Genomes and Genes
Summary: Dimers (homo and hetero) of FLAVONOIDS.
- Magos G, Mateos J, Páez E, Fernández G, Lobato C, Marquez C, et al. Hypotensive and vasorelaxant effects of the procyanidin fraction from Guazuma ulmifolia bark in normotensive and hypertensive rats. J Ethnopharmacol. 2008;117:58-68 pubmed publisher..was to investigate the in vivo and in vitro cardiovascular activity of a procyanidin fraction (PCF) obtained from acetone extract of Guazuma ulmifolia bark which has traditionally been used as an antihypertensive agent...
- Li B, Li X, Cai Q, Gao H, Cheng M, Zhang J, et al. Induction of lactadherin mediates the apoptosis of endothelial cells in response to advanced glycation end products and protective effects of grape seed procyanidin B2 and resveratrol. Apoptosis. 2011;16:732-45 pubmed publisher..Targeting lactadherin with antioxidant could be translated into clinical application in the fighting against DM complications. ..
- Corder R, Mullen W, Khan N, Marks S, Wood E, Carrier M, et al. Oenology: red wine procyanidins and vascular health. Nature. 2006;444:566 pubmed..These regions also happen to be associated with increased longevity in the population. ..
- Castrillejo V, Romero M, Esteve M, Ardevol A, Blay M, Bladé C, et al. Antioxidant effects of a grapeseed procyanidin extract and oleoyl-estrone in obese Zucker rats. Nutrition. 2011;27:1172-6 pubmed publisher..GSPE and OE improve oxidative stress in obese Zucker rats. The effect of GSPE + OE is comparable to GSPE for the liver and to OE for the kidney. Thus the effects of GSPE and OE are not additive and are organ dependent. ..
- Miki K, Nagai T, Suzuki K, Tsujimura R, Koyama K, Kinoshita K, et al. Anti-influenza virus activity of biflavonoids. Bioorg Med Chem Lett. 2007;17:772-5 pubmed..Ginkgetin was found to inhibit the influenza virus sialidase. Ginkgetin-sialic acid conjugates showed a significant survival effect in the influenza-virus-infected mice. ..
- Li B, Li X, Gao H, Zhang J, Cai Q, Cheng M, et al. Grape seed procyanidin B2 inhibits advanced glycation end product-induced endothelial cell apoptosis through regulating GSK3? phosphorylation. Cell Biol Int. 2011;35:663-9 pubmed publisher..GSPB2 therapy could become an effective approach to battling AGEs-induced endothelial apoptosis. ..
- Ryu Y, Jeong H, Kim J, Kim Y, Park J, Kim D, et al. Biflavonoids from Torreya nucifera displaying SARS-CoV 3CL(pro) inhibition. Bioorg Med Chem. 2010;18:7940-7 pubmed publisher..Following bioactivity-guided fractionation, eight diterpenoids (1-8) and four biflavonoids (9-12) were isolated and evaluated for SARS-CoV 3CL(pro) inhibition using fluorescence resonance energy ..
- Vermeer M, Mulder T, Molhuizen H. Theaflavins from black tea, especially theaflavin-3-gallate, reduce the incorporation of cholesterol into mixed micelles. J Agric Food Chem. 2008;56:12031-6 pubmed publisher..These results show that theaflavins can play a role in decreased intestinal cholesterol absorption via inhibition of micelle formation. ..
- Dhooghe L, Maregesi S, Mincheva I, Ferreira D, Marais J, Lemiere F, et al. Antiplasmodial activity of (I-3,II-3)-biflavonoids and other constituents from Ormocarpum kirkii. Phytochemistry. 2010;71:785-91 pubmed publisher..The compounds comprised seven (I-3,II-3)-biflavonoids, three (I-3,II-3)-bi-4-phenyldihydrocoumarins, an isoflavanone and a C-glucosylated flavone...
