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Статті в журналах з теми "Cyanidin-3-O-β-glucoside"

Автор: Grafiati

Опубліковано: 10 січня 2023

Оновлено: 28 січня 2023

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1

Hashimoto, Masanori, Toshisada Suzuki, and Tsukasa Iwashina. "New Acylated Anthocyanins and Other Flavonoids from the Red Flowers of Clematis Cultivars." Natural Product Communications 6, no. 11 (November 2011): 1934578X1100601. http://dx.doi.org/10.1177/1934578x1100601118.

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Анотація:

Six new acylated cyanidin glycosides, cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)-(1→2)- O-β-galactopyranoside (1), cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)-(1→2)- O-β-(6′′-malonylgalactopyranoside) (2), cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)- (1→2)- O-β-(6″-succinylgalactopyranoside) (3), cyanidin 3- O-β-(2′'- E-caffeoylglucopyranosyl)-(1→2)- O-β-galactopyranoside-3′- O-β-glucuronopyranoside (4), cyanidin 3- O-β-(2′′- E-caffeoylglucopyranosyl)-(1→2)- O-β-(6′'-malonylgalactopyranoside)-3′- O-β-glucuronopyranoside (5), and cyanidin 3- O-β-(2′'- E-feruloylglucopyranosyl)-(1→2)- O-β-(6′'-malonylgalactoside)-3′- O-β-glucuronopyranoside (6), were isolated from the red flowers of two Clematis cultivars, ‘Niobe'and ‘Madame Julia Correvon'. The chemical structures of the isolated anthocyanins were determined by UV, LC-MS, HPLC, TLC, characterization of hydrolysates, and 1H and 13C NMR spectroscopy, including H-H COSY, C-H COSY, HMBC, HMQC and NOESY. The last three anthocyanins were widely distributed in 37 red flower Clematis cultivars. On the other hand, the first three compounds were found only in two cultivars. Five known flavonol glycosides, kaempferol 3- O-glucoside, kaempferol 3- O-rutinoside, quercetin 3- O-galactoside, quercetin 3- O-glucoside and quercetin 3- O-rutinoside, were isolated from the flowers of ‘Madame Julia Correvon'.

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2

Kaume, Lydia, William Gilbert, Breda J. Smith та Latha Devareddy. "Cyanidin 3-O-β-d-Glucoside Improves Bone Indices". Journal of Medicinal Food 18, № 6 (червень 2015): 690–97. http://dx.doi.org/10.1089/jmf.2014.0029.

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3

Acquaviva, R., A. Russo, F. Galvano, G. Galvano, M. L. Barcellona, G. Li Volti та A. Vanella. "Cyanidin and cyanidin 3-O-β-D-glucoside as DNA cleavage protectors and antioxidants". Cell Biology and Toxicology 19, № 4 (серпень 2003): 243–52. http://dx.doi.org/10.1023/b:cbto.0000003974.27349.4e.

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4

Pop, Raluca, Adina Căta, Mariana Nela Ștefănuț, and Ioana Maria Carmen Ienașcu. "A computational study of the interactions between anthocyans and cyclodextrins." Zeitschrift für Naturforschung C 75, no. 11-12 (November 26, 2020): 433–41. http://dx.doi.org/10.1515/znc-2020-0072.

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Анотація:

AbstractThe interactions between six anthocyans (cyanidin-3-O-glucoside, delphinidin-3-O-glucoside, malvidin-3-O-glucoside, cyanidin-3-O-rutinoside, delphinidin-3-O-rutinoside, malvidin-3-O-rutinoside) and cyclodextrins were investigated by means of computational techniques. Four different structures of the aforementioned anthocyans were considered, as a result of the dependence structure – pH value (flavylium cations in acidic medium, hemiketals in neutral solutions and two tautomeric quinones in alkaline environment). The results outlined that the anthocyanidin-3-O-rutinoside are favored for the obtaining of inclusion complexes with the cyclodextrins, mostly due to the larger number of OH groups involved in the formation of hydrogen bonds. For all the four types of structures, best results have been obtained for β- and γ-cyclodextrins.

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5

Di Giacomo, Claudia, Rosaria Acquaviva, Rosa Santangelo, Valeria Sorrenti, Luca Vanella, Giovanni Li Volti, Nicolantonio D'Orazio, Angelo Vanella та Fabio Galvano. "Effect of Treatment with Cyanidin-3-O-β-D-Glucoside on Rat Ischemic/Reperfusion Brain Damage". Evidence-Based Complementary and Alternative Medicine 2012 (2012): 1–10. http://dx.doi.org/10.1155/2012/285750.

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This study investigated the effect of cyanidin-3-O-β-glucoside on an experimental model of partial/transient cerebral ischemia in the rats in order to verify the effectiveness of both pre- and posttreatments. Cyanidin-3-O-β-glucoside-pretreated rats were injected with 10 mg/Kg i.p. 1 h before the induction of cerebral ischemia; in posttreated rats, the same dosage was injected during reperfusion (30 min after restoring blood flow). Cerebral ischemia was induced by bilateral clamping of common carotid arteries for 20 min. Ischemic rats were sacrificed immediately after 20 min ischemia; postischemic reperfused animals were sacrificed after 3 or 24 h of restoring blood flow. Results showed that treatment with cyanidin increased the levels of nonproteic thiol groups after 24 h of postischemic reperfusion, significantly reduced the lipid hydroperoxides, and increased the expression of heme oxygenase andγ-glutamyl cysteine synthase; a significant reduction in the expression of neuronal and inducible nitric oxide synthases and the equally significant increase in the endothelial isoform were observed. Significant modifications were also detected in enzymes involved in metabolism of endogenous inhibitors of nitric oxide. Most of the effects were observed with both pre- and posttreatments with cyanidin-3-O-β-glucoside suggesting a role of anthocyanin in both prevention and treatment of postischemic reperfusion brain damage.

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6

Strack, Dieter, Ekkehard Busch, Victor Wray, Lutz Grotjahn, and Erich Klein. "Cyanidin 3-Oxalylglucoside in Orchids." Zeitschrift für Naturforschung C 41, no. 7-8 (August 1, 1986): 707–11. http://dx.doi.org/10.1515/znc-1986-7-808.

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Abstract A new acylated anthocyanin has been isolated from flowers of Nigritella and Orchis and identified as cyanidin 3-O-β-(6”-O-oxalyl)-glucoside on the basis of TLC , HPLC , FABMS, 1H and 13C NMR . This pigment was found to be present in various members of the Orchidaceae.

