Artículos de revistas: "Flavonoids Isoflavones Metabolites"

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Shen, Ting, Fengting Hu, Qianrui Liu, Haiyan Wang y Houhua Li. "Analysis of Flavonoid Metabolites in Chaenomeles Petals Using UPLC-ESI-MS/MS". Molecules 25, n.º 17 (2 de septiembre de 2020): 3994. http://dx.doi.org/10.3390/molecules25173994.

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Chaenomeles species are used for both ornamental decoration and medicinal purposes. In order to have a better understanding of the flavonoid profile of Chaenomeles, the petals of four Chaenomeles species, including Chaenomeles japonica (RB), Chaenomeles speciose (ZP), Chaenomeles sinensis (GP), and Chaenomeles cathayensis (MY), were selected as experimental material. The total flavonoid content of GP was found to be the highest, followed by MY, ZP, and RB. In total, 179 flavonoid metabolites (including 49 flavonols, 46 flavonoids, 19 flavone C-glycosides, 17 procyanidins, 15 anthocyanins, 10 flavanols, 10 dihydroflavonoids, 6 isoflavones, 5 dihydroflavonols, and 2 chalcones) were identified by Ultra-Performance Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry. Screening of differential flavonoid metabolites showed that GP had higher levels of metabolites when compared with the other three Chaenomeles species. Annotation and enrichment analysis of flavonoid metabolites revealed that cyanidin 3,5-diglucoside and pelargonidin-3,5-diglucoside anthocyanins are likely responsible for the color differences of the four Chaenomeles petals. Additionally, a large number of flavonoids, flavonols, and isoflavones were enriched in the petals of GP. This study provides new insights into the development and utilization of Chaenomeles petals and provides a basis for future investigations into their utilization.

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Wang, Jun-Fei, Si-Si Liu, Zhi-Qiang Song, Tang-Chang Xu, Chuan-Sheng Liu, Ya-Ge Hou, Rong Huang y Shao-Hua Wu. "Naturally Occurring Flavonoids and Isoflavonoids and Their Microbial Transformation: A Review". Molecules 25, n.º 21 (3 de noviembre de 2020): 5112. http://dx.doi.org/10.3390/molecules25215112.

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Flavonoids and isoflavonoids are polyphenolic secondary metabolites usually produced by plants adapting to changing ecological environments over a long period of time. Therefore, their biosynthesis pathways are considered as the most distinctive natural product pathway in plants. Seemingly, the flavonoids and isoflavones from fungi and actinomycetes have been relatively overlooked. In this review, we summarized and classified the isoflavones and flavonoids derived from fungi and actinomycetes and described their biological activities. Increasing attention has been paid to bioactive substances derived from microorganism whole-cell biotransformation. Additionally, we described the utilization of isoflavones and flavonoids as substrates by fungi and actinomycetes for biotransformation through hydroxylation, methylation, halogenation, glycosylation, dehydrogenation, cyclisation, and hydrogenation reactions to obtain rare and highly active biofunctional derivatives. Overall, among all microorganisms, actinomycetes are the main producers of flavonoids. In our review, we also summarized the functional genes involved in flavonoid biosynthesis.

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Chen, Qianru, Xianxian Wang, Xiaolong Yuan, John Shi, Chengsheng Zhang, Ning Yan y Changliang Jing. "Comparison of Phenolic and Flavonoid Compound Profiles and Antioxidant and α-Glucosidase Inhibition Properties of Cultivated Soybean (Glycine max) and Wild Soybean (Glycine soja)". Plants 10, n.º 4 (20 de abril de 2021): 813. http://dx.doi.org/10.3390/plants10040813.

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Wild soybean (Glycine soja Sieb.et Zucc; WS) has been used as a traditional food in China for many years and contains significantly higher levels of isoflavones than cultivated soybean (Glycine max; CS), but the secondary metabolites, including flavonoids and the phenolic composition differences between them, remain unclear. The results showed that WS possessed significantly higher total phenolic and flavonoid content and exhibited better antioxidant and α-glucosidase inhibition activities as well as excellent protective effects against H2O2-induced oxidative injury in a human endothelial cell line. Through metabolomic analysis, 642 metabolites were identified, and 238 showed differential expression, with 151 upregulated and 87 downregulated. A total of 79 flavonoid compounds were identified, 42 of which were upregulated in WS. 2′-Hydroxygenistein, garbanzol, protocatechuic aldehyde, ligustilide, and resveratrol were the most discriminated compounds in WS. The metabolic pathway analysis of differential metabolites related to the biosynthesis of flavonoids and phenolic acids were the biosynthesis of phenylpropanoids, flavonoids, isoflavonoids, flavones, and flavonols. This study substantially elucidated differences in the content of flavonoids and biological activities between WS and CS, which is useful information for the effective utilization of these two black soybean species in food processing.

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Wang, Tao, Fengjiao Zhang, Weibing Zhuang, Xiaochun Shu y Zhong Wang. "Metabolic Variations of Flavonoids in Leaves of T. media and T. mairei Obtained by UPLC-ESI-MS/MS". Molecules 24, n.º 18 (12 de septiembre de 2019): 3323. http://dx.doi.org/10.3390/molecules24183323.

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The needles of Taxus species contain a large number of bioactive compounds, such as flavonoids. In the present study, the total flavonoid content in leaves of Taxus media and Taxus mairei was 19.953 and 14.464 mg/g, respectively. A total of 197 flavonoid metabolites (70 flavones, 42 flavonols, 26 flavone C-glycosides, 20 flavanones, 15 anthocyanins, 13 isoflavones, 6 flavonolignans, and 5 proanthocyanidins) were identified for the first time by a widely targeted Ultra Performance Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry (UPLC-ESI-MS/MS) method within the two Taxus species, containing 160 common metabolites, with 37 unique metabolites merely determined in T. mairei or T. media. Moreover, 42 differential flavonoid metabolites were screened in the two Taxus species, which showed specific metabolic patterns in isoflavonoid biosynthesis, anthocyanin biosynthesis, and flavone and flavonol biosynthesis pathways. Compared to T. mairei, a more activated phenylpropanoid pathway was found in T. media, which could be responsible for the higher content of total flavonoids in T. media. Our results provide new insights into the diversity of flavonoid metabolites between T. mairei and T. media, and provide a theoretical basis for the sufficient utilization of Taxus species and the development of novel drugs.

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Zhang, Aiai, Jing Zheng, Xuemiao Chen, Xueyin Shi, Huaisong Wang y Qiushi Fu. "Comprehensive Analysis of Transcriptome and Metabolome Reveals the Flavonoid Metabolic Pathway Is Associated with Fruit Peel Coloration of Melon". Molecules 26, n.º 9 (10 de mayo de 2021): 2830. http://dx.doi.org/10.3390/molecules26092830.

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The peel color is an important external quality of melon fruit. To explore the mechanisms of melon peel color formation, we performed an integrated analysis of transcriptome and metabolome with three different fruit peel samples (grey-green ‘W’, dark-green ‘B’, and yellow ‘H’). A total of 40 differentially expressed flavonoids were identified. Integrated transcriptomic and metabolomic analyses revealed that flavonoid biosynthesis was associated with the fruit peel coloration of melon. Twelve differentially expressed genes regulated flavonoids synthesis. Among them, nine (two 4CL, F3H, three F3′H, IFS, FNS, and FLS) up-regulated genes were involved in the accumulation of flavones, flavanones, flavonols, and isoflavones, and three (2 ANS and UFGT) down-regulated genes were involved in the accumulation of anthocyanins. This study laid a foundation to understand the molecular mechanisms of melon peel coloration by exploring valuable genes and metabolites.

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Selvakumar, Priyanga, Aja Badgeley, Paige Murphy, Hina Anwar, Urvashi Sharma, Katharine Lawrence y Ashakumary Lakshmikuttyamma. "Flavonoids and Other Polyphenols Act as Epigenetic Modifiers in Breast Cancer". Nutrients 12, n.º 3 (13 de marzo de 2020): 761. http://dx.doi.org/10.3390/nu12030761.

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Breast cancer is a common cancer that occurs due to different epigenetic alterations and genetic mutations. Various epidemiological studies have demonstrated an inverse correlation between breast cancer incidence and flavonoid intake. The anti-cancer action of flavonoids, a class of polyphenolic compounds that are present in plants, as secondary metabolites has been a major topic of research for many years. Our review analysis demonstrates that flavonoids exhibit anti-cancer activity against breast cancer occurring in different ethnic populations. Breast cancer subtype and menopausal status are the key factors in inducing the flavonoid’s anti-cancer action in breast cancer. The dose is another key factor, with research showing that approximately 10 mg/day of isoflavones is required to inhibit breast cancer occurrence. In addition, flavonoids also influence the epigenetic machinery in breast cancer, with research demonstrating that epigallocatechin, genistein, and resveratrol all inhibited DNA methyltransferase and altered chromatin modification in breast cancer. These flavonoids can induce the expression of different tumor suppressor genes that may contribute to decreasing breast cancer progression and metastasis. Additional studies are required to confirm the contribution of epigenetic modifications by flavonoids to breast cancer prevention.

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Sak, K. "CURRENT EPIDEMIOLOGICAL KNOWLEDGE ABOUT THE ROLE OF FLAVONOIDS IN PROSTATE CARCINOGENESIS". Experimental Oncology 39, n.º 2 (22 de junio de 2017): 98–105. http://dx.doi.org/10.31768/2312-8852.2017.39(2):98-105.

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Numerous experimental studies have demonstrated anticancer action of polyphenolic plant metabolites. However, data about associations between dietary intake of plant-derived flavonoids and prostate cancer risk are still sparse and inconsistent. This minireview compiles the epidemiological findings published to date on the role of flavonoids in prostate tumorigenesis, discusses the reasons of inconsistencies and elicits the promising results for chemoprevention of this malignancy. Long-term consumption of high doses of soy isoflavones can be the reason of markedly lower clinically detectable prostate cancer incidence among Asian men compared to their counterparts in the Western world. The ability to metabolize daidzein to equol, the most biologically active isoflavone, by the certain intestinal bacteria also seems to contribute to this important health benefit. The increasing incidence rate of prostate cancer related to adoption of westernized lifestyle and dietary habits makes the issue of chemoprevention ever more important and directs the eyes to specific food components in the Eastern diet. If further large-scale epidemiological studies will confirm the protective effects of isoflavones against prostate cancer, this could provide an important way for prostate cancer prevention, as diet is a potentially modifiable factor in our behavioral pattern.

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Awouafack, Maurice Ducret, Pierre Tane, Michael Spiteller y Jacobus Nicolaas Eloff. "Eriosema (Fabaceae) Species Represent a Rich Source of Flavonoids with Interesting Pharmacological Activities". Natural Product Communications 10, n.º 7 (julio de 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000749.

