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

G. E. Raoelison, C. Terreaux, E. F. Queiroz, F. Zsila, M. Simonyi, S. Antus, A. Randriantsoa, K. Hostettmann

Research output: Contribution to journalArticle

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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 - 2001

Fingerprint

Pyrones
Pyrans
Cladosporium
Fractionation
Fungi
Nuclear magnetic resonance spectroscopy
Assays
Spectrum Analysis
Magnetic Resonance Spectroscopy
Spectroscopy
configurations
fungi
stems
fractionation
spectroscopy
nuclear magnetic resonance
(6R)-6-((4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl)-5,6-dihydro-2H-pyran-2-one

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Absolute configuration of two new 6-alkylated a-pyrones (= 2H-pyran-2-ones) from Ravensara crassifolia. / Raoelison, G. E.; Terreaux, C.; Queiroz, E. F.; Zsila, F.; Simonyi, M.; Antus, S.; Randriantsoa, A.; Hostettmann, K.

In: Helvetica Chimica Acta, Vol. 84, No. 11, 2001, p. 3470-3476.

Research output: Contribution to journalArticle

Raoelison, G. E. ; Terreaux, C. ; Queiroz, E. F. ; Zsila, F. ; Simonyi, M. ; Antus, S. ; Randriantsoa, A. ; Hostettmann, K. / Absolute configuration of two new 6-alkylated a-pyrones (= 2H-pyran-2-ones) from Ravensara crassifolia. In: Helvetica Chimica Acta. 2001 ; Vol. 84, No. 11. pp. 3470-3476.
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