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Journal articles on the topic 'Plant lignan'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Bolvig, Anne Katrine, Herman Adlercreutz, Peter Kappel Theil, Henry Jørgensen, and Knud Erik Bach Knudsen. "Absorption of plant lignans from cereals in an experimental pig model." British Journal of Nutrition 115, no. 10 (March 22, 2016): 1711–20. http://dx.doi.org/10.1017/s0007114516000829.

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AbstractPlant lignans are diphenolic compounds ingested with whole grains and seeds and converted to enterolignans by the colonic microbiota. In the present study, we investigated absorption and metabolism of plant lignans and enterolignansin vivoafter consumption of cereal-based diets. Six pigs fitted with catheters in the mesenteric artery and portal vein and with a flow probe attached to the portal vein along with twenty pigs for quantitative collection of urine were used for this study. The animals were fed bread based on wheat flour low in plant lignans and three lignan-rich breads based on whole-wheat grain, wheat aleurone flour or rye aleurone flour. Plant lignans and enterolignans in plasma were monitored daily at fast after 0–3 d of lignan-rich intake, and on the 4th day of lignan-rich intake a 10-h profile was completed. Urine samples were collected after 11 d of lignan-rich diet consumption. The concentrations of plant lignans were low at fast, and was 1·2–2·6 nmol/l after switching from the low-lignan diet to the lignan-rich diets. However, on the profile day, the concentration and quantitative absorption of plant lignans increased significantly from 33 nmol/h at fast to 310 nmol/h 0–2·5 h after ingestion with a gradual increase in the following periods. Quantitatively, the absorption of plant lignans across diets amounted to 7 % of ingested plant lignans, whereas the urinary excretion of plant lignans was 3 % across diets. In conclusion, there is a substantial postprandial uptake of plant lignans from cereals, suggesting that plant lignans are absorbed from the small intestine.

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2

Hamade, Kamar, Ophélie Fliniaux, Jean-Xavier Fontaine, Roland Molinié, Elvis Otogo Nnang, Solène Bassard, Stéphanie Guénin, et al. "NMR and LC-MS-Based Metabolomics to Study Osmotic Stress in Lignan-Deficient Flax." Molecules 26, no. 3 (February 2, 2021): 767. http://dx.doi.org/10.3390/molecules26030767.

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Lignans, phenolic plant secondary metabolites, are derived from the phenylpropanoid biosynthetic pathway. Although, being investigated for their health benefits in terms of antioxidant, antitumor, anti-inflammatory and antiviral properties, the role of these molecules in plants remains incompletely elucidated; a potential role in stress response mechanisms has been, however, proposed. In this study, a non-targeted metabolomic analysis of the roots, stems, and leaves of wild-type and PLR1-RNAi transgenic flax, devoid of (+) secoisolariciresinol diglucoside ((+) SDG)—the main flaxseed lignan, was performed using 1H-NMR and LC-MS, in order to obtain further insight into the involvement of lignan in the response of plant to osmotic stress. Results showed that wild-type and lignan-deficient flax plants have different metabolic responses after being exposed to osmotic stress conditions, but they both showed the capacity to induce an adaptive response to osmotic stress. These findings suggest the indirect involvement of lignans in osmotic stress response.

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3

Milder, Ivon E. J., Ilja C. W. Arts, Betty van de Putte, Dini P. Venema, and Peter C. H. Hollman. "Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol." British Journal of Nutrition 93, no. 3 (March 2005): 393–402. http://dx.doi.org/10.1079/bjn20051371.

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Enterolignans (enterodiol and enterolactone) can potentially reduce the risk of certain cancers and cardiovascular diseases. Enterolignans are formed by the intestinal microflora after the consumption of plant lignans. Until recently, only secoisolariciresinol and matairesinol were considered enterolignan precursors, but now several new precursors have been identified, of which lariciresinol and pinoresinol have a high degree of conversion. Quantitative data on the contents in foods of these new enterolignan precursors are not available. Thus, the aim of this study was to compile a lignan database including all four major enterolignan precursors. Liquid chromatography–tandem mass spectrometry was used to quantify lariciresinol, pinoresinol, secoisolariciresinol and matairesinol in eighty-three solid foods and twenty-six beverages commonly consumed in The Netherlands. The richest source of lignans was flaxseed (301 129 μg/100 g), which contained mainly secoisolariciresinol. Also, lignan concentrations in sesame seeds (29 331 μg/100 g, mainly pinoresinol and lariciresinol) were relatively high. For grain products, which are known to be important sources of lignan, lignan concentrations ranged from 7 to 764 μg/100 g. However, many vegetables and fruits had similar concentrations, because of the contribution of lariciresinol and pinoresinol.Brassicavegetables contained unexpectedly high levels of lignans (185–2321 μg/100 g), mainly pinoresinol and lariciresinol. Lignan levels in beverages varied from 0 (cola) to 91 μg/100 ml (red wine). Only four of the 109 foods did not contain a measurable amount of lignans, and in most cases the amount of lariciresinol and pinoresinol was larger than that of secoisolariciresinol and matairesinol. Thus, available databases largely underestimate the amount of enterolignan precursors in foods.

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Park, Woo Sung, Kyung Ah Koo, Ji-Yeong Bae, Hye-Jin Kim, Dong-Min Kang, Ji-Min Kwon, Seung-Mann Paek, Mi Kyeong Lee, Chul Young Kim, and Mi-Jeong Ahn. "Dibenzocyclooctadiene Lignans in Plant Parts and Fermented Beverages of Schisandra chinensis." Plants 10, no. 2 (February 13, 2021): 361. http://dx.doi.org/10.3390/plants10020361.

