Curvularin-type metabolites from the fungus curvularia sp. isolated from a marine alga

Jingqiu Dai, Karsten Krohn, Ulrich Flörke, Gennaro Pescitelli, Gábor Kerti, Tamás Papp, K. Kövér, A. Bényei, Sigfried Draeger, Barabara Schulz, T. Kurtán

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Two new curvularin-type macrolides, curvulone A (1) and B (2), and two known ones (3a, 4) of the rare 15R series have been isolated from the fungus Curvularia sp., which has been isolated from the marine alga Gracilaria folifera. Their structures were determined by extensive 2D NMR experiments and supported by the single-crystal X-ray analysis of 1. The structural elucidation of 1, which has a benzo[b]furanone moiety as part of a 12-membered macrolactone, has led to a revision of the structure of the previously reported (11S,15S)-11β-hydroxy-12-oxocurvularin. The absolute configuration of curvulone A was established independently by the solid-state TD-DFT ECD method and by measuring the anomalous dispersion effect. The absolute configuration of curvulone B was determined by TD-DFT ECD calculations on the computed solution conformers. Two different solid-state conformers of 4 were identified by X-ray analysis of the single crystals obtained from different solvents; TD-DFT ECD calculations were performed to reproduce the experimental ECD spectra. All four metabolites were biologically active against fungal, bacterial and algal test organisms. The 12-membered macrolide curvulone A (1) with a unique benzo[b]furanone moiety and the open-chain precursor curvulone B (2) have been isolated from the fungusCurvularia sp. Their absolute configurations are of the rare 15R type and were determined by a combination of single-crystal X-ray analysis and CD calculations (by the solid-state ECD TD-DFT method).

Original languageEnglish
Pages (from-to)6928-6937
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number36
DOIs
Publication statusPublished - Dec 2010

Fingerprint

fungi
metabolites
algae
Algae
Metabolites
Fungi
Discrete Fourier transforms
X ray analysis
Macrolides
X-Rays
solid state
single crystals
Single crystals
Gracilaria
configurations
x rays
organisms
nuclear magnetic resonance
Nuclear magnetic resonance
curvularin

Keywords

  • Configuration determination
  • Density functional calculations
  • Electronic circular dichroism
  • Fungal metabolites
  • Natural products

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Curvularin-type metabolites from the fungus curvularia sp. isolated from a marine alga. / Dai, Jingqiu; Krohn, Karsten; Flörke, Ulrich; Pescitelli, Gennaro; Kerti, Gábor; Papp, Tamás; Kövér, K.; Bényei, A.; Draeger, Sigfried; Schulz, Barabara; Kurtán, T.

In: European Journal of Organic Chemistry, No. 36, 12.2010, p. 6928-6937.

Research output: Contribution to journalArticle

Dai, Jingqiu ; Krohn, Karsten ; Flörke, Ulrich ; Pescitelli, Gennaro ; Kerti, Gábor ; Papp, Tamás ; Kövér, K. ; Bényei, A. ; Draeger, Sigfried ; Schulz, Barabara ; Kurtán, T. / Curvularin-type metabolites from the fungus curvularia sp. isolated from a marine alga. In: European Journal of Organic Chemistry. 2010 ; No. 36. pp. 6928-6937.
@article{4491a6f7aecb43df9d94e3ca7fc954b8,
title = "Curvularin-type metabolites from the fungus curvularia sp. isolated from a marine alga",
abstract = "Two new curvularin-type macrolides, curvulone A (1) and B (2), and two known ones (3a, 4) of the rare 15R series have been isolated from the fungus Curvularia sp., which has been isolated from the marine alga Gracilaria folifera. Their structures were determined by extensive 2D NMR experiments and supported by the single-crystal X-ray analysis of 1. The structural elucidation of 1, which has a benzo[b]furanone moiety as part of a 12-membered macrolactone, has led to a revision of the structure of the previously reported (11S,15S)-11β-hydroxy-12-oxocurvularin. The absolute configuration of curvulone A was established independently by the solid-state TD-DFT ECD method and by measuring the anomalous dispersion effect. The absolute configuration of curvulone B was determined by TD-DFT ECD calculations on the computed solution conformers. Two different solid-state conformers of 4 were identified by X-ray analysis of the single crystals obtained from different solvents; TD-DFT ECD calculations were performed to reproduce the experimental ECD spectra. All four metabolites were biologically active against fungal, bacterial and algal test organisms. The 12-membered macrolide curvulone A (1) with a unique benzo[b]furanone moiety and the open-chain precursor curvulone B (2) have been isolated from the fungusCurvularia sp. Their absolute configurations are of the rare 15R type and were determined by a combination of single-crystal X-ray analysis and CD calculations (by the solid-state ECD TD-DFT method).",
keywords = "Configuration determination, Density functional calculations, Electronic circular dichroism, Fungal metabolites, Natural products",
author = "Jingqiu Dai and Karsten Krohn and Ulrich Fl{\"o}rke and Gennaro Pescitelli and G{\'a}bor Kerti and Tam{\'a}s Papp and K. K{\"o}v{\'e}r and A. B{\'e}nyei and Sigfried Draeger and Barabara Schulz and T. Kurt{\'a}n",
year = "2010",
month = "12",
doi = "10.1002/ejoc.201001237",
language = "English",
pages = "6928--6937",
journal = "LIEBIGS ANN. CHEM.",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "36",

