Dimers (homo and hetero) of FLAVONOIDS.
A plant genus of the family CLUSIACEAE. Members contain XANTHONES.
A plant genus of the family THYMELAEACEAE. They are evergreen shrubs much cultivated in garden borders and rock gardens in mild climates. Members contain mezerein, flavonoids, and COUMARINS such as daphnetin and daphnin.
A plant genus of the family Cycadaceae, order Cycadales, class Cycadopsida, division CYCADOPHYTA of palm-like trees. It is a source of CYCASIN, the beta-D-glucoside of methylazoxymethanol.
Attachment of isoprenoids (TERPENES) to other compounds, especially PROTEINS and FLAVONOIDS.
Concentrated pharmaceutical preparations of plants obtained by removing active constituents with a suitable solvent, which is evaporated away, and adjusting the residue to a prescribed standard.
A group of phenyl benzopyrans named for having structures like FLAVONES.

Procyanidin oligomers selectively and intensively promote proliferation of mouse hair epithelial cells in vitro and activate hair follicle growth in vivo. (1/171)

We have previously reported that proanthocyanidins extracted from grape seeds possess growth-promoting activity toward murine hair epithelial cells in vitro and stimulate anagen induction in hair cycle progression in vivo. This report constitutes a comparison of the growth-promoting activity of procyanidin oligomers and the target cells of procyanidins in the skin. Results show that procyanidin dimer and trimer exhibit higher growth-promoting activity than the monomer. The maximum growth-promoting activity for hair epithelial cells with procyanidin B-2, an epicatechin dimer, reached about 300% (30 microM) relative to controls (= 100%) in a 5 d culture. Optimum concentration of procyanidin C-1, an epicatechin trimer, was lower than that of procyanidin B-2; the maximum growth-promoting activity of procyanidin C-1 was about 220% (3 microM). No other flavonoid compounds examined exhibit higher proliferative activities than the procyanidins. In skin constituent cells, only epithelial cells such as hair keratinocytes or epidermal keratinocytes respond to procyanidin oligomers. Topical application of 1% procyanidin oligomers on shaven C3H mice in the telogen phase led to significant hair regeneration [procyanidin B-2, 69.6% +/- 21.8% (mean +/- SD); procyanidin B-3, 80.9% +/- 13.0%; procyanidin C-1, 78.3% +/- 7.6%] on the basis of the shaven area; application of vehicle only led to regeneration of 41.7% (SD = 16.3%). In this paper, we demonstrate the hair-growing activity of procyanidin oligomers both in vitro and in vivo, and their potential for use as agents to induce hair growth.  (+info)

Suppression of extracellular signals and cell proliferation by the black tea polyphenol, theaflavin-3,3'-digallate. (2/171)

Previous studies in our laboratory have shown that the major green tea polyphenol, (-)-epigallocatechin-3-gallate (EGCG), suppressed autophosphorylation of epidermal growth factor (EGF) receptor induced by EGF in human A431 epidermoid carcinoma cells. In this study, we examined the inhibitory effects of black tea polyphenols, including theaflavin (TF-1), a mixture (TF-2) of theaflavin-3-gallate (TF-2a) and theaflavin-3'-gallate (TF-2b), theaflavin-3,3'-digallate (TF-3) and the thearubigin fraction on the autophosphorylation of the EGF and PDGF receptors in A431 cells and mouse NIH3T3 fibroblast cells, respectively. First, we examined the effects of these polyphenols on the proliferation of A431 and NIH3T3 cells. Both EGCG and TF-3 strongly inhibited the proliferation of A431 and NIH3T3 cells more than the other theaflavins did. In cultured cells with pre-treatment of tea polyphenol, TF-3 was stronger than EGCG on the reduction of EGF receptor and PDGF receptor autophosphorylation induced by EGF and PDGF, respectively. Other theaflavins slightly reduced the autophosphorylation of the EGF and PDGF receptors; furthermore, TF-3 could reduce autophosphorylation of the EGF receptor (or PDGF receptor) even with co-treatment with EGF (or PDGF) and TF-3, but EGCG was inactive under these conditions. In addition, TF-3 was stronger than EGCG in blocking EGF binding to its receptor. These results suggest that not only the green tea polyphenol, EGCG, but also the black tea polyphenol, TF-3, have an antiproliferative activity on tumor cells, and the molecular mechanisms of antiproliferation may block the growth factor binding to its receptor and thus suppress mitogenic signal transduction.  (+info)