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The fruit of Schisandra chinensis, Omija, is a well-known traditional medicine used as an anti-tussive and anti-diarrhea agent, with various biological activities derived from the dibenzocyclooctadiene-type lignans. A high-pressure liquid chromatography-diode array detector (HPLC-DAD) method was used to determine seven lignans (schisandrol A and B, tigloylgomisin H, angeloylgomisin H, schisandrin A, B, and C) in the different plant parts and beverages of the fruit of S. chinensis grown in Korea. The contents of these lignans in the plant parts descended in the following order: seeds, flowers, leaves, pulp, and stems. The total lignan content in Omija beverages fermented with white sugar for 12 months increased by 2.6-fold. Omija was fermented for 12 months with white sugar, brown sugar, and oligosaccharide/white sugar (1:1, w/w). The total lignan content in Omija fermented with oligosaccharide/white sugar was approximately 1.2- and 1.7-fold higher than those fermented with white sugar and brown sugar, respectively. A drink prepared by immersion of the fruit in alcohol had a higher total lignan content than these fermented beverages. This is the first report documenting the quantitative changes in dibenzocyclooctadiene-type lignans over a fermentation period and the effects of the fermentable sugars on this eco-friendly fermentation process.

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Szopa, Agnieszka, Michał Dziurka, Angelika Warzecha, Paweł Kubica, Marta Klimek-Szczykutowicz, and Halina Ekiert. "Targeted Lignan Profiling and Anti-Inflammatory Properties of Schisandra rubriflora and Schisandra chinensis Extracts." Molecules 23, no. 12 (November 27, 2018): 3103. http://dx.doi.org/10.3390/molecules23123103.

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Schisandra rubriflora is a dioecious plant of increasing importance due to its lignan composition, and therefore, possible therapeutic properties. The aim of the work was lignan profiling of fruits, leaves and shoots of female (F) and male (M) plants using UHPLC-MS/MS. Additionally, the anti-inflammatory activity of plant extracts and individual lignans was tested in vitro for the inhibition of 15-lipooxygenase (15-LOX), phospholipases A2 (sPLA2), cyclooxygenase 1 and 2 (COX-1; COX-2) enzyme activities. The extracts of fruits, leaves and shoots of the pharmacopoeial species, S. chinensis, were tested for comparison. Twenty-four lignans were monitored. Lignan contents in S. rubriflora fruit extracts amounted to 1055.65 mg/100 g DW and the dominant compounds included schisanhenol, aneloylgomisin H, schisantherin B, schisandrin A, gomisin O, angeloylgomisin O and gomisin G. The content of lignan in leaf extracts was 853.33 (F) and 1106.80 (M) mg/100 g DW. Shoot extracts were poorer in lignans—559.97 (F) and 384.80 (M) mg/100 g DW. Schisantherin B, schisantherin A, 6-O-benzoylgomisin O and angeloylgomisin H were the dominant compounds in leaf and shoot extracts. The total content of detected lignans in S. chinensis fruit, leaf and shoot extracts was: 1686.95, 433.59 and 313.83 mg/100 g DW, respectively. Gomisin N, schisandrin A, schisandrin, gomisin D, schisantherin B, gomisin A, angeloylgomisin H and gomisin J were the dominant lignans in S. chinensis fruit extracts were. The results of anti-inflammatory assays revealed higher activity of S. rubriflora extracts. Individual lignans showed significant inhibitory activity against 15-LOX, COX-1 and COX-2 enzymes.

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6

Rodríguez-García, Carmen, Cristina Sánchez-Quesada, Estefanía Toledo, Miguel Delgado-Rodríguez, and José Gaforio. "Naturally Lignan-Rich Foods: A Dietary Tool for Health Promotion?" Molecules 24, no. 5 (March 6, 2019): 917. http://dx.doi.org/10.3390/molecules24050917.

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Dietary guidelines universally advise adherence to plant-based diets. Plant-based foods confer considerable health benefits, partly attributable to their abundant micronutrient (e.g., polyphenol) content. Interest in polyphenols is largely focused on the contribution of their antioxidant activity to the prevention of various disorders, including cardiovascular disease and cancer. Polyphenols are classified into groups, such as stilbenes, flavonoids, phenolic acids, lignans and others. Lignans, which possess a steroid-like chemical structure and are defined as phytoestrogens, are of particular interest to researchers. Traditionally, health benefits attributed to lignans have included a lowered risk of heart disease, menopausal symptoms, osteoporosis and breast cancer. However, the intake of naturally lignan-rich foods varies with the type of diet. Consequently, based on the latest humans’ findings and gathered information on lignan-rich foods collected from Phenol Explorer database this review focuses on the potential health benefits attributable to the consumption of different diets containing naturally lignan-rich foods. Current evidence highlight the bioactive properties of lignans as human health-promoting molecules. Thus, dietary intake of lignan-rich foods could be a useful way to bolster the prevention of chronic illness, such as certain types of cancers and cardiovascular disease.

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7

Petit, Hélène V. "Antioxidants and dairy production: the example of flax." Revista Brasileira de Zootecnia 38, spe (July 2009): 352–61. http://dx.doi.org/10.1590/s1516-35982009001300035.

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This manuscript reports on the main problems decreasing productivity of dairy cows (e.g. fatty liver syndrome and poor fertility) and how antioxidants could enhance it. High producing dairy cows are prone to oxidative stress, and the situation can be exacerbated under certain environmental, physiological, and dietary conditions. Antioxidants have important effects on the expression of genes involved in the antioxidant status, which may enhance animal health and reproduction. Moreover, antioxidants may contribute to decrease the incidence of spontaneous oxidized flavour in milk enriched in polyunsaturated fatty acids. Plant lignans are strong antioxidants and flax is the richest source of plant lignans. Flax lignans are converted in the mammalian lignans enterolactone and enterodiol. The main mammalian lignan in milk is enterolactone and flax lignans are converted in enterolactone mainly under the action of ruminal microbiota. Therefore, ruminal microbiota may be the most important flora to target for plant lignan metabolism in order to increase concentration of mammalian lignan antioxidants in milk of dairy cows. However, more research is required to improve our knowledge on metabolism of other antioxidants in dairy cows and how they can contribute in decreasing milk oxidation.

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8

Xu, Xuan, Cédric Guignard, Jenny Renaut, Jean-Francois Hausman, Edoardo Gatti, Stefano Predieri, and Gea Guerriero. "Insights into Lignan Composition and Biosynthesis in Stinging Nettle (Urtica dioica L.)." Molecules 24, no. 21 (October 26, 2019): 3863. http://dx.doi.org/10.3390/molecules24213863.