- Jeong E, Seo H, Yang H, Kim J, Sung S, Kim Y. Anti-inflammatory phenolics isolated from Juniperus rigida leaves and twigs in lipopolysaccharide-stimulated RAW264.7 macrophage cells. J Enzyme Inhib Med Chem. 2012;27:875-9 pubmed publisher..Among the isolated compounds, phenylpropanoid glycosides with p-hydroxy group (2, 4) and massoniaside A (7), (+)-catechin (10), amentoflavone (11) effectively inhibited LPS-induced NO production in RAW264.7 cells...
- Oizumi Y, Mohri Y, Hirota M, Makabe H. Synthesis of procyanidin B3 and its anti-inflammatory activity. the effect of 4-alkoxy group of catechin electrophile in the Yb(OTf)(3)-catalyzed condensation with catechin nucleophile. J Org Chem. 2010;75:4884-6 pubmed publisher..The anti-inflammatory activity of 1 was stronger than that of indomethacin and glycyrrhetinic acid, the normally used anti-inflammatory agents. ..
- Sasaki H, Miki K, Kinoshita K, Koyama K, Juliawaty L, Achmad S, et al. beta-Secretase (BACE-1) inhibitory effect of biflavonoids. Bioorg Med Chem Lett. 2010;20:4558-60 pubmed publisherHere, we describe amentoflavone-type biflavonoids, which were isolated from natural sources and were found to inhibit beta-secretase (BACE-1)...
- Zhou H, Xie C, Jian R, Kang J, Li Y, Zhuang C, et al. Biflavonoids from Caper (Capparis spinosa L.) fruits and their effects in inhibiting NF-kappa B activation. J Agric Food Chem. 2011;59:3060-5 pubmed publisher..In this study, two biflavonoids, isoginkgetin, and ginkgetin, together with three other flavonoids, were isolated from caper fruits...
- Huang N, Rizshsky L, Hauck C, Nikolau B, Murphy P, Birt D. The inhibition of lipopolysaccharide-induced macrophage inflammation by 4 compounds in Hypericum perforatum extract is partially dependent on the activation of SOCS3. Phytochemistry. 2012;76:106-16 pubmed publisher..At the same time, these results also suggest that constituents in H. perforatum extract were alleviating LPS-induced macrophage response through SOCS3 independent mechanisms...
- Yang J, Li L, Tan S, Jin H, Qiu J, Mao Q, et al. A natural theaflavins preparation inhibits HIV-1 infection by targeting the entry step: potential applications for preventing HIV-1 infection. Fitoterapia. 2012;83:348-55 pubmed publisher..It has a potential to be developed as a safe and affordable topical microbicide for preventing sexual transmission of HIV. ..
- Cai Q, Li B, Gao H, Zhang J, Wang J, Yu F, et al. Grape seed procyanidin b2 inhibits human aortic smooth muscle cell proliferation and migration induced by advanced glycation end products. Biosci Biotechnol Biochem. 2011;75:1692-7 pubmed..GSPB2 may therefore have therapeutic potential in preventing and treating vascular complications of diabetes mellitus. ..
- Kumar G, Pillare S, Maru G. Black tea polyphenols-mediated in vivo cellular responses during carcinogenesis. Mini Rev Med Chem. 2010;10:492-505 pubmed..Overall, the mechanism(s) implicated in the BTPs-mediated inhibition are diverse and involve effects on multiple molecular pathways and genes. ..
- Zu M, Yang F, Zhou W, Liu A, Du G, Zheng L. In vitro anti-influenza virus and anti-inflammatory activities of theaflavin derivatives. Antiviral Res. 2012;94:217-24 pubmed publisher..These findings will provide important information for new drug design and development for the treatment of influenza virus infection. ..
- Lahiry L, Saha B, Chakraborty J, Bhattacharyya S, Chattopadhyay S, Banerjee S, et al. Contribution of p53-mediated Bax transactivation in theaflavin-induced mammary epithelial carcinoma cell apoptosis. Apoptosis. 2008;13:771-81 pubmed publisher..Together these findings suggest that in breast cancer cells, p53 promotes theaflavin-induced apoptosis in a transcription-dependent manner through mitochondrial death cascade. ..
