Bakuchiol

Bakuchiol
Chemical structure of bakuchiol
Names
IUPAC name
4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol
Other names
(+)-Bakuchiol
Identifiers
10309-37-2 N=
3D model (Jmol) Interactive image
ChEMBL ChEMBL262344 YesY
ChemSpider 4579217 YesY
PubChem 5468522
UNII OT12HJU3AR YesY
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 (aka Drupanol) 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]

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

External links

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