Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox

作者:Morikawa Toshio; Nakanishi Yusuke; Ninomiya Kiyofumi; Matsuda Hisashi; Nakashima Souichi; Miki Hisako; Miyashita Yu; Yoshikawa Masayuki; Hayakawa Takao; Muraoka Osamu*
来源:Journal of Natural Medicines, 2014, 68(3): 539-549.
DOI:10.1007/s11418-014-0832-1

摘要

A methanol extract of the flower buds of Chimonanthus praecox (L.) Link (Calycanthaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, five dimeric pyrrolidinoindoline alkaloids and four sesquiterpenes were isolated, together with 16 known compounds. Among them, (-)-chimonanthine (1, IC50 = 0.93 mu M), (-)-folicanthine (2, 1.4 mu M), and (-)-calycanthidine (3, 1.8 mu M) showed potent inhibitory effects without notable cytotoxicity at the effective concentrations. The most potent alkaloid (1) inhibited both tyrosinase and tyrosine-related protein-1 mRNA expressions, to which the melanogenesis inhibitory activity would be ascribable.

  • 出版日期2014-7