- Lee J, Sul J, Park J, Lee M, Cha E, Song I, et al. Fatty acid synthase inhibition by amentoflavone suppresses HER2/neu (erbB2) oncogene in SKBR3 human breast cancer cells. Phytother Res. 2013;27:713-20 pubmed publisher..These results suggest that amentoflavone modulated FASN expression by regulation of HER2-pathways, and induced cell death to enhance chemopreventive or chemotherapeutic activity in HER2-positive breast cancers. ..
- Park H, Kim Y, Chang H, Kim H. Anti-inflammatory activity of the synthetic C-C biflavonoids. J Pharm Pharmacol. 2006;58:1661-7 pubmedTo find anti-inflammatory agents based on plant constituents, the effects of six synthetic C-C biflavonoids connecting with different positions of C-C bond between flavone monomers (a: 4'-4', b: 4'-3', c: 4'-6, d: 3'-6, e: 6-6, f: 4'-3) ..
- Chen D, Cai X, Kwik Uribe C, Zeng R, Zhu X. Inhibitory effects of procyanidin B(2) dimer on lipid-laden macrophage formation. J Cardiovasc Pharmacol. 2006;48:54-70 pubmed..Many differentially expressed genes induced by B(2) help to uncover novel targets and may help to target disease interactions in atherosclerosis in the future. ..
- Yoon S, Shin S, Lee H, Chun H, Chung A. Isoginkgetin inhibits tumor cell invasion by regulating phosphatidylinositol 3-kinase/Akt-dependent matrix metalloproteinase-9 expression. Mol Cancer Ther. 2006;5:2666-75 pubmed..This suggests that isoginkgetin could be a potential candidate as a therapeutic agent against tumor invasion. ..
- Sang S, Lambert J, Ho C, Yang C. The chemistry and biotransformation of tea constituents. Pharmacol Res. 2011;64:87-99 pubmed publisher..Methylation, glucuronidation, sulfation, and ring-fission metabolism represent the major metabolic pathways for tea catechins. The present review summarizes the data concerning the chemistry and biotransformation of tea constituents. ..
- Zhang G, Jing Y, Zhang H, Ma E, Guan J, Xue F, et al. Isolation and cytotoxic activity of selaginellin derivatives and biflavonoids from Selaginella tamariscina. Planta Med. 2012;78:390-2 pubmed publisher..Spring plant. In addition, four known biflavonoids, namely neocryptomerin ( 6), hinokiflavone (7), pulvinatabiflavone (8), and 7''- O-methylamentoflavone (9), ..
- Ishola I, Agbaje O, Narender T, Adeyemi O, Shukla R. Bioactivity guided isolation of analgesic and anti-inflammatory constituents of Cnestis ferruginea Vahl ex DC (Connaraceae) root. J Ethnopharmacol. 2012;142:383-9 pubmed publisher..Cnestis ferruginea (CF) Vahl ex DC (Connaraceae) is a shrub widely used in Traditional African Medicine (TAM) for the treatment of various painful and inflammatory conditions...
- Hammerstone J, Lazarus S, Mitchell A, Rucker R, Schmitz H. Identification of procyanidins in cocoa (Theobroma cacao) and chocolate using high-performance liquid chromatography/mass spectrometry. J Agric Food Chem. 1999;47:490-6 pubmed
- Nunome S, Ishiyama A, Kobayashi M, Otoguro K, Kiyohara H, Yamada H, et al. In vitro antimalarial activity of biflavonoids from Wikstroemia indica. Planta Med. 2004;70:76-8 pubmed..Fractionation of the active extract led to the isolation of two biflavonoids, sikokianin B ( 1) and sikokianin C ( 2) with IC (50) values 0.54 microg/mL and 0...
- Kundu T, Dey S, Roy M, Siddiqi M, Bhattacharya R. Induction of apoptosis in human leukemia cells by black tea and its polyphenol theaflavin. Cancer Lett. 2005;230:111-21 pubmed..Such induction was found to be mediated through activation of caspases 3 and 8, particularly caspase 3 and by altering apoptosis related genes as evident by down-regulation of Bcl-2 and up-regulation of Bax proteins. ..
