| Title: | Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid-Producing Plants |
| Author(s): | Partridge SJ; Withall DM; Caulfield JC; Pickett JA; Stockman RA; Oldham NJ; Birkett MA; |
| Address: | "Biointeractions and Crop Protection Department, Rothamsted Research, Harpenden, Hertfordshire, AL5 2JQ, UK. School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK. School of Chemistry, Cardiff University, Cardiff, CF10 3AT, UK" |
| ISSN/ISBN: | 1521-3765 (Electronic) 0947-6539 (Linking) |
| 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 (2) H(4) -lactol 1 and (2) H(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" |
| Keywords: | Animals *Aphids Iridoids Monoterpenes Secondary Metabolism *Sex Attractants biosynthesis mass spectrometry molecular probe pea aphid sex pheromone; |
| Notes: | "MedlinePartridge, Suzanne J Withall, David M Caulfield, John C Pickett, John A Stockman, Robert A Oldham, Neil J Birkett, Michael A eng BBS/OS/CP/000001/BBSRC Rothamsted-University of Nottingham/ Biotechnology and Biological Sciences Research Council's Industrial Strategy Challenge Fund/ BB_/Biotechnology and Biological Sciences Research Council/United Kingdom Germany 2021/04/15 Chemistry. 2021 May 3; 27(25):7231-7234. doi: 10.1002/chem.202001356. Epub 2021 Apr 13" |
