Biosynthesis of linoleic acid in insects

Renobales, Mertxe de; Cripps, Colleen; Stanley-Samuelson, David W.; Jurenka, Russell A.; Blomquist, Gary J.

doi:10.1016/0968-0004(87)90167-8

Cited by 71 publications

(34 citation statements)

References 15 publications

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“…A few noticeable exceptions have been identified, such as the American cockroach (Periplaneta americana (L.)) and the house cricket (Beenakkers et al, 1985;Blomquist et al, 1991). It was originally assumed that bacterial fermentation was the source for C18:2 in these insect species, but more recent studies have shown that it can be synthesized de novo in these and other insect species distributed over four different orders Borgeson et al, 1991;Borgeson and Blomquist, 1993;de Renobales et al, 1987).…”

Section: Fats and Fatty Acidsmentioning

confidence: 99%

Insects as Food for Insectivores

Finke,

Oonincx

2014

Mass Production of Beneficial Organisms

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Section: Fats and Fatty Acidsmentioning

confidence: 99%

Insects as Food for Insectivores

Finke,

Oonincx

2014

Mass Production of Beneficial Organisms

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“…One uses Z9-14:COOH to make Z9,E12-14:COOH, which is then converted to Z9,E12-14:OAc, the sex pheromone of several moths (20). The other is found not in moths but in several other insects and uses oleic acid (Z9-18:COOH) to make linoleic acid (Z9,Z12-18:COOH) (21). Future research may yield comparisons of these unique desaturases, similar to those being made with other moth desaturases (22,23).…”

Section: Fig 2 Valine Incorporation Into the Alkene 2me-7-18:hc (A)mentioning

confidence: 99%

Sex pheromone biosynthetic pathway for disparlure in the gypsy moth, Lymantria dispar

Jurenka

Subchev

Abad

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

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The pheromone biosynthetic pathway for production of the sex pheromone disparlure, 2-methyl-7R,8S-epoxy-octadecane, was determined for the gypsy moth. Each step in the pathway was followed by using deuterium-labeled compounds that could be identified by using GC͞MS. This approach provides unequivocal determination of specific reactions in the pathway. It was shown that the alkene precursor, 2-methyl-Z7-octadecene, is most likely made in oenocyte cells associated with abdominal epidermal cells. The pathway begins with valine contributing carbons for chain initiation, including the methyl-branched carbon, followed by chain elongation to 19 carbons. The double bond is introduced with an unusual ⌬12 desaturase that utilizes a methyl-branched substrate. The resulting 18-methyl-Z12-nonadecenoate is decarboxylated to the hydrocarbon, 2-methyl-Z7-octadecene. The alkene is then transported to the pheromone gland through the hemolymph, most probably by lipophorin. At the pheromone gland, the alkene is unloaded and transformed into the epoxide disparlure for release into the environment. A chiral HPLC column was used to demonstrate that the (R,S)-stereoisomer of the epoxide, (؉)-disparlure is found in pheromone glands.

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“…Thus the Z12 desaturase found in pheromone glands of C. cautella and S. exigua will probably use only Z9-14:CoA as a substrate and produce only the E isomer. The other Z12 desaturase present in some insects (but not Lepidoptera) uses Z9-18:CoA as a substrate to produce Z9,Z12-18:CoA (linoleic acid) and is thought to be found in fat body and epidermal tissue throughout the body [18,19]. This desaturase also produces only the Z isomer, whereas the one in pheromone glands produces the E isomer.…”

Section: Research Articlesmentioning

confidence: 99%

Biosynthetic pathway for producing the sex pheromone component ( Z,E )-9,12-tetradecadienyl acetate in moths involves a ? 12 desaturase

Jurenka

1997

Cellular and Molecular Life Sciences (CMLS)

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Sex pheromones are used by insects as a form of chemical communication for the purpose of attracting conspecific mates. Female moths Cadra cautella and Spodoptera exigua use the diene (Z,E)-9,12-tetradecadienyl acetate as the major pheromone component. Biosynthesis of this pheromone component was demonstrated to occur through delta 11 desaturation of hexadecanoic acid (palmitate) to produce (Z)-11-hexadecenoic acid which is then chain-shortened to (Z)-9-tetradecenoic acid. A unique delta 12 desaturase uses the (Z)-9-tetradecenoic acid to produce (Z,E)-9,12-tetradecenoic acid which is reduced and acetylated to form the acetate ester pheromone component. Both moths also use a pheromonotropic peptide to stimulate pheromone biosynthesis.

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Biosynthesis of linoleic acid in insects

Cited by 71 publications

References 15 publications

Insects as Food for Insectivores

Insects as Food for Insectivores

Sex pheromone biosynthetic pathway for disparlure in the gypsy moth, Lymantria dispar

Biosynthetic pathway for producing the sex pheromone component ( Z,E )-9,12-tetradecadienyl acetate in moths involves a ? 12 desaturase

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