Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua

Ruangelie Edrada-Ebel, Markus Heubes, Gernot Brauers, Victor Wray, Albrecht Berg, Udo Grafe, Michael Wohlfarth, Jorg Muhlbacher, Karsten Schaumann, Sudarsono Sudarsono, Gerhard Bringmann, Peter Proksch

Research output: Contribution to journalArticle

99 Citations (Scopus)

Abstract

Fungal isolates of Penicillium cf. montanense were obtained from the marine sponge Xestospongia exiguacollected from the Bali Sea, Indonesia. Culture filtrates of the fungi yielded three novel decalactone metabolites, xestodecalactones A, B, and C (1, 2a, and 2b), consisting of 10-membered macrolides with a fused 1,3-dihydroxybenzene ring. Online HPLC-NMR, ESI-MS/MS, and -CD spectra were acquired, and the structures of the new compounds were established and confirmed on the basis of offline NMR spectroscopic ((1)H, (13)C, COSY, ROESY, (1)H-detected direct and long-range (13)C-(1)H correlations) and mass spectrometric (EIMS) data. Quantum chemical calculations of the CD spectra proved to be difficult because of the conformational flexibility of the xestodecalactones. These compounds, of which 2a and 2b, due to the additional stereocenter at C-9, are diastereomeric compounds, are structurally related to a number of biologically active metabolites found in terrestrial fungal strains. Compound 2a was found to be active against the yeast Candida albicans.

Original languageEnglish
Pages (from-to)1598-1604
Number of pages7
JournalJournal of Natural Products
Volume65
Issue number11
DOIs
Publication statusPublished - Nov 2002

Keywords

  • animals
  • antifungal agents
  • candida albicans
  • chromatography, high pressure liquid
  • circular dichroism
  • electron spin resonance spectroscopy
  • Indonesia
  • lactones
  • molecular conformation
  • molecular structure
  • penicillium
  • porifera
  • stereoisomerism

Fingerprint Dive into the research topics of 'Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua'. Together they form a unique fingerprint.

Cite this