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Many flavonoids have so far been isolated as main secondary metabolites in plant species of the genus Eriosema (Fabaceae), which contains approximately 160 species. A total of 52 flavonoids including isoflavones, dihydroflavonols, flavonols, flavanones, dihydrochalcones, isoflavanone and their pyrano or glucoside derivatives were isolated and characterized from the five species of this genus investigated to date. Total synthesis and semi-synthesis (acetylation, methylation, hydrogenation, and cyclization) of some isolated flavonoids were reported. Due to several significant pharmacological properties (antimicrobial, cytotoxicity, anti-mycobacterial, antioxidant, antiviral, erectile-dysfunction, vasodilatory and hypoglycemic) of the isolated flavonoids and derivatives, more scientists should be interested in investigating Eriosema species. The present review is the first to document all flavonoids that have been reported from the genus Eriosema to date together with their synthetic and semi-synthetic derivatives, and their pharmacological properties. Dihydrochalcones, which are precursors of other classes of flavonoids, are very rare in natural sources and their isolation from Eriosema species may explain the large number of flavonoids found in this genus. It appears that isoflavone could be a marker for species in this genus. The 83 flavonoids (1–83) documented include 52 isolates, 31 semi-synthetic and 3 totally synthetic derivatives. Data were obtained from Google scholar, Pubmed, Scifinder, Sciencedirect, and Scopus. With 52 different flavonoids isolated from only 5 of the approximately 160 species it shows the remarkable chemical diversity of this genus. This compilation of the biological activities and chemical composition may renew the interest of pharmacologists and phytochemists in this genus.

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Sasaki, Kanako, Yusuke Tsurumaru, Hirobumi Yamamoto y Kazufumi Yazaki. "Molecular Characterization of a Membrane-bound Prenyltransferase Specific for Isoflavone from Sophora flavescens". Journal of Biological Chemistry 286, n.º 27 (16 de mayo de 2011): 24125–34. http://dx.doi.org/10.1074/jbc.m111.244426.

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Prenylated isoflavones are secondary metabolites that are mainly distributed in legume plants. They often possess divergent biological activities such as anti-bacterial, anti-fungal, and anti-oxidant activities and thus attract much attention in food, medicinal, and agricultural research fields. Prenyltransferase is the key enzyme in the biosynthesis of prenylated flavonoids by catalyzing a rate-limiting step, i.e. the coupling process of two major metabolic pathways, the isoprenoid pathway and shikimate/polyketide pathway. However, so far only two genes have been isolated as prenyltransferases involved in the biosynthesis of prenylated flavonoids, namely naringenin 8-dimethylallyltransferase from Sophora flavescens (SfN8DT-1) specific for some limited flavanones and glycinol 4-dimethylallyltransferase from Glycine max (G4DT), specific for pterocarpan substrate. We have in this study isolated two novel genes coding for membrane-bound flavonoid prenyltransferases from S. flavescens, an isoflavone-specific prenyltransferase (SfG6DT) responsible for the prenylation of the genistein at the 6-position and a chalcone-specific prenyltransferase designated as isoliquiritigenin dimethylallyltransferase (SfiLDT). These prenyltransferases were enzymatically characterized using a yeast expression system. Analysis on the substrate specificity of chimeric enzymes between SfN8DT-1 and SfG6DT suggested that the determinant region for the specificity of the flavonoids was the domain neighboring the fifth transmembrane α-helix of the prenyltransferases.

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Faixová, D., G. Hrčková, T. Mačák Kubašková y D. Mudroňová. "Antiparasitic effects of selected isoflavones on flatworms". Helminthologia 58, n.º 1 (10 de febrero de 2021): 1–16. http://dx.doi.org/10.2478/helm-2021-0004.

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Summary Medicinal plants have been successfully used in the ethno medicine for a wide range of diseases since ancient times. The research on natural products has allowed the discovery of biologically relevant compounds inspired by plant secondary metabolites, what contributed to the development of many chemotherapeutic drugs. Flavonoids represent a group of therapeutically very effective plant secondary metabolites and selected molecules were shown to exert also antiparasitic activity. This work summarizes the recent knowledge generated within past three decades about potential parasitocidal activities of several flavonoids with different chemical structures, particularly on medically important flatworms such as Schistosoma spp., Fasciola spp., Echinococcus spp., Raillietina spp., and model cestode Mesocestoides vogae. Here we focus on curcumin, genistein, quercetin and silymarin complex of flavonolignans. All of them possess a whole spectrum of biological activities on eukaryotic cells which have multi-therapeutic effects in various diseases. In vitro they can induce profound alterations in the tegumental architecture and its functions as well as their activity can significantly modulate or damage worm´s metabolism directly by interaction with enzymes or signaling molecules in dose-dependent manner. Moreover, they seem to differentially regulate the RNA activity in numbers of worm´s genes. This review suggests that examined flavonoids and their derivates are promising molecules for antiparasitic drug research. Due to lack of toxicity, isoflavons could be used directly for therapy, or as adjuvant therapy for diseases caused by medically important cestodes and trematodes.

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Kicinska, Anna y Wieslawa Jarmuszkiewicz. "Flavonoids and Mitochondria: Activation of Cytoprotective Pathways?" Molecules 25, n.º 13 (4 de julio de 2020): 3060. http://dx.doi.org/10.3390/molecules25133060.

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A large number of diverse mechanisms that lead to cytoprotection have been described to date. Perhaps, not surprisingly, the role of mitochondria in these phenomena is notable. In addition to being metabolic centers, due to their role in cell catabolism, ATP synthesis, and biosynthesis these organelles are triggers and/or end-effectors of a large number of signaling pathways. Their role in the regulation of the intrinsic apoptotic pathway, calcium homeostasis, and reactive oxygen species signaling is well documented. In this review, we aim to characterize the prospects of influencing cytoprotective mitochondrial signaling routes by natural substances of plant origin, namely, flavonoids (e.g., flavanones, flavones, flavonols, flavan-3-ols, anthocyanidins, and isoflavones). Flavonoids are a family of widely distributed plant secondary metabolites known for their beneficial effects on human health and are widely applied in traditional medicine. Their pharmacological characteristics include antioxidative, anticarcinogenic, anti-inflammatory, antibacterial, and antidiabetic properties. Here, we focus on presenting mitochondria-mediated cytoprotection against various insults. Thus, the role of flavonoids as antioxidants and modulators of antioxidant cellular response, apoptosis, mitochondrial biogenesis, autophagy, and fission and fusion is reported. Finally, an emerging field of flavonoid-mediated changes in the activity of mitochondrial ion channels and their role in cytoprotection is outlined.

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Sood, Ankita, Bimlesh Kumar, Sachin Kumar Singh, Pankaj Prashar, Anamika Gautam, Monica Gulati, Narendra Kumar Pandey et al. "Flavonoids as Potential Therapeutic Agents for the Management of Diabetic Neuropathy". Current Pharmaceutical Design 26, n.º 42 (12 de diciembre de 2020): 5468–87. http://dx.doi.org/10.2174/1381612826666200826164322.

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Flavonoids are secondary metabolites that are widely distributed in plants. These phenolic compounds are classified into various subgroups based on their structures: flavones, flavonols, isoflavones, flavanones, and anthocyanins. They are known to perform various pharmacological actions like antioxidant, anti-inflammatory, anticancer, antimicrobial, antidiabetic and antiallergic, etc. Diabetes is a chronic progressive metabolic disorder that affects several biochemical pathways and leads to secondary complications such as neuropathy, retinopathy, nephropathy, and cardiomyopathy. Among them, the management of diabetic neuropathy is one of the major challenges for physicians as well as the pharmaceutical industries. Naturally occurring flavonoids are extensively used for the treatment of diabetes and its related complications due to their antioxidant properties. Moreover, flavonoids inhibit various pathways that are involved in the progression of diabetic neuropathy like the reduction of oxidative stress, decrease in glycogenolysis, increase glucose utilization, decrease in the formation of advanced glycation end products, and inhibition of the α-glucosidase enzyme. This review entails current updates on the therapeutic perspectives of flavonoids in the treatment of neuropathic pain. This manuscript explains the pathological aspects of neuropathic pain, the chemistry of flavonoids, and their application in amelioration of neuropathic pain through preclinical studies either alone or in combination with other therapeutic agents.

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AL-Ishaq, Abotaleb, Kubatka, Kajo y Büsselberg. "Flavonoids and Their Anti-Diabetic Effects: Cellular Mechanisms and Effects to Improve Blood Sugar Levels". Biomolecules 9, n.º 9 (1 de septiembre de 2019): 430. http://dx.doi.org/10.3390/biom9090430.

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Diabetes mellitus (DM) is a prevailing global health metabolic disorder, with an alarming incidence rate and a huge burden on health care providers. DM is characterized by the elevation of blood glucose due either to a defect in insulin synthesis, secretion, binding to receptor, or an increase of insulin resistance. The internal and external factors such as obesity, urbanizations, and genetic mutations could increase the risk of developing DM. Flavonoids are phenolic compounds existing as secondary metabolites in fruits and vegetables as well as fungi. Their structure consists of 15 carbon skeletons and two aromatic rings (A and B) connected by three carbon chains. Flavonoids are furtherly classified into 6 subclasses: flavonols, flavones, flavanones, isoflavones, flavanols, and anthocyanidins. Naturally occurring flavonoids possess anti-diabetic effects. As in vitro and animal model’s studies demonstrate, they have the ability to prevent diabetes and its complications. The aim of this review is to summarize the current knowledge addressing the antidiabetic effects of dietary flavonoids and their underlying molecular mechanisms on selected pathways: Glucose transporter, hepatic enzymes, tyrosine kinase inhibitor, AMPK, PPAR, and NF-κB. Flavonoids improve the pathogenesis of diabetes and its complications through the regulation of glucose metabolism, hepatic enzymes activities, and a lipid profile. Most studies illustrate a positive role of specific dietary flavonoids on diabetes, but the mechanisms of action and the side effects need more clarification. Overall, more research is needed to provide a better understanding of the mechanisms of diabetes treatment using flavonoids.

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Smeriglio, Antonella, Antonella Calderaro, Marcella Denaro, Giuseppina Laganà y Ersilia Bellocco. "Effects of Isolated Isoflavones Intake on Health". Current Medicinal Chemistry 26, n.º 27 (23 de octubre de 2019): 5094–107. http://dx.doi.org/10.2174/0929867324666171006143047.

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Background: Isoflavones are naturally occurring flavonoids, commonly found in the food consumed for centuries in the East-Asian population, characterized by a structure able to exert nonsteroidal estrogen-like activity on human cells. They have attracted researcher interest all around the word, following the results obtained in epidemiological and clinical studies. The involvement of isoflavones and their metabolites in various biological processes suggests that they can influence several metabolic pathways and can influence the gene expression at epigenetic level, involving effects that probably are due to early life exposure. They show positive health effects on several diseases, especially in the prevention of coronary heart and neurological diseases, hormone-related cancers, osteoporosis, and postmenopausal symptoms. Methods: We have performed a critical evaluation of available literature trough a structured search of bibliographic databases about isoflavones health promoting properties, risk assessment and mechanisms of action. In addition, we supplied useful information on their biochemical properties, sources and bioavailability. Results: Although these molecules have been the subjects of numerous researches, their role for the wellness of the human organism remains controversial. Moreover, there are substantial inconsistencies between the results obtained by epidemiologic studies conducted on Eastern population, which found high health promoting properties, and Western clinical trials, which found much less positive effects. Conclusion: Further epidemiologic studies and well-designed prospective human studies are to determine the beneficial effects of isoflavones exposure, as well as establishing its safe therapeutic.

