Absolute Configuration of (-)-Centratherin, a Sesquiterpenoid Lactone, Defined by Means of Chiroptical Spectroscopy.

Junior FM, Covington CL, de Albuquerque AC, Lobo JF, Borges RM, de Amorim MB, Polavarapu PL
J Nat Prod. 2015 78 (11): 2617-23

PMID: 26565920 · DOI:10.1021/acs.jnatprod.5b00546

(-)-Centratherin is a bioactive sesquiterpenoid lactone, whose absolute configuration (AC) was not established, but has been proposed based on those of germacrane precursors. To verify this proposal, the experimental electronic circular dichroism (ECD), electronic dissymmetry factor (EDF), optical rotatory dispersion (ORD), vibrational circular dichroism (VCD), and vibrational dissymmetry factor (VDF) spectra of (-)-centratherin have been analyzed with the corresponding density functional theoretical predictions. These analyses suggest the AC of naturally occurring (-)-centratherin to be (6R,7R,8S,10R,2'Z).

MeSH Terms (8)

Circular Dichroism Lactones Models, Chemical Molecular Structure Nuclear Magnetic Resonance, Biomolecular Optical Rotatory Dispersion Sesquiterpenes Stereoisomerism

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