Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid-Producing Plants

A - Papers appearing in refereed journals

Partridge, S., Withall, D., Caulfield, J. C., Pickett, J. A., Stockman, R. A,, Oldham, N. J. and Birkett, M. A. 2021. Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid-Producing Plants . Chemistry-A European Journal. 27 (25), pp. 7231-7234. https://doi.org/10.1002/chem.202001356

AuthorsPartridge, S., Withall, D., Caulfield, J. C., Pickett, J. A., Stockman, R. A,, Oldham, N. J. and Birkett, M. A.
Abstract

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 2H4-lactol 1 and 2H4-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.

Year of Publication2021
JournalChemistry-A European Journal
Journal citation27 (25), pp. 7231-7234
Digital Object Identifier (DOI)https://doi.org/10.1002/chem.202001356
Open accessPublished as green open access
FunderBiotechnology and Biological Sciences Research Council
Funder project or codeSWBio DTP PhD studentship
Publisher's version
Supplemental file
Output statusPublished
Publication dates
Online13 Apr 2021
Publication process dates
AcceptedMar 2021
PublisherWiley-V C H Verlag Gmbh
ISSN0947-6539

Permalink - https://repository.rothamsted.ac.uk/item/98392/iridoid-sex-pheromone-biosynthesis-in-aphids-mimics-iridoid-producing-plants

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