Anti-tumor-promoting activity of a polyphenolic fraction isolated from grape seeds in the mouse skin two-stage initiation-promotion protocol and identification of procyanidin B5-3'-gallate as the most effective antioxidant constituent. (3/171)

Procyanidins present in grape seeds are known to exert anti-inflammatory, anti-arthritic and anti-allergic activities, prevent skin aging, scavenge oxygen free radicals and inhibit UV radiation-induced peroxidation activity. Since most of these events are associated with the tumor promotion stage of carcinogenesis, these studies suggest that grape seed polyphenols and the procyanidins present therein could be anticarcinogenic and/or anti-tumor-promoting agents. Therefore, we assessed the anti-tumor-promoting effect of a polyphenolic fraction isolated from grape seeds (GSP) employing the 7,12-dimethylbenz[a]anthracene (DMBA)-initiated and 12-O-tetradecanoylphorbol 13-acetate (TPA)-promoted SENCAR mouse skin two-stage carcinogenesis protocol as a model system. Following tumor initiation with DMBA, topical application of GSP at doses of 0.5 and 1.5 mg/mouse/application to the dorsal initiated mouse skin resulted in a highly significant inhibition of TPA tumor promotion. The observed anti-tumor-promoting effects of GSP were dose dependent and were evident in terms of a reduction in tumor incidence (35 and 60% inhibition), tumor multiplicity (61 and 83% inhibition) and tumor volume (67 and 87% inhibition) at both 0.5 and 1.5 mg GSP, respectively. Based on these results, we directed our efforts to separate and identify the individual polyphenols present in GSP and assess their antioxidant activity in terms of inhibition of epidermal lipid peroxidation. Employing HPLC followed by comparison with authentic standards for retention times in HPLC profiles, physiochemical properties and spectral analysis, nine individual polyphenols were identified as catechin, epicatechin, procyanidins B1-B5 and C1 and procyanidin B5-3'-gallate. Five of these individual polyphenols with evident structural differences, namely catechin, procyanidin B2, procyanidin B5, procyanidin C1 and procyanidin B5-3'-gallate, were assessed for antioxidant activity. All of them significantly inhibited epidermal lipid peroxidation, albeit to different levels. A structure-activity relationship study showed that with an increase in the degree of polymerization in polyphenol structure, the inhibitory potential towards lipid peroxidation increased. In addition, the position of linkage between inter-flavan units also influences lipid peroxidation activity; procyanidin isomers with a 4-6 linkage showed stronger inhibitory activity than isomers with a 4-8 linkage. A sharp increase in the inhibition of epidermal lipid peroxidation was also evident when a gallate group was linked at the 3'-hydroxy position of a procyanidin dimer. Procyanidin B5-3'-gallate showed the most potent antioxidant activity with an IC(50) of 20 microM in an epidermal lipid peroxidation assay. Taken together, for the first time these results show that grape seed polyphenols possess high anti-tumor-promoting activity due to the strong antioxidant effect of procyanidins present therein. In summary, grape seed polyphenols in general, and procyanidin B5-3'-gallate in particular, should be studied in more detail to be developed as cancer chemopreventive and/or anticarcinogenic agents.  (+info)

Inhibition of activator protein 1 activity and cell growth by purified green tea and black tea polyphenols in H-ras-transformed cells: structure-activity relationship and mechanisms involved. (4/171)