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7

Jiang, Xinwei, Tianran Shen, Xilan Tang, Wenqi Yang, Honghui Guo та Wenhua Ling. "Cyanidin-3-O-β-glucoside combined with its metabolite protocatechuic acid attenuated the activation of mice hepatic stellate cells". Food & Function 8, № 8 (2017): 2945–57. http://dx.doi.org/10.1039/c7fo00265c.

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8

Trendafilova, Antoaneta, Viktoria Ivanova, Boryana Trusheva, Mariana Kamenova-Nacheva, Sava Tabakov, and Svetlana Simova. "Chemical Composition and Antioxidant Capacity of the Fruits of European Plum Cultivar “Čačanska Lepotica” Influenced by Different Rootstocks." Foods 11, no. 18 (September 14, 2022): 2844. http://dx.doi.org/10.3390/foods11182844.

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We investigated the influence of different rootstocks on the content of sugars, organic acids, and antioxidant phenolic compounds in the whole fruit and fruit skin of the European plum cultivar “Čačanska Lepotica”. 1H NMR of the fruit extracts allowed for the identification of sucrose, α- and β-glucose, sorbitol, fructose, and malic and quinic acids, while LC–DAD–ESIMS showed the presence of neochlorogenic and chlorogenic acids, cyanidin-3-O-glucoside, cyanidin-3-O-rutinoside, peonidin-3-O-glucoside, peonidin-3-O-rutinoside, hyperoside, isoquercitrin, rutin, and unidentified quercetin-3-diglycoside. The quantitation of the sugars, malic and quinic acids by 1H NMR and phenolic compounds by HPLC–DAD revealed that the rootstock significantly influenced the content of the individual compounds in the fruit skin and fruit. The fruit grafted on “Wavit” rootstock was characterized by significant amounts of neochlorogenic acid, peonidin-3-O-rutinoside, cyanidin-3-O-rutinoside, and sucrose, while the fruit on “GXN-15” was characterized by high levels of sugars, cyanidin-3-O-glucoside, and malic and chlorogenic acids. The fruit skins of plums grafted on “Wavit” were the richest in sugars, organic acids, and phenolic compounds. A good correlation was observed between the content of total phenolics (TPC), flavonoids (TFC), anthocyanins (TAC), and individual phenolic compounds in the extracts of the fruit and the fruit skins and their antioxidant capacity (DPPH, ABTS, and FRAP).

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9

Tsuda, Takanori, Fumihiko Horio та Toshihiko Osawa. "Absorption and metabolism of cyanidin 3-O -β-D -glucoside in rats". FEBS Letters 449, № 2-3 (23 квітня 1999): 179–82. http://dx.doi.org/10.1016/s0014-5793(99)00407-x.

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10

Li, Jiabai, David Percival, Jeff Hoyle, Jin Yue, Jane White, Krista Head, and Kris Pruski. "Environmental effects on fruit composition of cloudberry/bakeapple (Rubus chamaemorus L.) grown in southern Labrador, Canada." Canadian Journal of Plant Science 95, no. 6 (November 2015): 1167–75. http://dx.doi.org/10.4141/cjps-2015-130.

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Li, J., Percival, D., Hoyle, J., Yue, J., White, J., Head, K. and Pruski, K. 2015. Environmental effects on fruit composition of cloudberry/bakeapple (Rubus chamaemorus L.) grown in southern Labrador, Canada. Can. J. Plant Sci. 95: 1167–1175. The composition of fruit collected from three fields located near Lanse'au Clair, Red Bay and Cartwright in southern Labrador, Canada, was analyzed over the 2011 and 2012 growing seasons. Soluble solids, titratable acidity, total phenolics, total anthocyanins, chlorogenic acid, caffeic acid, quercetin-3-glucoside, cyanidin-3-glucoside and ellagic acid were determined after each harvest using standard laboratory procedures. Temperature, precipitation, wind and other environmental factors affected growth and deposition of nutrients in harvested fruit. Soluble solids content (TSS), titratable acidity (TA), total anthocyanin, chlorogenic acid, cyanidin, total phenolic compounds and total anthocyanins of cloudberry fruit were significantly (P<0.05) affected by the combination of the growing season and the location. The TSS, TA and total phenolics were higher in fruits from Cartwright (most northern location) in both seasons compared with the other two locations. The HPLC analysis of compounds showed the ellagic acid and quercetin 3-o-β-D-glucoside contents of fruits were significantly affected by the location and the growing season (higher in 2012 compared with 2011), while contents of chlorogenic acid, caffeic acids, and cyanidin-3-o-β-glucoside were not. To our knowledge this is the most comprehensive study of fruit composition of bakeapple conducted in southern Labrador, Canada.

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11

Seke, Faith, Vimbainashe E. Manhivi, Tinotenda Shoko, Retha M. Slabbert, Yasmina Sultanbawa, and Dharini Sivakumar. "Effect of Freeze Drying and Simulated Gastrointestinal Digestion on Phenolic Metabolites and Antioxidant Property of the Natal Plum (Carissa macrocarpa)." Foods 10, no. 6 (June 18, 2021): 1420. http://dx.doi.org/10.3390/foods10061420.

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Natal plums (Carissa macrocarpa) are a natural source of bioactive compounds, particularly anthocyanins, and can be consumed as a snack. This study characterized the impact of freeze drying and in vitro gastrointestinal digestion on the phenolic profile, antioxidant capacity, and α-glucosidase activity of the Natal plum (Carissa macrocarpa). The phenolic compounds were quantified using high performance liquid chromatography coupled to a diode-array detector HPLC-DAD and an ultra-performance liquid chromatograph (UPLC) with a Waters Acquity photodiode array detector (PDA) coupled to a Synapt G2 quadrupole time-of-flight (QTOF) mass spectrometer. Cyanidin-3-O-β-sambubioside (Cy-3-Sa) and cyanidin-3-O-glucoside (Cy-3-G) were the dominant anthocyanins in the fresh and freeze-dried Natal plum powder. Freeze drying did not affect the concentrations of both cyanidin compounds compared to the fresh fruit. Both cyanidin compounds, ellagic acid, catechin, epicatechin syringic acid, caffeic acid, luteolin, and quercetin O-glycoside from the ingested freeze-dried Natal plum powder was quite stable in the gastric phase compared to the small intestinal phase. Cyanidin-3-O-β-sambubioside from the ingested Natal plum powder showed bioaccessibility of 32.2% compared to cyanidin-3-O-glucoside (16.3%). The degradation of anthocyanins increased the bioaccessibility of gallic acid, protocatechuic acid, coumaric acid, and ferulic acid significantly, in the small intestinal digesta. The ferric reducing antioxidant power (FRAP), 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS) activities, and inhibitory effect of α-glucosidase activity decreased in the small intestinal phase. Indigenous fruits or freeze-dried powders with Cy-3-Sa can be a better source of anthocyanin than Cy-3-G due to higher bioaccessibility in the small intestinal phase.

