Jump to main content
Jump to site search

Issue 9, 2017, Issue in Progress
Previous Article Next Article

Daldinone derivatives from the mangrove-derived endophytic fungus Annulohypoxylon sp.

Author affiliations

Abstract

Two new benzo[j]fluoranthene metabolites, daldinones H, J (1 and 3), and the likewise undescribed artefact, daldinone I (2), along with six known compounds (4–9) were isolated from the endophytic fungus Annulohypoxylon sp. that was obtained from the Mangrove plant Rhizophora racemosa collected in Cameroon. The structures of the new compounds were elucidated by 1D and 2D NMR as well as by HRESIMS and ECD spectra analysis. Co-cultivation of this fungus with the actinomycetes Streptomyces lividans or with Streptomyces coelicolor resulted in an up to 38-fold increase of 1-hydroxy-8-methoxynaphthalene (9), while no significant induction was detected when the fungus was co-cultivated either with Bacillus subtilis or with Bacillus cereus. Compound 2 exhibited strong to moderate cytotoxicity against Ramos and Jurkat J16 cells with IC50 values of 6.6 and 14.1 μM, respectively. Mechanistic studies indicated that compound 2 induces apoptotic cell death caused by induction of intrinsic apoptosis. Moreover, 2 potently blocks autophagy, a potential pro-survival pathway for cancer cells. Feeding experiments with 1,8-dihydroxynaphthalene (DHN) led to an enhanced accumulation of daldinone B (6), which supported the proposed biogenetic pathway.

Graphical abstract: Daldinone derivatives from the mangrove-derived endophytic fungus Annulohypoxylon sp.

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 Nov 2016, accepted on 30 Dec 2016 and first published on 17 Jan 2017


Article type: Paper
DOI: 10.1039/C6RA27306H
Citation: RSC Adv., 2017,7, 5381-5393
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Daldinone derivatives from the mangrove-derived endophytic fungus Annulohypoxylon sp.

    Y. Liu, F. Stuhldreier, T. Kurtán, A. Mándi, S. Arumugam, W. Lin, B. Stork, S. Wesselborg, H. Weber, B. Henrich, G. Daletos and P. Proksch, RSC Adv., 2017, 7, 5381
    DOI: 10.1039/C6RA27306H

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements