Cadopherone and colomitide polyketides from Cadophora wood-rot fungi associated with historic expedition huts in Antarctica

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Abstract

Recent investigations of filamentous fungi isolated from coastal areas and historic wooden structures in the Ross Sea and Peninsula regions of Antarctica have identified the genus Cadophora as one of the most abundant fungal groups, comprising more than 30% of culturable fungi at some locations. A methanol extract of Cadophora luteo-olivacea grown on rice media yielded the known polyketides spiciferone A, spiciferol A, dihydrospiciferone A and dihydrospiciferol A. Additionally, nine related hexaketides were identified, including spiciferone F, two isomers of the known fungal bicyclic ketal colomitide B, cadopherones A-D, similin C, and spicifernin B. HPLC and NMR analysis of extracts from other isolates collected in Antarctica suggests that the spiciferones and colomitides are produced by at least two different Cadophora species. Preliminary precursor feeding experiments provided evidence for the biosynthesis of the colomitides from the same polyketide pathway as the spiciferone phytotoxins, possibly via a type III polyketide synthase (PKS). None of the compounds were active in a panel of anti-bacterial, anti-fungal, and mammalian cytotoxicity assays.

Original languageEnglish (US)
Pages (from-to)1-10
Number of pages10
JournalPhytochemistry
Volume148
DOIs
StatePublished - Apr 2018

Bibliographical note

Funding Information:
This research is supported in part by National Science Foundation grant #PLR0537143 to R. Blanchette. This work was also supported in part by the Center for Drug Design. We are grateful to J. Gloer, C. Aldrich, and M. Gearhart for helpful discussions, and to H. Irwin and J. Williams for conducting biological assays.

Funding Information:
This research is supported in part by National Science Foundation grant #PLR0537143 to R. Blanchette. This work was also supported in part by the Center for Drug Design. We are grateful to J. Gloer, C. Aldrich, and M. Gearhart for helpful discussions, and to H. Irwin and J. Williams for conducting biological assays.

Publisher Copyright:
© 2018 Elsevier Ltd

Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.

Keywords

  • Cadopherone
  • Cadophora
  • Colomitide
  • Fungus
  • PKS
  • Polyketide
  • Similin
  • Spiciferone

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