DEFENSE-MECHANISMS OF ARTHROPODS .61. LUCIBUFAGINS .2. ESTERS OF 12-OXO-2-BETA,5-BETA,11-ALPHA-TRIHYDROXYBUFALIN, THE MAJOR DEFENSIVE STEROIDS OF THE FIREFLY PHOTINUS-PYRALIS (COLEOPTERA, LAMPYRIDAE)

被引：54

作者：

MEINWALD, J ^{[1
]}

WIEMER, DF ^{[1
]}

EISNER, T ^{[1
]}

机构：

[1] CORNELL UNIV,NEUROBIOL & BEHAV SECT,ITHACA,NY 14853

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 11期

关键词：

D O I：

10.1021/ja00505a037

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fireflies of the species Photinus pyralis (Coleoptera: Lampyridae) are shown to contain a group of closely related steroidal pyrones, named lucibufagins, which serve a defensive role. The five major steroids from this insect are characterized as esters (5, 6, 7, 11, 12) of 12-oxo-2β, 5β, 11 α-trihydroxybufalin (9), chiefly on the basis of detailed spectral analyses. Selective proton decoupling 13C NMR experiments played a key role in making these structural assignments. These insect-derived steroids are the first bufadienolides to be isolated and characterized from an invertebrate source. © 1979, American Chemical Society. All rights reserved.

引用

页码：3055 / 3060

页数：6

共 19 条

[1]

BATTERHAM TJ, 1973, NMR SPECTRA SIMPLE H, P391

[2]

BROWN P, 1971, ORG MASS SPECTROM, V6, P47

[3]

CARLSON AD, 1978, AM SCI, V66, P340

[4] DEFENSE-MECHANISMS OF ARTHROPODS .59. LUCIBUFAGINS - DEFENSIVE STEROIDS FROM FIREFLIES PHOTINUS-IGNITUS AND PHOTINUS-MARGINELLUS (COLEOPTERA LAMPYRIDAE) [J].