BIOSYNTHESIS OF A DEFENSIVE INSECT ALKALOID - EPILACHNENE FROM OLEIC-ACID AND SERINE

被引:30
作者
ATTYGALLE, AB [1 ]
BLANKESPOOR, CL [1 ]
EISNER, T [1 ]
MEINWALD, J [1 ]
机构
[1] CORNELL UNIV,NEUROBIOL & BEHAV SECT,ITHACA,NY 14853
关键词
INSECTA; COCCINELLIDAE; MACROLIDE; STABLE ISOTOPE LABELING;
D O I
10.1073/pnas.91.26.12790
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
The biosynthesis of the azamacrolide epilachnene by the coccinellid beetle Epilachna varivestis has been studied with H-2-labeled oleic acid, H-2-labeled L-serine, and C-13,N-15-labeled L-serine. The incorporation of these precursors into epilachnene defines the origin of the alkaloid's entire carbon/nitrogen skeleton. GC/MS and GC/IR studies of alkaloid produced by Epilachna fed with deuteriated oleic acid show that oleic acid loses four carbon atoms from its carboxyl end during the biosynthesis. Other details, including the mechanism of carbon-nitrogen bond formation between the fatty acid and amino acid moieties, remain to be established.
引用
收藏
页码:12790 / 12793
页数:4
相关论文
共 7 条
[1]   BIOSYNTHESIS OF METHACRYLIC-ACID AND ISOBUTYRIC ACIDS IN A CARABID BEETLE, SCARITES-SUBTERRANEUS [J].
ATTYGALLE, AB ;
MEINWALD, J ;
EISNER, T .
TETRAHEDRON LETTERS, 1991, 32 (37) :4849-4852
[2]   AZAMACROLIDES - A FAMILY OF ALKALOIDS FROM THE PUPAL DEFENSIVE SECRETION OF A LADYBIRD BEETLE (EPILACHNA-VARIVESTIS) [J].
ATTYGALLE, AB ;
MCCORMICK, KD ;
BLANKESPOOR, CL ;
EISNER, T ;
MEINWALD, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (11) :5204-5208
[3]   GAS-PHASE INFRARED-SPECTROSCOPY FOR DETERMINATION OF DOUBLE-BOND CONFIGURATION OF MONOUNSATURATED COMPOUNDS [J].
ATTYGALLE, AB ;
SVATOS, A ;
WILCOX, C ;
VOERMAN, S .
ANALYTICAL CHEMISTRY, 1994, 66 (10) :1696-1703
[4]  
Blum M., 1981, CHEM DEFENSES ARTHRO
[5]  
Jones T. H., 1983, ALKALOIDS CHEM BIOL, V1, P33
[6]   SPERMATOPHORE SIZE AS DETERMINANT OF PATERNITY IN AN ARCTIID MOTH (UTETHEISA ORNATRIX) [J].
LAMUNYON, CW ;
EISNER, T .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (15) :7081-7084
[7]   THE CHEMICAL DEFENSE OF DORYPHORINA BEETLES (COLEOPTERA, CHRYSOMELIDAE) [J].
TIMMERMANS, M ;
RANDOUX, T ;
DALOZE, D ;
BRAEKMAN, JC ;
PASTEELS, JM ;
LESAGE, L .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1992, 20 (04) :343-349