130(P-76) カシューナット殻液に含まれるサリチル酸誘導体を用いた配糖体合成とその化粧品美白作用(ポスター発表の部)

概要

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Pollution by chlorofluorohydrocarbons from freezers and air conditioners has recently contributed to the destruction of the ozone layer and it has been suggested that excessive exposure to ultraviolet rays causes serious problems such as carcinogenesis, inflammation, and photo-aging. The investigation of natural products have been increased expecting the effectiveness and safety. We have previously reported that 6-[(8Z)-8-pentadecenyl] salicylic acid (1) (Anacardic acid monoene) and 6-[(8Z, 11Z)-8, 11, 14- pentadeca trienyl] salicylic acid (2) (Anacardic acid triene) were isolated from cashew nut shell oil and their derivatives showed strong tyrosinase inhibitory activity. In this report, we synthesized eight derivatives from (1), (2), 3-[(8Z)-8-pentadecenyl] phenol (3) (Cardanol monoene) and 3-[(8Z, 11Z)-8, 11, 14-pentadecatrienyl] phenol (4) (Cardanol triene) by condensation and hydrolysis reactions using 2,3,4,6-tetra-o-acetyl-α-D-glucopyranosyl bromide and 2,3,4,6-tetra-o-acetyl-α-D-e galactopyranosyl bromide. These derivatives were examined for their use as whitening agents which inhibit tyrosinase activity, superoxide scavenging activity and hyaluronidase activity. Compounds (1a) and (2a) were found to be inhibited by ca. 81-88% tyrosinase activity (L-Dopa). This inhibitory action considerably exceeded that of arbutin used in commercial cosmetics.
天然有機化合物討論会の論文
2000-10-01