Biosynthetic pathway for production of a conjugated dienyl sex pheromone of a Plusiinae moth, Thysanoplusia intermixta

Sex pheromone biosynthesis in the pine caterpillar moth, Dendrolimus punctatus (Lepidoptera: Lasiocampidae): pathways leading to Z5-monoene and 5,7-conjugated diene components

“…The fourth possible biosynthetic route of Z5,E7-12:OH: D7 desaturation of Z5-12:Acyl A final possibility comprises the formation of Z5,E7-12:Acyl by E7 desaturation of Z5-12:Acyl. A relatively large amount of Z5-12:Acyl occurs in the gland and could be the substrate for the second desaturation reaction, similar to what was reported in T. intermixta (Ono et al, 2002). A D7 desaturase has to our knowledge never been reported in any insect species or eukaryotic system so far.…”

“…production of Z9,E11-14:OAc, was reported in Spodoptera littoralis (Martinez et al, 1990). This type of route to a sex pheromone component with conjugated double bonds was also found for the production of E9,E11-14:OAc in Epiphyas postvittana (Foster and Roelofs, 1990) and E5,Z7-12:OAc in Thysanoplusia intermixta (Ono et al, 2002). In T. intermixta Z11 desaturation produces Z11-16:Acyl from 16:Acyl and after chain-shortening E5 desaturation of Z7-12:Acyl yields the doubly unsaturated precursor.…”

Lepidopteran Sex Pheromones

“…6). Biosynthetic experiments with T. intermixta revealed that the 5,7-dienyl structure was produced by D5-desaturation of the 7-12 acyl intermediate [42]. Instead of the 7-12 compounds, 5-12 compounds have been identified from Lasiocampidae species such as D. punctatus [43] and Gastropacha quercifolia [44], suggesting that dienyl structure of the Lasiocampidae pheromone might be produced via a 5-12 acyl or analogous intermediate in a manner different to the Plusiinae species.…”

Pheromone biosynthetic pathways: PBAN-regulated rate-limiting steps and differential expression of desaturase genes in moth species

“…These pheromone components are synthesized de novo in the pheromone gland, from acetyl-CoA [involving acetyl-CoA carboxylase (ACCase) and fatty acid synthetase] to fatty acids as a response to the neurohormonal signal transmitted by PBAN (Jurenka, 2003;Rafaeli and Jurenka, 2003). The production of fatty acid analogs is followed with the double bond positioning as a result of the action of unique desaturases to make mono-and di-unsaturated fatty acids (Tang et al, 1989;Roelofs, 1981, 1983;Rosell et al, 1992;Jurenka et al, 1994Jurenka et al, , 2003Foster and Greenwood, 1997;Jurenka, 1997;Wu et al, 1998;Svatos et al, 1999;Abad et al, 2001;Choi et al, 2002;Ono et al, 2002;Rodriguez et al, 2002;Villorbina et al, 2003). The involvement of desaturases in the production of sex pheromones is known to be a derived function found only in insects thus far (Roelofs and Rooney, 2003).…”

“…1 double bond in Z9,E12-14:Ac from Z9-14:Acid; and/or a D14 desaturase producing the second double bond in Z9,E12-14:Ac from Z11-16:Acid. Biosynthetic pathways have been studied in a number of moth species utilizing labeled precursor fatty acids in combination with the identification of possible fatty acid intermediates (Tang et al, 1989;Roelofs, 1981, 1983;Rosell et al, 1992;Jurenka et al, 1994Jurenka et al, , 2003Foster and Greenwood, 1997;Jurenka, 1997;Wu et al, 1998;Svatos et al, 1999;Abad et al, 2001;Choi et al, 2002;Ono et al, 2002;Rodriguez et al, 2002;Villorbina et al, 2003). Demonstrations of the rate-limiting enzyme primarily rely on experiments in which labeled precursors and intermediates are tracked into the pheromone component/s in the absence and presence of PBAN.…”