一种防御性昆虫生物碱的生物合成：源自油酸和丝氨酸的表毛链菌素
Biosynthesis of a defensive insect alkaloid: epilachnene from oleic acid and serine.
作者信息
Attygalle A B, Blankespoor C L, Eisner T, Meinwald J
机构信息
Department of Chemistry, Cornell University, Ithaca, NY 14853-1301.
出版信息
Proc Natl Acad Sci U S A. 1994 Dec 20;91(26):12790-3. doi: 10.1073/pnas.91.26.12790.
The biosynthesis of the azamacrolide epilachnene by the coccinellid beetle Epilachna varivestis has been studied with 2H-labeled oleic acid, 2H-labeled L-serine, and 13C,15N-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.
利用2H标记的油酸、2H标记的L-丝氨酸以及13C、15N标记的L-丝氨酸，对瓢虫Epilachna varivestis合成氮杂大环内酯类化合物表毛菌素的过程进行了研究。这些前体物质掺入表毛菌素的情况确定了该生物碱整个碳/氮骨架的来源。对用氘代油酸喂养的Epilachna所产生的生物碱进行的气相色谱/质谱（GC/MS）和气相色谱/红外光谱（GC/IR）研究表明，油酸在生物合成过程中从其羧基端失去了四个碳原子。包括脂肪酸和氨基酸部分之间碳氮键形成机制在内的其他细节仍有待确定。
Zotero 插件