90(P-97) Artocarpus incisusからのメラニン生成抑制成分(ポスター発表の部)

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The inhibitory effects of methanol extracts of heartwood of 23 Papua New Guinean wood species on tyrosinase activity were examined. The extract of Artocarpus incisus showed the strongest tyrosinase inhibitory activity which was equivalent to kojic acid. The extract apparently inhibited melanin biosynthesis of both cultured B16 melanoma cells without any cytotoxicity and back of brown guinea pig without skin irritation. Tyrosinase inhibitory activity-guided fractionation led to the isolation of seven active compounds including two new compounds which have been characterized as 6-(3"-methyl-1"-butenyl)-5,7,2',4'-tetrahydroxyflavone, named isoartocarpesin (19) and 3,2',4'-trihydroxy-6",6"-dimethyl-pyrano(3",2": 4,5)-trans-stilbene, named artocarbene (25). Other active compounds were (+)-dihydromorin (8), chlorophorin (24), (+)-norartocarpanone (9), 4-prenyloxyresveratrol (23) and artocarpesin (18). These compounds likely caused melanin biosynthesis inhibitory effects. Several flavonoids, stilbenes and related 4-substituted resorcinols, obtained from A. incisus and other plants or synthesized, were tested for their inhibitory activity against tyrosinase. The structure-activity relationships suggested that specific natural or synthesized compounds having 4-substituted resorcinol skeleton have potent tyrosinase inhibitory ability. Kinetic studies have indicated that specific compounds having 4-substituted resorcinol skeleton exhibit competitive inhibition of the oxidation of DL-β-(3,4-dihydroxyphenyl) alanine (DL-DOPA) by mushroom tyrosinase. These findings could lead to the design and discovery of new tyrosinase inhibitors.
天然有機化合物討論会の論文
2000-10-01

90(P-97) Artocarpus incisusからのメラニン生成抑制成分(ポスター発表の部)

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