ras gene mutation, which perpetually turns on the growth signal transduction pathway, occurs frequently in many cancer types. The mouse epidermal JB6 cell line has been transfected with a mutant H-ras gene to mimic carcinogenesis in vitro. These transformed cells (30.7b Ras 12) are able to grow in soft agar, exhibiting anchorage independence and high endogenous activator protein 1 (AP-1) activity, which can be detected by a stable AP-1 luciferase reporter. The present study investigated the ability of different pure green and black tea polyphenols to inhibit this ras signaling pathway. The major green tea polyphenols (catechins), (-)-epigallocatechin-3-gallate (EGCG), (-)-epigallocatechin, (-)-epicatechin-3-gallate, (-)-epicatechin, and their epimers, and black tea polyphenols, theaflavin, theaflavin-3-gallate, theaflavin-3'-gallate, and theaflavin-3,3'-digallate (TFdiG), were compared with respect to their ability to inhibit the growth of 30.7b Ras 12 cells and AP-1 activity. All of the tea polyphenols except (-)-epicatechin showed strong inhibition of cell growth and AP-1 activity. Among the catechins, both the galloyl structure on the B ring and the gallate moiety contributed to the growth inhibition and AP-1 activity; the galloyl structure appeared to have a stronger effect on the inhibitory action than the gallate moiety. The epimers of the catechins showed similar inhibitory effects on AP-1 activity. The addition of catalase to the incubation of the cells with EGCG or TFdiG did not prevent the inhibitory effect on AP-1 activity, suggesting that H2O2 does not play a significant role in the inhibition by tea polyphenols. Both EGCG and TFdiG inhibited the phosphorylation of p44/42 (extracellular signal-regulated kinase 1 and 2) and c-jun without affecting the levels of phosphorylated-c-jun-NH2-terminal kinase. TFdiG inhibited the phosphorylation of p38, but EGCG did not. EGCG lowered the level of c-jun, whereas TFdiG decreased the level of fra-1. These results suggest that tea polyphenols inhibited AP-1 activity and the mitogen-activated protein kinase pathway, which contributed to the growth inhibition; however, different mechanisms may be involved in the inhibition by catechins and theaflavins.  (+info)

Protection against peroxynitrite by cocoa polyphenol oligomers. (5/171)

Flavonoids, natural plant constituents, protect against peroxynitrite and can thereby play a role in defense against this mediator of inflammation. Procyanidin oligomers of different size (monomer through nonamer), isolated from the seeds of Theobroma cacao, were examined for their ability to protect against peroxynitrite-dependent oxidation of dihydrorhodamine 123 and nitration of tyrosine. By molarity, oligomers were more effective than the monomeric epicatechin; the tetramer was particularly efficient at protecting against oxidation and nitration reactions. These results suggest that epicatechin oligomers found in cocoa powder and chocolate may be a potent dietary source for defense against peroxynitrite.  (+info)

Procyanidin content and variation in some commonly consumed foods. (6/171)

Procyanidins are a subclass of flavonoids found in commonly consumed foods that have attracted increasing attention due to their potential health benefits. However, little is known regarding their dietary intake levels because detailed quantitative information on the procyanidin profiles present in many food products is lacking. Therefore, the procyanidin content of red wine, chocolate, cranberry juice and four varieties of apples has been determined. On average, chocolate and apples contained the largest procyanidin content per serving (164.7 and 147.1 mg, respectively) compared with red wine and cranberry juice (22.0 and 31.9 mg, respectively). However, the procyanidin content varied greatly between apple samples (12.3-252.4 mg/serving) with the highest amounts on average observed for the Red Delicious (207.7 mg/serving) and Granny Smith (183.3 mg/serving) varieties and the lowest amounts in the Golden Delicious (92.5 mg/serving) and McIntosh (105.0 mg/serving) varieties. The compositional data reported herein are important for the initial understanding of which foods contribute most to the dietary intake of procyanidins and may be used to compile a database necessary to infer epidemiological relationships to health and disease.  (+info)

Cocoa procyanidins and human cytokine transcription and secretion. (7/171)

