New lycorine-type alkaloid from Lycoris traubii and evaluation of antitrypanosomal and antimalarial activities of lycorine derivatives

被引：83

作者：

Toriizuka, Yosuke ^{[1
]}

Kinoshita, Eri ^{[1
]}

Kogure, Noriyuki ^{[1
]}

Kitajima, Mariko ^{[1
]}

Ishiyama, Aki ^{[2
]}

Otoguro, Kazuhiko ^{[2
]}

Yamada, Haruki ^{[2
]}

Omura, Satoshi ^{[2
]}

Takayama, Hiromitsu ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

[2] Kitasato Univ, Kitasato Inst Life Sci, Res Ctr Trop Dis, Minato Ku, Tokyo 1088641, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2008年 / 16卷 / 24期

基金：

日本学术振兴会;

关键词：

Lycorine; Alkaloid; Lycoris; Antitrypanosomal activity; Antimalarial activity; Structure elucidation; Structure-activity relationship;

D O I：

10.1016/j.bmc.2008.10.061

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new lycorine derivative LT1 (4) was isolated from the aerial part and bulbs of Lycoris traubii Hayward (Amaryllidaceae). Its structure including absolute con. guration was established by spectroscopic analysis and semi-synthesis to be 1-O-(3'S)-hydroxybutanoyllycorine. Some lycorine ester derivatives including LT1 were examined for their inhibitory activity against Trypanosoma brucei brucei, the parasite associated with sleeping sickness, and against Plasmodium falciparum, the causative agent of malaria. Among them, 2-O-acetyllycorine (6) showed the most potent activity against parasitic T. b. brucei, and LT1 (4), 1-O-(3'R)-hydroxybutanoyllycorine (8), 1,2-di-O-butanoyllycorine (11), and 1-O-propanoyllycorine (12) showed significant activity against P. falciparum in an in vitro experiment. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：10182 / 10189

页数：8

共 37 条

[1] Cytotoxic and antimalarial alkaloids from Brunsvigia littoralis [J].

Campbell, WE ;

Nair, JJ ;

Gammon, DW ;

Bastida, J ;

Codina, C ;

Viladomat, F ;

Smith, PJ ;

Albrecht, CF .

PLANTA MEDICA, 1998, 64 (01) :91-93

[2]

Citoglu G, 1998, PHYTOTHER RES, V12, P205, DOI 10.1002/(SICI)1099-1573(199805)12:3&lt

[3]

205::AID-PTR203&gt

[4]

3.0.CO

[5]

2-7

[6] CRYSTAL AND MOLECULAR STRUCTURE OF NARCISSIDINE [J].

CLARDY, JC ;

WILDMAN, WC ;

HAUSER, FM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (06) :1781-&

[7]

ESAMELDIN EE, 2004, PLANTA MED, V70, P260

[8] NARCICLASINE - H-1-NMR AND C-13-NMR DATA AND A NEW IMPROVED METHOD OF PREPARATION [J].

EVIDENTE, A .

PLANTA MEDICA, 1991, 57 (03) :293-295

[9] ISOLATION OF STERNBERGINE, A NEW ALKALOID FROM BULBS OF STERNBERGIA-LUTEA [J].

EVIDENTE, A ;

IASIELLO, I ;

RANDAZZO, G .

JOURNAL OF NATURAL PRODUCTS, 1984, 47 (06) :1003-1008

[10] H-1 AND C-13 NMR ANALYSIS OF LYCORINE AND ALPHA-DIHYDROLYCORINE [J].

EVIDENTE, A ;

CICALA, MR ;

GIUDICIANNI, I ;

RANDAZZO, G ;

RICCIO, R .

PHYTOCHEMISTRY, 1983, 22 (02) :581-584

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