Molecular structure and conformations of caramboxin, a natural neurotoxin from the star fruit: A computational study

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3 Citations (Scopus)

Abstract

Using density functional theory calculations we investigate the molecular structure and conformations of caramboxin, a neurotoxin recently isolated from the star fruit Averroha carambola. Among the seven conformers that exist within an energy window of ∼16.0 kcal/mol, two of them are the most favored ones with an energy difference of less than 2.0 kcal/mol. The computed chemical shifts of these two low-energy conformers are in good agreement with the experimental values determined in deuterated dimethylsulfoxide thus confirming the 2D chemical structure assigned to the neurotoxin. A topological analysis of the theoretical electronic charge density of four caramboxin conformers reveals the existence of intramolecular CH⋯O/N interactions which, in addition to the classical OH⋯O/N H-bonding interactions, contribute to decrease the conformational freedom of the neurotoxin.

Original languageEnglish
Pages (from-to)274-280
Number of pages7
JournalJournal of Molecular Structure
Volume1079
DOIs
Publication statusPublished - 2015

Keywords

  • Caramboxin
  • DFT
  • NMR
  • Natural products
  • QTAIM
  • Star fruit

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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