We examined whether cocoa, in its isolated procyanidin fractions (monomer through decamer), would modulate cytokine production at the levels of transcription and protein secretion in both resting and phytohemagglutinin (PHA)-stimulated peripheral blood mononuclear cells (PBMC). In resting cells, interleukin (IL)-1beta and IL-4 gene expression from cocoa-treated cells varied markedly among the subjects tested. However, at the protein level, the larger fractions (pentamer through decamer) stimulated a dramatic increase in IL-1beta concentration (up to ninefold) with increasing degree of polymerization. Similarly, these larger fractions augmented IL-4 concentration by as much as 2 pg/ml, whereas the control displayed levels nearly undetectable. In the presence of PHA, gene expression also seemed to be most affected by the larger procyanidin fractions. The pentameric through decameric fractions increased IL-1 beta expression by 7-19% compared with PHA control, whereas the hexameric through decameric fractions significantly inhibited PHA-induced IL-4 transcription in the range of 71-86%. This observation at the transcription level for IL-1 beta was reflected at the protein level in PHA-stimulated PBMC. Significant reductions in mitogen-induced IL-4 production were also seen at the protein level with the hexamer, heptamer and octamer. Individual oligomeric cocoa fractions were unstimulatory for IL-2 in resting PBMC. However, when induced with PHA, the pentamer, hexamer and heptamer fractions caused a 61-73% inhibition in IL-2 gene expression. This study offers additional data for the consideration of the health benefits of dietary polyphenols from a wide variety of foods, including those benefits associated specifically with cocoa and chocolate consumption.  (+info)

Reactions of peroxynitrite with cocoa procyanidin oligomers. (8/171)

Peroxynitrite is a mediator molecule in inflammation, and its biological properties are being studied extensively. Flavonoids, which are natural plant constituents, protect against peroxynitrite and thereby could play an anti-inflammatory role. Procyanidin oligomers of different sizes (monomer through nonamer), isolated from the seeds of Theobroma cacao, were recently examined for their ability to protect against peroxynitrite-dependent oxidation of dihydrorhodamine 123 and nitration of tyrosine and were found to be effective in attenuating these reactions. The tetramer was particularly efficient at protecting against oxidation and nitration reactions. Epicatechin oligomers found in cocoa powder and chocolate may be a potent dietary source for defense against peroxynitrite.  (+info)

