Sterostreins A–E, New Terpenoids from Cultures of the Basidiomycete <i>Stereum ostrea</i> BCC 22955

Isaka, Masahiko; Srisanoh, Urarat; Choowong, Wilunda; Boonpratuang, Thitiya

doi:10.1021/ol2019778

Cited by 48 publications

(27 citation statements)

References 15 publications

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“…compounds 39–42) biosynthesis. 89, 91 Stehi1|159379 and Stehi1|128017 are 1,6- and 1,10-cyclizing enzymes, respectively (Schemes 2 and 5). Within the clade of not yet characterized 1,11-cyclizing sesquiterpene synthases sequences identified in S. hirsutum , there may be enzymes that synthesize hirsutene 48 and sterpurene 43 (Scheme 4) for the above mentioned modified sesquiterpenoid compounds isolated from this fungal genus.…”

Section: Fungal Sesquiterpenoidsmentioning

confidence: 99%

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Traversing the fungal terpenome

2014

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Fungi (Ascomycota and Basidiomycota) are prolific producers of structurally diverse terpenoid compounds. Classes of terpenoids identified in fungi include the sesqui-, di- and triterpenoids. Biosynthetic pathways and enzymes to terpenoids from each of these classes have been described. These typically involve the scaffold generating terpene synthases and cyclases, and scaffold tailoring enzymes such as e.g. cytochrome P450 monoxygenases, NAD(P)+ and flavin dependent oxidoreductases, and various group transferases that generate the final bioactive structures. The biosynthesis of several sesquiterpenoid mycotoxins and bioactive diterpenoids has been well-studied in Ascomycota (e.g. filamentous fungi). Little is known about the terpenoid biosynthetic pathways in Basidiomycota (e.g. mushroom forming fungi), although they produce a huge diversity of terpenoid natural products. Specifically, many trans-humulyl cation derived sesquiterpenoid natural products with potent bioactivities have been isolated. Biosynthetic gene clusters responsible for the production of trans-humulyl cation derived protoilludanes, and other sesquiterpenoids, can be rapidly identified by genome sequencing and bioinformatic methods. Genome mining combined with heterologous biosynthetic pathway refactoring has the potential to facilitate discovery and production of pharmaceutically relevant fungal terpenoids.

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Section: Fungal Sesquiterpenoidsmentioning

confidence: 99%

“…89 Biosynthesis of the melleolides (e.g. 38 in Scheme 6) by Armillaria gallica requires the esterification Δ6-protoilludene 29 with orsillinic acid.…”

Section: Fungal Sesquiterpenoidsmentioning

confidence: 99%

Traversing the fungal terpenome

2014

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“…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

confidence: 99%

Biosynthesis of Terpenoid Natural Products in Fungi

Schmidt‐Dannert

2014

Advances in Biochemical Engineering/Biotechnology

108

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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.

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“…These gene clusters usually contain several P450s and GMC oxidoreductases presumably responsible for the scaffold rearrangements and oxygenations that lead to the bioactive products (Figure 3). Interestingly, Stereum makes protoilludene-derived bis-sesquiterpenoid stereostreins via a postulated Diels-Alder condensation reaction [77]. Agrocybone is another bis-sesquiterpenoid hypothesized to involve a Diels-Alder condensation reaction [78].…”

Section: Biocatalysts Of Secondary Metabolismmentioning

confidence: 99%

“…(B) Protoilludane-type sesquiterpenoids are coupled via a proposed Diels-Alder reaction in the biosynthesis of agrocybone [78] and stereostrein C [77]. Biosynthesis of melledonol involves cross-coupling of orsellenic acid with a hydroxylated protoilludene catalyzed by a polyketide synthase[66].…”

Section: Figurementioning

confidence: 99%