Identification of a Fungal 1,8-Cineole Synthase from Hypoxylon sp. with Specificity Determinants in Common with the Plant Synthases

Shaw, Jeffrey Jon; Berbasova, Tetyana; Sasaki, Tomoaki; Jefferson-George, Kyra; Spakowicz, Daniel; Dunican, Brian F.; Portero, Carolina E.; Narváez-Trujillo, Alexandra; Strobel, Scott A.

doi:10.1074/jbc.m114.636159

Cited by 78 publications

(86 citation statements)

References 82 publications

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“…This most important monoterpene is produced through extraction from peppermint oil as well as through some synthetic routes (Bedoukian 1986;Bauer et al 1997). Among the terpenes, fungi usually produce sesquiterpenes; however, recently a prized monoterpenoid, 1,8-cineole was found having been produced by several Hypoxylon/Nodulisporium species (Tomsheck et al 2010;Riyaz-Ul-Hassan et al 2013;Shaw et al 2015). There is also a previous report of isolation of menthol from a fungus, Phomopsis amygdale (Sassa et al 2003).…”

Section: Discussionmentioning

confidence: 86%

“…Very recently, the first monoterpene synthase genes were identified in the cineoleproducing Hypoxylon sp. which were distinct from the plant homologues but used the same mechanism (Shaw et al 2015). Earlier reports also suggest that there is only limited sequence similarity between plant and microbial enzymes/genes (Starks et al 1997;Yang et al 2014).…”

Section: Discussionmentioning

confidence: 95%

“…In addition to their ecological functions, microbial VOCs may serve as potential antimicrobials, biofuel molecules, commodity chemicals or their precursors (Fortman et al 2008, Alpha et al 2015Strobel 2015). Among the terpenes, fungi usually produce sesquiterpenes and diterpenes; however, some recent reports have revealed that they produce monoterpenoids as well (Tomsheck et al 2010;Strobel et al 2011;Riyaz-Ul-Hassan et al 2013;Shaw et al 2015). Monterpene biosynthetic pathways may remain silent under normal culture conditions (Riyaz-UlHassan et al 2012).…”

Section: Introductionmentioning

confidence: 97%

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An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds

Qadri

Deshidi

Shah

et al. 2015

World J Microbiol Biotechnol

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An endophytic fungus, PR4 was found in nature associated with the rhizome of Picrorhiza kurroa, a high altitude medicinal plant of Kashmir Himalayas. The fungus was found to inhibit the growth of several phyto-pathogens by virtue of its volatile organic compounds (VOCs). Molecular phylogeny, based on its ITS1-5.8S-ITS2 ribosomal gene sequence, revealed the identity of the fungus as Phomopsis/Diaporthe sp. This endophyte was found to produce a unique array of VOCs, particularly, menthol, phenylethyl alcohol, (+)-isomenthol, β-phellandrene, β-bisabolene, limonene, 3-pentanone and 1-pentanol. The purification of compounds from the culture broth of PR4 led to the isolation of 3-hydroxypropionic acid (3-HPA) as a major metabolite. This is the first report of a fungal culture producing a combination of biologically and industrially important metabolites—menthol, phenylethyl alcohol, and 3-HPA. The investigation into the monoterpene biosynthetic pathway of PR4 led to the partial characterization of isopiperitenone reductase (ipr) gene, which seems to be significantly distinct from the plant homologue. The biosynthesis of plant-like-metabolites, such as menthol, is of significant academic and industrial significance. This study indicates that PR4 is a potential candidate for upscaling of menthol, phenylethyl alcohol, and 3-HPA, as well as for understanding the menthol/monoterpene biosynthetic pathway in fungi.

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Section: Discussionmentioning

confidence: 86%

Section: Discussionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 97%

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An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds

Qadri

Deshidi

Shah

et al. 2015

World J Microbiol Biotechnol

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“…(CS Hyp3 ) (Shaw et al, 2015), and they both have been reported to produce 1,8-cineole as their main product. The cineole synthases were cloned into the 1P system (See Figure 1b), and the resulting plasmids (JBEI-15048 or JBEI-15049) were transformed into DH1 cells and tested for production in EZ rich defined media with 1% glucose.…”

Section: Acc E P Ted P R E P R I Ntmentioning

confidence: 99%

“…Monoterpene production in E. coli was achieved by heterologously expressing a nine-enzyme mevalonate pathway organized in three operons expressed in a single plasmid (See 1P system in Figure 1b); this arrangement has been shown to result in high production of limonene (Alonso-Gutierrez et al, 2013 Kampranis et al, 2007;Lis-Balchin, 2002;Nakano et al, 2011;Shaw et al, 2015). In this study we tested two cineole synthases (CSs); one from the bacterium Streptomyces clavuligerus (CS Str ) (Nakano et al, 2011) and the other from the fungus Hypoxylon sp.…”

Section: Acc E P Ted P R E P R I Ntmentioning

confidence: 99%

Production of jet fuel precursor monoterpenoids from engineered Escherichia coli

Mendez-Perez

Alonso-Gutierrez

et al. 2017

Biotech & Bioengineering

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Monoterpenes (C 10 isoprenoids) are the main components of essential oils and are possible precursors for many commodity chemicals and high energy density fuels. Monoterpenes are synthesized from geranyl diphosphate (GPP), which is also the precursor for the biosynthesis of farnesyl diphosphate (FPP). FPP biosynthesis diverts the carbon flux from monoterpene production to C 15 products and quinone biosynthesis. In this study, we tested a chromosomal mutation of E. coli's native FPP synthase (IspA) to improve GPP availability for the production of monoterpenes using a heterologous mevalonate pathway. Monoterpene production at high levels required not only optimization of GPP production but also a basal level of FPP to maintain growth. The optimized strains produced two jet fuel precursor monoterpenoids 1,8-cineole and linalool at the titer of 653 mg/L and 505 mg/L, respectively, in batch cultures with 1% glucose. The engineered strains developed in this work provide useful resources for the production of high-value monoterpenes. This article is protected by copyright. All rights reserved Acc e p ted P r e p r i nt

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Mechanistic Characterization of Two Chimeric Sesterterpene Synthases from Penicillium

Mitsuhashi

Rinkel

Okada

et al. 2017

Chemistry A European J

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The products of two bifunctional fungal sesterterpene synthases (StTPS), with prenyl transferase (PT) and terpene synthase (TPS) domains from Penicillium, were structurally characterized and their mechanisms studied in detail by labeling experiments. A phylogenetic analysis of the TPS domains of the new and previously characterized enzymes revealed six distinct clades. Enzymes from the same clade catalyze a common initial cyclization step, which suggests the potential for structural predictions from amino acid sequences.

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Identification of a Fungal 1,8-Cineole Synthase from Hypoxylon sp. with Specificity Determinants in Common with the Plant Synthases

Cited by 78 publications

References 82 publications

An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds

An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds

Production of jet fuel precursor monoterpenoids from engineered Escherichia coli

Mechanistic Characterization of Two Chimeric Sesterterpene Synthases from Penicillium

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