Leaflets also contain biflavonoids. Estragole is the primary volatile compound emitted from the male and female cones of C. ... Moderately Active Antibacterial Biflavonoids. Abeer Moawad, Mona Hetta, Jordan K. Zjawiony, Melissa R. Jacob, Mohamed Hifnawy, ...
The two biflavonoids, 3′-O-methyl loniflavone and loniflavone, along with luteolin and chrysin, can be isolated from the leaves ... Kumar, Neeraj; Singh, Bikram; Bhandari, Pamita; Gupta, Ajai P.; Uniyal, Sanjay K.; Kaul, Vijay K. (2005). "Biflavonoids from ...
Biflavonoids are a type of flavonoids with the general formula scheme (C6-C3-C6)2. Amentoflavone (bis-apigenin coupled at 8 and ... "Antimicrobial biflavonoids from the aerial parts of Ouratea sulcata". Phytochemistry. 66 (16): 1922-1926. doi:10.1016/j. ... revoluta contain biflavonoids such as (2S, 2′′S)-2,3,2′′,3′′-tetrahydro-4′,4′′′-di-O-methylamentoflavone ( ... Moderately active antibacterial biflavonoids". Planta Med. 76 (8): 796-802. doi:10.1055/s-0029-1240743. PMC 3711132. PMID ...
Biflavonoids in the primitive monocots Isophysis tasmanica and Xerophyta plicata. Christine A. Williams, Jeffrey B. Harborne ...
Williams, Christine A.; Harborne, Jeffrey B.; Tomas-Barberan A., Francisco (1987). "Biflavonoids in the primitive monocots ...
"Biflavonoids from the Unripe Fruits of Clusia Paralicola and their Antioxidant Activity". Natural Product Communications. 7 (12 ...
To date, the field of biochemistry of biflavonoids is still wide open. Little is known about Ochnaflavone of its natural ...
Chen, Li-Yin; Chen, Ih-Sheng; Peng, Chien-Fang (18 January 2012). "Structural Elucidation and Bioactivity of Biflavonoids from ...
Leaflets of C. circinalis contain biflavonoids such as (2S, 2′′S)-2,3,2′′,3′′-tetrahydro-4′,4′′′-di-O-methylamentoflavone ( ... Phytochemical Investigation of Cycas circinalis and Cycas revoluta Leaflets: Moderately Active Antibacterial Biflavonoids. ...
... a cytotoxic principle from Rhus succedanea and the cytotoxicity of the related biflavonoids". Planta Medica. 55 (2): 166-8. doi ...
Both biflavonoids were obtained in small quantities, and their structures show some new and unusual biflavonoid diversity. ... The leaves of Lophira alata afforded two new biflavonoids, lophirone L (1) and lophirone M (2), and the known luteolin and ...
... , an isolate of Garcinia dulcis, belongs to the family of biflavonoids and is an inhibitor of HMG-CoA reductase. ...
... biflavonoids MeSH D03.438.150.266.450.206 - catechin MeSH D03.438.150.266.450.221 - chalcones MeSH D03.438.150.266.450.221.500 ... biflavonoids MeSH D03.830.219.266.450.206 - catechin MeSH D03.830.219.266.450.221 - chalcones MeSH D03.830.219.266.450.221.500 ...
The biflavonoids 2",3"-dihydrohinokiflavone, 2,3,2",3"-tetrahydrohinokiflavone, 2,3-dihydroamentoflavone, 2,3,2",3"- ...
Biflavonoids from Ochna lanceolata v t e (Articles with short description, Short description is different from Wikidata, ...
... the potential toxicological effects of biflavonoids remains largely unknown. … ... Potential hepatic and renal toxicity induced by the biflavonoids from Ginkgo biloba Yun-Ying Li 1 , Xiao-Yan Lu 2 , Jia-Li Sun ... Potential hepatic and renal toxicity induced by the biflavonoids from Ginkgo biloba Yun-Ying Li et al. Chin J Nat Med. 2019 Sep ... Metabolic interaction between biflavonoids in Ginkgo biloba leaves and tacrolimus. Bai J, Zhang C. Bai J, et al. Biopharm Drug ...
Biflavonoids / analysis Actions. * Search in PubMed * Search in MeSH * Add to Search ...
MeSH Terms: Animals; Biflavonoids/chemistry; Biflavonoids/pharmacokinetics; Biotransformation; Catechin/analogs & derivatives; ...
Biflavonoids from. Lokhande K; Nawani N; K Venkateswara S; Pawar S. J Biomol Struct Dyn; 2022 Jul; 40(10):4376-4388. PubMed ID ...
Biflavonoids Preferred Concept UI. M0446742. Registry Number. 0. Scope Note. Dimers (homo and hetero) of FLAVONOIDS.. Terms. ... Biflavonoids Preferred Term Term UI T535060. Date03/11/2003. LexicalTag NON. ThesaurusID NLM (2004). ... Biflavonoids. Tree Number(s). D03.383.663.283.266.450.190. D03.633.100.150.266.450.190. Unique ID. D044946. RDF Unique ...
Advances in the Anti-Tumor Activity of Biflavonoids in Selaginella. Ren, Mengdie; Li, Sihui; Gao, Qiong; Qiao, Lei; Cao, ...
Improved solubility, dissolution rate, and oral bioavailability of main biflavonoids from Selaginella doederleinii extract by ... and delicaflavone are five major hydrophobic components in the total biflavonoids extract from Selaginella doederleinii (TBESD ...
