Genome Mining Reveals the Biosynthesis of Sativene and Its Oxidative Conversion to seco-Sativene

Abstract

Sativene (1) and seco-sativene are an important family of fungal sesquiterpenoids that feature unique tricyclo-[4.4.0.0 1,7 ]decane and bicyclo[3.2.1]octane skeletons, respectively. Herein, we identify a three-enzyme cassette: SatA cyclizes farnesyl diphosphate (FPP) to form compound 1; CYP450 SatB catalyzes C14−C15 dihydroxylations and subsequent bond cleavage; and reductase SatC regioselectively reduces C14 aldehyde and mediates hemiacetal ring closure to generate prehelminthosporol (2). Our findings clarify the synthetic step of sativene and its oxidative transformation processes into seco-sativene.

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“…Genome mining of Bipolaris sorokiniana ND90Pr has revealed a three-enzyme cassette that produces the important fungal sesquiterpenoids sativene 20 and prehelminthosporol 21 . 19 The enzyme SatA, a sativene synthase was shown to cyclise farnesyl diphosphate to give 20 , while the cytochrome P450 enzyme, SatB and reductase SatC convert this to 21 , via C14,C15 dihydroxylations, ring cleavage, aldehyde reduction and hemiacetal ring closure. Genome sequencing, terpenoid metabolomics and bioinformatics have been used to characterise ten novel type I terpene synthases from red algae such as Laurencia subopposita , which produces the halogenated terpenoid oppositol 22 .…”