- Weniger B, Vonthron Sénécheau C, Kaiser M, Brun R, Anton R. Comparative antiplasmodial, leishmanicidal and antitrypanosomal activities of several biflavonoids. Phytomedicine. 2006;13:176-80 pubmedThe antiplasmodial, leishmanicidal and antitrypanosomal activities of eight natural biflavonoids were estimated in vitro on a chloroquine-resistant strain of Plasmodium falciparum, axenically grown Leishmania donovani amastigotes and ..
- Mbwambo Z, Kapingu M, Moshi M, Machumi F, Apers S, Cos P, et al. Antiparasitic activity of some xanthones and biflavonoids from the root bark of Garcinia livingstonei. J Nat Prod. 2006;69:369-72 pubmed..ent-naringeninyl-(I-3alpha,II-8)-4'-O-methylnaringenin (6), along with five known xanthones and two known biflavonoids, was isolated from the root bark of Garcinia livingstonei collected in Tanzania...
- Lee M, Lim S, Yang H, Sung S, Lee H, Park M, et al. Osteoblast differentiation stimulating activity of biflavonoids from Cephalotaxus koreana. Bioorg Med Chem Lett. 2006;16:2850-4 pubmedSix amentoflavone-type biflavonoids, bilobetin (1), ginkgetin (2), 4',7''-di-O-methyl-amentoflavone (3), 7-O-methyl-isoginkgetin (4), sciadopitysin (5), and 7,4',7'',4'''-O-methyl-amentoflavone (6), were isolated from the EtOAc fraction ..
- Łuczaj W, Skrzydlewska E. Antioxidative properties of black tea. Prev Med. 2005;40:910-8 pubmed..Black tea consumed throughout the world is believed to be not only a popular beverage but also an antioxidative agent available in everyday life. ..
- Choi S, Oh H, Lee S, Jeong D, Ryu S, Son K, et al. Biflavonoids inhibited phosphatase of regenerating liver-3 (PRL-3). Nat Prod Res. 2006;20:341-6 pubmedTwo biflavonoids, ginkgetin (1) and sciadopitysin (2), were isolated from the MeOH extract of the young branches of Taxus cuspidata, which inhibited phosphatase of regenerating liver-3 (PRL-3) with IC50 values of 25.8 and 46...
- Woo E, Lee J, Cho I, Kim S, Kang K. Amentoflavone inhibits the induction of nitric oxide synthase by inhibiting NF-kappaB activation in macrophages. Pharmacol Res. 2005;51:539-46 pubmed
- Sang S, Lambert J, Tian S, Hong J, Hou Z, Ryu J, et al. Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities. Bioorg Med Chem. 2004;12:459-67 pubmed..7 cells. Their cytotoxic activities against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated. ..
- Sano A, Yamakoshi J, Tokutake S, Tobe K, Kubota Y, Kikuchi M. Procyanidin B1 is detected in human serum after intake of proanthocyanidin-rich grape seed extract. Biosci Biotechnol Biochem. 2003;67:1140-3 pubmed..Procyanidin B1 [epicatechin-(4beta-->8)-catechin] was detected in human serum 2 h after intake. Its concentration was 10.6 +/- 2.5 nmol/l. ..
- Leung L, Su Y, Chen R, Zhang Z, Huang Y, Chen Z. Theaflavins in black tea and catechins in green tea are equally effective antioxidants. J Nutr. 2001;131:2248-51 pubmed
- Kang S, Lee J, Choi Y, Song S, Kim J, Jeon S, et al. Neuroprotective effects of naturally occurring biflavonoids. Bioorg Med Chem Lett. 2005;15:3588-91 pubmedWe examined neuroprotective effects of naturally occurring biflavonoids on oxidative stress-induced and amyloid beta peptide-induced cell death in neuronal cells...