Biflavonoids D3.830.219.266.450.190 D3.383.663.283.266.450.190 Bignoniaceae B1.650.940.800.575.100.143 B1.650.940.800.575.100. ...
have led to the isolation of several compounds, such as diterpenes [47-49], flavonoids [50], biflavonoids [51] and tannins [52 ... Bahia MV, Dos Santos JB, Juceni PD, David JM: Biflavonoids and other phenolics from Caesalpinia pyramidalis (Fabaceae). J Braz ...
Biflavonoids Preferred Concept UI. M0446742. Registry Number. 0. Scope Note. Dimers (homo and hetero) of FLAVONOIDS.. Terms. ... Biflavonoids Preferred Term Term UI T535060. Date03/11/2003. LexicalTag NON. ThesaurusID NLM (2004). ... Biflavonoids. Tree Number(s). D03.383.663.283.266.450.190. D03.633.100.150.266.450.190. Unique ID. D044946. RDF Unique ...
Ab Initio Modeling and Garcinia Biflavonoids-Binding Study of Tyrosinase: The Signature Enzyme of Melanogenesis. Research ...
Biflavonoids - Preferred Concept UI. M0446742. Scope note. Dimers (homo and hetero) of FLAVONOIDS. ...
Preliminary structure-activity relationship studies of the isolated diterpenoids and biflavonoids are discussed. ... Preliminary structure-activity relationship studies of the isolated diterpenoids and biflavonoids are discussed.", ... Preliminary structure-activity relationship studies of the isolated diterpenoids and biflavonoids are discussed. ... Preliminary structure-activity relationship studies of the isolated diterpenoids and biflavonoids are discussed. ...
Anti-influenza virus activity of biflavonoids. Miki, K, Nagai, T, Suzuki, K, Tsujimura, R, Koyama, K, Kinoshita, K, Furuhata, K ...
The phenolic fraction contained biflavonoids: cupressuflavone (9), followed by minor amounts of amentoflavone (10) and ...
Natural biflavonoids as potential therapeutic agents against microbial diseases. Menezes José C J M D S, et al. The Science of ...
Heterocyclic N0000167032 Biflavonoids N0000182042 Biglycan N0000007698 Biguanides N0000006801 Bile Acids and Salts N0000007708 ...
The Homeopathic Agents Contain A Multitude Of Bioactive Constituents, Including Proanthocyanins, Flavonoids, Biflavonoids, ...
The compounds were flavonoids, flavones, flavonols, flavanones, bi-flavonoids, phenolics, glycosides, anthocyanins and amino- ...
These compounds seem to be the main constituents of Cuban Calophyllum species together xanthones and biflavonoids. Recently, ... These compounds seem to be the main constituents of Cuban Calophyllum species together xanthones and biflavonoids. Recently, ...
Inhibition of mast cell histamine release by flavonoids and biflavonoids. Planta Med. 1985;51:16-20. ...
AN - see SCR for organism specific terms HN - 2004 MH - Biflavonoids UI - D044946 MN - D3.438.150.266.450.190 MS - Dimers (homo ...
Biflavonoids D3.830.219.266.450.190 D3.383.663.283.266.450.190 Bignoniaceae B1.650.940.800.575.100.143 B1.650.940.800.575.100. ...
Biflavonoids D3.438.150.266.450.190 D3.633.100.150.266.450.190 Biglycan D9.698.735.700.500 D12.776.395.650.875.250 D12.776. ...
Biflavonoids D3.830.219.266.450.190 D3.383.663.283.266.450.190 Bignoniaceae B1.650.940.800.575.100.143 B1.650.940.800.575.100. ...
Biflavonoids. Biflavonoides. Co-fator PQQ. PQQ Cofactor. Cofactor PQQ. Corrinóides. Corrinoids. Corrinoides. ...
Phorbol 12-Myristate 13-Acetate Induced Toxicity Study and the Role of Tangeretin in Abrogating HIF-1a-NF-?B Crosstalk In Vitro and In Vivo. Int J Mol Sci. 2020 Dec 04; 21(23 ...
Biflavonoids Biglycan Bignoniaceae Biguanides Bilateral Vestibulopathy Bile Bile Acids and Salts Bile Canaliculi Bile Duct ...
  • Advances in the Anti-Tumor Activity of Biflavonoids in Selaginella . (bvsalud.org)
  • These compounds seem to be the main constituents of Cuban Calophyllum species together xanthones and biflavonoids. (unisa.it)
  • A new diterpene, 16-hydroxy communic acid (1), along with thirty one known compounds including five norditerpenes (2-6), twenty two flavonoids containing four biflavonoids (7-10), nine monoflavonoids (11-19) and nine flavanoid glycosides (20-28), as well as four phenolic constituents (29-32) were isolated from the 95% ethanolic extract of Podocarpus fasciculus. (tmu.edu.tw)
  • While biflavonoid is a subclass of the flavonoid family in Ginkgo biloba with a plenty of pharmacological properties, the potential toxicological effects of biflavonoids remains largely unknown. (nih.gov)
  • Natural biflavonoids as potential therapeutic agents against microbial diseases. (cdc.gov)
  • Natural biflavonoids as potential therapeutic agents against microbial diseases. (cdc.gov)