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.
引用
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页码:4426 / 4431
页数:6
相关论文
共 23 条
[11]   C-13 NUCLEAR MAGNETIC-RESONANCE OF POLY-HETERO-ATOMIC PENTAGONAL HETEROCYCLES - THIAZOLES AND THIAZOLO [2,3-E]TETRAZOLES [J].
FAURE, R ;
GALY, JP ;
VINCENT, EJ ;
ELGUERO, J .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (01) :46-55
[12]   NEW CYTO-TOXIC ACRIDINE ALKALOIDS FROM 2 DEEP-WATER MARINE SPONGES OF THE FAMILY PACHASTRELLIDAE [J].
GUNAWARDANA, GP ;
KOHMOTO, S ;
BURRES, NS .
TETRAHEDRON LETTERS, 1989, 30 (33) :4359-4362
[13]   DERCITIN, A NEW BIOLOGICALLY-ACTIVE ACRIDINE ALKALOID FROM A DEEP-WATER MARINE SPONGE, DERCITUS SP [J].
GUNAWARDANA, GP ;
KOHMOTO, S ;
GUNASEKERA, SP ;
MCCONNELL, OJ ;
KOEHN, FE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4856-4858
[14]  
Karuso P., 1987, BIOORGANIC MARINE CH, V1, P31, DOI DOI 10.1007/978-3-642-72726-9_2
[15]  
KLENAR VS, 1987, J MAGN RESON, V71, P379
[16]   ASCIDIDEMIN, A NOVEL PENTACYCLIC AROMATIC ALKALOID WITH POTENT ANTILEUKEMIC ACTIVITY FROM THE OKINAWAN TUNICATE DIDEMNUM SP [J].
KOBAYASHI, J ;
CHENG, JF ;
NAKAMURA, H ;
OHIZUMI, Y ;
HIRATA, Y ;
SASAKI, T ;
OHTA, T ;
NOZOE, S .
TETRAHEDRON LETTERS, 1988, 29 (10) :1177-1180
[17]   CYSTODYTIN-A, CYSTODYTIN-B, AND CYSTODYTIN-C, NOVEL TETRACYCLIC AROMATIC ALKALOIDS WITH POTENT ANTINEOPLASTIC ACTIVITY FROM THE OKINAWAN TUNICATE CYSTODYTES-DELLECHIAJEI [J].
KOBAYASHI, J ;
CHENG, JF ;
WALCHLI, MR ;
NAKAMURA, H ;
HIRATA, Y ;
SASAKI, T ;
OHIZUMI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1800-1804
[18]  
LAMBERT G, 1980, VELIGER, V22, P340
[19]   NEW ALKALOIDS OF THE LAMELLARIN CLASS FROM THE MARINE ASCIDIAN DIDEMNUM-CHARTACEUM (SLUITER, 1909) [J].
LINDQUIST, N ;
FENICAL, W ;
VANDUYNE, GD ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4570-4574
[20]   PETROSAMINE, A NOVEL PIGMENT FROM THE MARINE SPONGE PETROSIA SP [J].
MOLINSKI, TF ;
FAHY, E ;
FAULKNER, DJ ;
VANDUYNE, GD ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1340-1341