Synthesis and Cosmetic Whitening Effect of Glycosides Derived from Anacardic Acids.

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  • KASEMURA Kazuo
    School of Chemistry and Environmental Technology, Faculty of Engineering, Kinki University
  • NOMURA Masato
    School of Chemistry and Environmental Technology, Faculty of Engineering, Kinki University
  • SAWABE Akiyoshi
    Department of Agricultural Chemistry, Faculty of Agriculture, Kinki University
  • FUJIHARA Yoshihito
    School of Chemistry and Environmental Technology, Faculty of Engineering, Kinki University

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Anacardic acids, (6-[(8Z)-8-pentadecenyl] salicylic acid (1) and 6-[(8Z,11Z)-8,11,14-pentadecatrienyl] salicylic acid (2)) were isolated from the shell oil of Indonesian cashew nut and used to synthesize glycosides via glycosidation of the carboxyl group on the benzene ring. We examined these compounds for their inhibition of the enzyme tyrosinase, their superoxide scavenging activity and their inhibition of enzyme hyaluronidase. The glucosides derived from (1) and (2) were found to inhibit tyrosinase (using L-DOPA as a substrate) activity by more than 80%. The inhibitory rates exceeded that of arbutin, a compound that is used in commercial cosmetics. As the comparison, cardanols, (3-[(8Z)-8-pentadecenyl] phenol (3) and 3-[(8Z, 11Z)-8, 11, 14-pentadecatrienyl] phenol (4)) were isolated from the cashew nut shell oil and used to synthesize glycosides that we also examined for their inhibitory activity.<br>

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