期刊
JOURNAL OF CHEMICAL ECOLOGY
卷 33, 期 5, 页码 963-970出版社
SPRINGER
DOI: 10.1007/s10886-007-9276-3
关键词
biosynthesis; defensive allomones; tiglic acid; 2-methylbutyric acid; ethacrylic acid; isoleucine; Carabid beetles pterostichus (Hypherpes) californicus; Carabidae
Tiglic, 2-methylbutyric, and ethacrylic acids are found in the pygidial gland defensive fluid of many carabid beetles. By injecting a deuterium-labeled precursor into the carabid beetle Pterostichus (Hypherpes) californicus, and analyzing the defensive fluid by gas chromatography/mass spectrometry, we were able to demonstrate that tiglic and ethacrylic acids are biosynthesized from isoleucine via 2-methylbutyric acid. Moreover, we observed that the injection of L-isoleucine induces an increased production of tiglic acid in P. californicus. A strong primary kinetic isotope effect was found to operate in the dehydrogenation step of 2-methylbutyric acid to tiglic and ethacrylic acids. Consequently, ethacrylic acid was found to preferentially accumulate the deuterium labeling from [2,3,4,4(-2)H(4)]isoleucine during our biosynthetic experiments.
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