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Stinging nettle (Urtica dioica L.) has been used as herbal medicine to treat various ailments since ancient times. The biological activity of nettle is chiefly attributed to a large group of phenylpropanoid dimers, namely lignans. Despite the pharmacological importance of nettle lignans, there are no studies addressing lignan biosynthesis in this plant. We herein identified 14 genes encoding dirigent proteins (UdDIRs) and 3 pinoresinol-lariciresinol reductase genes (UdPLRs) in nettle, which are two gene families known to be associated with lignan biosynthesis. Expression profiling of these genes on different organs/tissues revealed a specific expression pattern. Particularly, UdDIR7, 12 and 13 displayed a remarkable high expression in the top internode, fibre tissues of bottom internodes and roots, respectively. The relatively high expression of UdPLR1 and UdPLR2 in the young internodes, core tissue of bottom internode and roots is consistent with the high accumulation of lariciresinol and secoisolariciresinol in these tissues. Lignan quantification showed a high abundance of pinoresinol in roots and pinoresinol diglucosides in young internodes and leaves. This study sheds light on lignan composition and biosynthesis in nettle, providing a good basis for further functional analysis of DIRs and PLRs and, ultimately, engineering lignan metabolism in planta and in cell cultures.

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9

Kim, A.-Young, Choong-In Yun, Joon-Goo Lee, and Young-Jun Kim. "Determination and Daily Intake Estimation of Lignans in Sesame Seeds and Sesame Oil Products in Korea." Foods 9, no. 4 (March 30, 2020): 394. http://dx.doi.org/10.3390/foods9040394.

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Sesame (Sesamum indicum L.) is a plant that belongs to the Pedaliaceae family which was first classified as a food source around 4000 years ago. Lignans (sesamin, sesamolin, sesamol, and sesaminol) present in sesame are the primary functional compounds that impart important health benefits. However, very little information is available on the lignan intake from sesame seeds and sesame oil products. Sesame oil is frequently and highly consumed in Korea and therefore is one of the important lignan intake sources due to the food eating habits of Koreans. Herein, we studied the distribution of lignans in sesame seeds (n = 21) and oil (n = 34) to estimate the daily lignan intake by the Korean population. High-performance liquid chromatography, in conjunction with statistical analysis, was used to determine the lignan content of seeds and oil. The estimated daily intake of total lignans from sesame seeds and oil, as estimated from the available domestic consumption data (Korea Nutrition and Health Examination Survey), is 18.39 mg/person/day for males and 13.26 mg/person/day for females. The contributions of lignan intake from sesame seeds and oil are 23.0% and 77.0%, respectively. This study provides preliminary information on lignan intake from sesame seeds and oil in the Korean population.

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10

Lampe, Johanna W., Charlotte Atkinson, and Meredith A. J. Hullar. "Assessing Exposure to Lignans and Their Metabolites in Humans." Journal of AOAC INTERNATIONAL 89, no. 4 (July 1, 2006): 1174–81. http://dx.doi.org/10.1093/jaoac/89.4.1174.

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Abstract Phytoestrogens occur naturally in plants and are structurally similar to mammalian estrogens. The lignans are a class of phytoestrogen and can be metabolized to the biologically active enterolignans, enterodiol, and enterolactone by a consortium of intestinal bacteria. Secoisolariciresinol diglucoside (SDG), a plant lignan, is metabolized to enterodiol and, subsequently, enterolactone. Matairesinol, another plant lignan, is metabolized to enterolactone. Other dietary enterolignan precursors include lariciresinol, pinoresinol, syringaresinol, arctigenin, and sesamin. Enterolignan exposure is determined in part by intake of these precursors, gut bacterial activity, and host conjugating enzyme activity. A single SDG dose results in enterolignan appearance in plasma 810 h latera timeframe associated with colonic bacterial metabolism and absorption. Conjugation of enterolignans with sulfate and glucuronic acid occurs in the intestinal wall and liver, with the predominant conjugates wall and liver, with the predominant conjugates have demonstrated dose-dependent urinary lignan excretion in response to flaxseed consumption (a source of SDG); however, even in the context of controlled studies, there is substantial interindividual variation in plasma concentrations and urinary excretion of enterolignans. The complex interaction between colonic environment and external and internal factors that modulate it likely contribute to this variation. Knowledge of this field, to date, indicates that understanding the sources of variation and measuring the relevant panel of compounds are important in order to use these measures effectively in evaluating the impact of lignans on human health.

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11

ZHANG, Xiaodong, Caixia LI, Chonlong CHIO, Ayyappa K. S. KAMESHWAR, Tianxiao MA, and Wensheng QIN. "Transcriptome analysis to identify genes involved in lignan, sesquiterpenoid and triterpenoid biosynthesis in medicinal plant Kadsura heteroclita." Notulae Botanicae Horti Agrobotanici Cluj-Napoca 48, no. 4 (December 22, 2020): 1802–31. http://dx.doi.org/10.15835/nbha48412044.

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Stems and roots of Kadsura plant species were the significant ingredients of traditional Chinese medicine. Kadsura heteroclita is one of the popular medicinal plants used in Tujia and Yao nationalities of China. Antioxidant compounds like lignan, sesquiterpenoid and triterpenoid are the major active components of K. hetroclita. Mass cultivation and bio-manufacturing strategies were being proposed to meet the increasing demand of Kadsura species plant parts. Therefore, it is important to reveal the molecular networks involved in biosynthesis of these highly efficient medicinal compounds. Here, transcriptomes of roots, stems and leaves in K. heteroclite seedling were sequenced by Hiseq2000 and unigenes involved in biosynthesis of lignan, sesquiterpenoid and triterpenoid biosynthesis were mined. As a result, 472 million clean reads were obtained which after aligning resulted in 160,248 transcripts and 98,005 genes. 191 and 279 unigenes were expected to be involved in biosynthesis of lignan, sesquiterpenoid and triterpenoid biosynthetic pathways respectively. Lignan, sesquiterpenoid and triterpenoid biosynthesis pathway genes were highly significant and differentially upregulated in roots and stems and downregulated in leaves. Also, genes encoding for MYB and bHLH transcription factors possibly involved in regulation of lignan, sesquiterpenoid and triterpenoid biosynthesis were discovered. These results provide the fundamental genomic resources for dissecting of biosynthetic pathways of the active components in K. hetroclita.