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Wyse, Jessica M., Sajid Latif, Saliya Gurusinghe, Erica D. Berntsen, Leslie A. Weston y Cyril P. Stephen. "Characterization of Phytoestrogens in Medicago sativa L. and Grazing Beef Cattle". Metabolites 11, n.º 8 (20 de agosto de 2021): 550. http://dx.doi.org/10.3390/metabo11080550.

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Phytoestrogens are plant-produced bioactive secondary metabolites known to play an integral role in plant defense that frequently accumulate in times of stress and/or microbial infection. Phytoestrogens typically belong to two distinct chemical classes; flavonoids (isoflavones) and non-flavonoids (lignans and coumestans). Upon consumption by livestock, high concentrations of phytoestrogens can cause long-term disruption in reproduction due to structural similarities with mammalian estrogens and their tendency to bind estrogen receptors. Wide variation in phytoestrogen concentration has been reported in pasture legumes and corresponding silage or hay. Lucerne is a common perennial pasture legume in temperate climates, but information on phytoestrogen production or accumulation in grazing livestock is currently limited. Therefore, metabolic profiling using UHPLC-MS-QToF was performed to identify and quantitate key phytoestrogens in both fresh and dried lucerne fodder from replicated field or controlled glasshouse environments. Phytoestrogens were also profiled in the blood plasma of Angus cattle grazing field-grown lucerne. Results revealed that phytoestrogens varied quantitatively and qualitatively among selected lucerne cultivars grown under glasshouse conditions. Fresh lucerne samples contained higher concentrations of coumestans and other phytoestrogenic isoflavones than did dried samples for all cultivars profiled, with several exceeding desirable threshold levels for grazing cattle. Coumestans and isoflavones profiled in plasma of Angus heifers grazing lucerne increased significantly over a 21-day sampling period following experimental initiation. Currently, threshold concentrations for phytoestrogens in plasma are unreported. However, total phytoestrogen concentration exceeded 300 mg·kg−1 in fresh and 180 mg·kg−1 in dried samples of selected cultivars, suggesting that certain genotypes may upregulate phytoestrogen production, while others may prove suitable sources of fodder for grazing livestock.

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Shafiq, Nusrat, Sahrish Shafiq, Naila Rafiq, Shagufta Parveen, Irum Javed, Humara Naz Majeed, Ayesha Mahmood, Nadia Noor y Abrar Anjum. "Review: Phytochemicals of the Seriphidium, Economically and Pharmaceutically Important Genus of Asteraceae Family". Mini-Reviews in Organic Chemistry 17, n.º 2 (28 de febrero de 2020): 158–68. http://dx.doi.org/10.2174/1570193x16666190319153647.

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Seriphidium plants were reported to be utilized by local communities to cure their ailments in the form of paste, tincture, tea, nutraceuticals due to their medicinal properties. Most of the species are used as food, forage and ornamentals, etc. Due to the significant properties of the Seriphidium plants, the present article was designed to compile the data of major aspects and chemical constituents of genus Seriphidium responsible for their significant uses. This review article comprehensively covers the biological potential of different plants with their secondary metabolites and describes an overview of the biological activities of the different species belonging to genus Seriphidium. The main secondary metabolites isolated from different species of the genus Seriphidium are triterpenoid, sesquiterpenes, flavonoids, coumarins, chromones, anthraquinones, polyphenols and their glycosides, phenolic derivatives, balchanins, costunolides, Vulgarin, pyridine derivatives, ceramides, biphenyls, isoflavones. All these compounds are used in the drug industry.

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Russell, Wendy y Garry Duthie. "Plant secondary metabolites and gut health: the case for phenolic acids". Proceedings of the Nutrition Society 70, n.º 3 (9 de mayo de 2011): 389–96. http://dx.doi.org/10.1017/s0029665111000152.

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Plant-based diets contain a plethora of secondary metabolites that may impact on health and disease prevention. Much attention has been focused on the potential bioactivity and nutritional relevance of several classes of phytochemicals such as flavonoids, carotenoids, phyto-oestrogens and glucosinolates. Less attention has been paid to simple phenolic acids that are widely found in fruit, vegetables, herbs, spices and beverages. Daily intakes may exceed 100 mg. In addition, bacteria in the gut can perform reactions that transform more complex plant phenolics such as anthocyanins, procyanidins, flavanones, flavonols, tannins and isoflavones into simple phenolic metabolites. The colon is thus a rich source of potentially active phenolic acids that may impact both locally and systemically on gut health. Both the small and large intestine (colon) contain absorption sites for phenolic acids but low post-prandial concentrations in plasma indicate minimal absorption early in the gastrointestinal tract and/or rapid hepatic metabolism and excretion. Therefore, any bioactivity that contributes to gut health may predominantly occur in the colon. Several phenolic acids affect the expression and activity of enzymes involved in the production of inflammatory mediators of pathways thought to be important in the development of gut disorders including colon cancer. However, at present, we remain largely ignorant as to which of these compounds are beneficial to gut health. Until we can elucidate which pro-inflammatory and potentially carcinogenetic changes in gene expression can be moderated by simple phenolic acids, it is not possible to recommend specific plant-based foods rich in particular phenolics to optimise gut health.

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Magiera, S., C. Uhlschmied, M. Rainer, Ch W. Huck, I. Baranowska y G. K. Bonn. "GC–MS method for the simultaneous determination of β-blockers, flavonoids, isoflavones and their metabolites in human urine". Journal of Pharmaceutical and Biomedical Analysis 56, n.º 1 (agosto de 2011): 93–102. http://dx.doi.org/10.1016/j.jpba.2011.04.024.

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Mei, Yuqi, Lifang Wei, Chuan Chai, Lisi Zou, Xunhong Liu, Jiali Chen, Mengxia Tan et al. "A Method to Study the Distribution Patterns for Metabolites in Xylem and Phloem of Spatholobi Caulis". Molecules 25, n.º 1 (31 de diciembre de 2019): 167. http://dx.doi.org/10.3390/molecules25010167.

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Spatholobi Caulis (SC), the vine stem of Spatholobus suberectus Dunn, is a widely used traditional Chinese medicine (TCM) for the treatment of blood stasis syndrome and related diseases. Xylem and phloem are the main structures of SC and the color of xylem in SC is red brown or brown while the phloem with resin secretions is reddish brown to dark brown. They are alternately arranged in a plurality of concentric or eccentric rings. In order to investigate the distribution patterns of metabolites in xylem and phloem of SC, an analytical method based on UFLC–QTRAP–MS/MS was established for simultaneous determination of 22 constituents including four flavanols, nine isoflavones, two flavonols, two dihydroflavones, one flavanonol, one chalcone, one pterocarpan, one anthocyanidin and one phenolic acid in the samples (xylem and phloem) from Laos. Furthermore, according to the contents of 22 constituents, heat map, principal components analysis (PCA), orthogonal partial least squares discriminant analysis (OPLS–DA) and t–test were used to evaluate the samples and discover the differences between xylem and phloem of SC. The results indicated that the measured ingredients in xylem and phloem were significantly different. To be specific, the contents of flavonoids in xylem were higher than that in phloem, while the content of protocatechuic acid showed a contrary tendency. This study will not only reveal the distribution patterns of metabolites in xylem and phloem of SC but also facilitate further study on their quality formation.

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Vargas-Medina, Lorena, Lydia F. Yamaguchi y Ericsson Coy-Barrera. "LC-ESI-HRMS-Based Chemical Characterization of Lupinus bogotensis Roots". Revista Facultad de Ciencias Básicas 12, n.º 2 (25 de julio de 2016): 200–211. http://dx.doi.org/10.18359/rfcb.2028.

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Plants of the genus Lupinus (Fabaceae) have been studied due to the occurrence of different compounds, especially those possessing quinolizidine and isoflavone-like structures. These kinds of compounds are characterized by both medical and industrial applications, providing various benefits to human being. However, organs such as roots have not been equally studied and there is a lack of such records for native species. Therefore, in the present study, the chemical composition of nodulated roots from greenhouse-established L. bogotensis plants was determined. The resulting crude ethanolic extract was then analyzed by LC/HRMS and chemical nature of most compounds was determined by analyzing the high resolution mass spectra. Recorded profile showed adequate separation allowing tentative identification of detected compounds. 47 secondary metabolites (mainly isoflavones and quinolizidine-type compounds) were thus identified. Most phenolic compounds were found to be conjugated flavonoids (e.g., genistin and genistein malonylglucoside) and lupanine, sparteine and hydroxylupanine were noticed as the main alkaloids. Among alkaloid-like compounds, dehydromitomycin C, a compound produced by Streptomyces caespitosus was identified. Lupadienediol (a lupane-type triterpene recognized for being involved in rhizobacteria:legumes symbiosis) was the only terpene-related component identified in the extract. The present work corresponds to the first report on the chemical composition of L. bogotensis root and constitutes an adequate basis for phytoconstituents finding from nature to support the use of native species.

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Sobeh, Mansour, Esraa ElHawary, Herbenya Peixoto, Rola M. Labib, Heba Handoussa, Noha Swilam, Ahmed H. El-Khatib et al. "Identification of phenolic secondary metabolites fromSchotia brachypetalaSond. (Fabaceae) and demonstration of their antioxidant activities inCaenorhabditis elegans". PeerJ 4 (15 de noviembre de 2016): e2404. http://dx.doi.org/10.7717/peerj.2404.

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BackgroundSchotia brachypetalaSond. (Fabaceae) is an endemic tree of Southern Africa whose phytochemistry and pharmacology were slightly studied. The present work aimed at profiling the major phenolics compounds present in the hydro-alcohol extract fromS. brachypetalaleaves (SBE) using LC/HRESI/MS/MS and NMR and prove their antioxidant capabilities using novel methods.MethodsIn vitroassays; DPPH, TEAC persulfate decolorizing kinetic and FRAP assays, andin vivoassays:Caenorhabditis elegansstrains maintenance, Intracellular ROS inC. elegans, Survival assay, GFP expression and Subcellular DAF-16 localization were employed to evaluate the antioxidant activity.ResultsMore than forty polyphenols, including flavonoid glycosides, galloylated flavonoid glycosides, isoflavones, dihydrochalcones, procyanidins, anthocyanins, hydroxy benzoic acid derivatives, hydrolysable tannins, and traces of methylated and acetylated flavonoid derivatives were identified. Three compounds were isolated and identified from the genusSchotiafor the first time, namely gallic acid, myricetin-3-O-α-L-1C4-rhamnoside and quercetin-3-O-L-1C4-rhamnoside. The total phenolics content of SBE was (376 mg CAE/g), followed by flavonoids (67.87 QE/g).In vitroantioxidant activity of SBE was evidenced by DPPH radical scavenging activity (IC50of 9 µg/mL), FRAP ferric reducing activity (5,000 mol Fe2+E/mg) and ABTS peroxide inhibiting activity (1,054 mM Trolox E/mg). The tested extract was able to protect the worms against juglone induced oxidative stress, an increased survival rate (up to 41%) was recorded, when compared with the control group (11%) and attenuate the reactive oxygen species (ROS) accumulation in dose-dependent and reached up to 72% for the highest tested concentration. SBE was also able to attenuate the levels of heat shock protein (HSP) expression in dose-dependent up to 60% in the 150 µg SBE/mL group. In DAF-16 Subcellular localization SBE treated worms showed nuclear localization pattern up to 78%, while it was only 5% in the untreated control group.DiscussionA pronounced antioxidant activityin vivo, which can be attributed to its ability to promote the nuclear translocation of DAF-16/FOXO, the main transcription factor regulating the expression of stress response genes. The remarkable antioxidant activityin vitroandin vivocorrelates to SBE rich phenolic profile.

