Ergosterimide, a new natural Diels-Alder adduct of a steroid and maleimide in the fungus Aspergillus niger

被引:42
作者
Zhang, Yi
Li, Xiao-Ming
Proksch, Peter
Wang, Bin-Gui [1 ]
机构
[1] Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
[3] Univ Dusseldorf, Inst Pharmazeut Biol & Biotechnol, D-40225 Dusseldorf, Germany
基金
中国国家自然科学基金;
关键词
brown alga; Colpomenia sinuosa; endophytic fungus; Aspergillus niger; ergosterimide; Diels-Alder adduct;
D O I
10.1016/j.steroids.2007.05.009
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
Ergosterimide (1), a natural Diels-Alder adduct of ergosteroid and maleimide, was characterized from the culture extract of Aspergillus niger EN-13, an endophytic fungus isolated from the marine brown alga Colpomenia sinuosa. In addition, four known steroids including (22E,24R)-ergosta-5,7,22-trien-3 beta-ol (2), (22E,24R)-ergosta-4,6,8(14),22-tetraen-3one (3), (22E,24R)-5 alpha,8 alpha-epidioxyergosta-6,22-dien-3 beta-ol (4), and (22E,24R)-ergosta-7,22dien-3 beta,5 alpha,6 beta-triol. (5) were also isolated and identified. The structures of these compounds were elucidated by extensive analysis of 1D and 2D NMR and IR spectra and MS data. The plausible biosynthetic pathway of 1 was also discussed. To the best of our knowledge, 1 is the first natural Diels-Alder adduct of steroid and maleimide reported so far. (C) 2007 Elsevier Inc. All rights reserved.
引用
收藏
页码:723 / 727
页数:5
相关论文
共 25 条
[1]   STRUCTURE OF ANTHERIDIOL A SEX HORMONE IN ACHLYA BISEXUALIS [J].
ARSENAULT, GP ;
BIEMANN, K ;
BARKSDALE, AW ;
MCMORRIS, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5635-+
[2]   A NEW STEROL FROM A STRAIN OF ASPERGILLUS-NIGER [J].
BARTON, DHR ;
BRUUN, T .
JOURNAL OF THE CHEMICAL SOCIETY, 1951, (OCT) :2728-2733
[3]  
Bondarenko-Gheorghiu LG, 2000, J SERB CHEM SOC, V65, P147
[4]   3-BETA,5-ALPHA,6-BETA-TRIHYDROXYSTEROLS FROM THE MEDITERRANEAN BRYOZOAN MYRIAPORA-TRUNCATA [J].
CAFIERI, F ;
FATTORUSSO, E ;
GAVAGNIN, M ;
SANTACROCE, C .
JOURNAL OF NATURAL PRODUCTS, 1985, 48 (06) :944-947
[5]   A modelling study of a non-concerted hydrolytic cycloaddition reaction by the catalytic antibody H11 [J].
Clark, RL ;
Johnston, BF ;
Suckling, CJ ;
Mackay, SP .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (08) :2674-2683
[6]   PERCEPTION OF FUNGAL STEROLS IN PLANTS - SUBNANOMOLAR CONCENTRATIONS OF ERGOSTEROL ELICIT EXTRACELLULAR ALKALINIZATION IN TOMATO CELLS [J].
GRANADO, J ;
FELIX, G ;
BOLLER, T .
PLANT PHYSIOLOGY, 1995, 107 (02) :485-490
[7]   STRUCTURES OF PHOSPHOLIPASE-A(2) INHIBITORS, ERGOPHILONE-A AND ERGOPHILONE-B [J].
HYODO, S ;
FUJITA, KI ;
KASUYA, O ;
TAKAHASHI, I ;
UZAWA, J ;
KOSHINO, H .
TETRAHEDRON, 1995, 51 (24) :6717-6724
[8]   Solanapyrones E-G, antialgal metabolites produced by a marine fungus [J].
Jenkins, KM ;
Toske, SG ;
Jensen, PR ;
Fenical, W .
PHYTOCHEMISTRY, 1998, 49 (08) :2299-2304
[9]   Enzymatic activity and partial purification of solanapyrone synthase: first enzyme catalyzing Diels-Alder reaction [J].
Katayama, K ;
Kobayashi, T ;
Oikawa, H ;
Honma, M ;
Ichihara, A .
BIOCHIMICA ET BIOPHYSICA ACTA-PROTEIN STRUCTURE AND MOLECULAR ENZYMOLOGY, 1998, 1384 (02) :387-395
[10]   Isolation of sterols from the marine fungus Corollospora lacera [J].
MacKenzie, SE ;
Gurusamy, GS ;
Piórko, A ;
Strongman, DB ;
Hu, TM ;
Wright, JLC .
CANADIAN JOURNAL OF MICROBIOLOGY, 2004, 50 (12) :1069-1072