Melanogenesis inhibitory activities of iridoid-, hemiterpene-, and fatty acid-glycosides from the fruits of Morinda citrifolia (Noni).
A new iridoid glycoside, 9-epi-6alpha-methoxy geniposidic acid (4), three new hemiterpene glycosides, 3-methylbut-3-enyl 2'-O-(beta-D-glucopyranosyl)-beta-D-glucopyranoside (nonioside K) (6), 3-methylbut-3-enyl 6'-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside (nonioside L) (8), and 3-methylbut-3-enyl 6'-O-(beta-D-xylofuranosyl)-beta-D-glucopyranoside (nonioside M) (9), and two new saccharide fatty acid esters, 6'-O-(beta-D-glucopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside N) (16) and 6'-O-(beta-D-xylopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside O) (17), were isolated from a methanol extract of the fruits of Morinda citrifolia (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 alpha-melanocyte-stimulating hormone (alpha-MSH), 13 compounds (1, 3, 4, 6-14, and 17) exhibited marked inhibitory effects with 34-49% reduction of melanin content at 100 muM with no or almost no toxicity to the cells (91-116% of cell viability at 100 microM).
Akihisa
Toshihiro
T
College of Science and Technology, Nihon University, Tokyo 101-8308, Japan. akihisa@chem.cst.nihon-u.ac.jp
Seino
Ken-ichi
K
Kaneko
Etsuyo
E
Watanabe
Kensuke
K
Tochizawa
Shun
S
Fukatsu
Makoto
M
Banno
Norihiro
N
Metori
Koichi
K
Kimura
Yumiko
Y
D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D005227:Fatty Acids / Q000737:chemistry* / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D039823:Iridoids / Q000737:chemistry* / Q000494:pharmacology; D008543:Melanins / Q000037:antagonists & inhibitors*; D015394:Molecular Structure; D032066:Morinda / Q000737:chemistry*; D008517:Phytotherapy; D010858:Pigmentation / Q000187:drug effects; D028321:Plant Preparations; D013729:Terpenes / Q000737:chemistry* / Q000494:pharmacology
D000970:Antineoplastic Agents; D005227:Fatty Acids; D006027:Glycosides; D039823:Iridoids; D008543:Melanins; D028321:Plant Preparations; D013729:Terpenes