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Qi, Yuting, Chuanshun Li, Chonghao Duan, Caihong Gu y Quan Zhang. "Integrated Metabolomic and Transcriptomic Analysis Reveals the Flavonoid Regulatory Network by Eutrema EsMYB90". International Journal of Molecular Sciences 22, n.º 16 (15 de agosto de 2021): 8751. http://dx.doi.org/10.3390/ijms22168751.

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Flavonoids are representative secondary metabolites with different metabolic functions in plants. Previous study found that ectopic expression of EsMYB90 from Eutremasalsugineum could strongly increase anthocyanin content in transgenic tobacco via regulating the expression of anthocyanin biosynthesis genes. In the present research, metabolome analysis showed that there existed 130 significantly differential metabolites, of which 23 metabolites enhanced more than 1000 times in EsMYB90 transgenic tobacco leaves relative to the control, and the top 10 of the increased metabolites included caffeic acid, cyanidin O-syringic acid, myricetin and naringin. A total of 50 markedly differential flavonoids including flavones (14), flavonols (13), flavone C-glycosides (9), flavanones (7), catechin derivatives (5), anthocyanins (1) and isoflavone (1) were identified, of which 46 metabolites were at a significantly enhanced level. Integrated analysis of metabolome and transcriptome revealed that ectopic expression of EsMYB90 in transgenic tobacco leaves is highly associated with the prominent up-regulation of 16 flavonoid metabolites and the corresponding 42 flavonoid biosynthesis structure genes in phenylpropanoid/flavonoid pathways. Dual luciferase assay documented that EsMYB90 strongly activated the transcription of NtANS and NtDFR genes via improving their promoter activity in transiently expressed tobacco leaves, suggesting that EsMYB90 functions as a key regulator on anthocyanin and flavonoid biosynthesis. Taken together, the crucial regulatory role of EsMYB90 on enhancing many flavonoid metabolite levels is clearly demonstrated via modulating flavonoid biosynthesis gene expression in the leaves of transgenic tobacco, which extends our understanding of the regulating mechanism of MYB transcription factor in the phenylpropanoid/flavonoid pathways and provides a new clue and tool for further investigation and genetic engineering of flavonoid metabolism in plants.

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Pambudi, Arief, Syaefudin, Nita Noriko, Risa Azhari y Purwanty Rara Azura. "Identifikasi Bioaktif Golongan Flavonoid Tanaman Anting-Anting (Acalypha indica L.)". JURNAL Al-AZHAR INDONESIA SERI SAINS DAN TEKNOLOGI 2, n.º 3 (2 de noviembre de 2015): 178. http://dx.doi.org/10.36722/sst.v2i3.139.

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Abstrak – Indonesia merupakan negara dengan kekayaan alam yang melimpah. Namun, untuk jenis tumbuhan, baru sekitar 8% yang dimanfaatkan sebagai tanaman pangan, obat-obatan, sumber kayu, dan tanaman hias. Salah satu tanaman yang berpotensi sebagai tanaman obat adalah Acalypha indica. Penelitian sebelumnya menunjukkan bahwa ekstrak tanaman ini memiliki aktivitas antibakteri Salmonella. Namun profil senyawa metabolit apa saja yang terkandung masih belum banyak diteliti. Fraksinasi senyawa metabolit dilakukan dengan kromatografi kertas pada ekstrak etanol (akar, batang, dan daun) tanaman Acalypha menggunakan eluen BAW (Butanol: Asam asetat: Air = 4:1:5) dan asam asetat 15%. Jumlah, letak, warna, dan nilai Rf bercak kemudian digunakan sebagai pedoman identifikasi dan menduga golongan flavonoid. Spektrofotometri serapan panjang gelombang maksimum dilakukan sebagai konfirmasi dugaan golongan flavonoid. Ketiga organ utama tanaman anting-anting (akar, batang, dan daun) memiliki distribusi kandungan senyawa yang berbeda-beda namun dengan jenis yang hampir sama. Golongan flavonoid yang berhasil teridentifikasi dari ketiga organ antara lain isoflavon, flavon, flavonol, flavanon, dihidroksiflavonol, khalkon, dan antosianidin. Organ daun memiliki keragaman kelas flavonoid lebih banyak dibanding akar dan batang. Abstract – Indonesia is a megabiodiversity country, but only about 8% of its plant diversity are utilized as food, medicine, timber, and ornamental plants. One plant species that potential to be used as a medicinal plant is Acalypha indica. Previous research showed this plant extract has some antibacterial activiting against Salmonella. However, the profile of the metabolites contained in the plant is not studied yet. Fractination of the metabolites was done by using paper chromatography in ethanol extract (roots, stems, and leaves) of Acalypha plants using BAW (butanol: acetic acid: water = 4:1:5) and 15% acetic acid eluent. Number, location, color, and Rf values of spots were used for identification of flavonoids class. Maximum absorption wavelength performed using spectrophotometry assay to confirm the flavonoid class. The three major plant organs (roots, stems, and leaves) have different compounds distribution, but with almost same class. Class of flavonoids which were identified from the three organs are isoflavones, flavones, flavonols, flavanones, dihidroxyflavonols, chalcones, and anthocyanidins. Leaf has more diverse flavonoid class than roots and stems. Keyword – Acalypha indica bioactive compound, chromatography, flavonoids.

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Moreira, Marco Aurélio Borba, Amilton Diniz Souza, Fernanda Barbosa Borges Jardim, Luís Carlos Scalon Cunha, Mário Machado Martins, Luiz Ricardo Goulart, Sérgio Antônio Lemos de Morais et al. "Chemical Profile and Chemometric Analysis of Genetically Modified Soybeans Produced in the Triângulo Mineiro Region (MG), Brazil". Journal of Agricultural Studies 9, n.º 2 (22 de febrero de 2021): 73. http://dx.doi.org/10.5296/jas.v9i2.18139.

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Soy production in Brazil is an important factor for the agro-industrial, economic, and social development of the country. The expansion of soy in the Brazilian territory is mainly due to the incorporation of new genetic characteristics into cultivars that granted resistance to the Cerrado conditions and to herbicides. Currently, Brazilian soy production is the result of genetically modified cultivars. Studies regarding the chemical composition of soybeans show that qualitative and quantitative variations can occur, depending on the region of production. This work aimed to investigate the chemical composition of soybeans produced in different cities of the Triângulo Mineiro region/MG, Brazil (Harvest 2017/2018) and stored in three warehouses located in the city of Uberaba/MG. The grain analysis was made by liquid chromatography coupled to electrospray ionization mass spectrometry (LC-MS-ESI). The classes of metabolites identified from methanolic extraction were organic acids, phenolic compounds, flavonoids, sugars, amino acids, dipeptides, nitrogenous bases, nucleosides, sphingolipids, and fatty acids. The isoflavones genistein, daidzein, glycitein, genistin, acetyldaidzin, and acetylgenistin were identified in soybeans from the three warehouses. The flavonoid eriodictyol-O-hexoside was also found. The Principal Component Analysis (PCA) from the mass spectrum data obtained by direct injection in the negative and positive modes evidenced the well-defined separation of three groups, indicating that there was variance among the soy samples from each warehouse. The samples from warehouses 1 and 3 showed greater similarity in the Hierarchical Cluster Analysis (HCA) in negative mode, while in positive mode, the samples from warehouses 2 and 3 presented greater similarity.

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Antipova, Ekaterina Alekseevna, Lyudmila Evdokimovna Kudrikova, Lyudmila Ivanovn Tikhomirova, Natalya Grigoryevna Bazarnova, Marina Yurievna Cheprasova y Elena Pavlovna Khanutova. "ASSESSMENT OF THE CONTENT OF POLYPHENOLS IN BIOTECHNOLOGICAL RAW MATERIAL IRIS SIBIRICA L. STAR VARIETY IN COMPARISON WITH INTACT PLANTS". chemistry of plant raw material, n.º 2 (1 de abril de 2019): 239–50. http://dx.doi.org/10.14258/jcprm.2019024799.

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Cultivation of plant raw materials in artificial conditions will inevitably lead to a change in the qualitative and quantitative composition of secondary metabolites in comparison with the composition of plants obtained in soil conditions. The study of the metabolic profile of such plants is very important on the one hand for our understanding of temporal (ontogenetic) and spatial changes in the metabolome of plants, on the other hand in the applied plan to obtain an alternative quality medicinal plant raw materials. In this regard, the aim of this study was to study the content of phenolic compounds in biotechnological raw materials Iris sibirica Grade Стерх in comparison with intact plants. As objects of study used plants propagated mikrokanale (regenerants), which were further grown under conditions of hydroponics (hydroponic). Intact plants were harvested in the field at the age of six years. As a result of research in raw materials Iris sibirica Grade Стерх, grown under different conditions, were found following a group of biologically active compound (БАС), corresponding to the genus Iris L.: fenilpropionovoy acid (Komarova and ferulic acid and their derivatives), flavonoids (glycosides of apigenin, apigenin-7-O-glycoside), isoflavones, and phenolic acids (vanillic acid), neytralizuya flavonoids-glycosides (glycosides of kaempferol and apigenin), stilbene. The qualitative composition of biologically active compounds of Iris sibirica Стерх depended on the growing conditions, while the biotechnological raw materials (hydroponic plants) are the closest to intact plants in terms of the content of biologically active compounds. This allows us to consider the biotechnology of obtaining the raw material Iris sibirica L. based on hydroponic cultivation coupled with the micropropagation in an alternative way.

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Wang, Fu, Lin Chen, Hongping Chen, Shiwei Chen y Youping Liu. "Analysis of Flavonoid Metabolites in Citrus Peels (Citrus reticulata “Dahongpao”) Using UPLC-ESI-MS/MS". Molecules 24, n.º 15 (24 de julio de 2019): 2680. http://dx.doi.org/10.3390/molecules24152680.

