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Chemical Compound Review:

Procyanidin B2 (2S,3R,4S)-2-(3,4- dihydroxyphenyl)-4-[(2S...

Synonyms: Procyanidol B2, CHEMBL38714, SureCN288579, CPD-1981, AG-K-50608, ...

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Disease relevance of AIDS-013365

Chromosomal aberration tests using CHL cells indicated that procyanidin B-2 caused polyploidy but no structural aberrations [1].
We report here the ability of HP and that of polyphenolic procyanidin B2 (PB-2) to inhibit the growth of leukemia K562 and U937 cells, brain glioblastoma cells LN229 and normal human astrocytes [2].
Procyanidin B-2 therapy shows potential as a promising cure for male pattern baldness [3].

High impact information on AIDS-013365

Experiments with calf thymus DNA also revealed that procyanidin B2 decreased 8-oxodG formation by Fe(II)/H2O2, whereas procyanidin B2 induced DNA damage in the presence of Cu(II), and H2O2 extensively enhanced it [4].
Our results raise the possibility that procyanidin B2 exerts both antioxidant and pro-oxidant properties by interacting with H2O2 and metal ions [4].
An electron spin resonance spin trapping study utilizing 3,3,5,5-tetramethyl-1-pyrroline-N-oxide (M4PO) demonstrated that procyanidin B2 decreased the signal of M4PO-OH from H2O2 and Fe(II), whereas procyanidin B2 enhanced the signal from H2O2 and Cu(II) [4].
We investigated the mechanism of preventive action of procyanidin B2 against oxidative DNA damage in human cultured cells and isolated DNA [4].
In contrast, a high concentration of procyanidin B2 increased the formation of 8-oxodG in HL-60 cells [4].

Biological context of AIDS-013365

As a pro-oxidant property, we examined DNA damage induced by procyanidin B2, using 32P-labeled DNA fragments obtained from genes relevant to human cancer [4].
We evaluated the bioavailability and plasma antioxidative activity after administration of procyanidin B2 [epicatechin-(4beta-8)-epicatechin] in rats [5].
OBJECTIVES: We discuss the hypothesis that the hair-growing activity of procyanidin B-2 is related to its downregulation or inhibition of translocation of PKC isozymes in hair epithelial cells [6].
The IC50 values for catechin, and procyanidin B-2 to inhibit oxygen consumption were 34.0 and 11.0 microM [7].
Addition of TGF-beta(1) or TGF-beta(2) to hair epithelial cell cultures dose-dependently decreased cell growth and induced apoptosis; however, addition of procyanidin B-2 to the culture neutralized the growth-inhibiting effects of both TGF-beta(1) and TGF-beta(2) and protected the cells from apoptosis [8].

Anatomical context of AIDS-013365

BACKGROUND: We have previously reported that several selective protein kinase C (PKC) inhibitors, including procyanidin B-2, promote hair epithelial cell growth and stimulate anagen induction [6].

Associations of AIDS-013365 with other chemical compounds

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%) [9].
Effects of proanthocyanidin (PA), procyanidin B-2 (B-2), and epigallocatechin gallate (EGCG) on azoxymethane (AOM)-induced colonic preneoplastic aberrant crypt foci (ACF) formation were investigated using F344 rats [10].
Daily treatment with either imipramine, Hypericum extract or hypericin alone or in combination with procyanidin B2 for 14 days significantly decreased plasma ACTH and corticosterone levels [11].
Roseoside and procyanidin B-2 were among the active compounds found in an in vitro assay; these compounds were further assessed for antitumor activity in vivo in a two-stage carcinogenesis assay on mouse skin [12].
Epicatechin gallate (IC50 = 0.029 microM), myricetin (0.39 microM), procyanidin B2 (PB2, 4.5 microM), and resveratrol (65.7 microM), constituents of the most bioactive mixed fraction from grape cell culture (TP-4), each individually provided potent catalytic inhibition of topoisomerase II [13].

Gene context of AIDS-013365

We confirmed that procyanidin B-2 upregulates the expression of MEK-1/2 in cultured murine hair epithelial cells [8].
RESULTS: We observed that procyanidin B-2 reduces the expression of PKC-alpha, -betaI, -betaII and -eta in cultured murine hair epithelial cells and also inhibits the translocation of these isozymes to the particulate fraction of hair epithelial cells [6].
Forskolin, an adenylate cyclase activator, promotes hair epithelial cell growth and boosts the growth-promoting effect of procyanidin B-2 [14].
RESULTS: (+) Catechin, procyanidin B2, procyanidin B5, procyanidin B5 3'-O-gallate, and amurensisin showed antioxidant activity with the IC50 values of 0.47, 0.25, 0.10, 0.02, and 0.03 mmol/L, respectively [15].