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12

Fernandes, Ana, Galya Ivanova, Natércia F. Brás, Nuno Mateus, Maria J. Ramos, Maria Rangel та Victor de Freitas. "Structural characterization of inclusion complexes between cyanidin-3-O-glucoside and β-cyclodextrin". Carbohydrate Polymers 102 (лютий 2014): 269–77. http://dx.doi.org/10.1016/j.carbpol.2013.11.037.

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13

Iwashina, Tsukasa, Hiroshi Tobe, Takahisa Nakane, Takayuki Mizuno, and Tanguy Jaffré. "Flavonoids and Phenolic Compounds From the Parasitic Gymnosperm Parasitaxus usta Endemic to New Caledonia." Natural Product Communications 17, no. 1 (January 2022): 1934578X2110697. http://dx.doi.org/10.1177/1934578x211069706.

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Parasitaxus usta (Podocarpaceae) is the only parasitic gymnosperm and endemic to New Caledonia. In this survey, 11 flavonoids and 6 phenolic compounds were isolated from the aerial parts. As for flavonoids, six flavones, apigenin 7- O-glucoside (1), luteolin (2), luteolin 7- O-glucoside (3), chrysoeriol (4), chrysoeriol 7- O-glucoside (5) and tricetin 3′- O-glucoside (6), one C-glycosylflavone, orientin (7), one flavonol, quercetin 3- O-glucoside (8), one anthocyanin, cyanidin 3- O-glucoside (9), and two biflavones, isoginkgetin (10) and agathisflavone (11) were identified by UV, liquid chromatograph–mass spectra (LC-MS), acid hydrolysis, NMR and/or HPLC comparisons with authentic samples. On the other hand, six phenolic compounds were identified as 5- O- E- p-coumaroyl quinic acid (12), 5- O- Z- p-coumaroyl quinic acid (13), 5- O- E- p-coumaroyl quinic acid methyl ester (14), 5- O- Z- p-coumaroyl quinic acid methyl ester (15), E-caffeic acid methyl ester 3- O-β-glucopyranoside (16), and Z-caffeic acid methyl ester 3- O-β-glucopyranoside (17) by UV, LC-MS and NMR. Chemical components of P usta were reported in this survey for the first time. Their chemical characters were chemotaxonomically compared with those of other Podocarpaceae species.

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14

Levy, Rachel, Zoya Okun, and Avi Shpigelman. "The Influence of Chemical Structure and the Presence of Ascorbic Acid on Anthocyanins Stability and Spectral Properties in Purified Model Systems." Foods 8, no. 6 (June 12, 2019): 207. http://dx.doi.org/10.3390/foods8060207.

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The loss of color pigment is an important quality factor of food products. This work aimed to systematically study, in purified model systems, the influence of anthocyanins’ structure (by increasing the size of the conjugated sugar) and the presence of ascorbic acid on their stability and spectral properties during storage at two pH levels relevant to medium and high acid foods (6.5 and 4.5, respectively). Anthocyanins (cyanidin (Cy), cyanidin 3-O-β-glucoside (Cy3G) and cyanidin 3-O-β-rutinoside (Cy3R)) displayed first-order degradation rates, presenting higher stability in acidic medium and enhanced stability with increasing size of conjugated sugar. The addition of ascorbic acid resulted in significantly enhanced degradation. Changes in ultra violet visible (UV-VIS) spectral properties presented a decrease in typical color intensity and pointed towards formation of degradation products. Identification and kinetics of formation for cyanidin degradation products were obtained by high performance liquid chromatography system-mass spectrometry (HPLC-MS).

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15

Fu, Yunhe, Zhengkai Wei, Ershun Zhou, Naisheng Zhang та Zhengtao Yang. "Cyanidin-3-O-β-glucoside inhibits lipopolysaccharide-induced inflammatory response in mouse mastitis model". Journal of Lipid Research 55, № 6 (21 квітня 2014): 1111–19. http://dx.doi.org/10.1194/jlr.m047340.

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16

Tsuda, Takanori, Katsumi Ohshima, Shunro Kawakishi та Toshihiko Osawa. "Oxidation products of cyanidin 3-O-β-d-glucoside with a free radical initiator". Lipids 31, № 12 (грудень 1996): 1259–63. http://dx.doi.org/10.1007/bf02587910.

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17

Sorrenti, Valeria, Francesco Mazza, Agata Campisi, Claudia Di Giacomo, Rosaria Acquaviva, Luca Vanella та Fabio Galvano. "Heme oxygenase induction by cyanidin-3-O-β-glucoside in cultured human endothelial cells". Molecular Nutrition & Food Research 51, № 5 (травень 2007): 580–86. http://dx.doi.org/10.1002/mnfr.200600204.

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18

Mphaphuli, Tshudufhadzo, Vimbainashe E. Manhivi, Retha Slabbert, Yasmina Sultanbawa, and Dharini Sivakumar. "Enrichment of Mango Fruit Leathers with Natal Plum (Carissa macrocarpa) Improves Their Phytochemical Content and Antioxidant Properties." Foods 9, no. 4 (April 4, 2020): 431. http://dx.doi.org/10.3390/foods9040431.