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Flavonoids are a kind of essential substance for the human body because of their antioxidant properties and extremely high medicinal value. Citrus reticulata “Dahongpao” (DHP) is a special citrus variety that is rich in flavonoids, however little is known about its systematic flavonoids profile. In the present study, the presence of flavonoids in five important citrus varieties, including DHP, Citrus grandis Tomentosa (HZY), Citrus ichangensis Swingle (YCC), Citrus sinensis (L.) Osbeck (TC), and Citrus reticulata ‘Buzhihuo’ (BZH), was determined using a UPLC-ESI-MS/MS-based, widely targeted metabolome. Results showed that a total of 254 flavonoid metabolites (including 147 flavone, 39 flavonol, 21 flavanone, 24 anthocyanins, 8 isoflavone, and 15 polyphenol) were identified. The total flavonoid content of peels from DHP was the highest. DHP could be clearly separated from other samples through clustering analysis and principal component analysis (PCA). Further, 169 different flavonoid metabolites were observed between DHP peels and the other four citrus peels, and 26 down-regulated differential metabolites displayed important biological activities in DHP. At the same time, a unique flavonoid component, tricin 4′-O-syringyl alcohol, was only found in DHP, which could be used as a marker to distinguish between other varieties. This work might facilitate a better understanding of flavonoid metabolites between DHP peels and the other four citrus peels and provide a reference for its sufficient utilization in the future.

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Li, Jing, Pu Yang, Qinghua Yang, Xiangwei Gong, Hongchi Ma, Ke Dang, Guanghua Chen, Xiaoli Gao y Baili Feng. "Analysis of Flavonoid Metabolites in Buckwheat Leaves Using UPLC-ESI-MS/MS". Molecules 24, n.º 7 (3 de abril de 2019): 1310. http://dx.doi.org/10.3390/molecules24071310.

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Flavonoids from plants are particularly important in our diet. Buckwheat is a special crop that is rich in flavonoids. In this study, four important buckwheat varieties, including one tartary buckwheat and three common buckwheat varieties, were selected as experimental materials. The total flavonoid content of leaves from red-flowered common buckwheat was the highest, followed by tartary buckwheat leaves. A total of 182 flavonoid metabolites (including 53 flavone, 37 flavonol, 32 flavone C-glycosides, 24 flavanone, 18 anthocyanins, 7 isoflavone, 6 flavonolignan, and 5 proanthocyanidins) were identified based on Ultra Performance Liquid Chromatography–Electrospray Ionization–Tandem Mass Spectrometry (UPLC-ESI-MS/MS) system. Through clustering analysis, principal component analysis (PCA), and orthogonal signal correction and partial least squares-discriminant analysis (OPLS-DA), different samples were clearly separated. Considerable differences were observed in the flavonoid metabolites between tartary buckwheat leaves and common buckwheat leaves, and both displayed unique metabolites with important biological functions. This study provides new insights into the differences of flavonoid metabolites between tartary buckwheat and common buckwheat leaves and provides theoretical basis for the sufficient utilization of buckwheat.

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Kim, Heon-Woong, Seon-Hye Lee, Min-Ki Lee, Gelila Asamenew, Suji Lee, Jin Ju Park, Youngmin Choi, Seon Mi Yoo y Sang Hoon Lee. "Characterization of Isoflavone Conjugated Metabolites in Human Plasma and Urine by Dietary Soybean Meals". Current Developments in Nutrition 4, Supplement_2 (29 de mayo de 2020): 414. http://dx.doi.org/10.1093/cdn/nzaa045_047.

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Abstract Objectives Soy isoflavones are one of the best studied secondary plant metabolites for the last 30 years and associated with potential health benefits such as prevention of cancer, cardiovascular diseases, and menopausal symptoms. The study aimed to identify isoflavone conjugated metabolites from human plasma and urine after dietary soybean meals using a targeted metabolomic approach and to investigate the effect of fermentation on bioavailability of soy isoflavones. Methods In the cross-over intervention design with 10 candidates (6 women and 4 men), standardized meals with fermented soybean (FS, Cheonggukjang, by Bacillus subtilis) and non-fermented soybean (NFS) were served over two weeks in two randomized groups. Flavonoid derivatives in each freeze-dried tested meal and isoflavone conjugated metabolites in plasma and urine collected before and after the consumption of each meal were evaluated by UPLC-DAD-QToF/MS. Results Twenty-two isoflavones, including genistein, daidzein, glycitein, and its glycosides, were identified in both tested meals. In particular, 6”-O-succinoyldadizin and 6”-O-succinoylgenistin produced newly as acylated forms with succinic acid in fermented process. Also, in levels of simple glycosidic forms (e.g., daidzin and genistin), the FS meal showed higher than NFS meal, which might be explained by the degradation of malonylglucosides during the fermentation. Fourteen metabolites conjugated with glucuronic acid and sulfuric acid were identified in plasma and urine, among them, genistein 4’,7-di-O-glucuronide and daidzein 7-O-glucuronide were confirmed as major metabolites in plasma and urine, respectively. The bioavailability was differentiated by personal characteristics after intake soy isoflavones, and it was considered that genistein class was more excellent as well as FS meal was more effective when compared to NFS meal on bioavailability. Conclusions The results may contribute to not only understanding the potential health effects of fermented foods by modifying the bioavailability of soybean bioactive components but also application of other traditional foods related with fermentation. Funding Sources This work was supported by the National Institute of Agricultural Science of Rural Development Administration, Republic of Korea.

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Saputra, Ajmi, Abdul Gani y Erlidawati Erlidawati. "UJI AKTIVITAS ANTIOKSIDAN DAUN GULMA SIAM (Chromoleana odorata L.) DENGAN METODE 1,1-DIFENIL-2-PIKRILHIDRAZIL". Jurnal IPA & Pembelajaran IPA 1, n.º 2 (1 de diciembre de 2017): 131–42. http://dx.doi.org/10.24815/jipi.v1i2.9687.

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Abstrak. Telah dilakukan penelitian uji aktivitas antioksidan daun gulma siam (Chromoleana odorata L.) dengan metode 1,1-difenil-2-pikrilhidrazil (DPPH). Tujuan penelitian ini untuk mengetahui kandungan senyawa metabolit sekunder, golongan flavonoid dan aktivitas antioksidan yang terdapat dalam daun gulma siam. Sebanyak 315 g daun gulma siam kering yang sudah dihaluskan, dimaserasi dengan etanol 95% diperoleh 100 g ekstrak kental etanol. Sebanyak 70 g ekstrak kental etanol difraksinasi dengan pelarut metanol dan n-heksana menghasilkan fraksi kental metanol 30,72 g dan n-heksana 14,62 g. Hasil skrining fitokimia ekstrak etanol menunjukkan positif mengandung senyawa alkaloid, flavonoid, saponin, tanin dan steroid. Fraksi metanol positif mengandung senyawa alkaloid, flavonoid, saponin, dan tanin. Fraksi metanol dilakukan isolasi dengan metode kromatografi kolom menggunakan eluen n-heksana : etil asetat : diklorometana (1:1:1) sebagai fase gerak pertama, kemudian ditingkatkan gradien kepolarannya untuk menghasilkan pemisahan secara sempurna. Hasil isolasi diperoleh 8 fraksi (A, B, C, D, E, F, G, H) dan hasil analisis secara KLT menunjukkan fraksi A dan B positif mengandung senyawa flavonoid. Senyawa flavonoid yang terkandung dalam fraksi A diperkirakan golongan isoflavon dan fraksi B diperkirakan golongan isoflavon, flavon, flavonol dan kalkon. Analisis FTIR menunjukkan fraksi A dan B mengandung gugus fungsi N-H, O-H (asam karboksilat), C=O (aldehid dan ester), C=C, C-H, C-X (flourida), C-O dan C-N. Hasil pengujian aktivitas antioksidan menggunakan metode DPPH, diperoleh Inhibitor concentrasi (IC50) untuk ekstrak etanol 15,5067 ppm, fraksi metanol 9,5671 ppm, fraksi A 82,7808 ppm dan fraksi B 16,2336 ppm, sedangkan untuk pembanding (asam askorbat) 0,8913 ppm. Dengan demikian, dapat disimpulkan aktivitas antioksidan yang paling kuat terdapat pada fraksi metanol.Kata kunci: daun gulma siam, Chromoleana odorata L., flavonoid, DPPH. Abstract. The antioxidant activity of siam weed leaf (Chromoleana odorata L.) has been done with 1,1-diphenyl-2-picrilhidrazil (DPPH) method. This study is intended to know the the content of secondary metabolite compounds, the group of flavonoid and antioxidant activity that found in siam weed leaf. The 315 g dry siam weed leaf that was refined, macerated with ethanol 96% produced 100 g of ethanol viscous extract. The 70 of ethanol viscous extract was fractionated with methanol and n-hexane solvent produced 30,72 g of methanol viscous fraction and 14,62 g n-hexane. The results of phytochemical screening of ethanol extract showed positive that contained compound of alkaloids, flavonoids, saponins, tannins and steroids. Methanol fraction showed positive that contained compound of alkaloids, flavonoids, saponins and tannins. The isolation in methanol fraction was made by coloumn chomatography method using eluent n-hexene : acetate ethyl : dichloromethane (1:1:1) as first mation phase. Then the polarity gradient was increased to produce complete separation. The result of isolation produced 8 fractions (A, B, C, D, E, F, G, H) and the analysis results with TLC showed fraction of A and B was positive contain flavonoids compound. Flaconoids compound that was contained in fraction A was estimated isoflvone group and fraction B was estimated group os isoflavone, flavone, flavonol and chalcone. Analysis FTIR showed that the fraction of A and B containing function group N-H, O-H (carboxylic acid), C=O (aldehyde and ester), C=C, C-H, C-X (flouride), C-O and C-N. The result of antioxidant activity test used DPPH method, obtained inhibitor concentration (IC50) for 15,5067 ppm of ethanol extract, 9,5671 of methanol fraction, 82,7808 ppm of fraction A and 16,2336 ppm of fraction B, while for comparison (ascorbic acid) is 0,8913 ppm. This, it can be concluded that strongert antioxidant activity was found in methanol fraction.Keywords: siam weed leaf, Chromoleana odorata L., DPPH.

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Wiseman, Helen. "The bioavailability of non-nutrient plant factors: dietary flavonoids and phyto-oestrogens". Proceedings of the Nutrition Society 58, n.º 1 (febrero de 1999): 139–46. http://dx.doi.org/10.1079/pns19990019.

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The bioavailability in human subjects of non-nutrient plant factors, including dietary flavonoids and phyto-oestrogens, is of great importance relative to their reported health protective effects. These effects include protection against heart disease, and also in the case of the phyto-oestrogens, hormone-dependent cancers. Epidemiological studies have shown flavonoid intake (mostly quercetin) to be inversely associated with mortality from CHD. Quercetin is a potent antioxidantin vitro, and protection against the oxidative damage to LDL implicated in atherogenesis has been suggested as a possible mechanism. Human subjects can absorb significant amounts of quercetin (particularly in the glucoside form) and it would appear to be sufficiently bioavailable to act as an antioxidantin vivo;however, following our recent study (J O'Reilly, TAB Sanders and H Wiseman, unpublished results), it is currently less clear whether quercetin really can act as an antioxidantin vivo. The isoflavone phyto-oestrogens genistein and daidzein are much less effective antioxidants than quercetinin vitro, however, they are well-absorbed by human subjects and appear to be sufficiently bioavailable to act as antioxidantsin vivo. In our recent study (O'Reillyet al.1998) lower plasma isoprostane concentrations and increased resistance of LDL to oxidation were observed following the high-isoflavone dietary phase compared with the low-isoflavone dietary phase. Considerable inter-individual variation in isoflavone metabolite excretion has been observed, in particular the production of equol (the gut bacterial metabolite of daidzein; a more potent antioxidant and more oestrogenic than daidzein), and this appears to be influenced by habitual diet. Further studies on the bioavailability of these non-nutrient plant factors and related influencing factors are clearly still required.

