Desaturases from the spotted fireworm moth (Choristoneura parallela) shed light on the evolutionary origins of novel moth sex pheromone desaturases

Liu, Weitian; Rooney, Alejandro P.; Xue, Bingye; Roelofs, Wendell L.

doi:10.1016/j.gene.2004.08.017

Cited by 60 publications

(59 citation statements)

References 23 publications

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“…Several ⌬ 9 desaturases have been cloned from moth pheromone glands and functionally expressed in yeast (6,8,10,18,24). However, none of the multiple clones from T. pityocampa pheromone glands analyzed corresponded to a ⌬ 9 desaturase.…”

Section: Discussionmentioning

confidence: 99%

“…The desaturases expressed in female sex-pheromone glands of different moth species have evolved to play a key role in the biosynthesis of sex pheromones, exhibiting an amazing diversity of substrate and regio-and stereospecifities. Unlike the metabolic ⌬ 9 acyl-CoA desaturases, pheromone gland desaturases catalyze the formation of uncommon unsaturated fatty acyl-CoA esters with variable chain lengths, different locations of unsaturations, and either the ordinary Z or the unusual E double bond geometry (3)(4)(5)(6)(7)(8)(9)(10).…”

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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: Discussionmentioning

confidence: 99%

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confidence: 99%

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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“…To identify the O. latipennis Δ11-desaturase that produces only the E isomer, we performed PCR using degenerate primers designed based on the histidine-cluster sequences conserved in nonheme desaturases (16,17). We cloned and sequenced ∼570-bp cDNA fragments, and found that 44 of 47 clones showed the same sequence, which was different from those of Δ11-desaturase genes identified from the congeners.…”

Section: Resultsmentioning

confidence: 99%

“…The sex pheromone components in Ostrinia are produced de novo in the pheromone gland (PG) of female moths from a common fatty acid, palmitic acid, through several enzymatic reactions (i.e., limited β oxidation, desaturation, reduction, and acetylation) (11)(12)(13)(14). A desaturase specifically expressed in the PG is the key enzyme that introduces a double bond into the pheromone molecules (15)(16)(17)(18)(19). A single Δ11-desaturase of O. nubilalis, OnubZ/ E11, has been shown to produce an ∼7:3 mixture of (E)-11-and (Z)-11-tetradecenoate (E11-and Z11-14:Acyl) from the substrate tetradecanoate (14:Acyl) (20).…”

Section: Sex Pheromone Desaturase Functioning In a Primitivementioning

confidence: 99%

Sex pheromone desaturase functioning in a primitive Ostrinia moth is cryptically conserved in congeners’ genomes

