KUANONIAMINE-A, KUANONIAMINE-B, KUANONIAMINE-C, AND KUANONIAMINE-D - PENTACYCLIC ALKALOIDS FROM A TUNICATE AND ITS PROSOBRANCH MOLLUSK PREDATOR CHELYNOTUS-SEMPERI

被引:141
作者
CARROLL, AR [1 ]
SCHEUER, PJ [1 ]
机构
[1] UNIV HAWAII,DEPT CHEM,HONOLULU,HI 96822
关键词
D O I
10.1021/jo00301a040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
From a Micronesian tunicate and its predator, a prosobranch mollusk Chelynotus semperi, we have isolated five alkaloids, the known shermilamine B (1) and four new pentacyclic compounds, kuanoniamines A-D (2–5). The structures were established by extensive NMR analysis and correlations. Cytotoxicity (IC50) against KB cells ranged from >10 ug/mL for 3 to 5 ug/mL for 1 and 5 to 1 ug/mL for 2. © 1990, American Chemical Society. All rights reserved.
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页码:4426 / 4431
页数:6
相关论文
共 23 条
[1]   METABOLITIES OF THE MARINE PROSOBRANCH MOLLUSK LAMELLARIA SP [J].
ANDERSEN, RJ ;
FAULKNER, DJ ;
HE, CH ;
VANDUYNE, GD ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5492-5495
[2]   H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].
BAX, A ;
SUMMERS, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094
[3]   STRUCTURE ELUCIDATION OF THE ANTIBIOTIC DESERTOMYCIN THROUGH THE USE OF NEW TWO-DIMENSIONAL NMR TECHNIQUES [J].
BAX, A ;
ASZALOS, A ;
DINYA, Z ;
SUDO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8056-8063
[4]  
BEHRENS DW, 1980, VELIGER, V22, P323
[5]  
Berger S., 1984, 13C NMR SPEKTROSKOPI
[6]   A NOVEL PENTACYCLIC AROMATIC ALKALOID FROM AN ASCIDIAN [J].
BLOOR, SJ ;
SCHMITZ, FJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :6134-6136
[7]   A 2ND SHERMILAMINE ALKALOID FROM A TUNICATE TRIDIDEMNUM SP [J].
CARROLL, AR ;
COORAY, NM ;
POINER, A ;
SCHEUER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4231-4232
[8]   DIPLAMINE, A CYTO-TOXIC POLYAROMATIC ALKALOID FROM THE TUNICATE DIPLOSOMA SP [J].
CHARYULU, GA ;
MCKEE, TC ;
IRELAND, CM .
TETRAHEDRON LETTERS, 1989, 30 (32) :4201-4202
[9]   CHEMISTRY OF 2-BROMOLEPTOCLINIDINONE, STRUCTURE REVISION [J].
DEGUZMAN, FS ;
SCHMITZ, FJ .
TETRAHEDRON LETTERS, 1989, 30 (09) :1069-1070
[10]   DISTORTIONLESS ENHANCEMENT OF NMR SIGNALS BY POLARIZATION TRANSFER [J].
DODDRELL, DM ;
PEGG, DT ;
BENDALL, MR .
JOURNAL OF MAGNETIC RESONANCE, 1982, 48 (02) :323-327