Absolute configuration of two new 6-alkylated a-pyrones (= 2H-pyran-2-ones) from Ravensara crassifolia

Guy Emmanuel Raoelison, Christian Terreaux, Emerson Ferreira Queiroz, Ferenc Zsila, Miklos Simonyi, Sandor Antus, Adolphe Randriantsoa, Kurt Hostettmann

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Abstract

The stem bark CH2Cl2 extract of Ravensara crassifolia showed antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum in a bioautographic TLC assay. Activity-guided fractionation afforded two new a-pyrones: (6S)-5, 6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one (1) and (6R)-6[(4R, 6R)-4, 6-dihydroxy-10-phenyldec-1-enyl]-5, 6-dihydro-2H-pyran-2-one (2). Their structures and absolute configurations were established by NMR spectroscopy, chemical methods, and CD spectroscopy. The antifungal activity against C. cucumerinum was determined for both compounds.

Original languageEnglish
Pages (from-to)3470-3476
Number of pages7
JournalHelvetica Chimica Acta
Volume84
Issue number11
DOIs
Publication statusPublished - Jan 1 2001

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ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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