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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 <i>flv</i> pathway produces flavunoidine <b>1</b>, an alkaloidal terpenoid. The core of <b>1</b> is a tetracyclic, cage-like, and oxygenated sesquiterpene that is connected to dimethylcadaverine via a C-N bond and is acylated with 5,  ...[more]

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