Relative configuration of yessotoxin and isolation of two new analogs from toxic scallops

被引:108
作者
Satake, M [1 ]
Terasawa, K [1 ]
Kadowaki, Y [1 ]
Yasumoto, T [1 ]
机构
[1] TOHOKU UNIV, FAC AGR, AOBA KU, SENDAI, MIYAGI 981, JAPAN
关键词
D O I
10.1016/0040-4039(96)01286-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The relative configuration of yessotoxin (YTX) and ring conformations were determined by NMR experiments. Additionally two new analogs, 45-hydroxy YTX and 45,46,47-trinorYTX were isolated from toxic scallops. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:5955 / 5958
页数:4
相关论文
共 9 条
[1]  
AUNE T, 1989, BIOACT MOL, V10, P461
[2]   THE RELATIONSHIP OF BREVETOXIN LENGTH AND A-RING FUNCTIONALITY TO BINDING AND ACTIVITY IN NEURONAL SODIUM-CHANNELS [J].
GAWLEY, RE ;
REIN, KS ;
JEGLITSCH, G ;
ADAMS, DJ ;
THEODORAKIS, EA ;
TIEBES, J ;
NICOLAOU, KC ;
BADEN, DG .
CHEMISTRY & BIOLOGY, 1995, 2 (08) :533-541
[3]   ISOLATION AND STRUCTURE OF BREVETOXIN-B FROM THE RED TIDE DINOFLAGELLATE PTYCHODISCUS-BREVIS (GYMNODINIUM, BREVE) [J].
LIN, YY ;
RISK, M ;
RAY, SM ;
VANENGEN, D ;
CLARDY, J ;
GOLIK, J ;
JAMES, JC ;
NAKANISHI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (22) :6773-6775
[4]   STRUCTURES AND CONFIGURATIONS OF CIGUATOXIN FROM THE MORAY EEL GYMNOTHORAX-JAVA']JAVANICUS AND ITS LIKELY PRECURSOR FROM THE DINOFLAGELLATE GAMBIERDISCUS-TOXICUS [J].
MURATA, M ;
LEGRAND, AM ;
ISHIBASHI, Y ;
FUKUI, M ;
YASUMOTO, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4380-4386
[5]   ISOLATION AND STRUCTURE OF YESSOTOXIN, A NOVEL POLYETHER COMPOUND IMPLICATED IN DIARRHETIC SHELLFISH POISONING [J].
MURATA, M ;
KUMAGAI, M ;
LEE, JS ;
YASUMOTO, T .
TETRAHEDRON LETTERS, 1987, 28 (47) :5869-5872
[6]   NEGATIVE-ION FAST-ATOM-BOMBARDMENT TANDEM MASS-SPECTROMETRY FOR THE STRUCTURAL STUDY OF POLYETHER COMPOUNDS - STRUCTURAL VERIFICATION OF YESSOTOXIN [J].
NAOKI, H ;
MURATA, M ;
YASUMOTO, T .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 1993, 7 (03) :179-182
[7]   CONFORMATIONAL-ANALYSIS OF THE SODIUM-CHANNEL MODULATOR, BREVETOXIN-A, COMPARISON WITH BREVETOXIN-B CONFORMATIONS, AND A HYPOTHESIS ABOUT THE COMMON PHARMACOPHORE OF THE SITE-5 TOXINS [J].
REIN, KS ;
BADEN, DG ;
GAWLEY, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) :2101-2106
[8]   STRUCTURE OF BREVETOXIN-A (GB-1 TOXIN), THE MOST POTENT TOXIN IN THE FLORIDA RED TIDE ORGANISM GYMNODINIUM-BREVE (PTYCHODISCUS-BREVIS) [J].
SHIMIZU, Y ;
CHOU, HN ;
BANDO, H ;
VANDUYNE, G ;
CLARDY, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (03) :514-515
[9]   HISTOPATHOLOGICAL STUDIES ON EXPERIMENTAL MARINE TOXIN POISONING .5. THE EFFECTS IN MICE OF YESSOTOXIN ISOLATED FROM PATINOPECTEN-YESSOENSIS AND OF A DESULFATED DERIVATIVE [J].
TERAO, K ;
ITO, E ;
OARADA, M ;
MURATA, M ;
YASUMOTO, T .
TOXICON, 1990, 28 (09) :1095-1104