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Structure Reassignment of Melonine and Quantum-Chemical Calculations-Based Assessment of Biosynthetic Scenari

  • Santé-Sciences-Technologie,
Date(s)

du 16 juillet 2021 au 31 mars 2026

Lieu(x)
BioCIS - Université Paris Saclay
Kouamé T, Bernadat G, Turpin V, Litaudon M, Okpekon AT, Gallard JF, Leblanc K, Rharrabti S, Champy P, Poupon E, Beniddir MA, Le Pogam P.  Org Lett. 2021 Aug 6;23(15):5964-5968. doi: 10.1021/acs.orglett.1c02055.
Abstract : Melonine is a basic monoterpene indole alkaloid (MIA) skeleton from Melodinus philliraeoides that was reported in 1983. The scarcity of its spectroscopic data questioned the validity of its structure. This prompted us to reisolate this molecule and to revise its structure into an unprecedented MIA scaffold. DFT-validated biosynthetic paths to both this new core and the originally reported form are proposed. The pathway to the original structure of melonine seems to be thermodynamically feasible, and that compound may exist as a natural product. linkage in the small group of vobasine/tryptamine hybrids, pyrrovobasine also represents the first pyrraline-containing representative in the whole monoterpene indole alkaloids group. Biosynthetic hypotheses possibly underpinning these structural oddities are proposed here.