TY - JOUR
T1 - Biosynthesis of a defensive insect alkaloid
T2 - Epilachnene from oleic acid and serine
AU - Attygalle, Athula B.
AU - Blankespoor, Curtis L.
AU - Eisner, Thomas
AU - Meinwald, Jerrold
PY - 1994/12/20
Y1 - 1994/12/20
N2 - 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.
AB - 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.
KW - Coccinellidae
KW - Insecta
KW - macrolide
KW - stable isotope labeling
UR - http://www.scopus.com/inward/record.url?scp=0028598677&partnerID=8YFLogxK
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U2 - 10.1073/pnas.91.26.12790
DO - 10.1073/pnas.91.26.12790
M3 - Article
C2 - 7809122
AN - SCOPUS:0028598677
SN - 0027-8424
VL - 91
SP - 12790
EP - 12793
JO - Proceedings of the National Academy of Sciences of the United States of America
JF - Proceedings of the National Academy of Sciences of the United States of America
IS - 26
ER -