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Natal plum fruit (Carissa macrocarpa) is indigenous to South Africa and a rich source of cyanidin derivatives. Indigenous fruits play a major role in food diversification and sustaining food security in the Southern African region. Agro-processing of indigenous are practiced adopted by the rural African communities in order to reduce the postharvest wastage of fruit commodities. In the current study, Natal plum was added to mango pulp at different ratios (mango and Natal plum (5:1, 3:1, 2:1)) to develop a healthy-functional snack (fruit leather). The effects of added Natal plum on the availability of antioxidant constituents and in vitro antioxidant properties of a mango-based fruit leather were evaluated by comparing with mango fruit leather. Fruit leather containing mango and Natal plum (2:1) retained the highest content of cyanidin-3-O-glucoside chloride, cyanidin- 3-O-β-sambubioside, epicatechin, apigenin, kaempferol, luteolin, quercetin-3-O-rhamnosyl glucoside, catechin, quinic, and chlorogenic acids, and in vitro antioxidant activity. Proximate analysis showed that 100 g of fruit leather (2:1) contained 63.51 g carbohydrate, 40.85 g total sugar, 0.36 g fat, and 269.88 cal. Therefore, enrichment of mango fruit leather with Natal plum (2:1) increases its phytochemical content and dietary phytochemical intake, especially for school children and adolescents.

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19

Zhang, Xuhuiqun, Amandeep Sandhu, Jiayi Fan, Di Xiao, Indika Edirisinghe, and Britt Burton-Freeman. "Metabolic Status and Gender Affect the Absorption and Metabolism of Red Raspberry (Poly)phenols." Current Developments in Nutrition 5, Supplement_2 (June 2021): 385. http://dx.doi.org/10.1093/cdn/nzab037_095.

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Abstract Objectives Red raspberries are rich in bioactive (poly)phenols, particularly anthocyanins and ellagitannins. A substantial amount of variability is observed in the bioavailability and metabolism of (poly)phenols in humans. This study aimed to investigate the potential factors, i.e., metabolic status, body mass index (BMI), age, gender and race, on (poly)phenol metabolism in individuals with different health statuses. Methods After 3-day wash-in and overnight fasting, subjects (n = 65, male: female 32:33, age 34 ± 1 years, BMI 27 ± 1 kg/m2, mean ± SEM) consumed 250 g red raspberries (2 cups equivalence). Plasma samples collected over 24 h were quantified for (poly)phenolic metabolites using an ultra-high performance liquid chromatography coupled with triple quadrupole (UHPLC-QQQ). Statistical analysis was performed using PC-SAS. Results Individuals with prediabetes and insulin-resistance (n = 45) had significantly higher bioavailability of cyanidin sophoroside (0.21 ± 0.02% vs. 0.14 ± 0.03%, P = 0.04) and cyanidin 3-O-glucoside (0.12 ± 0.01% vs. 0.09 ± 0.01%, P = 0.02), and lower area under the 24 h curve (AUC0–24h) of hippuric acid glucuronide (435 ± 123 nmol/L × h vs. 1011 ± 184 nmol/L × h, P = 0.01) compared to healthy individuals (n = 20). Females (n = 33) had significantly lower bioavailability of cyanidin 3-O-glucoside (0.09 ± 0.01% vs. 0.13 ± 0.01%, P = 0.04) compared to males (n = 32). Correlation analysis on all subjects (n = 65) identified that bioavailability of cyanidin sophoroside and cyanidin 3-O-glucoside negatively correlated with fasting plasma triglyceride and positively correlated with HOMA-IR, HOMA-β, and fasting insulin concentration (P < 0.05). The AUC0–24h of hippuric acid glucuronide negatively correlated with fasting plasma glucose and triglyceride concentrations. Conclusions Individuals with different metabolic status and gender have different capacity to absorb and metabolize red raspberry (poly)phenols. The data provide insight for personalized nutrition for optimal health benefits and suggest further research on possible mechanisms involved. Funding Sources This project was funded by the National Processed Raspberry Council and various donor funds to the Center for Nutrition Research, Illinois Institute of Technology.

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20

Tsuda, Takanori, Fumihiko Horio та Toshihiko Osawa. "Dietary cyanidin 3-O-β-d-glucoside increases ex vivo oxidation resistance of serum in rats". Lipids 33, № 6 (червень 1998): 583–88. http://dx.doi.org/10.1007/s11745-998-0243-5.

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21

Wang, Dongliang, Min Xia, Song Gao, Dan Li, Yuan Zhang, Tianru Jin та Wenhua Ling. "Cyanidin-3-O-β-glucoside upregulates hepatic cholesterol 7α-hydroxylase expression and reduces hypercholesterolemia in mice". Molecular Nutrition & Food Research 56, № 4 (квітень 2012): 610–21. http://dx.doi.org/10.1002/mnfr.201100659.

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22

Fan, Menglong, Ying Zhang, Meiying Yang, Si Wu, Hengfu Yin, Jiyuan Li, and Xinlei Li. "Transcriptomic and Chemical Analyses Reveal the Hub Regulators of Flower Color Variation from Camellia japonica Bud Sport." Horticulturae 8, no. 2 (January 30, 2022): 129. http://dx.doi.org/10.3390/horticulturae8020129.

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Camellia japonica is a woody ornamental plant with multiple flower color variations caused by bud sport; however, the molecular mechanism remains unclear. Here, chemical and transcriptomic analyses of C. japonica were performed with white, pink, red, and dark red flowers caused by bud sport. Seven anthocyanins were detected in these samples, except in C. japonica ‘YuDan’ (white petals). The total anthocyanin content of C. japonica ‘JinBiHuiHuang’ was the highest, and cyanidin 3-O-β-glucoside (Cy3G) was the main anthocyanin affecting the redness of petals. Furthermore, the ratio of Cy3G and cyanidin-3-O-(6-O-(E)-p-coumaroyl)-B-glucoside) was significantly correlated with the red petal phenotype. In total, 5673 genes were identified as differentially expressed genes (DEGs). The potential co-expression modules related to anthocyanin accumulation were established, which featured transcription factors, anthocyanin biosynthesis, and plant hormone signal transduction. Thirteen structural genes in the anthocyanin biosynthetic pathway were identified as DEGs, most of them were upregulated with deepening of flower redness. An integrated promoter and cluster analysis suggested that CjMYB62, CjMYB52, and CjGATA may play important roles in anthocyanin accumulation. These results provide insight and candidate genes for the transcriptional mechanism responsible for the bud sport phenotype.

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23

Jordheim, Monica, Kjersti Hasle Enerstvedt та Øyvind M. Andersen. "Identification of Cyanidin 3-O-β-(6″-(3-Hydroxy-3-methylglutaroyl)glucoside) and Other Anthocyanins from Wild and Cultivated Blackberries". Journal of Agricultural and Food Chemistry 59, № 13 (13 липня 2011): 7436–40. http://dx.doi.org/10.1021/jf201522b.

