Muricadienin, muridienins and chatenaytrienins, the early precursors of annonaceous acetogenins

被引:43
作者
Gleye, C
Raynaud, S
Hocquemiller, R
Laurens, A
Fourneau, C
Serani, L
Laprévote, O
Roblot, F
Leboeuf, M
Fournet, A
De Arias, AR
Figadère, B
Cavé, A
机构
[1] Univ Paris Sud, Fac Pharm, URA 1843 CNRS, BIOCIS,Lab Pharmacognosie, F-92296 Chatenay Malabry, France
[2] CNRS, Inst Chim Subst Nat, Lab Spectrometrie Masse, F-91198 Gif Sur Yvette, France
[3] IICS, Asuncion, Paraguay
关键词
Annona muricata; A-nutans; Annonaceae; acetogenins; oxidative degradation; enzymatic oxidation; tris-unsaturated fatty acid derivatives; biogenetic pathway;
D O I
10.1016/S0031-9422(97)00908-4
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
Chatenaytrienins-1,-2 and -3, muridienins-3 and -4 and muricadienin were characterized by tandem mass spectrometry (MS/MS) in a mixture of natural precursors of annonaceous acetogenins from Annona muricata. Chatenaytrienin-1, -2, -3 and -4 were then isolated from A. nutans and fully characterized by spectroscopic methods (NMR, MS) and by chemical and enzymatic oxidative processes. Isolation of these trienes confirmed the postulated biosynthetic pathway leading to the acetogenins. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:749 / 754
页数:6
相关论文
共 26 条
[1]   NEW DELTA(5,9)-FATTY-ACIDS IN THE PHOSPHOLIPIDS OF THE SEA-ANEMONE STOICHACTIS-HELIANTHUS [J].
CARBALLEIRA, NM ;
MEDINA, JR .
JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1994, 57 (12) :1688-1695
[2]  
Cave A, 1997, Fortschr Chem Org Naturst, V70, P81
[3]  
CAVE A, 1993, RECENT ADV PHYTOCHEM, V27, P167
[4]   Epomusenins A and B, two acetogenins from fruits of Rollinia mucosa [J].
Chen, YY ;
Chang, FR ;
Yen, HF ;
Wu, YC .
PHYTOCHEMISTRY, 1996, 42 (04) :1081-1083
[5]   VENEZENIN - A NEW BIOACTIVE ANNONACEOUS ACETOGENIN FROM THE BARK OF XYLOPIA-AROMATICA [J].
COLMANSAIZARBITORIA, T ;
GU, ZM ;
ZHAO, GX ;
ZENG, L ;
KOZLOWSKI, JF ;
MCLAUGHLIN, JL .
JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (04) :532-539
[6]   Coriadienin, the first Annonaceous acetogenin with two double bonds isolated from Annona coriaceae [J].
daSilva, ELM ;
Roblot, F ;
Mahuteau, J ;
Cave, A .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (05) :528-530
[7]   Assignment of absolute configuration of the alpha,beta-unsaturated gamma-methyl-gamma-lactone of the annonaceous acetogenins by a simple enzymatic method [J].
Duret, P ;
Waechter, AI ;
Figadere, B ;
Hocquemiller, R ;
Cave, A ;
Pierard, C ;
Peres, M .
TETRAHEDRON LETTERS, 1996, 37 (39) :7043-7046
[8]   NATURAL SUBSTANCES (ACETOGENINS) FROM THE FAMILY ANNONACEAE ARE POWERFUL INHIBITORS OF MITOCHONDRIAL NADH DEHYDROGENASE (COMPLEX-I) [J].
ESPOSTI, MD ;
GHELLI, A ;
RATTA, M ;
CORTES, D ;
ESTORNELL, E .
BIOCHEMICAL JOURNAL, 1994, 301 :161-167
[9]   A NEW-TYPE OF CYTOTOXIC ANNONACEOUS ACETOGENIN - GIGANIN FROM GONIOTHALAMUS-GIGANTEUS [J].
FANG, XP ;
SONG, R ;
GU, ZM ;
RIESER, MJ ;
MIESBAUER, LR ;
SMITH, DL ;
MCLAUGHLIN, JL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (06) :1153-1156
[10]   2 BINDING-SITES FOR NATURALLY-OCCURRING INHIBITORS IN MITOCHONDRIAL AND BACTERIAL NADH-UBIQUINONE OXIDOREDUCTASE (COMPLEX-I) [J].
FRIEDRICH, T ;
OHNISHI, T ;
FORCHE, E ;
KUNZE, B ;
JANSEN, R ;
TROWITZSCH, W ;
HOFLE, G ;
REICHENBACH, H ;
WEISS, H .
BIOCHEMICAL SOCIETY TRANSACTIONS, 1994, 22 (01) :226-230