Secondary metabolites isolated from an endophytic Phoma sp. - Absolute configuration of tetrahydropyrenophorol using the solid-state TDDFT CD methodology

Karsten Krohn, Umar Farooq, Ulrich Flörke, Barbara Schulz, Siegfried Draeger, Gennaro Pescitelli, Piero Salvadori, S. Antus, T. Kurtán

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

The known macrolide pyrenophorol (synonym helmidiol) (1), the new 2,3,10,11-tetrahydropyrenophorol (3), and (4S,7R)-4,7-dihydroxyoctanoic acid (4), the monomelic acid of the sixteen-membered cyclic diolide 1, were isolated from an endophytic Phoma sp. The relative configuration of tetrahydropyrenophorol (3) was confirmed by X-ray single crystal analysis and its absolute configuration determined by the solid-state TDDFT CD methodology. Compounds 1 and 4 show antifungal activity and the acid 4 is also an algicide.

Original languageEnglish
Pages (from-to)3206-3211
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number19
DOIs
Publication statusPublished - 2007

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Metabolites
Acids
Macrolides
X-Rays
Single crystals
X rays

Keywords

  • Absolute configuration
  • Algicidal activity
  • Antifungal activity
  • CD sector rules
  • Fungal metabolites
  • Pyrenophorol
  • Pyrenophorolic acid
  • Solid-state TDDFT CD methodology
  • Tetrahydropyrenophorol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Secondary metabolites isolated from an endophytic Phoma sp. - Absolute configuration of tetrahydropyrenophorol using the solid-state TDDFT CD methodology. / Krohn, Karsten; Farooq, Umar; Flörke, Ulrich; Schulz, Barbara; Draeger, Siegfried; Pescitelli, Gennaro; Salvadori, Piero; Antus, S.; Kurtán, T.

In: European Journal of Organic Chemistry, No. 19, 2007, p. 3206-3211.

Research output: Contribution to journalArticle

Krohn, Karsten ; Farooq, Umar ; Flörke, Ulrich ; Schulz, Barbara ; Draeger, Siegfried ; Pescitelli, Gennaro ; Salvadori, Piero ; Antus, S. ; Kurtán, T. / Secondary metabolites isolated from an endophytic Phoma sp. - Absolute configuration of tetrahydropyrenophorol using the solid-state TDDFT CD methodology. In: European Journal of Organic Chemistry. 2007 ; No. 19. pp. 3206-3211.
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