Biosynthesis of 10,12-dienoic fatty acids by a bifunctional Δ11desaturase in Spodoptera littoralis

Serra, Montserrat; Piña, Benjamı́n; Bujons, Jordi; Camps, Francisco; Fabriás, Gemma

doi:10.1016/j.ibmb.2006.05.005

Cited by 31 publications

(39 citation statements)

References 41 publications

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“…These results are similar to those found with the ⌬ 11 desaturase of S. littoralis (Fig. 5H), which produced the C11-monounsaturated hexa-and tetradecenoates, but did not make the corresponding C18 compound when expressed in yeast by using the pYEXTHS-BN vector (19). In contrast, (Z)-11-octadecenoic acid is synthesized by yeast transformed with either pYEXTHS-BN or the YEpOLEXbased plasmids containing the T. ni ⌬ 11 desaturase gene (5,19).…”

Section: Discussionsupporting

confidence: 87%

“…6 C and D) between the natural compound and an authentic synthetic standard. This compound was not produced in cells transformed with the S. littoralis ⌬ 11 desaturase, which did produce the previously reported (10,19) unsaturated intermediates (Fig. 5C).…”

Section: Resultssupporting

confidence: 42%

“…Likewise, another bifunctional desaturase/acetylenase enzyme has been reported in the moss C. purpureus (20,29). Bifunctional desaturases are not unusual in insects, as exemplified by the ⌬ 11 /⌬ 10,12 desaturases of B. mori (9) and S. littoralis (19). However, the case of the Tpi-PGFAD is unique because it exhibits not only dual ⌬ 11 /⌬ 13 desaturase activity, but also acetylenase activity, thus constituting a remarkable example of evolution of complex enzymatic activities to generate natural products in the most economical manner for the cell.…”

Section: Discussionmentioning

confidence: 96%

“…5H), which produced the C11-monounsaturated hexa-and tetradecenoates, but did not make the corresponding C18 compound when expressed in yeast by using the pYEXTHS-BN vector (19). In contrast, (Z)-11-octadecenoic acid is synthesized by yeast transformed with either pYEXTHS-BN or the YEpOLEXbased plasmids containing the T. ni ⌬ 11 desaturase gene (5,19). These differences suggest subtle dissimilarities in the tridimensional structure of the enzyme active sites, which result in different capabilities for accommodating long acyl substrates.…”

Section: Discussionmentioning

confidence: 99%

“…Cloned desaturases specifically involved in sex pheromone biosynthesis with unusual regiospecificities include the ⌬ 14 desaturase of Ostrinia species (18), the ⌬ 10 desaturase of Planotortrix octo (3), and the bifunctional desaturases of Bombyx mori (9) and Spodoptera littoralis (10,19). Because of the unique chemical structure of its sex pheromone, cloning the acyl-CoA desaturases from T. pityocampa pheromone gland might uncover new desaturases with activities, like ⌬ 11 acetylenase and ⌬ 13 desaturase, so far unreported in the Animal Kingdom.…”

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confidence: 99%

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A multifunctional desaturase involved in the biosynthesis of the processionary moth sex pheromone

Serra

Piña

Abad

et al. 2007

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

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The sex pheromone of the female processionary moth, Thaumetopoea pityocampa, is a unique C16 enyne acetate that is biosynthesized from palmitic acid. Three consecutive desaturation reactions transform this saturated precursor into the triunsaturated fatty acyl intermediate: formation of (Z)-11-hexadecenoic acid, acetylenation to 11-hexadecynoic acid, and final ⌬ 13 desaturation to (Z)-13-hexadecen-11-ynoic acid. By using degenerate primers common to all reported insect desaturases, a single cDNA sequence was isolated from total RNA of T. pityocampa female pheromone glands. The full-length transcript of this putative desaturase was expressed in elo1⌬/ole1⌬ yeast mutants (both elongase 1 and ⌬ 9 desaturase-deficient) for functional assays. The construct fully rescued the ⌬ole1 yeast phenotype, confirming its desaturase activity. Analysis of the unsaturated products from transformed yeast extracts demonstrated that the cloned enzyme showed ⌬ 11 desaturase, ⌬ 11 acetylenase, and ⌬ 13 desaturase activities. Therefore, this single desaturase may account for the three desaturation steps involved in the sex pheromone biosynthetic pathway of the processionary moth.acetylene ͉ cloning ͉ enyne ͉ Thaumetopoea pityocampa ͉ yeast

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Section: Discussionsupporting

confidence: 87%

Section: Resultssupporting

confidence: 42%

Section: Discussionmentioning

confidence: 96%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

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A multifunctional desaturase involved in the biosynthesis of the processionary moth sex pheromone

Serra

Piña

Abad

et al. 2007

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

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Bioproduction of (Z,E)‐9,12‐tetradecadienyl acetate (ZETA), the major pheromone component of Plodia, Ephestia, and Spodoptera species in yeast

Ding

Wang

Al-Saleh

et al. 2021

Pest Management Science

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BACKGROUND: (Z,E)-9,12-tetradecadienyl acetate (ZETA, Z9,E12-14:OAc) is a major sex pheromone component for many stored-product moth species. This pheromone is used worldwide for mating disruption, detection, monitoring, and mass trapping in raw and processed food storage facilities. In this study, we demonstrate the biological production of ZETA pheromone by engineered yeast Saccharomyces cerevisiae. RESULTS:We mined the pheromone gland transcriptome data of the almond moth, Ephestia (Cadra) cautella (Walker), to trace a novel E12 fatty acyl desaturase and expressed candidates heterologously in yeast and Sf9 systems. Furthermore, we demonstrated a tailor-made ZETA pheromone bioproduction in yeast through metabolic engineering using this E12 desaturase, in combination with three genes from various sources coding for a Z9 desaturase, a fatty acyl reductase, and an acetyltransferase, respectively. Electrophysiological assays (gas chromatography coupled to an electroantennographic detector) proved that the transgenic yeast-produced ZETA pheromone component elicits distinct antennal responses.CONCLUSION: The reconstructed biosynthetic pathway in yeast efficiently produces ZETA pheromone, leaves an undetectable level of biosynthetic intermediates, and paves the way for the economically competitive high-demand ZETA pheromone's bioproduction technology for high-value storage pest control.

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Δ11-fatty-acid desaturase 1.14.19.5

Schomburg

2013

Class 1 Oxidoreductases

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Biosynthesis of 10,12-dienoic fatty acids by a bifunctional Δ11desaturase in Spodoptera littoralis

Cited by 31 publications

References 41 publications

A multifunctional desaturase involved in the biosynthesis of the processionary moth sex pheromone

A multifunctional desaturase involved in the biosynthesis of the processionary moth sex pheromone

Bioproduction of (Z,E)‐9,12‐tetradecadienyl acetate (ZETA), the major pheromone component of Plodia, Ephestia, and Spodoptera species in yeast

Δ11-fatty-acid desaturase 1.14.19.5

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