Propionate as a Precursor of Juvenile Hormone in the Cecropia Moth

Abstract

Juvenile Hormone, Biosynthesis, Cecropia Moth Adult 3-4 day old males of the giant silk moth H yalophora cecropia incorporate the label of [1-14C] propionate and [1-14C]butyrate in JH-I and JH-II. [1-14C]propionate is used for the bio­ synthesis of the hormones as an intact C3-unit. Three possible intermediates in the biosynthesis of JH-I-(E,E,Z)-7-ethyl-3,11-dimethyl-2,6,10-tridecatrienoic acid, its methyl ester, and the cor­ responding alcohol - were converted in low yields to the hormone. Methyl 7-ethyl-3,11-dimethyl-tridecanoate was not incorporated. Mevalonate applied to larvae before pupation was not used for the synthesis of a hypothetical JH-I precursor.

High Versatility of IPP and DMAPP Methyltransferases Enables Synthesis of C6, C7and C8Terpenoid Building Blocks

“…It was shown that the respective pathway surprisingly accepts propionyl-CoA in addition to the normal starter unit acetyl-CoA, and in this way forms IPP and DMAPP derivatives with an additional methyl group. [7][8][9][10] In addition to the juvenile hormone derivatives, other terpene structures with additional methyl groups were then found in insects, which were usually referred to as homoterpenes in the literature (e. g. Ref. [11][12][13][14]).…”

“…The first exception was demonstrated with the discovery of different derivatives of the insect juvenile hormone containing extra methyl groups, [5–6] which in turn led to a closer inspection of the IPP‐ and DMAPP‐delivering mevalonate pathway in such organisms. It was shown that the respective pathway surprisingly accepts propionyl‐CoA in addition to the normal starter unit acetyl‐CoA, and in this way forms IPP and DMAPP derivatives with an additional methyl group [7–10] . In addition to the juvenile hormone derivatives, other terpene structures with additional methyl groups were then found in insects, which were usually referred to as homoterpenes in the literature (e. g. Ref.…”