Two novel pyrrole-imidazole alkaloids from the Mediterranean sponge Agelas oroides

被引:91
作者
Fattorusso, E [1 ]
Taglialatela-Scafati, O [1 ]
机构
[1] Univ Naples, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy
关键词
marine metabolites; biologically active compounds; alkaloids; stereochemistry;
D O I
10.1016/S0040-4039(00)01764-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The novel pyrrole-imidazole alkaloids cyclooroidin (7) and taurodispacamide A (8) have been isolated from the Mediterranean sponge Agelas oroides, and their structures established from spectroscopic data. Although both these alkaloids may be conceived as derivatives of the C11N5 skeleton of the known oroidin (1), remarkably cyclooroidin (7) possesses the unprecedented N1/C9 connection. Tauro-dispacamide A (8) exhibited a good antihistaminic activity, tested on the isolated guinea pig ileum. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9917 / 9922
页数:6
相关论文
共 16 条
[1]   Anti-histaminic activity of bromopyrrole alkaloids isolated from Caribbean Agelas sponges [J].
Cafieri, F ;
Carnuccio, R ;
Fattorusso, E ;
TaglialatelaScafati, O ;
Vallefuoco, T .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (17) :2283-2288
[2]   Dispacamides, anti-histamine alkaloids from Caribbean Agelas sponges [J].
Cafieri, F ;
Fattorusso, E ;
Mangoni, A ;
TaglialatelaScafati, O .
TETRAHEDRON LETTERS, 1996, 37 (20) :3587-3590
[3]   LONGAMIDE AND 3,7-DIMETHYLISOGUANINE, 2 NOVEL ALKALOIDS FROM THE MARINE SPONGE AGELAS-LONGISSIMA [J].
CAFIERI, F ;
FATTORUSSO, E ;
MANGONI, A ;
TAGLIALATELASCAFATI, O .
TETRAHEDRON LETTERS, 1995, 36 (43) :7893-7896
[4]   AGELASTATIN-A, A NEW SKELETON CYTOTOXIC ALKALOID OF THE OROIDIN FAMILY - ISOLATION FROM THE AXINELLID SPONGE AGELAS-DENDROMORPHA OF THE CORAL SEA [J].
DAMBROSIO, M ;
GUERRIERO, A ;
DEBITUS, C ;
RIBES, O ;
PUSSET, J ;
LEROY, S ;
PIETRA, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (16) :1305-1306
[5]   THE STRUCTURE OF DIBROMOISOPHAKELLIN FROM THE MARINE SPONGE ACANTHELLA-CARTERI [J].
FEDOREYEV, SA ;
UTKINA, NK ;
ILYIN, SG ;
RESHETNYAK, MV ;
MAXIMOV, OB .
TETRAHEDRON LETTERS, 1986, 27 (27) :3177-3180
[6]   THE STRUCTURE OF DIBROMOAGELASPONGIN - A NOVEL BROMINE-CONTAINING GUANIDINE DERIVATIVE FROM THE MARINE SPONGE AGELAS-SP [J].
FEDOREYEV, SA ;
ILYIN, SG ;
UTKINA, NK ;
MAXIMOV, OB ;
RESHETNYAK, MV ;
ANTIPIN, MY ;
STRUCHKOV, YT .
TETRAHEDRON, 1989, 45 (11) :3487-3492
[7]   NEW BROMO-PYRROLE DERIVATIVES FROM SPONGE AGELAS-OROIDES [J].
FORENZA, S ;
MINALE, L ;
RICCIO, R .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (18) :1129-&
[8]  
Jaffe H. H., 1962, THEORY APPL UV SPECT, P350
[9]   MAURITAMIDE-A AND ACCOMPANYING OROIDIN ALKALOIDS FROM THE SPONGE AGELAS-MAURITIANA [J].
JIMENEZ, C ;
CREWS, P .
TETRAHEDRON LETTERS, 1994, 35 (09) :1375-1378
[10]  
KITAGAWA I, 1983, CHEM PHARM BULL, V31, P2321