- Miyake M, Sasaki K, Ide K, Matsukura Y, Shijima K, Fujiwara D. Highly oligomeric procyanidins ameliorate experimental autoimmune encephalomyelitis via suppression of Th1 immunity. J Immunol. 2006;176:5797-804 pubmed..The results indicate that the suppression of development of EAE by the highly polymerized procyanidins resulted from an inhibition of Th1 and the effects might be associated with depression of Ag-presenting capability. ..
- Liu S, Lu H, Zhao Q, He Y, Niu J, Debnath A, et al. Theaflavin derivatives in black tea and catechin derivatives in green tea inhibit HIV-1 entry by targeting gp41. Biochim Biophys Acta. 2005;1723:270-81 pubmed..These results indicate that tea, especially black tea, may be used as a source of anti-HIV agents and theaflavin derivatives may be applied as lead compounds for developing HIV-1 entry inhibitors targeting gp41. ..
- Hibasami H, Shohji T, Shibuya I, Higo K, Kanda T. Induction of apoptosis by three types of procyanidin isolated from apple (Rosaceae Malus pumila) in human stomach cancer KATO III cells. Int J Mol Med. 2004;13:795-9 pubmed
- Busserolles J, Gueux E, Balasińska B, Piriou Y, Rock E, Rayssiguier Y, et al. In vivo antioxidant activity of procyanidin-rich extracts from grape seed and pine (Pinus maritima) bark in rats. Int J Vitam Nutr Res. 2006;76:22-7 pubmed..The results of the present experiment constitute positive evidence for an in vivo antioxidant effect at the plasma level of procyanidin-containing plant extracts. ..
- Leone M, Zhai D, Sareth S, Kitada S, Reed J, Pellecchia M. Cancer prevention by tea polyphenols is linked to their direct inhibition of antiapoptotic Bcl-2-family proteins. Cancer Res. 2003;63:8118-21 pubmed..These data suggest a strong link between the anticancer activities of these tea polyphenols and their inhibition of a crucial antiapoptotic pathway, which is implicated in the development of many human malignancies. ..
- Mulder T, van Platerink C, Wijnand Schuyl P, Van Amelsvoort J. Analysis of theaflavins in biological fluids using liquid chromatography-electrospray mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001;760:271-9 pubmed..The concentration in urine also peaked after 2 h at 4.2 microg l(-1). Hence, only minute amounts of theaflavins can be detected in plasma and urine samples of healthy volunteers after ingestion. ..
- Ma S, But P, Ooi V, He Y, Lee S, Lee S, et al. Antiviral amentoflavone from Selaginella sinensis. Biol Pharm Bull. 2001;24:311-2 pubmed..5 microg/ml. The contents of amentoflavone in nine species of Selaginella were determined by reversed-phase HPLC. S. sinensis showed a higher content of 1.13%. ..
- Henning S, Aronson W, Niu Y, Conde F, Lee N, Seeram N, et al. Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption. J Nutr. 2006;136:1839-43 pubmed..001) and GT (P = 0.025) consumption relative to baseline serum This is the first human study to show that tea polyphenols and theaflavins are bioavailable in the prostate where they may be active in the prevention of prostate cancer. ..
- Farombi E, Owoeye O. Antioxidative and chemopreventive properties of Vernonia amygdalina and Garcinia biflavonoid. Int J Environ Res Public Health. 2011;8:2533-55 pubmed publisher..The chemopreventive properties of Vernonia amygdalina and Garcinia biflavonoids have been attributed to their abilities to scavenge free radicals, induce detoxification, inhibit stress ..
- Quesada I, Bustos M, Blay M, Pujadas G, Ardevol A, Salvadó M, et al. Dietary catechins and procyanidins modulate zinc homeostasis in human HepG2 cells. J Nutr Biochem. 2011;22:153-63 pubmed publisher..We suggest that extracellular complexation of zinc cations and the elevation of cytoplasmic labile zinc may be relevant mechanisms underlying the modulation of diverse cell signaling and metabolic pathways by catechins and procyanidins. ..