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Pham, Thi Thanh My, Youbin Tu y Michel Sylvestre. "Remarkable Ability of Pandoraea pnomenusa B356 Biphenyl Dioxygenase To Metabolize Simple Flavonoids". Applied and Environmental Microbiology 78, n.º 10 (16 de marzo de 2012): 3560–70. http://dx.doi.org/10.1128/aem.00225-12.

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ABSTRACTMany investigations have provided evidence that plant secondary metabolites, especially flavonoids, may serve as signal molecules to trigger the abilities of bacteria to degrade chlorobiphenyls in soil. However, the bases for this interaction are largely unknown. In this work, we found that BphAEB356, the biphenyl/chlorobiphenyl dioxygenase fromPandoraea pnomenusaB356, is significantly better fitted to metabolize flavone, isoflavone, and flavanone than BphAELB400fromBurkholderia xenovoransLB400. Unlike those of BphAELB400, the kinetic parameters of BphAEB356toward these flavonoids were in the same range as for biphenyl. In addition, remarkably, the biphenyl catabolic pathway of strain B356 was strongly induced by isoflavone, whereas none of the three flavonoids induced the catabolic pathway of strain LB400. Docking experiments that replaced biphenyl in the biphenyl-bound form of the enzymes with flavone, isoflavone, or flavanone showed that the superior ability of BphAEB356over BphAELB400is principally attributable to the replacement of Phe336 of BphAELB400by Ile334 and of Thr335 of BphAELB400by Gly333 of BphAEB356. However, biochemical and structural comparison of BphAEB356with BphAEp4, a mutant of BphAELB400which was obtained in a previous work by the double substitution Phe336Met Thr335Ala of BphAELB400, provided evidence that other residues or structural features of BphAEB356whose precise identification the docking experiment did not allow are also responsible for the superior catalytic abilities of BphAEB356. Together, these data provide supporting evidence that the biphenyl catabolic pathways have evolved divergently among proteobacteria, where some of them may serve ecological functions related to the metabolism of plant secondary metabolites in soil.

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Di Lorenzo, Chiara, Francesca Colombo, Simone Biella, Creina Stockley y Patrizia Restani. "Polyphenols and Human Health: The Role of Bioavailability". Nutrients 13, n.º 1 (19 de enero de 2021): 273. http://dx.doi.org/10.3390/nu13010273.

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Polyphenols are a group of phytochemicals with potential health-promoting effects. They are classified as flavonoid (flavonols, flavanols, flavones, flavanones, isoflavones, and anthocyanins) and non-flavonoid molecules (phenolic acids, hydroxycinnamic acids, lignans, stilbenes, and tannins). Although an increasing number of trials have shown a correlation among polyphenol consumption and a reduction in risk factors for chronic diseases, discrepancies in explaining their positive effects have been found in terms of the bioavailability. In fact, polyphenols show a low bioavailability due to several factors: interaction with the food matrix, the metabolic processes mediated by the liver (phase I and II metabolism), intestine and microbiota. On the other hand, the biological activities of phenol compounds may be mediated by their metabolites, which are produced in vivo, and recent studies have confirmed that these molecules may have antioxidant and anti-phlogistic properties. This review discusses the studies performed in vivo, which consider the polyphenol bioavailability and their different food sources. Factors influencing the biological effects of the main classes of polyphenols are also considered.

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Shrestha, Lasata, Bishnu P. Marasini, Suman Prakash Pradhan, Rajib Kumar Shrestha, Suraj Shrestha, Kamal Prasad Regmi y Bishnu Prasad Pandey. "Biotransformation of Daidzein, Genistein, and Naringenin by Streptomyces Species Isolated from High-Altitude Soil of Nepal". International Journal of Microbiology 2021 (19 de junio de 2021): 1–8. http://dx.doi.org/10.1155/2021/9948738.

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Flavonoids have achieved widespread importance in pharmaceutical, food, and cosmetics industries. Furthermore, modification of these naturally occurring flavonoids to structurally diverse compounds through whole cell biotransformation with enhanced biological activities has numerous biotechnological applications. The present study investigated the biotransformation potential of Streptomyces species isolated from a high-altitude-soil sample towards selected flavonoid molecules. The biotransformed metabolites were confirmed by comparing the HPLC chromatogram with authentic compounds and LC-MS/MS analysis. Of these isolates, Streptomyces species G-18 (Accession number: MW663767.1) catalyzed isoflavone molecules daidzein and genistein to produce hydroxylated products at 24 h of reaction condition in a whole cell system. The hydroxylation of daidzein (4′,7-dihydroxyisoflavone) was confirmed at 3′-position of the B ring to produce 3′,4′,7-trihydroxyisoflavone. In addition, Streptomyces species G-14 (Accession number: MW663770.1) and Streptomyces species S4L (Accession number: MW663769.1) also revealed the transformation of daidzein (4′,7-dihydroxyisoflavone) to hydroxy daidzein at a distinct position than that of G-18 isolates, whereas thee Streptomyces species S4L reaction mixture with naringenin as a substrate also revealed the hydroxylated product. Our results demonstrated that microorganisms isolated from different ecological niches have broad application.

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D'Angiolillo, Francesca, Laura Pistelli, Cecilia Noccioli, Barbara Ruffoni, Simona Piaggi, Roberto Scarpato y Luisa Pistelli. "In vitro Cultures of Bituminaria bituminosa: Pterocarpan, Furanocoumarin and Isoflavone Production and Cytotoxic Activity Evaluation". Natural Product Communications 9, n.º 4 (abril de 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900411.

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Bituminaria bituminosa L. is known for producing several compounds with considerable pharmaceutical interest, such as phenylpropanoids, furanocoumarins and pterocarpans. In vitro cultures of seedlings, shoots, and callus have been produced to obtain plant materials useful for the production of these metabolites. The secondary metabolite profile was evaluated by HPLC-DAD. The extracts of all the in vitro material contained the flavonoid daidzein, while plicatin B, erybraedin C and bitucarpin A were found only in the extracts of the in vitro shoots and in wild shoots. The furanocoumarins angelicin and psoralen were found in in vivo and in vitro plants, but in the callus were not detectable. The extracts were also tested for cytotoxic activity in HeLa cell culture; the highest level of cytotoxicity was found in in vitro shoot extracts.

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França, S. C., P. G. Roberto, M. A. Marins, R. D. Puga, A. Rodrigues y J. O. Pereira. "Biosynthesis of secondary metabolites in sugarcane". Genetics and Molecular Biology 24, n.º 1-4 (diciembre de 2001): 243–50. http://dx.doi.org/10.1590/s1415-47572001000100032.

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A set of genes related to secondary metabolism was extracted from the sugarcane expressed sequence tag (SUCEST) database and was used to investigate both the gene expression pattern of key enzymes regulating the main biosynthetic secondary metabolism pathways and the major classes of metabolites involved in the response of sugarcane to environmental and developmental cues. The SUCEST database was constructed with tissues in different physiological conditions which had been collected under varied situation of environmental stress. This database allows researchers to identify and characterize the expressed genes of a wide range of putative enzymes able to catalyze steps in the phenylpropanoid, isoprenoid and other pathways of the special metabolic mechanisms involved in the response of sugarcane to environmental changes. Our results show that sugarcane cDNAs encoded putative ultra-violet induced sesquiterpene cyclases (SC); chalcone synthase (CHS), the first enzyme in the pathway branch for flavonoid biosynthesis; isoflavone synthase (IFS), involved in plant defense and root nodulation; isoflavone reductase (IFR), a key enzyme in phenylpropanoid phytoalexin biosynthesis; and caffeic acid-O-methyltransferase, a key enzyme in the biosynthesis of lignin cell wall precursors. High levels of CHS transcripts from plantlets infected with Herbaspirillum rubri or Gluconacetobacter diazotroficans suggests that agents of biotic stress can elicit flavonoid biosynthesis in sugarcane. From this data we have predicted the profile of isoprenoid and phenylpropanoid metabolism in sugarcane and pointed the branches of secondary metabolism activated during tissue-specific stages of development and the adaptive response of sugarcane to agents of biotic and abiotic stress, although our assignment of enzyme function should be confirmed by careful biochemical and genetic supporting evidence.

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Nishanbaev, Sabir Zaripbaevich, Il'dar Dzhamil'yevich Shamyanov, Khayrulla Mamadievich Bobakulov y Shamansur Shahsaidovich Sagdullaev. "CHEMICAL COMPOSITION AND BIOLOGICAL ACTIVITY OF METABOLITES OF THE GENUS ALHAGI". chemistry of plant raw material, n.º 4 (27 de diciembre de 2019): 5–28. http://dx.doi.org/10.14258/jcprm.2019045117.

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In the review summarized the scientific literature on geographical distribution, the degree of knowledge of the chemical composition and biological activity of extracts and isolated individual compounds of the genus Alhagi Tourn. ex Adans. of the world flora. The structures of the isolated 300 compounds are presented belonging to the alkaloids, terpenoids, carbohydrates, hydrocarbons, lipids, and phenolic compounds. In quantitative terms, the phenolic compounds dominate, among which flavonoids belonging to the group flavone, flavonol, flavanone, isoflavone, isoflavonolignan and flavan-3-ols groups are prevails. Among them, to the chemotoxonomic markers can be include flavonols narcissin and its aglycone isorhamnetin, which are produced in major quantities in practically all species of the genus Alhagi. It was revealed that the qualitative composition of the metabolites of the same species of this genus depends on the ecological-geographical and soil-climatic conditions of their growth place. The data on the biological activity of extracts and isolated individual metabolites are considered. The main biologically active substances of the genus Alhagi are phenolic compounds. The presented information in the review shows that the plants of the genus Alhagi are promising for the creation of new pharmaceuticals. It was noted that in present time are being conducted in-depth preclinical pharmacological studies of the antioxidant preparation "Yantacin", the anti-inflammatory "Alkakhin", the biologically active complex "Alkhidin", and the antioxidant and antibacterial preparation "Zhantharid". Cited in the review information may be used as reference literature by phytochemists, biologists, and pharmacologists.

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Ibrahim, Ragai K. "A forty-year journey in plant research: original contributions to flavonoid biochemistry". Canadian Journal of Botany 83, n.º 5 (1 de mayo de 2005): 433–50. http://dx.doi.org/10.1139/b05-030.

