Literature DB >> 24668298

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

Toshio Morikawa1, Yusuke Nakanishi, Kiyofumi Ninomiya, Hisashi Matsuda, Souichi Nakashima, Hisako Miki, Yu Miyashita, Masayuki Yoshikawa, Takao Hayakawa, Osamu Muraoka.   

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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Year:  2014        PMID： 24668298     DOI： 10.1007/s11418-014-0832-1

Source DB:  PubMed          Journal:  J Nat Med        ISSN： 1340-3443            Impact factor:   2.343


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  10 in total

1.  Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis.

Authors:  Toshio Morikawa; Kiyofumi Ninomiya; Hiroyuki Kuramoto; Iyori Kamei; Masayuki Yoshikawa; Osamu Muraoka
Journal:  J Nat Med       Date:  2016-01       Impact factor: 2.343

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Authors:  Yoshiaki Manse; Fenglin Luo; Kazuhiro Kato; Akane Okazaki; Eriko Okada-Nishida; Mitsuhiro Yanagida; Sho Nakamura; Toshio Morikawa
Journal:  J Nat Med       Date:  2021-01-08       Impact factor: 2.343

3.  Simultaneous quantitative analysis of 12 methoxyflavones with melanogenesis inhibitory activity from the rhizomes of Kaempferia parviflora.

Authors:  Kiyofumi Ninomiya; Taku Matsumoto; Saowanee Chaipech; Sohachiro Miyake; Yushi Katsuyama; Akihiro Tsuboyama; Yutana Pongpiriyadacha; Takao Hayakawa; Osamu Muraoka; Toshio Morikawa
Journal:  J Nat Med       Date:  2015-12-28       Impact factor: 2.343

4.  Labdane-Type Diterpenes, Galangalditerpenes A-C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga.

Authors:  Yoshiaki Manse; Kiyofumi Ninomiya; Ryosuke Nishi; Yoshinori Hashimoto; Saowanee Chaipech; Osamu Muraoka; Toshio Morikawa
Journal:  Molecules       Date:  2017-12-20       Impact factor: 4.411

Review 5.  Studies on the alkaloids of the calycanthaceae and their syntheses.

Authors:  Jin-Biao Xu; Ke-Jun Cheng
Journal:  Molecules       Date:  2015-04-15       Impact factor: 4.411

6.  Inhibition of melanin production by anthracenone dimer glycosides isolated from Cassia auriculata seeds.

Authors:  Weicheng Wang; Yi Zhang; Souichi Nakashima; Seikou Nakamura; Tao Wang; Masayuki Yoshikawa; Hisashi Matsuda
Journal:  J Nat Med       Date:  2019-03-07       Impact factor: 2.343

7.  Physical Map of FISH 5S rDNA and (AG3T3)3 Signals Displays Chimonanthus campanulatus R.H. Chang & C.S. Ding Chromosomes, Reproduces its Metaphase Dynamics and Distinguishes Its Chromosomes.

Authors:  Xiaomei Luo; Jingyuan Chen
Journal:  Genes (Basel)       Date:  2019-11-07       Impact factor: 4.096

8.  Anti-oxidative and anti-inflammatory activities of the ethanol extract of edible flower from Chimonanthus praecox.

Authors:  Yuan Kang; Zhuangzhuang Liu; Wenjing Li; Ximeng Li; Xiaoyu Zhang; Zhenlu Xu; Yuan Gao; Yun Qi
Journal:  Front Pharmacol       Date:  2022-09-27       Impact factor: 5.988

9.  Structural Requirements of Alkylglyceryl-l-Ascorbic Acid Derivatives for Melanogenesis Inhibitory Activity.

Authors:  Norihisa Taira; Yushi Katsuyama; Masato Yoshioka; Osamu Muraoka; Toshio Morikawa
Journal:  Int J Mol Sci       Date:  2018-04-10       Impact factor: 5.923

10.  Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity.

Authors:  Toshio Morikawa; Niichiro Kitagawa; Genzoh Tanabe; Kiyofumi Ninomiya; Shuhei Okugawa; Chiaki Motai; Iyori Kamei; Masayuki Yoshikawa; I-Jung Lee; Osamu Muraoka
Journal:  Molecules       Date:  2016-07-19       Impact factor: 4.411
  10 in total

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