“…[32,33,35,36] and from culture media, [37,38] indicating that members of this genus produce 1,11-cyclizing sesquiterpene synthases. Additionally, sesquiterpenoids derived from a 1,6-cyclization [34] as well as a 1,10-cyclization mechanism [31,35] have also been isolated from Stereum sp. (Scheme 1).…”
Section: Resultsmentioning
confidence: 99%
“…Stereum strains also produce the stereumins, which are derived from a modified δ-cadinene scaffold, [31,35] and methoxylaricinolic acid, which is derived from a modified drimane scaffold, [34] suggesting that Stereum strains have several highly active secondary metabolic pathways. Gene clustering of biosynthetic secondary metabolic pathways is a hallmark characteristic of fungi.…”
Basidiomycota represent a diverse source of natural products, particularly the sesquiterpenoids. Recently, the genome sequencing, mining, and subsequent discovery of a suite of sesquiterpene synthases was described in Omphalotus olearius. A predictive framework was developed to facilitate the discovery of sesquiterpene synthases in Basidiomycota. Phylogenetic analyses indicated a conservation of both sequence and initial cyclization mechanisms used. Here, the first robust application of this predictive framework is reported. It is used to pursue and selectively identify sesquiterpene synthases that follow a 1,6-, 1,10-, and 1,11-cyclization mechanism in the crust fungus Stereum hirsutum. The successful identification and characterization of a 1,6- and a 1,10-cyclizing sesquiterpene synthase, as well as three 1,11-cyclizing Δ-6 protoilludene synthases, is described. This study verifies the accuracy and utility of the predictive framework as a roadmap for the discovery of specific sesquiterpene synthases from Basidiomycota, representing an important step forward in natural product discovery.
“…[32,33,35,36] and from culture media, [37,38] indicating that members of this genus produce 1,11-cyclizing sesquiterpene synthases. Additionally, sesquiterpenoids derived from a 1,6-cyclization [34] as well as a 1,10-cyclization mechanism [31,35] have also been isolated from Stereum sp. (Scheme 1).…”
Section: Resultsmentioning
confidence: 99%
“…Stereum strains also produce the stereumins, which are derived from a modified δ-cadinene scaffold, [31,35] and methoxylaricinolic acid, which is derived from a modified drimane scaffold, [34] suggesting that Stereum strains have several highly active secondary metabolic pathways. Gene clustering of biosynthetic secondary metabolic pathways is a hallmark characteristic of fungi.…”
Basidiomycota represent a diverse source of natural products, particularly the sesquiterpenoids. Recently, the genome sequencing, mining, and subsequent discovery of a suite of sesquiterpene synthases was described in Omphalotus olearius. A predictive framework was developed to facilitate the discovery of sesquiterpene synthases in Basidiomycota. Phylogenetic analyses indicated a conservation of both sequence and initial cyclization mechanisms used. Here, the first robust application of this predictive framework is reported. It is used to pursue and selectively identify sesquiterpene synthases that follow a 1,6-, 1,10-, and 1,11-cyclization mechanism in the crust fungus Stereum hirsutum. The successful identification and characterization of a 1,6- and a 1,10-cyclizing sesquiterpene synthase, as well as three 1,11-cyclizing Δ-6 protoilludene synthases, is described. This study verifies the accuracy and utility of the predictive framework as a roadmap for the discovery of specific sesquiterpene synthases from Basidiomycota, representing an important step forward in natural product discovery.
“…This wood-rotting mushroom was primarily sequenced to elucidate its lignin decomposition biochemistry. However, it is also among the few Basidiomycota with a sequenced genome for which a number of bioactive natural products have been isolated, including many humulyl-pathway derived sesquiterpenoids [138,[172][173][174][175][176][177][178].…”
Section: Sesquiterpenoid Biosynthetic Pathways In Basidiomycotamentioning
Tens of thousands of terpenoid natural products have been isolated from plants and microbial sources. Higher fungi (Ascomycota and Basidiomycota) are known to produce an array of well-known terpenoid natural products, including mycotoxins, antibiotics, antitumor compounds, and phytohormones. Except for a few well-studied fungal biosynthetic pathways, the majority of genes and biosynthetic pathways responsible for the biosynthesis of a small number of these secondary metabolites have only been discovered and characterized in the past 5-10 years. This chapter provides a comprehensive overview of the current knowledge on fungal terpenoid biosynthesis from biochemical, genetic, and genomic viewpoints. Enzymes involved in synthesizing, transferring, and cyclizing the prenyl chains that form the hydrocarbon scaffolds of fungal terpenoid natural products are systematically discussed. Genomic information and functional evidence suggest differences between the terpenome of the two major fungal phyla--the Ascomycota and Basidiomycota--which will be illustrated for each group of terpenoid natural products.
“…This is detected and characterized by GC–MS following comparison to the standards included in the database. The product peak at 18.68 min generated the dominant mass segments at m/z 161, 119, 204 and 105 perfectly matching δ-cadinol (also torreyol) in mass spectra of the database and the authentic δ-cadinol in publications [13, 25] (Electronic supplementary material).Fig. 2Expression of BvCS /pET32a+ in E. coli and purification of recombinant fusion proteins.…”
Section: Resultsmentioning
confidence: 89%
“…torreyol). Moreover, production of (+)-δ-cadinol was observed in mycelial of Stereum hirsutum which falls into the same genus with B. vibrans [13]. Thus we speculate that a sesquiterpene synthase catalyzing the conversion of farnesyl diphosphate (FPP, 1 ) into δ-cadinol ( 6 ) is probably responsible for the production of boreovibrins (Fig.…”
Sesquiterpenoids are very common among natural products. A large number of sesquiterpene synthase genes have been cloned and functionally characterized. However, until now there is no report about the δ-cadinol synthase predominantly forming δ-cadinol (syn. torreyol) from farnesyl diphosphate. Sesquiterpenoids boreovibrins structurally similar to δ-cadinol were previously isolated from culture broths of the basidiomycete fungus Boreostereum vibrans. This led us to expect a corresponding gene coding for a δ-cadinol synthase that may be involved in the biosynthesis of boreovibrins in B. vibrans. Here we report the cloning and heterologous expression of a new sesquiterpene synthase gene from B. vibrans. The crude and purified recombinant enzymes, when incubating with farnesyl diphosphate as substrate, gave δ-cadinol as its principal product and thereby identified as a δ-cadinol synthase.Graphical AbstractA new sesquiterpene synthase gene was cloned from the basidiomycete fungus Boreostereum vibrans and heterologously expressed in E. coli. The purified recombinant enzyme gave δ-cadinol as its principal product from farnesyl diphosphate and thereby identified as a δ-cadinol synthase (BvCS).
Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0096-4) contains supplementary material, which is available to authorized users.
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