Fujii

Ito

Tatematsu

et al. 2011

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

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(E)-11-and (Z)-11-tetradecenyl acetate are the most common female sex pheromone components in Ostrinia moths. The Δ11-desaturase expressed in the pheromone gland (PG) of female moths is a key enzyme that introduces a double bond into pheromone molecules. A single Δ11-desaturase of Ostrinia nubilalis, OnubZ/ E11, has been shown to produce an ∼7:3 mixture of (E)-11-and (Z)-11-tetradecenoate from the substrate tetradecanoate. In contrast, the sex pheromone of Ostrinia latipennis, a primitive species of Ostrinia, is (E)-11-tetradecenol. This pheromone is unique in that it is not acetylated, and includes no Z isomer. In the present study, through the cloning and functional analysis of a PG-specific Δ11-desaturase in O. latipennis, we showed that the absence of the Z isomer in the pheromone is attributable to the strict product specificity of the Δ11-desaturase in this species, LATPG1. Phylogenetic analysis revealed that LATPG1 was not closely related to OnubZ/ E11. Rather, it was closely related to retroposon-linked cryptic Δ11-desaturases (ezi-Δ11) found in the genomes of O. nubilalis and Ostrinia furnacalis. Taken together, the results showed that an unusual Δ11-desaturase is functionally expressed in O. latipennis, although the genes encoding this enzyme appear to be cryptic in congeners.baculovirus expression system | speciation M ost moths use a mate-finding system that involves the longdistance attraction of males with female sex pheromones (1). The great majority of moth pheromones are a blend of unsaturated C 10 -C 18 primary acetates, alcohols, or aldehydes, and the combination of components and the blend ratios confer high species specificity to the signal (1). Given the primary role of sex pheromones in reproductive behavior, the divergence of pheromone signals should have profoundly affected premating reproductive isolation and speciation in moths (for a review, see ref.2). Moths of the genus Ostrinia (Lepidoptera: Crambidae), which show distinct differences in sex pheromones (3), are useful for studying the evolution of sex pheromone communication systems. The European corn borer Ostrinia nubilalis has long been a model for studies on this subject (4-7). Given the wealth of information available on the genetic, biochemical, and molecular aspects of sex pheromone production and reception in this species, comparative studies using congeners should shed new light on the subject. Among the 21 species of Ostrinia recorded worldwide (4, 8), the sex pheromones of nine species, including O. nubilalis, have been characterized to date (8,9). (E)-11-and (Z)-11-tetradecenyl acetate (E11-and Z11-14:OAc) are the most common female sex pheromone components in Ostrinia (10). The sex pheromone components in Ostrinia are produced de novo in the pheromone gland (PG) of female moths from a common fatty acid, palmitic acid, through several enzymatic reactions (i.e., limited β oxidation, desaturation, reduction, and acetylation) (11)(12)(13)(14). A desaturase specifically expressed in the PG is the key enzyme that introduces ...

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“…In addition to the ability to introduce Z-double bonds, moth mFADs can catalyze the introduction of rather uncommon E-double bond in nature [64][65][66][67][68] or produce a mixture of E-and Z-unsaturated FAs [69,70]. The preferred fatty acyl chain length may be C14 [27,[66][67][68][70][71][72][73], C16 [74], or C18 [63,75,76], but some mFADs can desaturate a broad range of fatty acyl chain lengths, such as C14-C20 [67,77]. The positions of the introduced double bond include ∆9, ∆4 [33], ∆5 [72], ∆6 [64,78], ∆8 [65], ∆10 [69,78], ∆11 [10, 63, 65-67, 74-76, 79, 80], ∆13 [81], and ∆14 [70,82].…”

Section: Mfad Propertiesmentioning

confidence: 99%

Biotechnological potential of insect fatty acid-modifying enzymes

Tupec

Buček

Valterová

2017

Zeitschrift Für Naturforschung C

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There are more than one million described insect species. This species richness is reflected in the diversity of insect metabolic processes. In particular, biosynthesis of secondary metabolites, such as defensive compounds and chemical signals, encompasses an extraordinarily wide range of chemicals that are generally unparalleled among natural products from other organisms. Insect genomes, transcriptomes and proteomes thus offer a valuable resource for discovery of novel enzymes with potential for biotechnological applications. Here, we focus on fatty acid (FA) metabolism-related enzymes, notably the fatty acyl desaturases and fatty acyl reductases involved in the biosynthesis of FA-derived pheromones. Research on insect pheromone-biosynthetic enzymes, which exhibit diverse enzymatic properties, has the potential to broaden the understanding of enzyme specificity determinants and contribute to engineering of enzymes with desired properties for biotechnological production of FA derivatives. Additionally, the application of such pheromone-biosynthetic enzymes represents an environmentally friendly and economic alternative to the chemical synthesis of pheromones that are used in insect pest management strategies.

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Desaturases from the spotted fireworm moth (Choristoneura parallela) shed light on the evolutionary origins of novel moth sex pheromone desaturases

Cited by 60 publications

References 23 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

Sex pheromone desaturase functioning in a primitive Ostrinia moth is cryptically conserved in congeners’ genomes

Biotechnological potential of insect fatty acid-modifying enzymes

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