Melanogenesis inhibitory activity of monoterpene glycosides from Gardeniae Fructus.
A new iridoid glycoside, 10-O-(4"-O-methylsuccinoyl)geniposide (7), and two new pyronane glycosides, jasminosides Q and R (13 and 14, resp.), along with nine known iridoid glycosides, 1-6 and 8-10, and two known pyronane glycosides, 11 and 12, were isolated from a MeOH extract of Gardeniae Fructus, the dried ripe fruit of Gardenia jasminoides (Rubiaceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Upon evaluation of compounds 1-14 on the melanogenesis in B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three compounds, i.e., 6-O-p-coumaroylgeniposide (3), 7, and 6'-O-sinapoyljasminoside (12), exhibited inhibitory effects with 21.6-41.0 and 37.5-47.7% reduction of melanin content at 30 and 50 μM, respectively, with almost no toxicity to the cells (83.7-106.1% of cell viability at 50 μM).
College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Tokyo 101-8308, Japan. akihisa.toshihiro@nihon-u.ac.jp
Toshihiro
T
Akihisa
Kensuke
K
Watanabe
Ayako
A
Yamamoto
Jie
J
Zhang
Masahiro
M
Matsumoto
Makoto
M
Fukatsu
D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D005638:Fruit / Q000737:chemistry; D032062:Gardenia / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D008546:Melanoma, Experimental / Q000378:metabolism; D039821:Monoterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D006027:Glycosides; D008543:Melanins; D039821:Monoterpenes