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Umezawa, Toshiaki. "Diversity in lignan biosynthesis." Phytochemistry Reviews 2, no. 3 (January 2003): 371–90. http://dx.doi.org/10.1023/b:phyt.0000045487.02836.32.

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13

Bylund, Annika, Niina Saarinen, Jie-xian Zhang, Anders Bergh, Anders Widmark, Anders Johansson, Eva Lundin, et al. "Anticancer Effects of a Plant Lignan 7-Hydroxymatairesinol on a Prostate Cancer Model In Vivo." Experimental Biology and Medicine 230, no. 3 (March 2005): 217–23. http://dx.doi.org/10.1177/153537020523000308.

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Clinical intervention studies and experimental studies with lignan-rich diets suggest that lignans may have inhibitory effects on prostate cancer, but no clinical or experimental studies with purified lignans have been published. The purpose of this study was to investigate the effect of a plant lignan 7-hydroxymatairesinol (HMR) on LNCaP human prostate cancer xenografts in athymic mice. Athymic nude male mice were injected subcutaneously with LNCaP cells. Starting 3 days after tumor cell injections, a control diet or a control diet supplemented with 0.15% or 0.30% of HMR was administered to mice and the tumor take rate and growth was observed for 9 weeks. HMR diet inhibited the growth of LNCaP tumors. Mice treated with HMR had smaller tumor volume, lower tumor take rate, increased proportion of nongrowing tumors, and higher tumor cell apoptotic index compared with controls. Furthermore, the cell proliferation index was reduced in mice receiving the 0.30% HMR diet compared with mice receiving the control diet. Our results suggest that dietary HMR started at the early phase of the tumor development inhibits the growth of the LNCaP human prostate cancer xenografts in athymic male mice.

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14

Fucassi, Flavia, Adam Heikal, Lyuba I. Mikhalovska, Guy Standen, Iain U. Allan, Sergey V. Mikhalovsky, and Peter J. Cragg. "Metal chelation by a plant lignan, secoisolariciresinol diglucoside." Journal of Inclusion Phenomena and Macrocyclic Chemistry 80, no. 3-4 (April 18, 2014): 345–51. http://dx.doi.org/10.1007/s10847-014-0411-9.

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15

Liu, Jianbin, Lishu Wang, Daqing Zhao, Dongyan Cheng, Tunhai Xu, Xuefeng Zhou, Xianwen Yang, and Yonghong Liu. "A new lignan from Saururus chinensis." Chemistry of Natural Compounds 46, no. 4 (August 28, 2010): 631–33. http://dx.doi.org/10.1007/s10600-010-9695-1.

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16

Xiao, Xin-min, Zhi-qin Ji, Ji-wen Zhang, Bao-jun Shi, Shao-peng Wei, and Wen-jun Wu. "A new lignan from Phryma leptostachya." Chemistry of Natural Compounds 49, no. 1 (March 2013): 21–23. http://dx.doi.org/10.1007/s10600-013-0495-2.

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17

Bankova, V., N. Nikolova, and M. Marcucci. "A New Lignan from Brazilian Propolis." Zeitschrift für Naturforschung C 51, no. 9-10 (October 1, 1996): 735–37. http://dx.doi.org/10.1515/znc-1996-9-1019.

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The known flavonoid kaempferid 4 and a new benzofurane lignan 1 were isolated from Brazilian propolis. The new lignan is a suitable taxonomic marker and gives new possibilities for identification of propolis plant sources in the tropical regions

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18

Cushman, Kent E., Muhammad Maqbool, Hemant Lata, Ebru Bedir, Ikhlas A. Khan, and Rita M. Moraes. "Podophyllotoxin Content and Yield of American Mayapple Leaves in Sun and Shade." HortScience 40, no. 1 (February 2005): 60–63. http://dx.doi.org/10.21273/hortsci.40.1.60.

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Four levels of shade (0%, 30%, 55%, and 80%) were used to determine their effect on growth and lignan content of american mayapple (Podophyllum peltatum L.). Mayapple rhizomes were harvested from the wild and transplanted into plant beds on 20 Dec. 2001 using a randomized complete block design with four blocks. Growth and lignan content were recorded during spring of 2002 and 2003. Leaf samples were analyzed for the following lignans: podophyllotoxin, alpha-peltatin, and beta-peltatin. Increasing levels of shade increased shoot longevity, leaf area per plant (cm2/plant), and shoot height. Shade did not affect shoot emergence, total leaf area (cm2·m-2), or leaf dry mass (g·m-2 or g/plant). Regardless of year, podophyllotoxin and total lignan contents at 0% shade were significantly greater than those at 80% shade, and the overall trend was for decreasing contents with increasing shade. Shade did not affect alpha-peltatin content. Content of beta-peltatin was greatest at 0% shade compared to the other three shade treatments. Year affected alpha-peltatin and beta-peltatin contents, with less content of each in 2003 than in 2002. There were large numerical decreases in podophyllotoxin yield (podophyllotoxin content per unit area, mg·m-2) as shade increased from 0% to 80%, but these differences were only marginally significant (P = 0.0897). In contrast, podophyllotoxin yield was significantly greater in 2003 than in 2002 as total leaf area and dry mass significantly increased. Increasing levels of shade slightly decreased air and soil temperatures. Our results indicate that american mayapple is not a shade-requiring species. Under full sun (0% shade) shoots did not persist as long as under shade and leaves were smaller and thicker, but total lignan content was significantly greater than under shade. It appears that growers of specialty crops serving the pharmaceutical industry can establish and cultivate american mayapple under full sun, thus providing leaf biomass with high podophyllotoxin content while avoiding the cost of expensive shade structures.

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Zhao, Changqi, Akito Nagatsu, Keiichiro Hatano, Naohiro Shirai, Setsuko Kato, and Yukio Ogihara. "New Lignan Glycosides from Chinese Medicinal Plant, Sinopodophillum emodi." CHEMICAL & PHARMACEUTICAL BULLETIN 51, no. 3 (2003): 255–61. http://dx.doi.org/10.1248/cpb.51.255.

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20

Elfahmi, Komar Ruslan, Sieb Batterman, Rein Bos, Oliver Kayser, Herman J. Woerdenbag, and Wim J. Quax. "Lignan profile of Piper cubeba, an Indonesian medicinal plant." Biochemical Systematics and Ecology 35, no. 7 (July 2007): 397–402. http://dx.doi.org/10.1016/j.bse.2007.01.003.

