Bakuchiol

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Bakuchiol
Chemical structure of 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
ECHA InfoCard 100.211.101
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 was first isolated in 1966 by Mehta et al. from Psoralea corylifolia seed and was called Bakuchiol based on the sanskrit name Bakuchi of the plant.[1] Bakuchiol is mainly obtained from the seeds of the plant Psoralea corylifolia,[2][3][4] which is widely used in Indian as well as in Chinese medicine to treat a variety of diseases.[5] It has also been isolated from other plants, such as P. grandulosa,[6][7] P. drupaceae,[8] Ulmus davidiana,[9]Otholobium pubescens,[10] Piper longum [11] and Aerva sangulnolenta Blum.[12]

Even if the first complete synthesis of Bakuchiol has been described in 1973[13], its first commercial use in topical applications did not occur until 2007 when it was introduced to the market under the trade name Sytenol® A by Sytheon Ltd.[14]

It has been reported to have anticancer activity in pre-clinical models, possibly due to its structural similarity with resveratrol.[15] One study in rats suggested that bakuchiol and ethanol extracts of the Chinese medicinal plant Psoralea corylifolia could protect against bone loss.[16]

Bakuchiol possesses antioxidant,[17][18] anti-inflammatory [19][20] and anti-bacterial [21] properties. 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.[22]

Despite having no structural resemblance to retinol, Bakuchiol was found to have retinol functionality through retinol-like regulation of gene expression.[23] In 2018, a randomized, double-blind, 12-week clinical study with 44 volunteers demonstrated that Bakuchiol is comparable with retinol in its ability to improve photoageing (wrinkles, hyperpigmentation) but has a better skin tolerance.[24]

Bakuchiol has been found to possess antiandrogenic activity in prostate cancer cells, which inhibited cell proliferation.[25]

See also[edit]

References[edit]

