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Genome Mining of Alkaloidal Terpenoids from a Hybrid Terpene and Nonribosomal Peptide Biosynthetic Pathway.

ABSTRACT: Biosynthetic pathways containing multiple core enzymes have potential to produce structurally complex natural products. Here we mined a fungal gene cluster that contains two predicted terpene cyclases (TCs) and a nonribosomal peptide synthetase (NRPS). We showed the flv pathway produces flavunoidine 1, an alkaloidal terpenoid. The core of 1 is a tetracyclic, cage-like, and oxygenated sesquiterpene that is connected to dimethylcadaverine via a C-N bond and is acylated with 5,5-dimethyl-l-pipecolate. The roles of all flv enzymes are established on the basis of metabolite analysis from heterologous expression.

SUBMITTER: Yee DA

PROVIDER: S-EPMC7000236 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Genome Mining of Alkaloidal Terpenoids from a Hybrid Terpene and Nonribosomal Peptide Biosynthetic Pathway.

Yee Danielle A DA Kakule Thomas B TB Cheng Wei W Chen Mengbin M Chong Christine T Y CTY Hai Yang Y Hang Leibniz F LF Hung Yiu-Sun YS Liu Nicholas N Ohashi Masao M Okorafor Ikechukwu C IC Song Yongxiang Y Tang Mancheng M Zhang Zhuan Z Tang Yi Y

Journal of the American Chemical Society 20200103 2

Biosynthetic pathways containing multiple core enzymes have potential to produce structurally complex natural products. Here we mined a fungal gene cluster that contains two predicted terpene cyclases (TCs) and a nonribosomal peptide synthetase (NRPS). We showed the flv pathway produces flavunoidine 1, an alkaloidal terpenoid. The core of 1 is a tetracyclic, cage-like, and oxygenated sesquiterpene that is connected to dimethylcadaverine via a C-N bond and is acylated with 5, ...[more]

PMID: 31885262

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