Neofunctionalization in an ancestral insect desaturase lineage led to rare Δ6 pheromone signals in the Chinese tussah silkworm

Wang, Honglei; Liénard, Marjorie A.; Zhao, Congcong; Wang, Chen-Zhu; Löfstedt, Christer

doi:10.1016/j.ibmb.2010.07.009

Cited by 72 publications

(52 citation statements)

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“…Pheromone biosynthesis involves modifications of fatty acyl substrates, such as chain shortening and elongation, reduction, acetylation, oxidation, and desaturation (11). SP biosynthetic enzymes [i.e., FA reductases (8), FA chain-shortening enzymes (12, 13), and particularly FA desaturases (FADs) (7,9,(14)(15)(16)(17)] are the most commonly discovered traits underlying SP divergence in moths.Manduca sexta females attract males by releasing an SP containing in addition to mono-and diunsaturated aldehydes, which are typical structural themes in SPs of Bombycoidea moths (10), also uncommon conjugated triunsaturated aldehydes. The production of triunsaturated SPCs represents an easily traceable phenotype, thus making M. sexta a convenient yet unexploited model organism for unraveling the mechanisms of chemical communication evolution via novel SPC recruitment.…”

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Evolution of moth sex pheromone composition by a single amino acid substitution in a fatty acid desaturase

Buček

Matoušková

Vogel

et al. 2015

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

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For sexual communication, moths primarily use blends of fatty acid derivatives containing one or more double bonds in various positions and configurations, called sex pheromones (SPs). To study the molecular basis of novel SP component (SPC) acquisition, we used the tobacco hornworm (Manduca sexta), which uses a blend of mono-, di-, and uncommon triunsaturated fatty acid (3UFA) derivatives as SP. We identified pheromone-biosynthetic fatty acid desaturases (FADs) MsexD3, MsexD5, and MsexD6 abundantly expressed in the M. sexta female pheromone gland. Their functional characterization and in vivo application of FAD substrates indicated that MsexD3 and MsexD5 biosynthesize 3UFAs via E/Z14 desaturation from diunsaturated fatty acids produced by previously characterized Z11-desaturase/conjugase MsexD2. Site-directed mutagenesis of sequentially highly similar MsexD3 and MsexD2 demonstrated that swapping of a single amino acid in the fatty acyl substrate binding tunnel introduces E/Z14-desaturase specificity to mutated MsexD2. Reconstruction of FAD gene phylogeny indicates that MsexD3 was recruited for biosynthesis of 3UFA SPCs in M. sexta lineage via gene duplication and neofunctionalization, whereas MsexD5 representing an alternative 3UFA-producing FAD has been acquired via activation of a presumably inactive ancestral MsexD5. Our results demonstrate that a change as small as a single amino acid substitution in a FAD enzyme might result in the acquisition of new SP compounds.fatty acid desaturase | Manduca sexta | sex pheromone biosynthesis | pheromone evolution | substrate specificity S ex pheromones (SPs) are a diverse group of chemical compounds that are central to mate-finding behavior in insects (1). Variation in SP composition between closely related species and among populations is well documented. Despite this variation, SPs are presumed to be under strong stabilizing selection, and thus the genetic mechanisms driving SP diversification represented an enigma (2). Research on SPs in moths (Insecta: Lepidoptera) helped establish the hypothesis of asymmetric tracking as a major driving force in SP diversification. In this scenario, abrupt changes in female SP composition via a shift in component ratio or the inclusion or loss of a component result in a distinct SP that attracts males with more broadly or differentially tuned SP preference (3). Assortative mating, the preferential mating of females producing a novel SP with males attracted to this SP, restricts gene flow between subpopulations with differing SP compositions. This can ultimately lead to speciation and fixation of novel communication channels (4). Work in insect models such as wasps (5), fruit flies (6), and especially moths (7-9) is helping uncover the genetic basis of SP diversification.In the majority of moth species, females use species-specific mixtures of SP components (SPCs) consisting of volatile fatty acid (FA) derivatives to attract conspecific males at long range. These SPCs are predominantly long-chain aliphatic (C12-C18) acetates, alcoh...

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confidence: 99%

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confidence: 99%

Evolution of moth sex pheromone composition by a single amino acid substitution in a fatty acid desaturase

Buček

Matoušková

Vogel

et al. 2015

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

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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].…”

Section: Mfad Propertiesmentioning

confidence: 99%

“…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]. Δ12 mFADs have also been identified, but they are involved in primary metabolism during the production of methylene-interrupted PUFAs [31] rather than pheromone biosynthesis.…”

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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“…Plenty of genes coding this enzyme have been isolated and characterized in other various organisms e.g. Mortierella alpina (Sakuradani et al 1999b), Amylomyces rouxii (Laoteng et al 2005a) Saccharomyces cerevisiae (Stuckey et al 1990), Yarrowia lipolytica (Xue et al 2009), Arabidopsis thaliana (Fukuchi-Mizutani et al 1998), Rattus norvegicus (Baba et al 1994), Xenopus laevis (Klein et al 2002), Antheraea pernyi (Wang et al 2010) etc. Figure 6 represents the alignment of these sequences where the cytochrome b 5 domain is located at C-terminal end of protein.…”

Section: δ9-desaturasementioning

confidence: 99%

Characterization of membrane-bound fatty acid desaturases

Klempová

Mihálik²,

Čertı́k³

2013

gpb

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Abstract. Membrane-bound desaturases play key role in metabolism of polyunsaturated fatty acids. Characterization of these enzymes and their genes is the first step in basic understanding of their proper functioning in living cells as well as in tailor-made preparation of highly-specific and highlyproductive strains of microorganisms interesting for applied biotechnology. It is also the crucial step in creation of transgenic agricultural crops with enhanced content of individual polyunsaturated fatty acids. Properties and applications of identified membrane-bound desaturases genes and enzymes are discussed in this review.

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Neofunctionalization in an ancestral insect desaturase lineage led to rare Δ6 pheromone signals in the Chinese tussah silkworm

Cited by 72 publications

References 51 publications

Evolution of moth sex pheromone composition by a single amino acid substitution in a fatty acid desaturase

Evolution of moth sex pheromone composition by a single amino acid substitution in a fatty acid desaturase

Biotechnological potential of insect fatty acid-modifying enzymes

Characterization of membrane-bound fatty acid desaturases

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