学术探索
学术期刊
新闻热点
数据分析
智能评审

New clerodane diterpenoids from Laetia procera (Poepp.) Eichler (Flacourtiaceae), with antiplasmodial and antileishmanial activities

被引：39
作者：
Jullian, V
Bonduelle, C
Valentin, A
Acebey, L
Duigou, AG
Prévost, MF
Sauvain, M
机构：
[1] Univ Toulouse 3, Fac Pharm, UMR 152, Inst Rech Dev,IRD,UPS, F-31062 Toulouse, France
[2] Ctr IRD Cayenne, US 084 IRD, Cayenne 97323, French Guiana
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 22期
关键词：
Laetia procera; Flacourtiaceae; clerodane diterpenoids; butanolide; Plasmodium falciparum; leishmania;
D O I：
10.1016/j.bmcl.2005.07.090
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Extracts of Laetia procera (Flacourtiaceac) displayed significant in vitro activity against Plasmodium falciparum. P. falciparum bioassay guided fractionation of a trunk bark extract of this plant led to the isolation of six clerodane diterpenoids (1-6) and a butanolide (7). Five of these compounds are new and called Laetiaprocerine A-D (3-6) and Laetianolide A (7). Their structures were established on the basis of 1D and 2D NMR experiments. Absolute configurations of 1 and 2 were determined by a modified Mosher's method and the absolute configuration of 5 by chemical correlation. The clerodane diterpenoids displayed activities against P. falciparum with an IC50 down to 0.5 mu M on FCb1 and F32 strains, and also cytotoxicity toward human tumor cell line MCF7. The most active compound showed a selectivity index of 6.8. Some of these compounds also displayed activities against Leishmania amazonensis amastigote axenic stages and promastigote. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5065 / 5070
页数：6
相关论文
共 22 条
[1]   ANTIMALARIAL ACTIVITY IN-VITRO OF COCHLOSPERMUM-TINCTORIUM TUBERCLE EXTRACTS [J].
BENOIT, F ;
VALENTIN, A ;
PELISSIER, Y ;
MARION, C ;
MALLIE, M ;
BASTIDE, JM .
TRANSACTIONS OF THE ROYAL SOCIETY OF TROPICAL MEDICINE AND HYGIENE, 1995, 89 (02) :217-218
[2]   Novel cytotoxic diterpenes from Casearia arborea [J].
Beutler, JA ;
McCall, KL ;
Herbert, K ;
Herald, DL ;
Pettit, GR ;
Johnson, T ;
Shoemaker, RH ;
Boyd, MR .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (05) :657-661
[3]   Cytotoxic clerodane diterpene esters from Laetia corymbulosa [J].
Beutler, JA ;
McCall, KL ;
Herbert, K ;
Johnson, T ;
Shoemaker, RH ;
Boyd, MR .
PHYTOCHEMISTRY, 2000, 55 (03) :233-236
[4]   Acetogenins from Porcelia macrocarpa: Stereochemical determination of 2-alkyl-3-hydroxy-4-methyl gamma-lactones by C-13 NMR spectroscopy [J].
Chaves, MH ;
Roque, NF .
PHYTOCHEMISTRY, 1997, 44 (03) :523-528
[5]   QUANTITATIVE ASSESSMENT OF ANTI-MALARIAL ACTIVITY INVITRO BY A SEMIAUTOMATED MICRODILUTION TECHNIQUE [J].
DESJARDINS, RE ;
CANFIELD, CJ ;
HAYNES, JD ;
CHULAY, JD .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 16 (06) :710-718
[6]   Trypanocidal activity of a new diterpene from Casearia sylvestris var. lingua [J].
Espindola, LS ;
Vasconcelos, JRE ;
de Mesquita, ML ;
Marquié, P ;
de Paula, JE ;
Mambu, L ;
Santana, JM .
PLANTA MEDICA, 2004, 70 (11) :1093-1095
[7]   Clerodane diterpenes from the leaves of Laetia procera [J].
Gibbons, S ;
Gray, AI ;
Waterman, PG .
PHYTOCHEMISTRY, 1996, 43 (03) :635-638
[8]   Antitumor agents.: Part 212:: Bucidarasins A-C, three new cytotoxic clerodane diterpenes from Bucida buceras [J].
Hayashi, K ;
Nakanishi, Y ;
Bastow, KF ;
Cragg, G ;
Nozaki, H ;
Lee, KH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (03) :345-348
[9]   Four new clerodane diterpenes from the leaves of Casearia guianensis which inhibit the interaction of leukocyte function antigen 1 with intercellular adhesion molecule 1 [J].
Hunter, MS ;
Corley, DG ;
Carron, CP ;
Rowold, E ;
Kilpatrick, BF ;
Durley, RC .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (09) :894-899
[10]   NEW ANTITUMOR PRINCIPLES, CASEARINS-A-F, FOR CASEARIA-SYLVESTRIS SW (FLACOURTIACEAE) [J].
ITOKAWA, H ;
TOTSUKA, N ;
MORITA, H ;
TAKEYA, K ;
IITAKA, Y ;
SCHENKEL, EP ;
MOTIDOME, M .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (12) :3384-3388
123