Analytical, diagnostic and therapeutic context of AIDS-013365

The lethal dose of procyanidin B-2 is greater than 2000 mg/kg (subcutaneous injection) [1].
Mutagenicity tests using bacteria showed procyanidin B-2 to be non-mutagenic [1].
Nineteen men in the procyanidin B-2 group and 10 men in the placebo control group were subjected to analyses [16].

References

Toxicological studies on procyanidin B-2 for external application as a hair growing agent. Takahashi, T., Yokoo, Y., Inoue, T., Ishii, A. Food Chem. Toxicol. (1999) [Pubmed]
Hyperforin a constituent of St John's wort (Hypericum perforatum L.) extract induces apoptosis by triggering activation of caspases and with hypericin synergistically exerts cytotoxicity towards human malignant cell lines. Hostanska, K., Reichling, J., Bommer, S., Weber, M., Saller, R. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft für Pharmazeutische Verfahrenstechnik e.V. (2003) [Pubmed]
The first clinical trial of topical application of procyanidin B-2 to investigate its potential as a hair growing agent. Takahashi, T., Kamimura, A., Yokoo, Y., Honda, S., Watanabe, Y. Phytotherapy research : PTR. (2001) [Pubmed]
Procyanidin B2 has anti- and pro-oxidant effects on metal-mediated DNA damage. Sakano, K., Mizutani, M., Murata, M., Oikawa, S., Hiraku, Y., Kawanishi, S. Free Radic. Biol. Med. (2005) [Pubmed]
Absorption and urinary excretion of procyanidin B2 [epicatechin-(4beta-8)-epicatechin] in rats. Baba, S., Osakabe, N., Natsume, M., Terao, J. Free Radic. Biol. Med. (2002) [Pubmed]
Procyanidin B-2, extracted from apples, promotes hair growth: a laboratory study. Kamimura, A., Takahashi, T. Br. J. Dermatol. (2002) [Pubmed]
The inhibitory effect of tannins on lipid peroxidation of rat heart mitochondria. Hong, C.Y., Wang, C.P., Huang, S.S., Hsu, F.L. J. Pharm. Pharmacol. (1995) [Pubmed]
Procyanidin oligomers counteract TGF-beta1- and TGF-beta2-induced apoptosis in hair epithelial cells: an insight into their mechanisms. Kamimura, A., Takahashi, T., Morohashi, M., Takano, Y. Skin pharmacology and physiology. (2006) [Pubmed]
Procyanidin oligomers selectively and intensively promote proliferation of mouse hair epithelial cells in vitro and activate hair follicle growth in vivo. Takahashi, T., Kamiya, T., Hasegawa, A., Yokoo, Y. J. Invest. Dermatol. (1999) [Pubmed]
Chemoprevention of colorectal cancer by grape seed proanthocyanidin is accompanied by a decrease in proliferation and increase in apoptosis. Nomoto, H., Iigo, M., Hamada, H., Kojima, S., Tsuda, H. Nutrition and cancer. (2004) [Pubmed]
Pharmacological and endocrine effects of Hypericum perforatum and hypericin after repeated treatment. Butterweck, V., Korte, B., Winterhoff, H. Pharmacopsychiatry (2001) [Pubmed]
Antitumor activity of compounds isolated from leaves of Eriobotrya japonica. Ito, H., Kobayashi, E., Li, S.H., Hatano, T., Sugita, D., Kubo, N., Shimura, S., Itoh, Y., Tokuda, H., Nishino, H., Yoshida, T. J. Agric. Food Chem. (2002) [Pubmed]
Catalytic inhibition of human DNA topoisomerase II by interactions of grape cell culture polyphenols. Jo, J.Y., Gonzalez de Mejia, E., Lila, M.A. J. Agric. Food Chem. (2006) [Pubmed]
Several selective protein kinase C inhibitors including procyanidins promote hair growth. Takahashi, T., Kamimura, A., Shirai, A., Yokoo, Y. Skin Pharmacol. Appl. Skin Physiol. (2000) [Pubmed]
Antioxidant activity of polyphenols from seeds of Vitis amurensis in vitro. Wang, J.N., Chen, Y.J., Hano, Y., Nomura, T., Tan, R.X. Acta Pharmacol. Sin. (2000) [Pubmed]
Investigation of topical application of procyanidin B-2 from apple to identify its potential use as a hair growing agent. Kamimura, A., Takahashi, T., Watanabe, Y. Phytomedicine (2000) [Pubmed]

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