Absolute stereochemistry of cicutoxin and related toxic polyacetylenic alcohols from Cicuta virosa

被引：30

作者：

Ohta, T ^{[1
]}

Uwai, K

Kikuchi, R

Nozoe, S

Oshima, Y

Sasaki, K

Yoshizaki, F

机构：

[1] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9200934, Japan

[2] Tohoku Univ, Grad Sch Pharmaceut Sci, Sendai, Miyagi 9800856, Japan

[3] Tohoku Coll Pharm, Sendai, Miyagi 9810905, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 41期

关键词：

polyacetylenic alcohols; optical properties; stereochemistry;

D O I：

10.1016/S0040-4020(99)00706-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute stereostructures of cicutoxin (1) and related toxic polyacetylenic alcohols, isocicutoxin (2), and virols A (3) and C (4), from Cicuta virosa were determined on the basis of spectroscopic analysis. The CD exciton chirality method was successfully applied to 4-methoxybenzoates of dyne-conjugated polyenyl alcohol systems. Fatal doses of these compounds on mice are also reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：12087 / 12098

页数：12

共 19 条

[1]

ANET E, 1952, CHEM IND-LONDON, P757

[2] OENANTHOTOXIN AND CICUTOXIN - ISOLATION AND STRUCTURES [J].

ANET, EFLJ ;

LYTHGOE, B ;

SILK, MH ;

TRIPPETT, S .

JOURNAL OF THE CHEMICAL SOCIETY, 1953, (JAN) :309-322

[3] POLYACETYLENE COMPOUNDS .168. POLYYNES FROM CICUTA VIROSA L [J].

BOHLMANN, F ;

HANEL, P .

CHEMISCHE BERICHTE-RECUEIL, 1969, 102 (10) :3293-&

[4] POLYACETYLENE COMPOUNDS .147. POLYINES FROM OENANTHE CROCATA L [J].

BOHLMANN, F ;

RODE, KM .

CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (04) :1163-&

[5]

Harada N., 1983, CIRCULAR DICHROIC SP

[6] Cicutoxin - The poisonous principle in water hemlock (Cicuta) [J].

Jacobson, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1915, 37 :916-934

[7]

KNUTSEN OH, 1984, CLIN TOXICOL, V22, P157

[8] ANTITUMOR AGENTS .85. CICUTOXIN, AN ANTILEUKEMIC PRINCIPLE FROM CICUTA-MACULATA, AND THE CYTOTOXICITY OF THE RELATED DERIVATIVES [J].

KONOSHIMA, T ;

LEE, KH .

JOURNAL OF NATURAL PRODUCTS, 1986, 49 (06) :1117-1121

[9]

NORTH DS, 1985, WESTERN J MED, V143, P250

[10] HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].

OHTANI, I ;

KUSUMI, T ;

KASHMAN, Y ;

KAKISAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096

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