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21

Mohagheghzadeh, Abdolali, Azra Gholami, Mohammad Soltani, Shiva Hemmati, and Wilhelm Alfermann. "Linum mucronatum: Organ to Organ Lignan Variations." Zeitschrift für Naturforschung C 60, no. 5-6 (June 1, 2005): 508–10. http://dx.doi.org/10.1515/znc-2005-5-622.

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The percentage of podophyllotoxin (PTOX) and its congener lignans were measured by HPLC in Linum mucronatum ssp. mucronatum (Linaceae) fresh plant organs. The highest amounts of PTOX (0.595 ± 0.060% g/g dry wt) and 6-methoxypodophyllotoxin (MPTOX) (1.491 ± 0.125% g/g dry wt) were found in the plant sexual organs. Whereas, the highest levels of β-peltatin, 5′-demethoxy-MPTOX and yatein were found in not developed buds, petals and sepals, respectively.

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22

Zanella, Isabella, Giorgio Biasiotto, Finn Holm, and Diego di Lorenzo. "Cereal Lignans, Natural Compounds of Interest for Human Health?" Natural Product Communications 12, no. 1 (January 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200139.

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Cereals are suggested to be the most important sources of lignan in the diets of western populations. Recent epidemiological studies show that European subpopulations in which the major source of lignans are cereals, display lower disease frequency regarding metabolic and cardiovascular diseases. The biological mechanisms of lignan are several. Beyond their antioxidant and anti-inflammatory actions at nutritional doses some lignans regulate the activity of specific nuclear receptors (NRs), such as the estrogen receptors (ERs), and also NRs that are central switches in glucose and fatty acid metabolism such as PPARα, PPARγ and LXRs, highlighting them as selective nuclear receptor modulators (SNRMs). These include enterodiol (END) and enterolactone (ENL), the metabolites produced by the gut microbiota from food lignans. The available knowledge suggests that given some additional research it should be possible to make ‘function' claims for a regular intake of lignans-rich foods related to maintaining a healthy metabolism.

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Mazur, W. M., K. Wähälä, S. Rasku, A. Salakka, T. Hase, and H. Adlercreutz. "Lignan and isoflavonoid concentrations in tea and coffee." British Journal of Nutrition 79, no. 1 (January 1998): 37–45. http://dx.doi.org/10.1079/bjn19980007.

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Tea is a beverage consumed widely throughout the world. The existence in tea of chemopreventing compounds possessing antimutagenic, anticarcinogenic and antioxidative properties has been reported. High intakes of tea and foods containing flavonoids have recently been shown to be negatively correlated to the occurrence of CHD. However, tea may contain other compounds with similar activities. Using a new gas chromatographic–mass spectrometric method we measured lignans and isoflavonoids in samples of twenty commercial teas (black, green and red varieties) and, for comparison, six coffees. Both unbrewed and brewed tea were investigated. The analysis of the teas yielded relatively high levels of the lignans secoisolariciresinol (5.6–28.9 mg/kg; 15.9–81.9 μmol/kg) and matairesinol (0.56–4.13 mg/kg; 1.6–11.5 μmol/kg) but only low levels of isoflavonoids. Because the plant lignans, as well as their mammalian metabolites enterolactone and enterodiol, have antioxidative properties and these mammalian lignans occur in high concentrations in plasma, we hypothesize that lignan polyphenols may contribute to the protective effect of tea on CHD.

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Zhang, Jin, Yaojie Guo, Jiushi Liu, Xiaoguang Jia, Bengang Zhang, and Haitao Liu. "A New Dibenzocyclooctadiene Lignan from Kadsura longipedunculata." Chemistry of Natural Compounds 54, no. 5 (September 2018): 837–40. http://dx.doi.org/10.1007/s10600-018-2494-9.

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Li, Yue, Yue-Li Wei, Jun-Ju Xu, Yan-Li Liang, and Yu-Peng Li. "Two New Lignan Derivatives from Jatropha curcas." Chemistry of Natural Compounds 55, no. 4 (July 2019): 614–17. http://dx.doi.org/10.1007/s10600-019-02761-0.

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Chen, C. Y., C. T. Chen, S. L. Liu, C. L. Kao, W. J. Li, H. C. Yeh, H. T. Li, and H. W. Chang. "A New Dimeric Lignan from Machilus philippinensis." Chemistry of Natural Compounds 56, no. 4 (July 2020): 611–13. http://dx.doi.org/10.1007/s10600-020-03105-z.

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Batirov, É. Kh, A. D. Matkarimov, V. M. Malikov, and M. R. Yagudaev. "Versicoside — A new lignan glycoside fromHaplophyllum versicolor." Chemistry of Natural Compounds 21, no. 5 (September 1985): 584–87. http://dx.doi.org/10.1007/bf00579057.

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Pan, Yaping, Yan Zhang, Chao Fan, Yu Zhang, Shikai Yan, Huizi Jin, and Weidong Zhang. "Lignans from the Whole Plants of Hedyotis uncinella." Natural Product Communications 11, no. 8 (August 2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100821.

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Two new lignans, named (7R, 8 S)-balanophonin (1) and (7R, 8 S)-tomentosanan A (2), together with eight known lignans, burselignan (3), (+)-isolariciresinol (4), (+)-lyoniresinol (5), 5-methoxy-(+)-isolariciresinol (6), (-)-syringaresinol (7), (+)-epipinoresinol (8), (-)-(7′ S, 8 S, 8′ R)-4,4′-dihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9-epoxy-lignan-9′-ol-7-one (9), and (-)-(7 R, 8 S)-dihydrodehydrodiconiferyl alcohol (10) were isolated from the whole plants of Hedyotis uncinella Hook. et Arn. Structures of these compounds were elucidated through 1H NMR, 13C NMR, 2D NMR, ESI-MS and CD data.

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Li, Chang, Qian Wei, Zhi-Hao Zou, Chen-Zhi Sun, Qin Wang, Gang Zhao, Xin-Jia Yan, Tian-Yi Yu, and Chun-Li Gan. "A lignan and a lignan derivative from the fruit of Forsythia suspensa." Phytochemistry Letters 32 (August 2019): 115–18. http://dx.doi.org/10.1016/j.phytol.2019.05.009.

