IRCINOL-A AND IRCINOL-B, FIRST ANTIPODES OF MANZAMINE-RELATED ALKALOIDS FROM AN OKINAWAN MARINE SPONGE

被引：53

作者：

TSUDA, M ^{[1
]}

KAWASAKI, N ^{[1
]}

KOBAYASHI, J ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO 060,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 27期

关键词：

D O I：

10.1016/S0040-4020(01)85280-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new manzamine-related alkaloids, ircinols A (1) and B (2), have been isolated from the Okinawan marine sponge Amphimedon sp. and the structures elucidated to be enantiomers of alcoholic forms at C-1 of ircinals A and B, respectively, on the basis of extensive 2D NMR data and chemical correlations. Compounds 1 and 2 are the first examples possessing opposite absolute configurations to those of manzamine alkaloids.

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页码：7957 / 7960

页数：4

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共 10 条

[1] LANKALAPUOL-A AND LANKALAPUOL-B - 2 CIS-EUDESMANES FROM THE SEA HARE APLYSIA-DACTYLOMELA [J].

BAKER, B ;

RATNAPALA, L ;

MAHINDARATNE, MPD ;

DESILVA, ED ;

TILLEKERATNE, LMV ;

JEONG, JH ;

SCHEUER, PJ ;

SEFF, K .

TETRAHEDRON, 1988, 44 (15) :4695-4701

[2] ON THE BIOSYNTHESIS OF MANZAMINES [J].

BALDWIN, JE ;

WHITEHEAD, RC .

TETRAHEDRON LETTERS, 1992, 33 (15) :2059-2062

[3] MARINE-INVERTEBRATES FROM NEO-CALEDONIAN LAGOONS .5. ISOLATION AND IDENTIFICATION OF METABOLITES FROM A NEW SPECIES OF SPONGE, PSEUDAXINYSSA-CANTHARELLA [J].

DENANTEUIL, G ;

AHOND, A ;

GUILHEM, J ;

POUPAT, C ;

DAU, ETH ;

POTIER, P ;

PUSSET, M ;

PUSSET, J ;

LABOUTE, P .

TETRAHEDRON, 1985, 41 (24) :6019-6033

[4] 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

[5] NEW MANZAMINE ALKALOIDS FROM A SPONGE OF THE GENUS XESTOSPONGIA [J].

ICHIBA, T ;

SAKAI, R ;

KOHMOTO, S ;

SAUCY, G ;

HIGA, T .

TETRAHEDRON LETTERS, 1988, 29 (25) :3083-3086

[6] 8-HYDROXYMANZAMINE-A, A BETA-CARBOLINE ALKALOID FROM A SPONGE, PACHYPELLINA SP [J].

ICHIBA, T ;

CORGIAT, JM ;

SCHEUER, PJ ;

KELLYBORGES, M .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (01) :168-170

[7] IRCINAL-A AND IRCINAL-B FROM THE OKINAWAN MARINE SPONGE-IRCINIA SP - PLAUSIBLE BIOGENETIC PRECURSORS OF MANZAMINE ALKALOIDS [J].

KONDO, K ;

SHIGEMORI, H ;

KIKUCHI, Y ;

ISHIBASHI, M ;

SASAKI, T ;

KOBAYASHI, J .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2480-2483

[8] PHYSIOLOGICALLY ACTIVE MARINE NATURAL-PRODUCTS FROM PORIFERA .15. KERAMAMINE-A AND KERAMAMINE-B, NOVEL ANTIMICROBIAL ALKALOIDS FROM THE OKINAWAN MARINE SPONGE PELLINA SP [J].

NAKAMURA, H ;

DENG, SZ ;

KOBAYASHI, J ;

OHIZUMI, Y ;

TOMOTAKE, Y ;

MATSUZAKI, T ;

HIRATA, Y .

TETRAHEDRON LETTERS, 1987, 28 (06) :621-624

[9] MANZAMINE-A, A NOVEL ANTITUMOR ALKALOID FROM A SPONGE [J].

SAKAI, R ;

HIGA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6404-6405

[10] MANZAMINE-B AND MANZAMINE-C, 2 NOVEL ALKALOIDS FROM THE SPONGE HALICLONA SP [J].

SAKAI, R ;

KOHMOTO, S ;

HIGA, T .

TETRAHEDRON LETTERS, 1987, 28 (45) :5493-5496