Insect-synthesised retronecine ester alkaloids: precursors of the common arctiine (Lepidoptera) pheromone hydroxydanaidal.
Many pyrrolizidine alkaloid (PA)-adapted insects convert PAs sequestered from their larval host plants into "insect-PAs" in which the acid components of the alkaloids are replaced by small, branched aliphatic 2-hydroxy acids of insect origin. It has been proposed that insect-PAs are precursors of the pheromone hydroxydanaidal in male Estigmene acrea moths, but it is not clear why they are specifically required or what the structural features or chemical properties are that make insect-PAs more suitable for conversion into hydroxydanaidal than superficially similar alkaloids of plant origin. Evidence is presented that insect-PAs are also precursors of hydroxydanaidal in the polyphageous arctiine, Creatonotos transiens, and a new biosynthetic pathway to hydroxydanaidal is proposed that has a mandatory requirement for insect-PAs as intermediates.
Edgar
John A
JA
CSIRO Livestock Industries, Private Bag 24, Geelong, Victoria, 3220, Australia.
Boppré
Michael
M
Kaufmann
Eva
E
D000470:Alkaloids / Q000096:biosynthesis*; D000818:Animals; D002853:Chromatography, Liquid; D002855:Chromatography, Thin Layer; D008401:Gas Chromatography-Mass Spectrometry; D007915:Lepidoptera / Q000378:metabolism*; D010675:Pheromones / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000378:metabolism*
D000470:Alkaloids; D010675:Pheromones; D011763:Pyrrolizidine Alkaloids; C014795:retronecine; C071252:hydroxydanaidal