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Müller, Ulrike, Yahya Mrestani, Reinhard Neubert, and Birgit Dräger. "Chiral separation of the plant lignan matairesinol by capillary electrophoresis." ELECTROPHORESIS 29, no. 17 (August 2008): 3582–87. http://dx.doi.org/10.1002/elps.200700800.

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Petit, Hélène V., Nathalie Gagnon, Priyadarshini S. Mir, Rong Cao, and Steve Cui. "Milk concentration of the mammalian lignan enterolactone, milk production, milk fatty acid profile, and digestibility in dairy cows fed diets containing whole flaxseed or flaxseed meal." Journal of Dairy Research 76, no. 3 (March 2, 2009): 257–64. http://dx.doi.org/10.1017/s0022029909003999.

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A total of 24 lactating Holstein cows averaging 620 (se=29) kg of body weight were allotted at week 17 of lactation to eight groups of three cows blocked for similar days in milk to determine the effects of feeding two sources of the plant lignan precursor secoisolariciresinol diglucoside, whole flaxseed and flaxseed meal, on concentrations of the mammalian lignans (enterodiol and enterolactone) in milk. Feed intake, digestion, milk production and milk composition were also determined to compare the use of whole flaxseed and flaxseed meal for milk production. Cows within each block were assigned to one of the three isonitrogenous and isoenergetic total mixed diets: no flaxseed product; 10% flaxseed meal; or 10% whole flaxseed in the dry matter. The experiment was carried out from week 17 to week 21 of lactation and diets were fed at ad-libitum intake. The mammalian lignan, enterodiol, was not detected in the milk of cows. Cows fed whole flaxseed and flaxseed meal had greater concentrations of enterolactone in milk than those fed the control diet. Feed intake, milk production and milk composition were also similar for all diets, indicating that both flaxseed meal and whole flaxseed are suitable feed ingredients for milk production of cows in mid lactation. The results provide new information on the conversion of plant secoisolariciresinol diglucoside from two flaxseed products into mammalian lignans in dairy cows.

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Lee, Yeong-Geun, Kyeong-Hwa Seo, Jung Eun Gwag, Hyoung-Geun Kim, Jung-Hwan Ko, Dae Young Lee, and Nam-In Baek. "New Lignan from the Flowers of Forsythia koreana." Chemistry of Natural Compounds 55, no. 3 (May 2019): 432–34. http://dx.doi.org/10.1007/s10600-019-02707-6.

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Medvedova, S. A., S. Z. Ivanova, V. A. Babkin, A. I. Rezvukhin, and I. V. Volkova. "A lignan glycoside from the needles ofPinus sibirica." Chemistry of Natural Compounds 21, no. 4 (July 1985): 525–26. http://dx.doi.org/10.1007/bf00579152.

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34

Baldi, Ashish, Sunita Farkya, Abhishek Jain, Nishant Gupta, Rahul Mehra, Vatsala Datta, Ashok Kumar Srivastava, and Virendra Swarup Bisaria. "Enhanced production of podophyllotoxins by co-culture of transformed Linum album cells with plant growth-promoting fungi." Pure and Applied Chemistry 82, no. 1 (January 5, 2010): 227–41. http://dx.doi.org/10.1351/pac-con-09-02-09.

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To investigate the plant growth-promoting effect and stimulation of lignan biosynthesis, the effect of culture filtrates/live co-culture of two arbuscular mycorrhizae-like fungi, Piriformospora indica and Sebacina vermifera, on growth of Linum album cells and on production of podophyllotoxin (PT) and 6-methoxypodophyllotoxin (6-MPT) was studied. For elicitation studies, different volumes of culture filtrates (autoclaved and membrane-filtered) of P. indica/S. vermifera were added to suspension cultures of L. album. The culture filtrates of both the fungi exhibited a positive effect on product formation. For co-culture experiments, both fungi were individually co-cultivated at different concentrations with L. album in suspension cultures for different time periods. This resulted in significant enhancement of PT and 6-MPT content in the plant cells. The activity of phenylalanine ammonia lyase (PAL) was observed to be related to the lignan accumulation, indicating its role as the key enzyme of the phenylpropanoid pathway. The study resulted in total lignan (PT and 6-MPT) production of 745.6 mg/l with a very high PT productivity of 52.4 mg/(l.d).

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Navarro, Sandi L., Lisa Levy, Keith R. Curtis, Isaac Elkon, Orsalem J. Kahsai, Hamza S. Ammar, Timothy W. Randolph, et al. "Effect of a Flaxseed Lignan Intervention on Circulating Bile Acids in a Placebo-Controlled Randomized, Crossover Trial." Nutrients 12, no. 6 (June 19, 2020): 1837. http://dx.doi.org/10.3390/nu12061837.

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Plant lignans and their microbial metabolites, e.g., enterolactone (ENL), may affect bile acid (BA) metabolism through interaction with hepatic receptors. We evaluated the effects of a flaxseed lignan extract (50 mg/day secoisolariciresinol diglucoside) compared to a placebo for 60 days each on plasma BA concentrations in 46 healthy men and women (20–45 years) using samples from a completed randomized, crossover intervention. Twenty BA species were measured in fasting plasma using LC-MS. ENL was measured in 24-h urines by GC-MS. We tested for (a) effects of the intervention on BA concentrations overall and stratified by ENL excretion; and (b) cross-sectional associations between plasma BA and ENL. We also explored the overlap in bacterial metabolism at the genus level and conducted in vitro anaerobic incubations of stool with lignan substrate to identify genes that are enriched in response to lignan metabolism. There were no intervention effects, overall or stratified by ENL at FDR < 0.05. In the cross-sectional analysis, irrespective of treatment, five secondary BAs were associated with ENL excretion (FDR < 0.05). In vitro analyses showed positive associations between ENL production and bacterial gene expression of the bile acid-inducible gene cluster and hydroxysteroid dehydrogenases. These data suggest overlap in community bacterial metabolism of secondary BA and ENL.

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Hallmans, Göran, Jie-Xian Zhang, Eva Lundin, PäR Stattin, Anders Johansson, Ingegerd Johansson, Kerstin Hultén, et al. "Rye, lignans and human health." Proceedings of the Nutrition Society 62, no. 1 (February 2003): 193–99. http://dx.doi.org/10.1079/pns2002229.

