著者

Akihisa Toshihiro Seino Ken-ichi Kaneko Etsuyo Watanabe Kensuke Tochizawa Shun Fukatsu Makoto Banno Norihiro Metori Koichi Kimura Yumiko

出版者

Japan Oil Chemists' Society

雑誌

Journal of Oleo Science (ISSN:13458957)

巻号頁・発行日

vol.59, no.1, pp.49-57, 2010

被引用文献数

56

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A new iridoid glycoside, 9-<I>epi</I>-6α-methoxy geniposidic acid (4), three new hemiterpene glycosides, 3-methylbut-3-enyl 2′-O-(β-D-glucopyranosyl)-β-D-glucopyranoside (nonioside K) (6), 3-methylbut-3-enyl 6′-O-(β-D-xylopyranosyl)-β-D-glucopyranoside (nonioside L) (8), and 3-methylbut-3-enyl 6′-O-(β-D-xylofuranosyl)-β-D-glucopyranoside (nonioside M) (9), and two new saccharide fatty acid esters, 6′-O-(β-D-glucopyranosyl)-1′-<I>O</I>-[(2ξ)-2-methylbutanoyl]-β-D-glucopyranose (nonioside N) (16) and 6′-<I>O</I>-(β-D-xylopyranosyl)-1′-<I>O</I>-[(2ξ)-2-methylbutanoyl]-β-D-glucopyranose (nonioside O) (17), were isolated from a methanol extract of the fruits of <I>Morinda citrifolia</I> (noni), along with 11 known compounds, namely, three iridoid glycosides (1-3), two hemiterpene glycosides (5 and 7), and five saccharide fatty acid esters (10-15). Upon evaluation of compounds 1-17 on the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), 13 compounds (1, 3, 4, 6-14, and 17) exhibited marked inhibitory effects with 34-49% reduction of melanin content at 100 μM with no or almost no toxicity to the cells (91-116% of cell viability at 100 μM).