P-49 Chlorophytum arundinaceum由来のビベンジル配糖体の化学合成とチロシナーゼ阻害活性(ポスター発表の部)

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The enzymic oxidation of phenols to o-quinones is observed in the early stage of various browning phenomena in nature, is mainly catalyzed by tyrosinase, a copper containing enzyme. Therefore, efficient tyrosinase inhibitor can be applied to antioxidant for fruits and vegetables, pest control agent, and skin lightening cosmetic. Bibenzyl xyloside 1 was isolated from the extract of Chlorophytum arundinaceum and the structure was determined by Tandon et al. in 1993. However, the synthetic study and the biological evaluation of 1 have not been carried out. We report here the concise chemical syntheses and tyrosinase inhibitory activity of 1 and its derivatives 2, 3 and 4. As shown in Scheme 1, 1 was synthesized using Wittig reaction and Lewis acid-catalyzed glycosylation as key steps. The total synthetic yield of 1 was 65% and the reaction sequence possessed seven steps from aldehyde 5. The synthetic pathway of bibenzyl derivatives 2 and 3 are shown in Scheme 2. By adjusting the amount of imidate 12, bibenzyl 18 was selectively converted into the key intermediates 19 or 20 in high yields. Consequently, 2 and 3 were furnished from aldehyde 14 via six steps in 39% and 37% overall yields respectively. In order to obtain bibenzyl 4, aldehyde 15 was used as the starting material (Scheme 3). Finally, the synthesis of bibenzyl 4 was achieved by two steps in 36% yield. Tyrosinase inhibitory activity of 1, 2, 3 and 4 was evaluated using mushroom tyrosinase. As a result, all the derivatives were more effective than kojic acid which is one of the typical tyrosinase inhibitors. This is the first report concerning potent tyrosinase inhibitors with glycosyl moiety. Hence, their derivatives can be useful tools from agricultural and medicinal perspectives.
天然有機化合物討論会の論文
2006-09-15

P-49 Chlorophytum arundinaceum由来のビベンジル配糖体の化学合成とチロシナーゼ阻害活性(ポスター発表の部)

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