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Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid‐Producing Plants
Author(s) -
Partridge Suzanne J.,
Withall David M.,
Caulfield John C.,
Pickett John A.,
Stockman Robert A.,
Oldham Neil J.,
Birkett Michael A.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001356
Subject(s) - acyrthosiphon pisum , nerol , biosynthesis , iridoid , lactol , stereochemistry , geraniol , chemistry , enol , citronellol , cyclase , biochemistry , biology , enzyme , aphididae , botany , lactone , glycoside , pest analysis , homoptera , essential oil , catalysis
Biosynthesis of (1 R ,4a S ,7 S ,7a R )‐nepetalactol ( 1 ) and (4a S ,7 S ,7a R) ‐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.