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Biosynthesis of an Anti-Addiction Agent from the Iboga Plant.

ABSTRACT: (-)-Ibogaine and (-)-voacangine are plant derived psychoactives that show promise as treatments for opioid addiction. However, these compounds are produced by hard to source plants, making these chemicals difficult for broad-scale use. Here we report the complete biosynthesis of (-)-voacangine, and de-esterified voacangine, which is converted to (-)-ibogaine by heating, enabling biocatalytic production of these compounds. Notably, (-)-ibogaine and (-)-voacangine are of the opposite enantiomeric configuration compared to the other major alkaloids found in this natural product class. Therefore, this discovery provides insight into enantioselective enzymatic formal Diels-Alder reactions.

SUBMITTER: Farrow SC

PROVIDER: S-EPMC6706869 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Biosynthesis of an Anti-Addiction Agent from the Iboga Plant.

Farrow Scott C SC Kamileen Mohamed O MO Caputi Lorenzo L Bussey Kate K Mundy Julia E A JEA McAtee Rory C RC Stephenson Corey R J CRJ O'Connor Sarah E SE

Journal of the American Chemical Society 20190806 33

(-)-Ibogaine and (-)-voacangine are plant derived psychoactives that show promise as treatments for opioid addiction. However, these compounds are produced by hard to source plants, making these chemicals difficult for broad-scale use. Here we report the complete biosynthesis of (-)-voacangine, and de-esterified voacangine, which is converted to (-)-ibogaine by heating, enabling biocatalytic production of these compounds. Notably, (-)-ibogaine and (-)-voacangine are of the opposite enantiomeric ...[more]

PMID: 31364847

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