Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 25, Pages 7231-7234Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001356
Keywords
biosynthesis; mass spectrometry; molecular probe; pea aphid; sex pheromone
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Funding
- BBSRC Rothamsted-University of Nottingham Doctoral Training Programme (DTP) studentship
- Biotechnology and Biological Sciences Research Council's Industrial Strategy Challenge Fund [BBS/OS/CP/000001]
- Biotechnology and Biological Sciences Research Council [BBS/OS/CP/000001] Funding Source: researchfish
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This study investigated the biosynthesis of nepetalactol and nepetalactone in pea aphids using isotopically-labeled monoterpenoids as molecular probes. The results suggest that iridoid biosynthesis in animals, specifically aphids, may follow a broadly similar route to that characterized for plants.
Biosynthesis of (1R,4aS,7S,7aR)-nepetalactol (1) and (4aS,7S,7aR)-nepetalactone (2) in plants involves iridoid synthase (ISY), an atypical reductive cyclase that catalyses the reduction of 8-oxogeranial into the reactive enol of (S)-8-oxocitronellal, and cyclization of this enol intermediate, either non-enzymatically or by a nepetalactol-related short chain dehydrogenase enzyme (NEPS) that yields the nepetalactols. In this study, we investigated the biosynthesis in vivo of 1 and 2 in the pea aphid, Acyrthosiphon pisum, using a library of isotopically-labelled monoterpenoids as molecular probes. Topical application of deuterium-labelled probes synthesized from geraniol and nerol resulted in production of H-2(4)-lactol 1 and H-2(4)-lactone 2. However, deuterium incorporation was not evident using labelled probes synthesized from (S)-citronellol. These results suggest that iridoid biosynthesis in animals, specifically aphids, may follow a broadly similar route to that characterised for plants.
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