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Rye bran contains a high content not only of dietary fibre, but also of plant lignans and other bioactive compounds in the so-called dietary fibre complex. Blood concentrations of lignans such as enterolactone have been used as biomarkers of intake of lignan-rich plant food. At present, evidence from studies in human subjects does not warrant the conclusion that rye, whole grains or phyto-oestrogens protect against cancer. Some studies, however, have pointed in that direction, especially in relation to cancers of the upper digestive tract. A number of prospective epidemiological studies have clearly shown a protective effect of whole-grain cereals against myocardial infarctions. A corresponding protective effect against diabetes and ischaemic stroke (brain infarct) has also been demonstrated. It seems reasonable to assume that these protective effects are associated with one or more factors in the dietary fibre complex.

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37

Taavitsainen, Eveliina, Maarit Kortesoja, Tanja Bruun, Niklas G. Johansson, and Leena Hanski. "Assaying Chlamydia pneumoniae Persistence in Monocyte-Derived Macrophages Identifies Dibenzocyclooctadiene Lignans as Phenotypic Switchers." Molecules 25, no. 2 (January 11, 2020): 294. http://dx.doi.org/10.3390/molecules25020294.

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Antibiotic-tolerant persister bacteria involve frequent treatment failures, relapsing infections and the need for extended antibiotic treatment. The virulence of an intracellular human pathogen C. pneumoniae is tightly linked to its propensity for persistence and means for its chemosensitization are urgently needed. In the current work, persistence of C. pneumoniae clinical isolate CV6 was studied in THP-1 macrophages using quantitative PCR and quantitative culture. A dibenzocyclooctadiene lignan schisandrin reverted C. pneumoniae persistence and promoted productive infection. The concomitant administration of schisandrin and azithromycin resulted in significantly improved bacterial eradication compared to sole azithromycin treatment. In addition, the closely related lignan schisandrin C was superior to azithromycin in eradicating the C. pneumoniae infection from the macrophages. The observed chemosensitization of C. pneumoniae was associated with the suppression of cellular glutathione pools by the lignans, implying to a previously unknown aspect of chlamydia–host interactions. These data indicate that schisandrin lignans induce a phenotypic switch in C. pneumoniae, promoting the productive and antibiotic-susceptible phenotype instead of persistence. By this means, these medicinal plant -derived compounds show potential as adjuvant therapies for intracellular bacteria resuscitation.

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Nurmi, Tarja, Jaakko Mursu, José L. Peñalvo, Henrik E. Poulsen, and Sari Voutilainen. "Dietary intake and urinary excretion of lignans in Finnish men." British Journal of Nutrition 103, no. 5 (October 8, 2009): 677–85. http://dx.doi.org/10.1017/s0007114509992261.

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Intake of lignans has been assessed in different study populations, but so far none of the studies has compared the daily intake of lignans and the urinary excretion of plant and enterolignans. We assessed the intake of lariciresinol, pinoresinol, secoisolariciresinol and matairesinol in 100 Finnish men consuming their habitual omnivorous diet, and measured the 24 h urinary excretion of plant and enterolignans to compare the intake and metabolism. Dietary determinants of lignan intake and their urinary excretion were also determined. The mean intake of lignans was 1224 (sd 539) μg/d, of which lariciresinol and pinoresinol covered 78 %. Almost half (47 %) of the intake of lignans was explained by the intake of rye products, berries, coffee, tea and roots. The urinary excretion of plant lignans corresponded to 17 % and enterolignans to 92 % of the intake of lignans. The urinary excretion of plant lignans was explained 14 % by the intake of rye products and intake of coffee, and consequently 3–7 % by the intake of water-insoluble fibre. The urinary excretion of enterolactone was explained 11 % by the intake of vegetables and rye products, 14 % by the intake of water-soluble fibre and only 4 % by the intake of lariciresinol. Although the assessed intake of lignans corresponded well with the urinary excretion of lignans, the enterolactone production in the human body depended more on the dietary sources of lignans than the absolute intake of lignans.

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Bhatt, Vinod, Sushila Sharma, Neeraj Kumar, and Bikram Singh. "A New Lignan from the Leaves of Zanthoxylum armatum." Natural Product Communications 12, no. 1 (January 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200128.

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A new furofuran lignan, zanthonin (1) together with 13 known compounds including seven furofuran lignans (2–8), one isobutyl amide (9), a furanocoumarin (10) and four flavonoids (11–14) have been isolated from the leaves of Zanthoxylum armatum. The chemical structures of these compounds were elucidated mainly on the basis of NMR (1D and 2D) and MS data. This is the first report on the isolation of methylxanthoxylol (4) from Z. armatum.

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Zhu, Yan Hui, Na Li, and Ming-Wei Wang. "A new lignan glycoside fromPeperomia duclouxii." Natural Product Research 22, no. 17 (November 20, 2008): 1483–86. http://dx.doi.org/10.1080/14786410802236432.

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41

Mo, Xiaoyu, Yinning Chen, Yu Han, Huili Hao, and Riming Huang. "A New Benzylbutane Lignan from the Stems of Schisandra bicolor." Chemistry of Natural Compounds 54, no. 5 (September 2018): 872–74. http://dx.doi.org/10.1007/s10600-018-2502-0.

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42

Wang, Qing-hu, Jun-hua Gong, Jun-sheng Hao, and Yan-hua Xu. "Structure Elucidation of a New Lignan Glycoside from Artemisia ordosica." Chemistry of Natural Compounds 55, no. 6 (November 2019): 1007–9. http://dx.doi.org/10.1007/s10600-019-02880-8.

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43

Zeng, Jin, Sheng-Nan Zhang, Hong-Zhi Song, Rui-Jing Ma, and Qin-Gang Tan. "Flavonoid and Lignan Glycosides from the Leaves of Melia Azedarach." Chemistry of Natural Compounds 56, no. 2 (March 2020): 323–24. http://dx.doi.org/10.1007/s10600-020-03019-w.

