Bakuchiol
Bakuchiol is a prenylated phenolic terpene originally sourced from many plants, including Psoralea coryfolia. Bakuchiol exhibits estrogenic, antibacterial, anti-inflammatory, anti-diabetic, anti-hyperlipidemic, and anti-fibrotic activities. Bakuchiol activates estrogen receptors, displaying preference for ERα over ERβ. Bakuchiol shows antimicrobial activity against species of Streptococcus, Enterococcus, Lactobacillus, Actinomyces, and Porphyromonas. In macrophages, bakuchiol inhibits LPS-induced production of NO and prostaglandin E2 (PGE2); in other cellular models, it decreases formation of leukotriene B4 (LTB4) and thromboxane B2 (TXB2). In vivo, bakuchiol decreases PGE2 levels, myeloperoxidase activity, and neutrophil degranulation, decreasing edema. In multiple animal models of diabetes, this compound decreases plasma glucose and triglyceride levels. Across several cellular models of fibrosis, bakuchiol activates ERK 1/2, JNK, p38 MAPK, caspase-3, cytochrome c release, and cleavage of poly(ADP)-ribose polymerase (PARP). Bakuchiol may also inhibit protein phosphatase 1B (PP1B)
References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18842994
Cas No. |
10309-37-2 |
---|---|
Purity |
≥98% |
Formula |
C18H24O |
Formula Wt. |
256.38 |
Chemical Name |
Phenol,4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadien-1-yl] |
IUPAC Name |
4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol |
Synonym |
Bakuchiol(7CI); Phenol, 4-(3-ethenyl-3,7-dimethyl-1,6-octadienyl)-, [S-(E)]-; Phenol,4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadienyl]- (9CI); (+)-Bakuchiol;(S)-(+)-Bakuchiol; (S)-Bakuchiol; Drupanol; UP 256 |
Appearance |
Yellow liquid |
Lim SH, Ha TY, Ahn J, et al. Estrogenic activities of Psoralea corylifolia L. seed extracts and main constituents. Phytomedicine. 2011 Mar 15;18(5):425-30. PMID: 21382704.
Choi SY, Lee S, Choi WH, et al. Isolation and anti-inflammatory activity of Bakuchiol from Ulmus davidiana var. japonica. J Med Food. 2010 Aug;13(4):1019-23. PMID: 20553183.
Park EJ, Zhao YZ, Kim YC, et al. Bakuchiol-induced caspase-3-dependent apoptosis occurs through c-Jun NH2-terminal kinase-mediated mitochondrial translocation of Bax in rat liver myofibroblasts. Eur J Pharmacol. 2007 Mar 22;559(2-3):115-23. PMID: 17292878.
Katsura H, Tsukiyama RI, Suzuki A, et al. In vitro antimicrobial activities of bakuchiol against oral microorganisms. Antimicrob Agents Chemother. 2001 Nov;45(11):3009-13. PMID: 11600349.
Krenisky JM, Luo J, Reed MJ, et al. Isolation and antihyperglycemic activity of bakuchiol from Otholobium pubescens (Fabaceae), a Peruvian medicinal plant used for the treatment of diabetes. Biol Pharm Bull. 1999 Oct;22(10):1137-40. PMID: 10549873.
Ferrándiz ML, Gil B, Sanz MJ, et al. Effect of bakuchiol on leukocyte functions and some inflammatory responses in mice. J Pharm Pharmacol. 1996 Sep;48(9):975-80. PMID: 8910867.