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24

Giacomo, Claudia Di, Rosaria Acquaviva, Andrea Piva, Valeria Sorrenti, Luca Vanella, Gianfranco Piva, Gabriele Casadei та ін. "Protective effect of cyanidin 3-O-β-d-glucoside on ochratoxin A-mediated damage in the rat". British Journal of Nutrition 98, № 5 (листопад 2007): 937–43. http://dx.doi.org/10.1017/s0007114507756908.

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The aim of the present study was to verify whether the oral administration of cyanidin 3-O-β-d-glucoside (C3G) might counteract damage induced by chronic exposure (28 d) to ochratoxin A (OTA) in rats and if its effect may be mediated by haeme oxygenase-1 (HO-1). Forty male Sprague–Dawley rats, individually caged, were divided into four groups of ten animals. A control group received a commercial diet, group C3G received the control diet supplemented with C3G (1 g/kg feed), group OTA received the control diet supplemented with 200 parts per billion of OTA, and group OTA+C3G received the OTA group diet supplemented with C3G (1 g/kg feed). After 4 weeks of treatment animals were killed and the liver, kidneys and brain of each rat were collected and homogenised to evaluate non-proteic thiol groups (RSH), lipid hydroperoxide (LOOH) levels, HO-1 expression and DNA fragmentation. Rats of the OTA group showed a significant (P < 0·001) decrease in RSH content of kidney and liver and a significant (P < 0·001) increase of LOOH in all the examined tissues compared with the control group. In the OTA+C3G group both RSH content and LOOH levels were similar to those observed in the control group, demonstrating that C3G was able to counteract the effects of OTA. A significant (P < 0·001) induction of HO-1 was evident in kidney and liver of both OTA and C3G groups. DNA damage occurred in all the examined tissues of the OTA group, whereas C3G was able to prevent it. The present study confirmed that the effects of OTA are mediated by oxidative stress and demonstrated that C3G efficiently counteracted deleterious effects of OTA because of its antioxidant and HO-1-inducing properties.

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Russo, Alessandra, Luca La Fauci, Rosaria Acquaviva, Agata Campisi, Giuseppina Raciti, Christian Scifo, Marcella Renis, Giacomo Galvano, Angelo Vanella та Fabio Galvano. "Ochratoxin A-induced DNA damage in human fibroblast: protective effect of cyanidin 3-O-β-d-glucoside". Journal of Nutritional Biochemistry 16, № 1 (січень 2005): 31–37. http://dx.doi.org/10.1016/j.jnutbio.2004.05.005.

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Wang, Yun, Yuhua Zhang, Xiaoming Wang, Yan Liu та Min Xia. "Cyanidin-3-O-β-glucoside induces oxysterol efflux from endothelial cells: Role of liver X receptor alpha". Atherosclerosis 223, № 2 (серпень 2012): 299–305. http://dx.doi.org/10.1016/j.atherosclerosis.2012.06.004.

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27

Tsuda, Takanori, Fumihiko Horio, Junzoh Kitoh та Toshihiko Osawa. "Protective Effects of Dietary Cyanidin 3-O-β-d-Glucoside on Liver Ischemia–Reperfusion Injury in Rats". Archives of Biochemistry and Biophysics 368, № 2 (серпень 1999): 361–66. http://dx.doi.org/10.1006/abbi.1999.1311.

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Laganà, Giuseppina, Davide Barreca, Antonella Smeriglio, Maria Paola Germanò, Valeria D'Angelo, Antonella Calderaro, Ersilia Bellocco, and Domenico Trombetta. "Evaluation of Anthocyanin Profile, Antioxidant, Cytoprotective, and Anti-Angiogenic Properties of Callistemon citrinus Flowers." Plants 9, no. 8 (August 17, 2020): 1045. http://dx.doi.org/10.3390/plants9081045.

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Lemon bottlebrush (Callistemon citrinus (Curtis) Skeels) is one of the most common ornamental plants, diffused worldwide, and characterized by the presence of flowers with an intense red/purple coloration. There is increasing interest in the use and application of anthocyanins for their unique structural/chemical features in both food and pharmaceutical applications. RP-HPLC-DAD-ESI-MS/MS analysis of an enriched fraction of acidified methanolic extract of C. citrinus flowers allow the possibility of identifying, for the first time, the presence of four anthocyanins: cyanidin-3,5-O-diglucoside (cyanin), peonidin-3,5-O-diglucoside (peonin), cyanidin-3-O-glucoside, and cyanidin-coumaroylglucoside-pyruvic acid. Moreover, the evaluation of antioxidant and biological potential showed a remarkable activity of this fraction, able to actively scavenge DPPH, AAPH, and ABTS radicals, and to counteract the β-carotene-bleaching. In addition, it protects human mononuclear cells from oxidative injuries and prevents angiogenesis (acting in the range of few μg/ml); furthermore, it does not show significant iron-chelating ability (up to 200 µg/mL). The easy way of cultivation, robustness, and adaptability to different environments make the flowers of this plant a useful source of anthocyanins, with remarkable health promoting properties.

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Norris, Katie M., Whitney Okie, Claire L. Yakaitis та Robert Pazdro. "The anthocyanin cyanidin-3- O -β-glucoside modulates murine glutathione homeostasis in a manner dependent on genetic background". Redox Biology 9 (жовтень 2016): 254–63. http://dx.doi.org/10.1016/j.redox.2016.08.014.

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Fu, Yunhe, Ershun Zhou, Zhengkai Wei, Wei Wang, Tiancheng Wang, Zhengtao Yang та Naisheng Zhang. "Cyanidin-3-O-β-glucoside ameliorates lipopolysaccharide-induced acute lung injury by reducing TLR4 recruitment into lipid rafts". Biochemical Pharmacology 90, № 2 (липень 2014): 126–34. http://dx.doi.org/10.1016/j.bcp.2014.05.004.

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Tsuda, Takanori, Fumihiko Horio, Koji Uchida, Hiromitsu Aoki та Toshihiko Osawa. "Dietary Cyanidin 3-O-β-D-Glucoside-Rich Purple Corn Color Prevents Obesity and Ameliorates Hyperglycemia in Mice". Journal of Nutrition 133, № 7 (1 липня 2003): 2125–30. http://dx.doi.org/10.1093/jn/133.7.2125.