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This review highlights original contributions by the author to the field of flavonoid biochemistry during his research career of more than four decades. These include elucidation of novel aspects of some of the common enzymatic reactions involved in the later steps of flavonoid biosynthesis, with emphasis on methyltransferases, glucosyltransferases, sulfotransferases, and an oxoglutarate-dependent dioxygenase, as well as cloning, and inferences about phylogenetic relationships, of the genes encoding some of these enzymes. The three-dimensional structure of a flavonol O-methyltransferase was studied through homology-based modeling, using a caffeic acid O-methyltransferase as a template, to explain their strict substrate preferences. In addition, the biological significance of enzymatic prenylation of isoflavones, as well as their role as phytoanticipins and inducers of nodulation genes, are emphasized. Finally, the potential application of knowledge about the genes encoding these enzyme reactions is discussed in terms of improving plant productivity and survival, modification of flavonoid profiles, and the search for new compounds with pharmaceutical and (or) nutraceutical value.Key words: flavonoid enzymology, metabolite localization, gene cloning, 3-D structure, phylogeny.

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Yusnawan, Eriyanto, Novita Nugrahaeni y Joko Susilo Utomo. "Changes of Phenolic Contents and Antioxidant Activity in Soybean Seeds Harvested from Phakopsora pachyrhizi Infected Crops". Biosaintifika: Journal of Biology & Biology Education 10, n.º 2 (29 de agosto de 2018): 369–78. http://dx.doi.org/10.15294/biosaintifika.v10i2.14481.

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Asian soybean rust caused by Phakopsora pachyrhizi is one of the most destructive foliar diseases on soybean. Severe infection of this disease causes early defoliation and reduces the yield. To determine the response of soybean genotypes to this disease and the changes of metabolites in seeds, a greenhouse study was conducted using eight Indonesian soybean cultivars, i.e. Malabar, Wilis, Ringgit, Pangrango, Argomulyo, Grobogan, Dena 1, and Dena 2. The experiment was arranged in a randomized completely block design and repeated three times. The soybean crops were inoculated with the pathogen and another set was not inoculated. Infection of P. pachyrhizi reduced fresh biomass, seed weight per plant, and weight of 100 seeds. However, total flavonoid contents in seeds increased from 12 to 50% in all infected genotypes. The increase of daidzein from 27 to 67% in seeds was observed, except for Malabar and Argomulyo . The increase of genistein was genotypic dependence. The increase of total phenolic contents as well as antioxidant activity was also depending on the genotypes. P. pachyrhizi could be one of the biotic elicitors to increase total flavonoid contents in soybean seeds. Dena 1 less suffered from the rust infection as represented by the least pustule number, less reduction in seed weight and weight of 100 seeds. Secondary metabolites particularly phenolics and isoflavones in seeds of this cultivar increased significantly after the rust infection. This cultivar could be considered as an alternative tolerant genotype where cultivated area is favorable for soybean rust infection.

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Chiang, Chien-Min, Tzi-Yuan Wang, Szu-Yi Yang, Jiumn-Yih Wu y Te-Sheng Chang. "Production of New Isoflavone Glucosides from Glycosylation of 8-Hydroxydaidzein by Glycosyltransferase from Bacillus subtilis ATCC 6633". Catalysts 8, n.º 9 (10 de septiembre de 2018): 387. http://dx.doi.org/10.3390/catal8090387.

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8-Hydroxydaidzein (8-OHDe) has been proven to possess some important bioactivities; however, the low aqueous solubility and stability of 8-OHDe limit its pharmaceutical and cosmeceutical applications. The present study focuses on glycosylation of 8-OHDe to improve its drawbacks in solubility and stability. According to the results of phylogenetic analysis with several identified flavonoid-catalyzing glycosyltransferases (GTs), three glycosyltransferase genes (BsGT110, BsGT292 and BsGT296) from the genome of the Bacillus subtilis ATCC 6633 strain were cloned and expressed in Escherichia coli. The three BsGTs were then purified and the glycosylation activity determined toward 8-OHDe. The results showed that only BsGT110 possesses glycosylation activity. The glycosylated metabolites were then isolated with preparative high-performance liquid chromatography and identified as two new isoflavone glucosides, 8-OHDe-7-O-β-glucoside and8-OHDe-8-O-β-glucoside, whose identity was confirmed by mass spectrometry and nuclear magnetic resonance spectroscopy. The aqueous solubility of 8-OHDe-7-O-β-glucoside and 8-OHDe-8-O-β-glucoside is 9.0- and 4.9-fold, respectively, higher than that of 8-OHDe. Moreover, more than 90% of the initial concentration of the two 8-OHDe glucoside derivatives remained after 96 h of incubation in 50 mM of Tris buffer at pH 8.0. In contrast, the concentration of 8-OHDe decreased to 0.8% of the initial concentration after 96 h of incubation. The two new isoflavone glucosides might have potential in pharmaceutical and cosmeceutical applications.

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Gu, Fenglin, Guiping Wu, Yiming Fang y Hongying Zhu. "Nontargeted Metabolomics for Phenolic and Polyhydroxy Compounds Profile of Pepper (Piper nigrum L.) Products Based on LC-MS/MS Analysis". Molecules 23, n.º 8 (9 de agosto de 2018): 1985. http://dx.doi.org/10.3390/molecules23081985.

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In the present study, nontargeted metabolomics was used to screen the phenolic and polyhydroxy compounds in pepper products. A total of 186 phenolic and polyhydroxy compounds, including anthocyanins, proanthocyanidins, catechin derivatives, flavanones, flavones, flavonols, isoflavones and 3-O-p-coumaroyl quinic acid O-hexoside, quinic acid (polyhydroxy compounds), etc. For the selected 50 types of phenolic compound, except malvidin 3,5-diglucoside (malvin), l-epicatechin and 4′-hydroxy-5,7-dimethoxyflavanone, other compound contents were present in high contents in freeze-dried pepper berries, and pinocembrin was relatively abundant in two kinds of pepper products. The score plots of principal component analysis indicated that the pepper samples can be classified into four groups on the basis of the type pepper processing. This study provided a comprehensive profile of the phenolic and polyhydroxy compounds of different pepper products and partly clarified the factors responsible for different metabolite profiles in ongoing studies and the changes of phenolic compounds for the browning mechanism of black pepper.

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Manoharlal, Raman y G. V. S. Saiprasad. "Assessment of germination, phytochemicals, and transcriptional responses to ethephon priming in soybean [Glycine max (L.) Merrill]". Genome 62, n.º 12 (diciembre de 2019): 769–83. http://dx.doi.org/10.1139/gen-2019-0013.

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The present work aims to dissect the underlying signaling pathways associated with soybean [Glycine max (L.) Merrill] seed hormo-priming with ethephon (Eth). Our results demonstrated that soybean germination improved significantly upon Eth priming (Ethp). Phytohormone quantification shows relative enhanced endogenous gibberellin A4 (GA4) levels concomitant with impaired biogenesis and signaling of auxin, viz., indole acetic acid (IAA) and abscisic acid (ABA). Phytochemical analysis revealed relative reduced levels of individual and total raffinose family oligosaccharide (RFO) components, starch, soluble sugars, and sucrose concomitant with enhanced levels of reducing sugars, glucose, cellular ATP, and acetyl-CoA pools. Secondary metabolite analysis revealed the activation of the mevalonate (MVA) pathway with a concomitant suppression of the plastidal 2-methyl-d-erythritol-4-phosphate/1-deoxy-d-xylulose-5-phosphate (MEP/DOX) and phenylpropanoid pathways, substantiated by relative reduced levels of total phenolics, tannins, and proanthocyanidin. Ethp also enhances the in vitro antioxidative activity (viz., 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging ability and ferric reducing antioxidant power (FRAP)) and endogenous antioxidants levels (viz., flavonoids, isoflavones, β-carotene, vitamin C, and vitamin E). Further quantitative real-time polymerase chain reaction (qRT-PCR) analysis showed transcriptional pattern of representative genes in agreement with these metabolic alterations.

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Ngadni, Muhammad Afiq, Muhammad Tayyab Akhtar, Intan Safinar Ismail, Anis Irfan Norazhar, Soo Yee Lee, Maulidiani Maulidiani y Khozirah Shaari. "Clitorienolactones and Isoflavonoids of Clitorea ternatea Roots Alleviate Stress-Like Symptoms in a Reserpine-Induced Zebrafish Model". Molecules 26, n.º 14 (7 de julio de 2021): 4137. http://dx.doi.org/10.3390/molecules26144137.

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Clitorea ternatea has been used in Ayurvedic medicine as a brain stimulant to treat mental illnesses and mental functional disorders. In this study, the metabolite profiles of crude C. ternatea root extract (CTRE), ethyl acetate (EA), and 50% aqueous methanol (50% MeOH) fractions were investigated using ultrahigh-performance liquid chromatography–diode array detector–tandem mass spectrometry (UHPLC–DAD–MS/MS), while their effect on the stress-like behavior of zebrafish, pharmacologically induced with reserpine, was investigated. A total of 32 compounds were putatively identified, among which, a series of norneolignans, clitorienolactones, and various flavonoids (flavone, flavonol, isoflavone, and isoflavanone) was found to comprise the major constituents, particularly in the EA and 50% MeOH fractions. The clitorienolactones, presently unique to the species, were present in both the free and glycosylated forms in the roots. Both the EA and 50% MeOH fractions displayed moderate effects on the stress-induced zebrafish model, significantly decreasing freezing duration and elevating the total distance travelled and average velocity, 72 h post-treatment. The results of the present study provide further evidence that the basis for the use of C. ternatea roots in traditional medicine to alleviate brain-related conditions, such as stress and depression, is attributable to the presence of clitorienolactones and the isoflavonoidal constituents.

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El-Sakhawy, Fatma, Hanaa Kassem, Dina Abou-Hussein, Sabah El-Gayed, Mayy Mostafa y Rania Ahmed. "Phytochemical investigation of the bioactive extracts of the leaves of Ficus cyathistipula Warb." Zeitschrift für Naturforschung C 71, n.º 5-6 (1 de mayo de 2016): 141–54. http://dx.doi.org/10.1515/znc-2015-0274.

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Abstract Ethanolic and aqueous leaf extracts of Ficus cyathistipula significantly reduced blood-glucose level, improved triglycerides and cholesterol levels of dyslipidemia in diabetic-rats. They similarly reduced the inflammation of paw-edema and stomach-ulcers in rats. Fractions obtained by successive partition of ethanolic extract were assessed for their cytotoxicity, antioxidant and antimicrobial activities; Petroleum ether fraction was the most cytotoxic (IC50 = 4.43 ± 0.2, 17.3 ± 2.22 and 15.5 ± 3.67 μg/ml on MCF7, HepG2 and HeLa cell lines, respectively). Ethyl acetate fraction was the strongest antioxidant in DPPH assay (IC50 = 100 μg/ml). All samples exhibited low to strong antimicrobial activity. Chemical investigation of leaf extracts led to the isolation of α-amyrin palmitate (1), lupeol acetate (2), taraxerol (3), β-sitosterol (4), protocatechuic acid (5) and 3-O-caffeoyl quinic acid (6) that were identified via spectral and chromatographic analyses. Metabolite profiling was performed via UPLC-PDA-MS and revealed the presence of flavonoid glycosides, phenolic acids, isoflavones, coumarins and fatty acids. Quantitative determination revealed 593 ± 0.5 mg BSE, 348.1 ± 0.09 mg GAE, 238.7 ± 0.5 mg rutin and 9 ± 0.5 g tannins per 100 g d.wt. of leaves. GLC analysis of lipid fraction revealed identification of phytosterols (15.6%), saturated (51.71%) and unsaturated (41.9%) fatty acids. Galactose, glucose, arabinose and glucoronic acid (36.98%, 28.86%, 22.56% and 1.06%, respectively) were identified by HPLC analysis of mucilage-hydrolysate.

