Two 6-substituted 5,6-dihydro-α-pyrones from Ravensara anisata

被引:31
作者
Andrianaivoravelona, JO
Sahpaz, S
Terreaux, C
Hostettmann, K [1 ]
Stoeckli-Evans, H
Rasolondramanitra, J
机构
[1] Ecole Polytech Fed Lausanne, Inst Pharmacognosie & Phytochim, BEP, CH-1015 Lausanne, Switzerland
[2] Ctr Natl Rech Ind & Technol, Antananarivo 101, Madagascar
[3] Univ Neuchatel, Inst Chim, CH-2000 Neuchatel, Switzerland
[4] Ecole Super Polytech, Antananarivo 101, Madagascar
关键词
Ravensara anisata; Lauraceae; antifungal activity; Cladosporium cucumerinum; Candida albicans; alpha-pyrones; X-ray analysis;
D O I
10.1016/S0031-9422(99)00158-2
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
The leaves and bark dichloromethane extracts of Ravensara anisata showed antifungal activity against the yeast Candida albicans and the phytopathogenic fungus Cladosporium cucumerinum in bioautographic TLC assays. Activity-guided fractionation afforded two new alpha-pyrones: 6R(*)-(4R(*)-acetoxy-2S(*)-hydroxy-8-phenyloctyl)-5, 6-dihydro-2-H-pyran-2-one and 6R(*)(2S(*)-acetoxy-4R(*)-hydroxy-8-phenyloctyl)-5,6-dihydro-2-H-pyran-2-one. Their structures have been established by NMR spectroscopy, chemical methods and X-ray crystallographic analysis. The antifungal activity against C. albicans and C. cucumerinum was determined for both compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:265 / 269
页数:5
相关论文
共 18 条
[1]  
De Medici D., 1992, Flavour and Fragrance Journal, V7, P275, DOI 10.1002/ffj.2730070509
[2]  
DREWES SE, 1994, PHYTOCHEMISTRY, V44, P333
[3]   NOVEL BIOACTIVE STYRYL-LACTONES - GONIOFUFURONE, GONIOPYPYRONE, AND 8-ACETYLGONIOTRIOL FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) - X-RAY MOLECULAR-STRUCTURE OF GONIOFUFURONE AND OF GONIOPYPYRONE [J].
FANG, XP ;
ANDERSON, JE ;
CHANG, CJ ;
FANWICK, PE ;
MCLAUGHLIN, JL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06) :1655-1661
[4]  
FU X, 1993, PHYTOCHEMISTRY, V33, P1272, DOI 10.1016/0031-9422(93)85065-Y
[5]   A NEW SPRAY REAGENT FOR PAPER CHROMATOGRAPHY OF POLYOLS AND CETOSES [J].
GODIN, P .
NATURE, 1954, 174 (4420) :134-134
[6]   COMPONENTS OF RAVENSARA-AROMATICA, A LAURACEA FROM MADAGASCAR [J].
GROEBEL, A ;
LENOIR, D ;
PERNET, R .
PLANTA MEDICA, 1970, 18 (01) :66-+
[7]   DIRECT BIOAUTOGRAPHY ON THIN-LAYER CHROMATOGRAMS AS A METHOD FOR DETECTING FUNGITOXIC SUBSTANCES [J].
HOMANS, AL ;
FUCHS, A .
JOURNAL OF CHROMATOGRAPHY, 1970, 51 (02) :327-&
[8]   SITOSTEROL 3-O-BETA-D-XYLOPYRANOSIDE FROM BAUHINIA-CANDICANS [J].
IRIBARREN, AM ;
POMILIO, AB .
PHYTOCHEMISTRY, 1984, 23 (09) :2087-2088
[9]  
Kostermans AJGH, 1950, FLORE MADAGASCAR COM, P46
[10]   EXOCARPIC ACID AND OTHER COMPOUNDS FROM TUBERS AND INFLORESCENCES OF SARCOPHYTE-SANGUINEA [J].
NAIDOO, LAC ;
DREWES, SE ;
VANSTADEN, J ;
HUTCHINGS, A .
PHYTOCHEMISTRY, 1992, 31 (11) :3929-3931