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Zhou, Yujia, Sufan Wang, Ting Wan, Yuanling Huang, Nengzhi Pang, Xuye Jiang, Yingying Gu, Zhenfeng Zhang, Jing Luo та Lili Yang. "Cyanidin-3-O-β-glucoside inactivates NLRP3 inflammasome and alleviates alcoholic steatohepatitis via SirT1/NF-κB signaling pathway". Free Radical Biology and Medicine 160 (листопад 2020): 334–41. http://dx.doi.org/10.1016/j.freeradbiomed.2020.08.006.

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Cheng, Jing, Jian-Hua Liu, Govindarajan Prasanna та Pu Jing. "Spectrofluorimetric and molecular docking studies on the interaction of cyanidin-3- O -glucoside with whey protein, β-lactoglobulin". International Journal of Biological Macromolecules 105 (грудень 2017): 965–72. http://dx.doi.org/10.1016/j.ijbiomac.2017.07.119.

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Ya, Fuli, Qing Li, Dongliang Wang, Shuangfeng Xie, Fenglin Song, Reid Gallant, Zezhong Tian, Jianbo Wan, Wenhua Ling та Yan Yang. "Cyanidin-3-o-β-Glucoside Induces Megakaryocyte Apoptosis via PI3K/Akt- and MAPKs-Mediated Inhibition of NF-κB Signalling". Thrombosis and Haemostasis 118, № 07 (4 червня 2018): 1215–29. http://dx.doi.org/10.1055/s-0038-1656551.

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AbstractApoptotic-like phase is an essential step in thrombopoiesis from megakaryocytes. Anthocyanins are natural flavonoid pigments that possess a wide range of biological activities, including protection against cardiovascular diseases and induction of tumour cell apoptosis. We investigated the effects and underlying mechanisms of cyanidin-3-o-β-glucoside (Cy-3-g, the major bioactive compound in anthocyanins) on the apoptosis of human primary megakaryocytes and Meg-01 cell line in vitro. We found that Cy-3-g dose-dependently increased the dissipation of the mitochondrial membrane potential, caspase-9 and caspase-3 activity in megakaryocytes from patients with newly diagnosed acute myeloid leukaemia but not in those from healthy volunteers. In Meg-01 cells, Cy-3-g regulated the distribution of Bak, Bax and Bcl-xL proteins in the mitochondria and cytosol, subsequently increasing cytochrome c release and stimulating caspase-9 and caspase-3 activation and phosphatidylserine exposure. However, Cy-3-g did not exert significant effects on factor-associated suicide (Fas), Fas ligand, caspase-8 or Bid expression. Cy-3-g inhibited nuclear factor kappa B (NF-κB) p65 activation by down-regulating inhibitor of NF-κB kinase (IKK)α and IKKβ expression, followed by the inhibition of inhibitor of NF-κB (IκB)α phosphorylation and degradation and subsequent inhibition of the translocation of the p65 sub-unit into the nucleus, and finally stimulating caspase-3 activation and phosphatidylserine exposure. The inhibitory effect of Cy-3-g on NF-κB activation was mediated by the activation of extracellular signal-regulated kinases (Erk1/2) and p38 mitogen-activated protein kinase (MAPK) and the inhibition of phosphoinositide 3-kinase (PI3K)/Akt signalling. U0126 (Erk1/2 inhibitor), SB203580 (p38 MAPK inhibitor) and 740 Y-P (PI3K agonist) significantly reversed Cy-3-g-reduced phosphorylation of p65. Taken together, our data indicate that Cy-3-g induces megakaryocyte apoptosis via the inhibition of NF-κB signalling, which may play important roles in regulating thrombopoiesis.

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Stebbins, Nathan B., Luke R. Howard, Ronald L. Prior, Cindi Brownmiller, Rohana Liyanage, Jackson O. Lay, Xiaoyu Yang та Steven Y. Qian. "Ascorbic acid-catalyzed degradation of cyanidin-3-O-β-glucoside: Proposed mechanism and identification of a novel hydroxylated product". Journal of Berry Research 6, № 2 (16 червня 2016): 175–87. http://dx.doi.org/10.3233/jbr-160132.

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Ya, Fuli, Jinju Tian, Qing Li, Liyi Chen, Jing Ren, Yimin Zhao, Jianbo Wan, Wenhua Ling та Yan Yang. "Cyanidin-3-O-β-glucoside, a Natural Polyphenol, Exerts Proapoptotic Effects on Activated Platelets and Enhances Megakaryocytic Proplatelet Formation". Journal of Agricultural and Food Chemistry 66, № 41 (18 вересня 2018): 10712–20. http://dx.doi.org/10.1021/acs.jafc.8b03266.

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Wei, Xiaoyi, Dongliang Wang, Yan Yang, Min Xia, Dan Li, Guilan Li, Yanna Zhu, Yunjun Xiao та Wenhua Ling. "Cyanidin-3-O -β-glucoside improves obesity and triglyceride metabolism in KK-Ay mice by regulating lipoprotein lipase activity". Journal of the Science of Food and Agriculture 91, № 6 (24 лютого 2011): 1006–13. http://dx.doi.org/10.1002/jsfa.4275.

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38

Kaume, Lydia, William C. Gilbert, Cindi Brownmiller, Luke R. Howard та Latha Devareddy. "Cyanidin 3-O-β-d-glucoside-rich blackberries modulate hepatic gene expression, and anti-obesity effects in ovariectomized rats". Journal of Functional Foods 4, № 2 (квітень 2012): 480–88. http://dx.doi.org/10.1016/j.jff.2012.02.008.

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39

Talagavadi, Veena, Paolo Rapisarda, Fabio Galvano, Piergiuseppe Pelicci та Marco Giorgio. "Cyanidin-3- O -β-glucoside and protocatechuic acid activate AMPK/mTOR/S6K pathway and improve glucose homeostasis in mice". Journal of Functional Foods 21 (березень 2016): 338–48. http://dx.doi.org/10.1016/j.jff.2015.12.007.

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40

Chen, Jialong, Heng Ye, Jie Wang, and Lu Zhang. "Relationship between Anthocyanin Composition and Floral Color of Hibiscus syriacus." Horticulturae 9, no. 1 (January 3, 2023): 48. http://dx.doi.org/10.3390/horticulturae9010048.