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Jakimiuk, Katarzyna, Michael Wink y Michał Tomczyk. "Flavonoids of the Caryophyllaceae". Phytochemistry Reviews, 17 de abril de 2021. http://dx.doi.org/10.1007/s11101-021-09755-3.

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AbstractThe plant family Caryophyllaceae, commonly known as the pink family, is divided into 3 subfamilies and contains over 80 genera with more than 2600 species that are widely distributed in temperate climate zones. Plants belonging to this family produce a variety of secondary metabolites important in an ecological context; however, some of these metabolites also show health-promoting activities. The most important classes of phytochemicals include saponins, phytoecdysteroids, other sterols, flavonoids, lignans, other polyphenols, essential oils, andN-containing compounds such as vitamins, alkaloids or cyclopeptides. Flavonoids are polyphenolic compounds that remain one of the most extensively studied constituents of the Caryophyllaceae family. Numerous structurally diverse aglycones, including flavones, flavonols, flavonones (dihydroflavones), flavonols, isoflavones, and theirO- orC-glycosides, exhibit multiple interesting biological and pharmacological activities, such as antioxidant, anti-inflammatory, anti-oedemic, antimicrobial, and immunomodulatory effects. Thus, this review analysed the flavonoid composition of 26 different genera and more than 120 species of Caryophyllaceae for the first time.

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Tian, Ruru, Qianqian Li, Shupei Rao, Aike Wang, Hechen Zhang, Liangsheng Wang, Yue Li y Jinhuan Chen. "Metabolic profiling and gene expression analysis provides insights into flavonoid and anthocyanin metabolism in poplar". Tree Physiology, 9 de noviembre de 2020. http://dx.doi.org/10.1093/treephys/tpaa152.

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Abstract Poplar, a woody perennial model, is a common and widespread tree genus. We cultivated two red leaf poplar varieties from bud mutation of Populus sp. Linn. ‘2025’ (also known as Zhonglin 2025, L2025 for shot): Populus deltoides varieties with bright red leaves (LHY) and completely red leaves (QHY). After measuring total contents of flavonoid, anthocyanin, chlorophyll, and carotenoid metabolites, a liquid chromatography-electrospray ionization-tandem mass spectrometry system was used for the relative quantification of widely targeted metabolites in leaves of three poplar varieties. A total of 210 flavonoid metabolites (89 flavones, 40 flavonols, 25 flavanones, 18 anthocyanins, 16 isoflavones, 7 dihydroflavonols, 7 chalcones, 5 proanthocyanidins, and 3 other flavonoid metabolites) were identified. Compared with L2025, 48 and 8 flavonoids were more and less abundant, respectively, in LHY, whereas 51 and 9 flavonoids were more and less abundant in QHY, respectively. On the basis of a comprehensive analysis of the metabolic network, gene expression levels were analyzed by deep-sequencing to screen for potential reference genes for the red leaves. Most phenylpropanoid biosynthesis pathway involved genes were differentially expressed among the examined varieties. Gene expression analysis also revealed several potential anthocyanin biosynthesis regulators including three MYB genes. The study results provide new insights into poplar flavonoid metabolites and represent the theoretical basis for future studies on leaf coloration in this model tree species.

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Baky, Mostafa H., Mostafa S. Elshahed, Ludger A. Wessjohann y Mohamed A. Farag. "Interactions between dietary flavonoids and the gut microbiome: A comprehensive review". British Journal of Nutrition, 13 de septiembre de 2021, 1–46. http://dx.doi.org/10.1017/s0007114521003627.

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Abstract Flavonoids are natural polyphenol secondary metabolites that are widely produced in planta. Flavonoids are ubiquities in human dietary intake and exhibit a myriad of health benefits. Flavonoids-induced biological activities are strongly influenced by their in-situ availability in the human GI tract, as well as the levels of which are modulated by interaction with the gut bacteria. As such, assessing flavonoids-microbiome interactions is considered a key to understand their physiological activities. Here, we review the interaction between the various classes of dietary flavonoids (flavonols, flavones, flavanones, isoflavones, flavan-3-ols, and anthocyanins) and gut microbiota. We aim to provide a holistic overview of the nature and identity of flavonoids on diet, and highlight how flavonoids chemical structure, metabolism, and impact on humans and their microbiomes are interconnected. Emphasis is placed on how flavonoids and their biotransformation products affect gut microbiota population, influence gut homeostasis, and induce measurable physiological changes and biological benefits.

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Shao, Fenjuan, Lisha Zhang, Juan Guo, Xiaochun Liu, Wenhui Ma, Iain W. Wilson y Deyou Qiu. "A comparative metabolomics analysis of the components of heartwood and sapwood in Taxus chinensis (Pilger) Rehd." Scientific Reports 9, n.º 1 (27 de noviembre de 2019). http://dx.doi.org/10.1038/s41598-019-53839-2.

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AbstractTaxus chinensis is a well-known gymnosperm with great ornamental and medicinal value. Its purple red brown heartwood (HW) has many attributes such as straight texture, high density, mechanical strength, rich elasticity and corrosion resistance that is highly prized commercially. T. chinensis sapwood (SW), in comparison, lacks these important traits. At present, little is known about the differences of metabolites between the SW and HW in T. chinensis. Widely targeted metabolic profiling was performed to analyze the metabolic profiles of HW and SW in T. chinensis using Liquid Chromatography-Electrospray Ionization-Mass Spectrometry (LC-EI-MS). A total of 607 metabolites were detected in HW and SW. Among them, 146 metabolites were significantly higher, and 167 metabolites significantly lower, in HW as compared to SW. These differential metabolites were mainly involved in metabolic pathways and biosynthesis of secondary metabolites, such as flavonoids, flavone and flavonol, phenylpropanoids and antibiotics. Moreover, 71 flavonoids and isoflavones were found to be significantly different between HW and SW. Our results show the difference of components between the HW and SW, which has potential significance to further elucidate the mechanism of HW color formation. The results will provide insight into the metabolites associated with wood color formation and useful information for understanding the metabolites associated with wood quality.

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Tawfeek, Nora, Mona F. Mahmoud, Dalia I. Hamdan, Mansour Sobeh, Nawaal Farrag, Michael Wink y Assem M. El-Shazly. "Phytochemistry, Pharmacology and Medicinal Uses of Plants of the Genus Salix: An Updated Review". Frontiers in Pharmacology 12 (12 de febrero de 2021). http://dx.doi.org/10.3389/fphar.2021.593856.

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The Willows (genus Salix), with more than 330–500 species and 200 hybrids, are trees, shrubs or prostrate plants that are widely distributed in Africa, North America, Europe, and Asia. The genus is traditionally used in folk medicine and represents a valuable source of biologically active compounds among them salicin, a prodrug for salicylic acid. Altogether, 322 secondary metabolites were characterized in the genus including flavonoids 94) (flavonols, flavones, flavanones, isoflavones, flavan-3-ols (catechins and procyanidins), chalcones, dihydrochalcone, anthocyanins, dihydroflavonols), phenolic glycosides (76), organic acids (28), and non-phenolic glycosides (17), sterols and terpenes (17), simple phenolics 13) and lignans 7) in addition to volatiles and fatty acids (69). Furthermore, willows exert analgesic, anti-inflammatory, antioxidant, anticancer, cytotoxic, antidiabetic, antimicrobial, antiobesity, neuroprotective and hepatoprotective activities. The current review provides an updated summary of the importance of willows, their chemical composition and pharmacological activities.

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Zhang, Xiang, Yan Zhu, Jun Ye, Ziyu Ye, Ruirui Zhu, Guoyong Xie, Yucheng Zhao y Minjian Qin. "Iris domestica (iso)flavone 7- and 3′-O-Glycosyltransferases Can Be Induced by CuCl2". Frontiers in Plant Science 12 (9 de febrero de 2021). http://dx.doi.org/10.3389/fpls.2021.632557.

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In many plants, isoflavones are the main secondary metabolites that have various pharmacological activities, but the low water solubility of aglycones limits their usage. The O-glycosylation of (iso)flavones is a promising way to overcome this barrier. O-glycosyltransferases (UGTs) are key enzymes in the biosynthesis of (iso)flavonoid O-glycosides in plants. However, limited investigations on isoflavonoid O-UGTs have been reported, and they mainly focused on legumes. Iris domestica (L.) Goldblatt et Mabberley is a non-legume plant rich in various isoflavonoid glycosides. However, there are no reports regarding its glycosylation mechanism, despite the I. domestica transcriptome previously being annotated as having non-active isoflavone 7-O-UGTs. Our previous experiments indicated that isoflavonoid glycosides were induced by CuCl2 in I. domestica calli; therefore, we hypothesized that isoflavone O-UGTs may be induced by Cu2+. Thus, a comparative transcriptome analysis was performed using I. domestica seedlings treated with CuCl2, and eight new active BcUGTs were obtained. Biochemical analyses showed that most of the active BcUGTs had broad substrate spectra; however, substrates lacking 5-OH were rarely catalyzed. Real-time quantitative PCR results further indicated that the transcriptional levels of BcUGTs were remarkably induced by Cu2+. Our study increases the understanding of UGTs and isoflavone biosynthesis in non-legume plants.

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Breitinger, Ulrike, Heinrich Sticht y Hans-Georg Breitinger. "Modulation of recombinant human alpha 1 glycine receptor by flavonoids and gingerols". Biological Chemistry, 22 de marzo de 2021. http://dx.doi.org/10.1515/hsz-2020-0360.

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Abstract The inhibitory glycine receptor (GlyR) is a principal mediator of fast synaptic inhibition in mammalian spinal cord, brainstem, and higher brain centres. Flavonoids are secondary plant metabolites that exhibit many beneficial physiological effects, including modulatory action on neuronal receptors. Using whole-cell current recordings from recombinant human α1 GlyRs, expressed in HEK293 cells, we compared the flavonols kaempferol and quercetin, the flavanone naringenin, the flavones apigenin and nobiletin, the isoflavone genistein, and two gingerols, 6-gingerol and 8-gingerol for their modulation of receptor currents. All compounds were inhibitors of the GlyR with IC50 values ranging between 9.3 ± 2.6 µM (kaempferol) and 46.7 ± 6.5 µM (genistein), following a mixed mode of inhibition. Co-application of two inhibitors revealed distinct binding sites for flavonoids and gingerols. Pore-lining mutants T258A and T258S were strongly inhibited by quercetin and naringenin, but not by 6-gingerol, confirming the existence of distinct binding sites for flavonoids and gingerols. Apigenin, kaempferol, nobiletin, naringenin and 6-gingerol showed biphasic action, potentiating glycine-induced currents at low concentration of both, modulator and glycine, and inhibiting at higher concentrations. Identification of distinct modulatory sites for flavonoids and related compounds may present pharmacological target sites and aid the discovery of novel glycinergic drugs.

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