Bakuchiol

Bakuchiol
Names
IUPAC name
4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol
Other names
(+)-Bakuchiol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
Properties
C18H24O
Molar mass 256.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Bakuchiol is a meroterpene (a chemical compound having a partial terpenoid structure) in the class terpenophenol. It is found in Psoralea corylifolia[1][2][3] and in Otholobium pubescens.[4]

It has been reported to have anticancer activity in pre-clinical models, possibly due to its structural similarity with resveratrol.[5] One study in rats suggested that bakuchiol and ethanol extracts of the Chinese medicinal plant Psoralea corylifolia could protect against bone loss.[6] Bakuchiol isolated from P. corylifolia has shown activity against numerous Gram-positive and Gram-negative oral pathogens. It was able to inhibit the growth of Streptococcus mutans under a range of sucrose concentrations, pH values and in the presence of organic acids in a temperature-dependent manner and also inhibited the growth of cells adhered to a glass surface.[7] Bakuchiol was also found to have retinol functionality.[8]

Bakuchiol has been found to possess antiandrogenic activity in prostate cancer cells, which inhibited cell proliferation.[9]

See also

References

  1. Biosynthesis of bakuchiol, a meroterpene from Psoralea corylifolia. Asok Banerji and Chintalwar G. J., Phytochemistry, 1983, vol. 22, no9, pp. 1945-1947, INIST:9311490
  2. Amyloglucosidase Catalyzed Syntheses of Bakuchiol Glycosides in Supercritical Carbon Dioxide. Balaraman Manohar, Soundar Divakar and Kadimi Udaya Sankar, Bull. Korean Chem. Soc. 2009, Vol. 30, No. 8, pp. 1760-1766, INIST:22343814
  3. Bakuchiol: A Hepatoprotective Compound of Psoralea corylifolia on Tacrine-Induced Cytotoxicity in Hep G2 Cells. Hyun Cho, Jung-Yang Jun, Eun-Kyoung Song, Ki-Hong Kang, Hum-Young Baek, Yong-Suk Ko and Youn-Chul Kim, Planta Med., 2001, 67(8), pp. 750-751, doi:10.1055/s-2001-18347
  4. Isolation and antihyperglycemic activity of bakuchiol from Otholobium pubescens (fabaceae), a peruvian medicinal plant used for the treatment of diabetes. Krenisky J. M., Luo J., Reed M. J. and Carney J. R., Biological & pharmaceutical bulletin, 1999, vol. 22, no10, pp. 1137-1140, INIST:1198639
  5. Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line. Chen Z, Jin K, Gao L, Lou G, Jin Y, Yu Y, Lou Y. Eur J Pharmacol. 2010 Sep 25;643(2-3):170-9. doi: 10.1016/j.ejphar.2010.06.025.
  6. Ethanol extract of Psoralea corylifolia L. and its main constituent, bakuchiol, reduce bone loss in ovariectomised Sprague-Dawley rats. Lim SH, Ha TY, Kim SR, Ahn J, Park HJ and Kim S, Br J Nutr., 2009 Apr, 101(7), pp. 1031-1039
  7. Dental Caries and Medicinal Plants –An Overview. Parimala Devi B. and Ramasubramaniaraj R., Journal of Pharmacy Research, 2009, 2(11), pp. 1669-1675 http://jpronline.info/article/view/906/708
  8. Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects. Chaudhuri RK and Bojanowski K. Int J Cosmet Sci. 2014 Jun;36(3):221-30 doi:10.1111/ics.12117
  9. Miao, L., Ma, S. W., Fan, G. W., Wang, H., Wang, Y. F., & Chai, L. J. (2013). Bakuchiol inhibits the androgen induced-proliferation of prostate cancer cell line LNCaP through suppression of AR transcription activity. Tianjin Journal of Traditional Chinese Medicine, 5, 012.


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