1. Structure Reassignment of Melonine and Quantum-Chemical Calculations-Based Assessment of Biosynthetic Scenarios Leading to Its Revised and Original Structures
- Author
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Aboua Timothée Okpekon, Jean-François Gallard, Somia Rharrabti, Marc Litaudon, Karine Leblanc, Pierre Champy, Pierre Le Pogam, Mehdi A. Beniddir, Victor Turpin, Guillaume Bernadat, Erwan Poupon, Tapé Kouamé, Centre National de la Recherche Scientifique (CNRS), Université Paris-Saclay, Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
Quantum chemical ,Biological Products ,Molecular Structure ,biology ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Structure (category theory) ,010402 general chemistry ,biology.organism_classification ,01 natural sciences ,Biochemistry ,Indole Alkaloids ,0104 chemical sciences ,Apocynaceae ,Melodinus ,Computational chemistry ,Monoterpenes ,[CHIM]Chemical Sciences ,Physical and Theoretical Chemistry ,ComputingMilieux_MISCELLANEOUS - 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.
- Published
- 2021