Iridoid sex pheromone biosynthesis in aphids mimics iridoid‐producing plants

Partridge, Suzanne J., Withall, David M., Caulfield, John C., Pickett, John A. ORCID: https://orcid.org/0000-0002-1008-6595, Stockman, Robert A., Oldham, Neil J. and Birkett, Michael A. 2021. Iridoid sex pheromone biosynthesis in aphids mimics iridoid‐producing plants. Chemistry - A European Journal 27 (25) , pp. 7231-7234. 10.1002/chem.202001356

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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	0947-6539
Funders:	BBSRC Rothamsted-University of Nottingham Doctoral Training Programme (DTP) studentship
Date of First Compliant Deposit:	20 April 2021
Date of Acceptance:	11 March 2021
Last Modified:	16 Nov 2024 11:00
URI:	https://orca.cardiff.ac.uk/id/eprint/140555

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