Dihydrofurochromones from Prionosciadium thapsoides

J. Martín Torres-Valencia, O. Esther Chávez-Ríos, Carlos M. Cerda-García-Rojas, Eleuterio Burgueño-Tapia, Pedro Joseph-Nathan

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20 Scopus citations

Abstract

Chemical investigations of Prionosciadium thapsoides roots led to the isolation of the new dihydrofurochromones (S)-(+)-4′-O-angeloyl-5-O- methylvisamminol (1) and (S)-(+)-4′-O-senecioyl-5-O-methylvisamminol (2), together with the known coumarins jatamansin, buchtormin, isopteryxin, isosamidin, psoralen, and bergapten. The structures of 1 and 2 were determined by 1D and 2D NMR experiments, and their absolute configuration was established by chemical correlation with (+)-5-O-methylvisamminol (3), whose structure was secured by single-crystal X-ray diffraction analysis and its absolute configuration was established as S by vibrational circular dichroism spectroscopy in comparison to DFT B3LYP/DGDZVP calculations.

Original languageEnglish
Pages (from-to)1956-1960
Number of pages5
JournalJournal of Natural Products
Volume71
Issue number11
DOIs
StatePublished - Nov 2008

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