- Schuck A, Ausubel M, Zuckerbraun H, Babich H. Theaflavin-3,3'-digallate, a component of black tea: an inducer of oxidative stress and apoptosis. Toxicol In Vitro. 2008;22:598-609 pubmed publisher..Apoptosis was not noted in GN46 fibroblasts treated with TF-3. ..
- Chukwujekwu J, de Kock C, Smith P, van Heerden F, van Staden J. Antiplasmodial and antibacterial activity of compounds isolated from Ormocarpum trichocarpum. Planta Med. 2012;78:1857-60 pubmed publisherUsing activity-guided fractionation based on in vitro antibacterial assays, five biflavonoids, among them two new ones, were isolated from the aerial parts of Ormocarpum trichocarpum...
- Tsujita T, Shintani T, Sato H. α-Amylase inhibitory activity from nut seed skin polyphenols. 1. Purification and characterization of almond seed skin polyphenols. J Agric Food Chem. 2013;61:4570-6 pubmed publisher..The results suggest almond seed skin contains highly polymerized polyphenols with strong α-amylase inhibitory activity, which retard absorption of carbohydrate. ..
- Akpanika G, Winters A, Wilson T, Ayoola G, Adepoju Bello A, Hauck B. Polyphenols from Allanblackia floribunda seeds: Identification, quantification and antioxidant activity. Food Chem. 2017;222:35-42 pubmed publisher..profile revealed six predominant compounds which were identified by HPLC-PDA-ESI/MSn as the biflavonoids morelloflavone, Gb-2a and volkensiflavone and their respective glucosides...
- Hu X, Wu J, Wang M, Yu M, Zhao Q, Wang H, et al. 2-Arylbenzofuran, flavonoid, and tyrosinase inhibitory constituents of Morus yunnanensis. J Nat Prod. 2012;75:82-7 pubmed publisherTwo novel 2-arylbenzofuran dimers, morusyunnansins A and B (1 and 2), two new biflavonoids, morusyunnansins C and D (3 and 4), two new flavans, morusyunnansins E and F (5 and 6), and four known flavans (7-10) were isolated from the leaves ..
- Panickar K, Polansky M, Graves D, Urban J, Anderson R. A procyanidin type A trimer from cinnamon extract attenuates glial cell swelling and the reduction in glutamate uptake following ischemia-like injury in vitro. Neuroscience. 2012;202:87-98 pubmed publisher..Thus, the effects of trimer 1 in attenuating the reduction in glutamate uptake are likely mediated through their action on the mitochondria. ..
- Lluís L, Muñoz M, Nogués M, Sánchez Martos V, Romeu M, Giralt M, et al. Toxicology evaluation of a procyanidin-rich extract from grape skins and seeds. Food Chem Toxicol. 2011;49:1450-4 pubmed publisher..Our results indicated slight mutagenicity under the study conditions, so further studies should be conducted at lower doses to demonstrate that this extract is not toxic. ..
- He L, Mu C, Shi J, Zhang Q, Shi B, Lin W. Modification of collagen with a natural cross-linker, procyanidin. Int J Biol Macromol. 2011;48:354-9 pubmed publisher..The present study reveals that procyanidin stabilizes collagen as a cross-linker and preserves its triple helical structure. ..
- Paulsen B, Souza C, Chicaybam L, Bonamino M, Bahia M, Costa S, et al. Agathisflavone enhances retinoic acid-induced neurogenesis and its receptors ? and ? in pluripotent stem cells. Stem Cells Dev. 2011;20:1711-21 pubmed publisher..This is the first report to describe that naturally occurring biflavonoids regulate apoptosis and neuronal differentiation in pluripotent stem cells.
- Wang W, Chen R, Wang J. Procyanidin B2 ameliorates carrageenan-induced chronic nonbacterial prostatitis in rats via anti-inflammatory and activation of the Nrf2 pathway. Biochem Biophys Res Commun. 2017;493:794-799 pubmed publisher..In conclusion, treatment with PB attenuates carrageenan-induced chronic nonbacterial prostatitis via anti-inflammatory and activation of the Nrf2 pathway. ..