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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 based on metabolite analysis from heterologous expression.

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