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

  • J Nat Med. 2014 Jul;68(3):539-49. doi: 10.1007/s11418-014-0832-1.
Toshio Morikawa  1 ,  Yusuke Nakanishi ,  Kiyofumi Ninomiya ,  Hisashi Matsuda ,  Souichi Nakashima ,  Hisako Miki ,  Yu Miyashita ,  Masayuki Yoshikawa ,  Takao Hayakawa ,  Osamu Muraoka
Affiliations
  • 1. Pharmaceutical Research and Technology Institute, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan.
PMID: 24668298 DOI: 10.1007/s11418-014-0832-1
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.

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