RRC ID 44985
Author Morikawa T, Nakanishi Y, Ninomiya K, Matsuda H, Nakashima S, Miki H, Miyashita Y, Yoshikawa M, Hayakawa T, Muraoka O.
Title Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox.
Journal J Nat Med
Abstract 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 μM), (-)-folicanthine (2, 1.4 μM), and (-)-calycanthidine (3, 1.8 μM) 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.
Volume 68(3)
Pages 539-49
Published 2014-7-1
DOI 10.1007/s11418-014-0832-1
PMID 24668298
MeSH Alkaloids / chemistry Alkaloids / pharmacology* Animals Calycanthaceae / chemistry* Cell Line, Tumor Dimerization Flowers / chemistry Indoles / chemistry Indoles / pharmacology* Melanins / biosynthesis* Mice Monophenol Monooxygenase / metabolism Pyrroles / chemistry Pyrroles / pharmacology* Sesquiterpenes / chemistry Sesquiterpenes / pharmacology
IF 2.055
Times Cited 17
WOS Category CHEMISTRY, MEDICINAL PHARMACOLOGY & PHARMACY
Resource
Human and Animal Cells