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44

Côrtes, Cristiano, Daniele da Silva-Kazama, Ricardo Kazama, Chaouki Benchaar, Geraldo dos Santos, Lucia M. Zeoula, N. Gagnon, and Hélène V. Petit. "Effects of abomasal infusion of flaxseed (Linum usitatissimum) oil on microbial β-glucuronidase activity and concentration of the mammalian lignan enterolactone in ruminal fluid, plasma, urine and milk of dairy cows." British Journal of Nutrition 109, no. 3 (May 1, 2012): 433–40. http://dx.doi.org/10.1017/s0007114512001341.

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Ruminal microbiota plays an important role in the conversion of plant lignans into mammalian lignans. The main mammalian lignan present in the milk of dairy cows fed flax products is enterolactone (EL). The objectives of the present study were to investigate the effects of abomasal infusion of flax oil on the metabolism of flax lignans and concentrations of EL in biological fluids of dairy cows. A total of six rumen-cannulated dairy cows were assigned within a 2 × 3 factorial arrangement of six treatments utilising flax hulls (0 and 15·9 % of DM) and abomasal infusion of flax oil (0, 250 and 500 g/d). There were six periods of 21 d each. Samples were collected during the last 7 d of each period and subjected to chemical analysis. Flax hull supplementation increased concentrations of EL in ruminal fluid, plasma, urine and milk, while flax oil infusion had no effect. Post-feeding, β-glucuronidase activity in the ruminal fluid of cows infused with 250 g flax oil was significantly lower for cows fed hulls than for those fed the control diet. The present study demonstrated that the presence of a rich source of n-3 fatty acids such as flax oil in the small intestine does not interfere with the absorption of the mammalian lignan EL and that lower ruminal β-glucuronidase activity had no effect on the conversion of flax lignans into EL in the rumen of dairy cows.

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45

Mukherjee, Tulika, Sayan Chowdhury, Ashish Kumar, Hemanta K. Majumder, Parasuraman Jaisankar, and Sibabrata Mukhopadhyay. "Saracoside: A New Lignan Glycoside from Saraca indica, a Potential Inhibitor of DNA Topoisomerase IB." Natural Product Communications 7, no. 6 (June 2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700619.

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Chemical investigation of the stem bark of Saraca indica has resulted in the isolation of a new lignan glycoside, saracoside, along with four known lignan glycosides lyoniside, icariside E3, (+)5′methoxyisolarciresinol-9′- O-β-D-glucopyranoside and nudiposide, and a phenolic glucopyranoside, 3,4,5– trimethoxyphenyl-β-D-glucopyranoside, which has been isolated for the first time from this species. The isolated lignan glycosides exhibit potent DNA topoisomerase IB inhibitory activity.

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46

Westcott, Neil D., and Alister D. Muir. "Flax seed lignan in disease prevention and health promotion." Phytochemistry Reviews 2, no. 3 (October 2003): 401–17. http://dx.doi.org/10.1023/b:phyt.0000046174.97809.b6.

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47

Sepulveda-Boza, Silvia, Sualaheen Delhvi, and Bruce K. Cassels. "An aryltetralin lignan from Persea lingue." Phytochemistry 29, no. 7 (January 1990): 2357–58. http://dx.doi.org/10.1016/0031-9422(90)83075-c.

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48

Mulabagala, Vanisree, Gottumukkala V. Subbaraju, Modukuri V. Ramani, David L. DeWitt, and Muraleedharan G. Nair. "Lipid Peroxidation, Cyclooxygenase Enzyme and Tumor Cell Proliferation Inhibitory Lignans from Justicia Species." Natural Product Communications 3, no. 11 (November 2008): 1934578X0800301. http://dx.doi.org/10.1177/1934578x0800301109.

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The genus Justicia is a rich source of lignans, especially aryl naphthalide lignans. Lignans are biologically active phytochemicals, and are reported to possess antiplatelet, antiviral, anti-tumor, antidepressant, and insect antifeedant activities. In the present study, we report lipid peroxidation (LPO), cyclooxygenase (COX-1 and −2) enzyme and tumor cell proliferation inhibitory activities of lignans, namely, lariciresinol (1), isolariciresinol (2), neesiinoside A (3), justirumalin (4), justalakonin (5), justicidin G (6), sesamin (7), sesamolin (8), jusmicranthin methyl ether (9), taiwanin E methyl ether (10), lignan J1 (11), jusneesiinol (12), jusmicranthin ethyl ether (13), tiruneesiin (14), justicidin E (15) and simplexolin (16). Lignans 1 and 2 were isolated from J. tranquebariensis, 3, 4, 6, 9, 10, 11, 12, 13 and 14 from J. neesii Ramamoorthy, 5 from J. purpurea and 7, 8, 15 and 16 from J. orbiculata. Among the lignans assayed, 1, 2, 12 and 14 showed 79.6, 86.2, 90.8 and 95.9% and 3 41.3% inhibition of LPO at 25 μg/mL. The lignans 4, 9 and 16 inhibited COX-2 enzyme by 67.2, 73.0 and 72.8%, respectively, when tested at 25 μg/mL. Similarly, lignans 3, 4, 10, 11 and 15 inhibited COX-1 enzyme by 59.9, 89.2, 69.6, 73.9, and 80.1%, respectively, at 25 μg/mL. When assayed at 25 μg/mL, 4 inhibited human stomach and breast cancer cell lines by 42.8 and 42.1%, respectively. Also, at 25 μg/mL the lignan 7 inhibited the growth of CNS, lung and breast cancer cell lines by 50.0, 41.3, and 42.0 %, respectively, and 15 inhibited the proliferation of lung, breast and colon cell lines by 40–53%.

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Markulin, Lucija, Cyrielle Corbin, Sullivan Renouard, Samantha Drouet, Laurent Gutierrez, Ivan Mateljak, Daniel Auguin, Christophe Hano, Elisabeth Fuss, and Eric Lainé. "Pinoresinol–lariciresinol reductases, key to the lignan synthesis in plants." Planta 249, no. 6 (March 20, 2019): 1695–714. http://dx.doi.org/10.1007/s00425-019-03137-y.

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Swarup, V., J. Ghosh, M. K. Mishra, and A. Basu. "Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan." Journal of Antimicrobial Chemotherapy 61, no. 3 (February 4, 2008): 679–88. http://dx.doi.org/10.1093/jac/dkm503.

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