  1. ^ Mehta, G.; Nayak, U.Ramdas; Dev, Sukh (January 1966). "Bakuchiol, a novel monoterpenoid". Tetrahedron Letters. 7 (38): 4561–4567. doi:10.1016/s0040-4039(00)70078-5. ISSN 0040-4039.
  2. ^ Banerji, A; Chintalwar, G (1983). "Biosynthesis of bakuchiol, a meroterpene from Psoralea corylifolia". Phytochemistry. 22 (9): 1945–1947. doi:10.1016/0031-9422(83)80019-3. INIST:9311490
  3. ^ Cho, Hyun; Jun, Jung-Yang; Song, Eun-Kyoung; et al. (2001). "Bakuchiol: a hepatoprotective compound of Psoralea corylifolia on tacrine-induced cytotoxicity in Hep G2 cells". Planta Medica. 67 (8): 750–751. doi:10.1055/s-2001-18347. PMID 11731920.
  4. ^ Manohar, B., Divakar, S., Udaya Sankar, K (2009). "Amyloglucosidase Catalyzed Syntheses of Bakuchiol Glycosides in Supercritical Carbon Dioxide". Bulletin of the Korean Chemical Society. 30 (8): 1760–1766. doi:10.5012/bkcs.2009.30.8.1760.CS1 maint: multiple names: authors list (link) INIST:22343814
  5. ^ Uikey, Shilandra; Yadav, A.S.; Sharma, Ajit K.; Rai, Atul K.; Raghuwanshi, D.K.; Badkhane, Yogesh (2010-06-22). "The Botany, Chemistry, Pharmacological and Therapeutic Application of Psoralea corylifolia L. – A Review". International Journal of Phytomedicine. 2 (2): 100–107. doi:10.5138/ijpm.2010.0975.0185.02016. ISSN 0975-0185.
  6. ^ Labbé, Cecilia; Faini, Francesca; Coll, Joseph; Connolly, Joseph D. (July 1996). "Bakuchiol derivatives from the leaves of Psoralea glandulosa". Phytochemistry. 42 (5): 1299–1303. doi:10.1016/0031-9422(96)00144-6. ISSN 0031-9422.
  7. ^ Nadine Backhouse, C; Delporte, Carla L; Negrete, Rosa E; Erazo, Silvia; Zuñiga, Alexandra; Pinto, Alvaro; Cassels, Bruce K (November 2001). "Active constituents isolated from Psoralea glandulosa L. with antiinflammatory and antipyretic activities". Journal of Ethnopharmacology. 78 (1): 27–31. doi:10.1016/s0378-8741(01)00309-9. ISSN 0378-8741.
  8. ^ Lystvan, Kateryna; Belokurova, Valeria; Sheludko, Yuriy; Ingham, John L.; Prykhodko, Valeria; Kishchenko, Olena; Paton, Evgenija; Kuchuk, Mykola (2009-12-20). "Production of bakuchiol by in vitro systems of Psoralea drupacea Bge". Plant Cell, Tissue and Organ Culture (PCTOC). 101 (1): 99–103. doi:10.1007/s11240-009-9657-0. ISSN 0167-6857.
  9. ^ Choi, Sang Yoon; Lee, Sanghyun; Choi, Won-Hee; Lee, Yeonmi; Jo, Youn Ock; Ha, Tae-Youl (August 2010). "Isolation and Anti-Inflammatory Activity of Bakuchiol from Ulmus davidiana var. japonica". Journal of Medicinal Food. 13 (4): 1019–1023. doi:10.1089/jmf.2009.1207. ISSN 1096-620X. PMID 20553183.
  10. ^ Krenisky, Joann M.; Luo, Jian; Reed, Michael J.; et al. (1999). "Isolation and Antihyperglycemic Activity of Bakuchiol from Otholobium pubescens(Fabaceae), a Peruvian Medicinal Plant Used for the Treatment of Diabetes". Biological & Pharmaceutical Bulletin. 22 (10): 1137–1140. doi:10.1248/bpb.22.1137. PMID 10549873. INIST:1198639
  11. ^ OHNO, Osamu; WATABE, Taeko; NAKAMURA, Kazuhiko; KAWAGOSHI, Masaru; UOTSU, Nobuo; CHIBA, Tomohiro; YAMADA, Masayoshi; YAMAGUCHI, Kohji; YAMADA, Kaoru (2010-07-23). "Inhibitory Effects of Bakuchiol, Bavachin, and Isobavachalcone Isolated fromPiper longumon Melanin Production in B16 Mouse Melanoma Cells". Bioscience, Biotechnology, and Biochemistry. 74 (7): 1504–1506. doi:10.1271/bbb.100221. ISSN 0916-8451. PMID 20622433.
  12. ^ "Aerva Sanguinolenta (L.) Blume, Extract 116425-35-5", Sax's Dangerous Properties of Industrial Materials, John Wiley & Sons, Inc., 2012-10-15, doi:10.1002/0471701343.sdp26534, ISBN 978-0471701347
  13. ^ Damodaran, N.P.; Dev, Sukh (January 1973). "Meroterpenoids—III". Tetrahedron. 29 (9): 1209–1213. doi:10.1016/0040-4020(73)80103-6. ISSN 0040-4020.
