Bioactive metabolites from Chaetomium aureum: Structure elucidation and inhibition of the Hsp90 machine chaperoning activity

Fatima Zahra Kabbaj, Su Lu, My El Abbés Faouzi, Bouchra Meddah, Peter Proksch, Yahya Cherrah, Hans Josef Altenbach, Amal H. Aly, Ahmed Chadli, Abdessamad Debbab

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Chemical investigation of the EtOAc extract of the fungus Chaetomium aureum, an endophyte of the Moroccan medicinal plant Thymelaea lythroides, afforded one new resorcinol derivative named chaetorcinol, together with five known metabolites. The structures of the isolated compounds were determined on the basis of one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry as well as by comparison with the literature. All compounds were tested for their activity towards the Hsp90 chaperoning machine in vitro using the progesterone receptor (PR) and rabbit reticulocyte lysate (RRL). Among the isolated compounds, only sclerotiorin efficiently inhibited the Hsp90 machine chaperoning activity. However, sclerotiorin showed no cytotoxic effect on breast cancer Hs578T, MDA-MB-231 and prostate cancer LNCaP cell lines. Interestingly, deacetylation of sclerotiorin increased its cytotoxicity toward the tested cell lines over a period of 48 h.

Original languageEnglish (US)
Pages (from-to)126-131
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume23
Issue number1
DOIs
StatePublished - Jan 1 2015

Fingerprint

Chaetomium
Metabolites
Cells
Endophytes
Cell Line
Reticulocytes
Progesterone Receptors
Cytotoxicity
Medicinal Plants
Fungi
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Mass Spectrometry
Prostatic Neoplasms
Magnetic Resonance Spectroscopy
Breast Neoplasms
Rabbits
Derivatives
sclerotiorin

Keywords

  • Bioactive metabolites
  • Chaetomium aureum
  • Cytotoxicity
  • Structure elucidation Hsp90

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Bioactive metabolites from Chaetomium aureum : Structure elucidation and inhibition of the Hsp90 machine chaperoning activity. / Kabbaj, Fatima Zahra; Lu, Su; Faouzi, My El Abbés; Meddah, Bouchra; Proksch, Peter; Cherrah, Yahya; Altenbach, Hans Josef; Aly, Amal H.; Chadli, Ahmed; Debbab, Abdessamad.

In: Bioorganic and Medicinal Chemistry, Vol. 23, No. 1, 01.01.2015, p. 126-131.

Research output: Contribution to journalArticle

Kabbaj, FZ, Lu, S, Faouzi, MEA, Meddah, B, Proksch, P, Cherrah, Y, Altenbach, HJ, Aly, AH, Chadli, A & Debbab, A 2015, 'Bioactive metabolites from Chaetomium aureum: Structure elucidation and inhibition of the Hsp90 machine chaperoning activity', Bioorganic and Medicinal Chemistry, vol. 23, no. 1, pp. 126-131. https://doi.org/10.1016/j.bmc.2014.11.021
Kabbaj, Fatima Zahra ; Lu, Su ; Faouzi, My El Abbés ; Meddah, Bouchra ; Proksch, Peter ; Cherrah, Yahya ; Altenbach, Hans Josef ; Aly, Amal H. ; Chadli, Ahmed ; Debbab, Abdessamad. / Bioactive metabolites from Chaetomium aureum : Structure elucidation and inhibition of the Hsp90 machine chaperoning activity. In: Bioorganic and Medicinal Chemistry. 2015 ; Vol. 23, No. 1. pp. 126-131.
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