Efficient exploration of terpenoid biosynthetic gene clusters in filamentous fungi

Yuan, Yujie; Cheng, Shu; Bian, Guangkai; Yan, Pan; Ma, Zhengning; Dai, Wen; Chen, Rong; Fu, Shuai; Huang, He; Chi, Haoming; Cai, Yuanfeng; Deng, Zixin; Liu, Tiangang

doi:10.1038/s41929-022-00762-x

Cited by 56 publications

(52 citation statements)

References 49 publications

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“…Because of their potential to synthesize diverse hydrocarbon skeletons, subsequent genome mining efforts focused on identifying additional cryptic type I bifunctional terpene synthases. As a result, a number of fungal type I sesterterpene synthases were characterized. − However, since the discovery of PaFS, only a limited number of type I diterpene synthases have been identified, including those responsible for the production of variediene ( 3 ), phomopsene ( 4 ), brassicicene ( 5 ), a precursor to the cyclopiane-type diterpenes ( 6 ), and dolasta-1(15),8-diene ( 7 ) (Figure ). Given our limited knowledge of type I diterpene synthases, the discovery and biochemical characterization of new enzymes would bring to light cryptic natural products, unveil novel cyclization reactions, and allow for more informed bioinformatic predictions.…”

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confidence: 99%

Identification and Characterization of a Cryptic Bifunctional Type I Diterpene Synthase Involved in Talaronoid Biosynthesis from a Marine-Derived Fungus

Zhang

Heard

et al. 2022

Org. Lett.

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We report the identification of the tnd biosynthetic cluster from the marine-derived fungus Aspergillus flavipes and the in vivo characterization of a cryptic type I diterpene synthase. The heterologous expression of the bifunctional terpene synthase led to the discovery of a diterpene backbone, talarodiene, harboring a benzo[ a ]cyclopenta[ d ]cyclooctane tricyclic fused ring system. The conversion of geranylgeranyl diphosphate to talarodiene was investigated using 13 C-labeling studies, and stable isotope tracer experiments showed the biotransformation of talarodiene into talaronoid C.

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confidence: 99%

Identification and Characterization of a Cryptic Bifunctional Type I Diterpene Synthase Involved in Talaronoid Biosynthesis from a Marine-Derived Fungus

Zhang

Heard

et al. 2022

Org. Lett.

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“…Terpenoids constitute the largest and most diverse group of natural products, with more than 100 000 discovered to date . The diverse structural variations endow terpenoids with a wide range of bioactivities . Sesquiterpenoids are a major class of terpenoids, with more than 300 sesquiterpene scaffolds reported .…”

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confidence: 99%

Characterization of Tremulane Sesquiterpene Synthase from the Basidiomycete Irpex lacteus

Chen

Feng

et al. 2022

Org. Lett.

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Tremulane sesquiterpenoids are key secondary metabolites of the basidiomycete Irpex lacteus, which displays structural diversity and various bioactivities. However, tremulane sesquiterpene synthases have not been reported to date. The tremulane sesquiterpene synthase of I. lacteus was characterized by genome mining, heterologous expression, an in vitro assay, and substrate feeding. Moreover, the structures of the corresponding products were elucidated by NMR spectroscopy and X-ray diffraction analysis.Letter pubs.acs.org/OrgLett

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“…As a result, a number of fungal type I sesterterpene synthases were characterized. [9][10][11][12][13][14][15][16][17] However, since the discovery of PaFS, only a limited number of type I diterpene synthases have been identified and include those responsible for the production of variediene 3, 18 phomopsene 4, 19 brassicicene 5, 20 a precursor to the cyclopiane-type diterpenes 6, 21 and dolasta-1(15),8-diene 7 22 (Figure 1). Given our limited knowledge of type I diterpene synthases, the discovery and biochemical characterization of new enzymes would bring to light cryptic natural products, unveil novel cyclization reactions, and allow for more informed bioinformatic predictions.…”

mentioning

confidence: 99%

Biochemical Characterization of a Fungal Bifunctional Type I Diterpene Synthase Brings a Cryptic Natural Product to Light

Zhang¹,

Heard³

et al. 2022

Preprint

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We report the identification of the tnd biosynthetic cluster from the marine-derived fungal strain Aspergillus flavipes CNL-338 and in vivo characterization of a cryptic type I diterpene synthase. Heterologous expression of the bifunctional terpene synthase TndC in Saccharomyces cerevisiae led to the discovery of a new diterpene backbone, talarodiene 8, harboring a benzo[a]cyclopenta[d]cyclooctane tricyclic fused ring system. The cyclization mechanism that converts geranylgeranyl diphosphate to the tricyclic hydrocarbon skeleton was investigated using 13C-labeling studies and stable isotope tracer experiments showed the biotransformation of 8 into the natural product talaronoid C.

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Efficient exploration of terpenoid biosynthetic gene clusters in filamentous fungi

Cited by 56 publications

References 49 publications

Identification and Characterization of a Cryptic Bifunctional Type I Diterpene Synthase Involved in Talaronoid Biosynthesis from a Marine-Derived Fungus

Identification and Characterization of a Cryptic Bifunctional Type I Diterpene Synthase Involved in Talaronoid Biosynthesis from a Marine-Derived Fungus

Characterization of Tremulane Sesquiterpene Synthase from the Basidiomycete Irpex lacteus

Biochemical Characterization of a Fungal Bifunctional Type I Diterpene Synthase Brings a Cryptic Natural Product to Light

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