  14. ^ Chaudhuri, Ratan (2015-09-18), Sivamani, Raja; Jagdeo, Jared; Elsner, Peter; Maibach, Howard (eds.), "Bakuchiol: A Retinol-Like Functional Compound, Modulating Multiple Retinol and Non-Retinol Targets", Cosmeceuticals and Active Cosmetics, Third Edition, CRC Press, pp. 1–18, doi:10.1201/b18895-2, ISBN 9781482214161, retrieved 2019-08-02
  15. ^ Chen, Zhe; Jin, Ke; Gao, Lingyan; et al. (2010). "Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line". European Journal of Pharmacology. 643 (2–3): 170–9. doi:10.1016/j.ejphar.2010.06.025. PMID 20599920.
  16. ^ Lim, Sun-Hye; Ha, Tae-Youl; Kim, Sung-Ran; et al. (2008). "Ethanol extract of Psoralea corylifolia L. and its main constituent, bakuchiol, reduce bone loss in ovariectomised Sprague–Dawley rats". British Journal of Nutrition. 101 (7): 1031–1039. doi:10.1017/S0007114508066750. PMID 18801207.
  17. ^ Adhikari, S.; Joshi, R.; Patro, B. S.; Ghanty, T. K.; Chintalwar, G. J.; Sharma, A.; Chattopadhyay, S.; Mukherjee, T. (September 2003). "Antioxidant Activity of Bakuchiol:  Experimental Evidences and Theoretical Treatments on the Possible Involvement of the Terpenoid Chain". Chemical Research in Toxicology. 16 (9): 1062–1069. doi:10.1021/tx034082r. ISSN 0893-228X. PMID 12971793.
  18. ^ Haraguchi, Hiroyuki; Inoue, Junji; Tamura, Yukiyoshi; Mizutani, Kenji (2002). "Antioxidative components of Psoralea corylifolia (Leguminosae)". Phytotherapy Research. 16 (6): 539–544. doi:10.1002/ptr.972. ISSN 0951-418X. PMID 12237811.
  19. ^ Ferrándiz, María Luisa; Gil, Blanca; Sanz, María Jesús; Ubeda, Amalia; Erazo, Silvia; González, Ernesto; Negrete, Rosa; Pacheco, Sergio; Payáa, Miguel (September 1996). "Effect of Bakuchiol on Leukocyte Functions and Some Inflammatory Responses in Mice". Journal of Pharmacy and Pharmacology. 48 (9): 975–980. doi:10.1111/j.2042-7158.1996.tb06016.x. ISSN 0022-3573. PMID 8910867.
  20. ^ Nadine Backhouse, C; Delporte, Carla L; Negrete, Rosa E; Erazo, Silvia; Zuñiga, Alexandra; Pinto, Alvaro; Cassels, Bruce K (November 2001). "Active constituents isolated from Psoralea glandulosa L. with antiinflammatory and antipyretic activities". Journal of Ethnopharmacology. 78 (1): 27–31. doi:10.1016/s0378-8741(01)00309-9. ISSN 0378-8741.
  21. ^ Katsura, H.; Tsukiyama, R.-I.; Suzuki, A.; Kobayashi, M. (2001-11-01). "In Vitro Antimicrobial Activities of Bakuchiol against Oral Microorganisms". Antimicrobial Agents and Chemotherapy. 45 (11): 3009–3013. doi:10.1128/aac.45.11.3009-3013.2001. ISSN 0066-4804. PMC 90775. PMID 11600349.
  22. ^ Parimala Devi B, Ramasubramaniaraj R (2009). "Dental Caries and Medicinal Plants – An Overview". Journal of Pharmacy Research. 2 (11): 1669–1675.
  23. ^ Chaudhuri RK, Bojanowski K (2014). "Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects". International Journal of Cosmetic Science. 36 (3): 221–230. doi:10.1111/ics.12117. PMID 24471735.
  24. ^ Dhaliwal, S.; Rybak, I.; Ellis, S.R.; Notay, M.; Trivedi, M.; Burney, W.; Vaughn, A.R.; Nguyen, M.; Reiter, P. (February 2019). "Prospective, randomized, double‐blind assessment of topical bakuchiol and retinol for facial photoageing". British Journal of Dermatology. 180 (2): 289–296. doi:10.1111/bjd.16918. ISSN 0007-0963. PMID 29947134.
  25. ^ Miao L., Ma S, Fan G et al. (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. 30 (5): 291–293. doi:10.11656/j.issn.1672-1519.2013.05.13.CS1 maint: uses authors parameter (link) original title: 补骨脂酚拮抗AR转录活性抑制雄激素诱导的前列腺癌细胞LNCaP的增殖

External links[edit]