}

TY - JOUR

T1 - Curvularin-type metabolites from the fungus curvularia sp. isolated from a marine alga

AU - Dai, Jingqiu

AU - Krohn, Karsten

AU - Flörke, Ulrich

AU - Pescitelli, Gennaro

AU - Kerti, Gábor

AU - Papp, Tamás

AU - Kövér, K.

AU - Bényei, A.

AU - Draeger, Sigfried

AU - Schulz, Barabara

AU - Kurtán, T.

PY - 2010/12

Y1 - 2010/12

N2 - Two new curvularin-type macrolides, curvulone A (1) and B (2), and two known ones (3a, 4) of the rare 15R series have been isolated from the fungus Curvularia sp., which has been isolated from the marine alga Gracilaria folifera. Their structures were determined by extensive 2D NMR experiments and supported by the single-crystal X-ray analysis of 1. The structural elucidation of 1, which has a benzo[b]furanone moiety as part of a 12-membered macrolactone, has led to a revision of the structure of the previously reported (11S,15S)-11β-hydroxy-12-oxocurvularin. The absolute configuration of curvulone A was established independently by the solid-state TD-DFT ECD method and by measuring the anomalous dispersion effect. The absolute configuration of curvulone B was determined by TD-DFT ECD calculations on the computed solution conformers. Two different solid-state conformers of 4 were identified by X-ray analysis of the single crystals obtained from different solvents; TD-DFT ECD calculations were performed to reproduce the experimental ECD spectra. All four metabolites were biologically active against fungal, bacterial and algal test organisms. The 12-membered macrolide curvulone A (1) with a unique benzo[b]furanone moiety and the open-chain precursor curvulone B (2) have been isolated from the fungusCurvularia sp. Their absolute configurations are of the rare 15R type and were determined by a combination of single-crystal X-ray analysis and CD calculations (by the solid-state ECD TD-DFT method).

AB - Two new curvularin-type macrolides, curvulone A (1) and B (2), and two known ones (3a, 4) of the rare 15R series have been isolated from the fungus Curvularia sp., which has been isolated from the marine alga Gracilaria folifera. Their structures were determined by extensive 2D NMR experiments and supported by the single-crystal X-ray analysis of 1. The structural elucidation of 1, which has a benzo[b]furanone moiety as part of a 12-membered macrolactone, has led to a revision of the structure of the previously reported (11S,15S)-11β-hydroxy-12-oxocurvularin. The absolute configuration of curvulone A was established independently by the solid-state TD-DFT ECD method and by measuring the anomalous dispersion effect. The absolute configuration of curvulone B was determined by TD-DFT ECD calculations on the computed solution conformers. Two different solid-state conformers of 4 were identified by X-ray analysis of the single crystals obtained from different solvents; TD-DFT ECD calculations were performed to reproduce the experimental ECD spectra. All four metabolites were biologically active against fungal, bacterial and algal test organisms. The 12-membered macrolide curvulone A (1) with a unique benzo[b]furanone moiety and the open-chain precursor curvulone B (2) have been isolated from the fungusCurvularia sp. Their absolute configurations are of the rare 15R type and were determined by a combination of single-crystal X-ray analysis and CD calculations (by the solid-state ECD TD-DFT method).

KW - Configuration determination

KW - Density functional calculations

KW - Electronic circular dichroism

KW - Fungal metabolites

KW - Natural products

UR - http://www.scopus.com/inward/record.url?scp=78650088261&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=78650088261&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201001237

DO - 10.1002/ejoc.201001237

M3 - Article

AN - SCOPUS:78650088261

SP - 6928

EP - 6937

JO - LIEBIGS ANN. CHEM.

JF - LIEBIGS ANN. CHEM.

SN - 1434-193X

IS - 36

ER -