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

被引：36

作者：

Morikawa, Toshio ^{[1
,2
]}

Nakanishi, Yusuke ^{[1
]}

Ninomiya, Kiyofumi ^{[1
,2
]}

Matsuda, Hisashi ^{[3
]}

Nakashima, Souichi ^{[3
]}

Miki, Hisako ^{[3
]}

Miyashita, Yu ^{[3
]}

Yoshikawa, Masayuki ^{[3
]}

Hayakawa, Takao ^{[1
]}

Muraoka, Osamu ^{[1
,2
]}

机构：

[1] Kinki Univ, Pharmaceut Res & Technol Inst, Higashiosaka, Osaka 5778502, Japan

[2] Kinki Univ, Antiaging Ctr, Higashiosaka, Osaka 5778502, Japan

[3] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078412, Japan

来源：

JOURNAL OF NATURAL MEDICINES | 2014年 / 68卷 / 03期

关键词：

Chimonanthus praecox; Melanogenesis inhibitor; (-)-Chimonanthine; (-)-Folicanthine; (-)-Calycanthidine; Dimeric pyrrolidinoindoline alkaloid; MELANOCYTE-STIMULATING HORMONE; TYROSINASE INHIBITORS; CONSTITUENTS; GLYCOSIDES; MECHANISM; LEAVES; SESQUITERPENES; EXPRESSION; ALCOHOLS; ROOT;

D O I：

10.1007/s11418-014-0832-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

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.

引用

页码：539 / 549

页数：11

共 16 条

[1] Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox
Toshio Morikawa
Yusuke Nakanishi
Kiyofumi Ninomiya
Hisashi Matsuda
Souichi Nakashima
Hisako Miki
Yu Miyashita
Masayuki Yoshikawa
Takao Hayakawa
Osamu Muraoka
Journal of Natural Medicines, 2014, 68 : 539 - 549
[2] Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity
Morikawa, Toshio
Kitagawa, Niichiro
Tanabe, Genzoh
Ninomiya, Kiyofumi
Okugawa, Shuhei
Motai, Chiaki
Kamei, Iyori
Yoshikawa, Masayuki
Lee, I-Jung
Muraoka, Osamu
MOLECULES, 2016, 21 (07)
[3] Quantitative Determination of Principal Alkaloid and Flavonoid Constituents in Wintersweet, the Flower Buds of Chimonanthus praecox
Kitagawa, Niichiro
Ninomiya, Kiyofumi
Okugawa, Shuhei
Motai, Chiaki
Nakanishi, Yusuke
Yoshikawa, Masayuki
Muraoka, Osamu
Morikawa, Toshio
NATURAL PRODUCT COMMUNICATIONS, 2016, 11 (07) : 953 - 956
[4] Lignan Dicarboxylates and Terpenoids from the Flower Buds of Cananga odorata and Their Inhibitory Effects on Melanogenesis
Matsumoto, Takahiro
Nakamura, Seikou
Nakashima, Souichi
Fujimoto, Katsuyoshi
Yoshikawa, Masayuki
Ohta, Tomoe
Ogawa, Keiko
Matsuda, Hisashi
JOURNAL OF NATURAL PRODUCTS, 2014, 77 (04): : 990 - 999
[5] Melanogenesis inhibitory daphnane diterpenoids from the flower buds of Daphne genkwa
Bang, Kwon Ki
Yun, Cheong-Yong
Lee, Chul
Jin, Qinghao
Lee, Jin Woo
Jung, Sang-Hun
Lee, Dongho
Lee, Mi Kyeong
Hong, Jin Tae
Kim, Youngsoo
Hwang, Bang Yeon
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (11) : 3334 - 3337
[6] Medicinal Flowers. XXXV. Nor-Oleanane-Type and Acylated Oleanane-Type Triterpene Saponins from the Flower Buds of Chinese Camellia japonica and Their Inhibitory Effects on Melanogenesis
Fujimoto, Katsuyoshi
Nakamura, Seikou
Nakashima, Souichi
Matsumoto, Takahiro
Uno, Kaoru
Ohta, Tomoe
Miura, Tomoko
Matsuda, Hisashi
Yoshikawa, Masayuki
CHEMICAL & PHARMACEUTICAL BULLETIN, 2012, 60 (09) : 1188 - 1194
[7] Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells
Nakamura, Seikou
Nakashima, Souichi
Tanabe, Genzo
Oda, Yoshimi
Yokota, Nami
Fujimoto, Katsuyoshi
Matsumoto, Takahiro
Sakuma, Rika
Ohta, Tomoe
Ogawa, Keiko
Nishida, Shino
Miki, Hisako
Matsuda, Hisashi
Muraoka, Osamu
Yoshikawa, Masayuki
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (03) : 779 - 787
[8] Medicinal Flowers. XXXVI. Acylated Oleanane-Type Triterpene Saponins with Inhibitory Effects on Melanogenesis from the Flower Buds of Chinese Camellia japonica
Nakamura, Seikou
Fujimoto, Katsuyoshi
Nakashima, Souichi
Matsumoto, Takahiro
Miura, Tomoko
Uno, Kaoru
Matsuda, Hisashi
Yoshikawa, Masayuki
CHEMICAL & PHARMACEUTICAL BULLETIN, 2012, 60 (06) : 752 - 758
[9] Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis
Nakamura, Seikou
Fujimoto, Katsuyoshi
Matsumoto, Takahiro
Nakashima, Souichi
Ohta, Tomoe
Ogawa, Keiko
Matsuda, Hisashi
Yoshikawa, Masayuki
PHYTOCHEMISTRY, 2013, 92 : 128 - 136
[10] Labdane-Type Diterpenes, Galangalditerpenes A-C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga
Manse, Yoshiaki
Ninomiya, Kiyofumi
Nishi, Ryosuke
Hashimoto, Yoshinori
Chaipech, Saowanee
Muraoka, Osamu
Morikawa, Toshio
MOLECULES, 2017, 22 (12):

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