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Hibiscus syriacus is a highly ornamental flowering shrub widely grown in East Asia. Its abundant flower colors mainly reflect the accumulation of anthocyanins. Classifying H. syriacus petals and identifying the relationship between flower color and anthocyanins can provide references for flower color breeding. With eight cultivars of H. syriacus as experimental materials, the floral color was described using the Royal Horticultural Society Color Chart and the CIEL*a*b* coordinate. The anthocyanin in petals was qualitatively and quantitatively analyzed by using ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS), and the relationships between flower color and anthocyanin were analyzed by using stepwise regression analysis. We divided eight cultivars of hibiscus into five color lines: red-purple, white, violet, purple, and blue-purple, and then into two groups: purple and red-purple. The results showed that the L* had a significant negative correlation with a* and C*. A total of 52 anthocyanin components were detected in the petals of H. syriacus, including cyanidin, delphinidin, malvidin, petunidin, peonidin, and pelargonidin derivatives. Cyanidin derivatives accounted for the highest proportion, and pelargonidin derivatives accounted for the lowest proportion of the total anthocyanins. Petals of ‘Pink Giant’ contained the largest number of types of anthocyanin components and the highest total anthocyanin content, while the petals of ‘Albus Single’ contained the smallest. Petunidin-3-O-glucoside showed a significant negative correlation with L* in the red-purple group and in all cultivars, whereas it showed a significant negative correlation with b* in the purple group. Delphinidin-3-O-(6-O-Malonyl-β-D-glucoside) exhibited a significant positive correlation with a* in the red-purple group, and delphinidin-3-O-glucoside showed a significant negative correlation with L* in the purple group. Therefore, our results suggest that changing the content of these three anthocyanin components may have the potential to alter the flower color. This research provides scientific guidance and a foundation for the molecular breeding of H. syriacus cultivars with new floral colors.

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Yanuar, Arry, Rezi Riadhi Syahdi, and Widya Dwi Aryati. "PARAMETER OPTIMIZATION AND VIRTUAL SCREENING INDONESIAN HERBAL DATABASE AS HUMAN IMMUNODEFICIENCY VIRUS -1 INTEGRASE INHIBITOR USING AUTODOCK AND VINA." International Journal of Applied Pharmaceutics 9 (October 30, 2017): 90. http://dx.doi.org/10.22159/ijap.2017.v9s1.51_57.

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Objective: Human immunodeficiency virus (HIV-1) is a virus that causes acquired immunodeficiency syndrome, a disease considered to be one of themost dangerous because of its high mortality, morbidity, and infectivity. The emergence of mutant HIV strains has led treatment to target proteaseas reverse transcriptase and integrase enzyme become less effective. This study aims to provide knowledge about the potential of HIV-1 integraseinhibitors for use as guiding compounds in the development of new anti-HIV drugs.Methods: This study used AutoDock and AutoDock Vina for virtual screening of the Indonesian herbal database for inhibitors of HIV-1 integrase andis validated using a database of the directory of useful decoys. Optimization was accomplished by selecting the grid size, the number of calculations,and the addition of two water molecules and a magnesium atom as cofactor.Results: This study determined that the best grid box size is 21.1725×21.1725×21.1725 in unit space size (1 unit space equals to macromolecules 1Ǻ),using AutoDock Vina with EF and AUC values, 3.93 and 0.693, respectively. Three important water molecules have meaning in molecular dockingaround the binding pocket.Conclusions: This study obtained the top ten ranked compounds using AutoDock Vina. The compounds include: Casuarinin; Myricetin-3-O-(2’’,6’’-di-O-α-rhamnosyl)-β-glucoside; 5,7,2’,4’-tetrahydroxy-6,3’-diprenylisoflavone 5-O-(4’’-rhamnosylrhamnoside); myricetin 3-robinobioside; cyanidin3-[6-(6-ferulylglucosyl)-2-xylosylgalactoside]; mesuein, cyanidin 7-(3-glucosyl-6-malonylglucoside)-4’-glucoside; kaempferol 3-[glucosyl-(1→3)-rhamnosyl-(1→6)-galactoside]; 3-O-galloylepicatechin-(4-β→8)-epicatechin-3-O-gallate; and quercetin 4’-glucuronide.

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Wang, Xin, Junhong Bai, Wei Wang, and Guangliang Zhang. "Leaf metabolites profiling between red and green phenotypes of Suaeda salsa by widely targeted metabolomics." Functional Plant Biology 46, no. 9 (2019): 845. http://dx.doi.org/10.1071/fp18182.

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The Chenopodiaceae Suaeda salsa (L.) Pall. is a traditional Chinese medicine and food with green and red phenotypes in the Yellow River Delta. We identified 521 metabolites using widely targeted metabolomics, of which 165 were selected as significantly differential metabolites which could be related to the leaf traits of different phenotypes of S. salsa. Two anthocyanins (i.e. cyanidin O-acetylhexoside and delphinidin-3-O-(6ʹ-O-α-rhamnopyranosy l-β-glucopyranoside)) were responsible for red colour in red leaves of S. salsa. Gallic acid, which existed only in red one, was the main reason for leaf succulence. D-arabitol and ribitol were two significantly upregulated carbohydrates in red phenotype. Four alkaloids (i.e. harmaline, aminophylline, pipecolate and trigonelline) were upregulated in red leaves. Hormonal changed involved a decrease in indoleacetic acid-valine (IAA-Val), N6-isopentenyladenosine-5ʹ-monophosphate (iPRMP), isopentenyladenineriboside (iPR), trans-abscisic acid (S-ABA), salicylic acid O-hexoside, methyl jasmonate, N6-isopentenyladenine (iP), trans-zeatin riboside-O-glucoside iso2, trans-zeatin riboside-O-glucoside, and a tendency for dihydrozeatin 9-O-glucoside (DZ9G) down accumulation. In addition, the regulation of amino acids and lipids also contributed to the adaptation of red phenotype to harsh environment. Generally, our findings provide a comprehensive comparison of the metabolites between two phenotypes of S. salsa and an interpretation of phenotypic differences from the point of metabolomics.

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Cabrita, Luis. "A Novel Acylated Anthocyanin with a Linear Trisaccharide from Flowers of Convolvulus althaeoides." Natural Product Communications 10, no. 11 (November 2015): 1934578X1501001. http://dx.doi.org/10.1177/1934578x1501001140.

