Bromotyrosine-derived metabolites from the sponge Aiolochroia crassa

被引:35
作者
Gao, HF
Kelly, M
Hamann, MT [1 ]
机构
[1] Univ Mississippi, Dept Pharmacognosy, University, MS 38677 USA
[2] Univ Mississippi, Sch Pharm, Nat Ctr Dev Nat Prod, University, MS 38677 USA
[3] UNITEC Inst Technol, Fac Hlth Sci & Technol, Auckland, New Zealand
关键词
antibiotics; marine metabolites; spiro compounds;
D O I
10.1016/S0040-4020(99)00553-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A chemical investigation of secondary metabolites from the sponge Aiolochroia crassa has been performed and five bromotyrosine derivatives (1-5) were identified. Their structures have been assigned on the basis of spectroscopic analysis, of which araplysillin III (2) and hexadellin C (3) possess new structures. The absolute configurations of dibromotyrosine moieties of 2 were determined by HPLC analysis of derivatized constituent amino acids obtained from acid hydrolysis. The stereochemistry of the spirocyclohexadienylisoxazoline moiety of compounds 1-3 was deduced from spectroscopic comparison of the same moiety of aerothionin, of which the absolute configuration was previously assigned by X-ray and CD analysis. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9717 / 9726
页数:10
相关论文
共 14 条
[1]   CHEMISTRY OF VERONGIDA SPONGES .1. CONSTITUENTS OF THE CARIBBEAN SPONGE PSEUDOCERATINA-CRASSA [J].
ALBRIZIO, S ;
CIMINIELLO, P ;
FATTORUSSO, E ;
MAGNO, S ;
PANSINI, M .
TETRAHEDRON, 1994, 50 (03) :783-788
[2]   NEW METHOD OF QUATERNIZING AMINES AND ITS USE IN AMINO-ACID AND PEPTIDE CHEMISTRY [J].
CHEN, FCM ;
BENOITON, NL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (20) :3310-3311
[3]   Chemistry of Verongida sponges.: 9.: Secondary metabolite composition of the Caribbean sponge Aplysina cauliformis [J].
Ciminiello, P ;
Dell'Aversano, C ;
Fattorusso, E ;
Magno, S ;
Pansini, M .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (04) :590-593
[4]   THE SYNTHESIS OF [C-14] AND [H-3(2)] SK-AND-F L-94901 - A NOVEL THYROMIMETIC [J].
CROWE, AM ;
LAWRIE, KWM ;
SAUNDERS, D .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1988, 25 (07) :763-772
[5]   Structurally novel bioconversion products of the marine natural product sarcophine effectively inhibit JB6 cell transformation [J].
El Sayed, KA ;
Hamann, MT ;
Waddling, CA ;
Jensen, C ;
Lee, SK ;
Dunstan, CA ;
Pezzuto, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7449-7455
[6]  
Gopichand Y., 1979, TETRAHEDRON LETT, V20, P3921
[7]   2 NEW DIBROMOTYROSINE DERIVATIVES FROM THE CARIBBEAN SPONGE PSEUDOCERATINA-CRASSA [J].
KASSUHLKE, KE ;
FAULKNER, DJ .
TETRAHEDRON, 1991, 47 (10-11) :1809-1814
[8]   IANTHELLINE, A NEW DERIVATIVE OF 3,5-DIBROMO-TYROSINE ISOLATED FROM THE SPONGE IANTHELLA-ARDIS FROM THE BAHAMAS [J].
LITAUDON, M ;
GUYOT, M .
TETRAHEDRON LETTERS, 1986, 27 (37) :4455-4456
[9]   ARAPLYSILLIN-I AND ARAPLYSILLIN-II - BIOLOGICALLY-ACTIVE DIBROMOTYROSINE DERIVATIVES FROM THE SPONGE PSAMMAPLYSILLA-ARABICA [J].
LONGEON, A ;
GUYOT, M ;
VACELET, J .
EXPERIENTIA, 1990, 46 (05) :548-550
[10]   COMPARATIVE-STUDY OF THE HALOGENATED TYROSINE DERIVATIVES FROM DEMOSPONGIAE (PORIFERA) [J].
MAKARIEVA, TN ;
STONIK, VA ;
ALCOLADO, P ;
ELYAKOV, YB .
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY, 1981, 68 (03) :481-484