Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid‐Producing Plants

Partridge, Suzanne J.; Withall, David M.; Caulfield, John C.; Pickett, John A.; Stockman, Robert A.; Oldham, Neil J.; Birkett, Michael 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.

Citation

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

• Journal Article Type: Article
• Acceptance Date: Mar 10, 2021
• Online Publication Date: Apr 13, 2021
• Publication Date: May 3, 2021
• Deposit Date: Apr 21, 2021
• Publicly Available Date: Apr 14, 2022
• Journal: Chemistry - A European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 27
• Issue: 25
• Pages: 7231-7234
• DOI: https://doi.org/10.1002/chem.202001356
• Keywords: General Chemistry
• Public URL: https://nottingham-repository.worktribe.com/output/5469919
• Publisher URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202001356
• Additional Information: This is the peer reviewed version of the following article: Partridge, S.J., Withall, D.M., 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. Chem. Eur. J.., which has been published in final form at https://doi.org/10.1002/chem.202001356. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.