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Анотація:

An acylated anthocyanin trioside was isolated from pink flowers of Convolvulus althaeoides using a combination of chromatographic techniques. On the basis of MS (MALDI-TOF) and NMR (1H NMR, 1H-1H COSY, 1D TOCSY, HSQC, HMBC, 13C CAPT) its structure was determined as cyanidin 3- O-[6- O-(4- O-(6- O-( E-caffeoyl)-β-D-glucopyranosyl)-α-L-rhamnopyranosyl)-β-D-glucopyranoside]-5- O-β-D-glucopyranoside. The absolute configuration of the aldose enantiomer moieties was determined from the separation of the corresponding thiazolidine diastereoisomer derivatives by HPLC-DAD. This is a novel trisaccharide within the flavonoids, and the first complete characterization of a linear glucosyl-rhamnosyl-glucoside (4′-glucosylrutinoside) within the anthocyanins. Whilst acylation of rhamnose moieties in position 4 is quite common, the occurrence in anthocyanins of a glycosylated rhamnose is a unique trait. Although many complex anthocyanins have been found amongst the Convolvulaceae, the genus Convolvulus had not yet been surveyed for anthocyanins and thus this account could be of significance within the current chemotaxonomy of this family.

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Yang, Zixin, Ting Huang, Ping Li, Jian Ai, Jiaxin Liu, Weibin Bai, and Lingmin Tian. "Dietary Fiber Modulates the Fermentation Patterns of Cyanidin-3-O-Glucoside in a Fiber-Type Dependent Manner." Foods 10, no. 6 (June 16, 2021): 1386. http://dx.doi.org/10.3390/foods10061386.

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The interactions between cell-wall polysaccharides and polyphenols in the gastrointestinal tract have attracted extensive attention. We hypothesized that dietary fiber modulates the fermentation patterns of cyanidin-3-O-glucoside (C3G) in a fiber-type-dependent manner. In the present study, the effects of four dietary fibers (fructose-oligosaccharides, pectin, β-glucan and arabinoxylan) on the modulation of C3G fermentation patterns were investigated through in vitro fermentation inoculated with human feces. The changes in gas volume, pH, total carbohydrate content, metabolites of C3G, antioxidant activity, and microbial community distribution during in vitro fermentation were analyzed. After 24 h of fermentation, the gas volume and total carbohydrate contents of the four dietary-fiber-supplemented groups respectively increased and decreased to varying degrees. The results showed that the C3G metabolites after in vitro fermentation mainly included cyanidin, protocatechuic acid, 2,4,6-trihydroxybenzoic acid, and 2,4,6-trihydroxybenzaldehyde. Supplementation of dietary fibers changed the proportions of C3G metabolites depending on the structures. Dietary fibers increased the production of short-chain fatty acids and the relative abundance of gut microbiota Bifidobacterium and Lactobacillus, thus potentially maintaining colonic health to a certain extent. In conclusion, the used dietary fibers modulate the fermentation patterns of C3G in a fiber-type-dependent manner.

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45

Zhang, Yuhua, Xiaoming Wang, Yun Wang, Yan Liu та Min Xia. "Supplementation of Cyanidin-3-O-β-Glucoside Promotes Endothelial Repair and Prevents Enhanced Atherogenesis in Diabetic Apolipoprotein E–Deficient Mice". Journal of Nutrition 143, № 8 (12 червня 2013): 1248–53. http://dx.doi.org/10.3945/jn.113.177451.

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46

Han, S. J., S. N. Ryu, H. T. Trinh, E. H. Joh, S. Y. Jang, M. J. Han та D. H. Kim. "Metabolism of Cyanidin-3-O-β-D-Glucoside Isolated from Black Colored Rice and Its Antiscratching Behavioral Effect in Mice". Journal of Food Science 74, № 8 (жовтень 2009): H253—H258. http://dx.doi.org/10.1111/j.1750-3841.2009.01327.x.

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47

Ren, Cong, Wenfei Xiong, Jing Li та Bin Li. "Comparison of binding interactions of cyanidin-3-O-glucoside to β-conglycinin and glycinin using multi-spectroscopic and thermodynamic methods". Food Hydrocolloids 92 (липень 2019): 155–62. http://dx.doi.org/10.1016/j.foodhyd.2019.01.053.

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48

Zhang, Yinghui, Fuzhi Lian, Yanna Zhu, Min Xia, Qing Wang, Wenhua Ling та Xiang-Dong Wang. "Cyanidin-3-O-β-glucoside inhibits LPS-induced expression of inflammatory mediators through decreasing IκBα phosphorylation in THP-1 cells". Inflammation Research 59, № 9 (23 березня 2010): 723–30. http://dx.doi.org/10.1007/s00011-010-0183-7.

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49

Gao, Jihui, Jiahui Fu, Xiaoyu Gao та Dong Yang. "Molecular Mechanism of Cyanidin-3-O-Glucoside Disassembling Aβ Fibril In Silico". Nutrients 15, № 1 (26 грудня 2022): 109. http://dx.doi.org/10.3390/nu15010109.

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Анотація:

The deposition of β-amyloid (Aβ) in the brain leads to neurotoxic effects and subsequent Alzheimer’s disease (AD). While AD is becoming more and more prevalent in modern society, therapeutic efforts targeting Aβ could be a promising solution. Currently, two natural products are reported to disintegrate preformed Aβ fibril in vitro. Meanwhile, the chemical driving force behind this phenomenon remains unknown. Taking cyanidin-3-O-glucoside (Cy-3G) as an example, here we studied its interaction with different Aβ polymorphs in silico. Negative charges on different Aβ polymorphs draw the interaction with the flavylium cation on Cy-3G. Our results show that Aβ in a single peptide form in solution exposed more hydrophobic solvent accessible surface area than its fibril structure (per protomer), and Cy-3G interacts more intensively with the single peptide form than fibril as indicated by more hydrogen bonding formed and more amino acid residues involved in their hydrophobic interactions. Thus, the single Aβ peptide aggregation into fibril and fibril dissociation into single peptide equilibrium could be disturbed by the preferential binding of Cy-3G to the monomeric Aβ peptide, which leads to the disassembly of the pathogenic Aβ fibril. This study offers a novel perspective of Cy-3G alleviated AD syndrome beyond its dogmatic antioxidant activity.

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50

Kondo, Tadao, Kin-ichi Oyama, Saki Nakamura, Daisuke Yamakawa, Kazunari Tokuno та Kumi Yoshida. "Novel and Efficient Synthesis of Cyanidin 3-O-β-d-Glucoside from (+)-Catechin via a Flav-3-en-3-ol as a Key Intermediate". Organic Letters 8, № 16 (серпень 2006): 3609–12. http://dx.doi.org/10.1021/ol0614976.

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