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

94 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.

LanguageEnglish
Pages1598-1604
Number of pages7
JournalJournal of Natural Products
Volume65
Issue number11
DOIs
Publication statusPublished - Nov 2002

Fingerprint

Xestospongia
Indonesia
Penicillium
Macrolides
Porifera
Metabolites
Fungi
Candida albicans
Oceans and Seas
Yeasts
High Pressure Liquid Chromatography
Nuclear magnetic resonance
Candida
Yeast
catechol
xestodecalactone C
xestodecalactone A
xestodecalactone B

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

Cite this

Edrada-Ebel, Ruangelie ; Heubes, Markus ; Brauers, Gernot ; Wray, Victor ; Berg, Albrecht ; Grafe, Udo ; Wohlfarth, Michael ; Muhlbacher, Jorg ; Schaumann, Karsten ; Sudarsono, Sudarsono ; Bringmann, Gerhard ; Proksch, Peter. / Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua. In: Journal of Natural Products. 2002 ; Vol. 65, No. 11. pp. 1598-1604.
@article{8dc8d203faf44582b168355f451f9758,
title = "Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua",
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.",
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",
author = "Ruangelie Edrada-Ebel and Markus Heubes and Gernot Brauers and Victor Wray and Albrecht Berg and Udo Grafe and Michael Wohlfarth and Jorg Muhlbacher and Karsten Schaumann and Sudarsono Sudarsono and Gerhard Bringmann and Peter Proksch",
year = "2002",
month = "11",
doi = "10.1021/np020085c",
language = "English",
volume = "65",
pages = "1598--1604",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "11",

}

Edrada-Ebel, R, Heubes, M, Brauers, G, Wray, V, Berg, A, Grafe, U, Wohlfarth, M, Muhlbacher, J, Schaumann, K, Sudarsono, S, Bringmann, G & Proksch, P 2002, 'Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua' Journal of Natural Products, vol. 65, no. 11, pp. 1598-1604. https://doi.org/10.1021/np020085c

Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua. / Edrada-Ebel, Ruangelie; Heubes, Markus; Brauers, Gernot; Wray, Victor; Berg, Albrecht; Grafe, Udo; Wohlfarth, Michael; Muhlbacher, Jorg; Schaumann, Karsten; Sudarsono, Sudarsono; Bringmann, Gerhard; Proksch, Peter.

In: Journal of Natural Products, Vol. 65, No. 11, 11.2002, p. 1598-1604.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua

AU - Edrada-Ebel, Ruangelie

AU - Heubes, Markus

AU - Brauers, Gernot

AU - Wray, Victor

AU - Berg, Albrecht

AU - Grafe, Udo

AU - Wohlfarth, Michael

AU - Muhlbacher, Jorg

AU - Schaumann, Karsten

AU - Sudarsono, Sudarsono

AU - Bringmann, Gerhard

AU - Proksch, Peter

PY - 2002/11

Y1 - 2002/11

N2 - 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.

AB - 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.

KW - animals

KW - antifungal agents

KW - candida albicans

KW - chromatography, high pressure liquid

KW - circular dichroism

KW - electron spin resonance spectroscopy

KW - Indonesia

KW - lactones

KW - molecular conformation

KW - molecular structure

KW - penicillium

KW - porifera

KW - stereoisomerism

U2 - 10.1021/np020085c

DO - 10.1021/np020085c

M3 - Article

VL - 65

SP - 1598

EP - 1604

JO - Journal of Natural Products

T2 - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 11

ER -