Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel

Elazar Cohen, Liat Koch, Kathy Myint Thu, Yocheved Rahamim, Yaniv Aluma, Micha Ilan, Oded Yarden, Shmuel Carmeli*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

68 Scopus citations

Abstract

Three novel meroterpenoids, insuetolides A-C (1-3) and four drimane sesquiterpenes, the new (E)-6-(4′-hydroxy-2′-butenoyl)-strobilactone A (4) and the known 2α, 9α, 11-trihydroxy-6-oxodrim-7-ene (5), strobilactone A (6) and (E,E)-6-(6′,7′-dihydroxy-2′,4′- octadienoyl)-strobilactone A (7), were isolated from the EtOAc extract of the culture medium of the marine-derived fungus Aspergillus insuetus (OY-207), which was isolated from the Mediterranean sponge Psammocinia sp. The structures of the compounds were determined by spectroscopic methods. Insuetolides A-C reveal a new carbon skeleton derived from the cyclization of farnesyl and 3, 5-dimethylorsellinic acid. Compounds 1, 6, and 7 exhibited anti-fungal activity towards Neurospora crassa with MIC values of 140, 242, and 162 μM, respectively; and compounds 3, 4, and 7 exhibited mild cytotoxicity towards MOLT-4 human leukemia cells.

Original languageAmerican English
Pages (from-to)6587-6593
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume19
Issue number22
DOIs
StatePublished - 15 Nov 2011

Bibliographical note

Funding Information:
We thank Noam Tal, The Mass Spectrometry Laboratory of The School of Chemistry, Tel Aviv University, for the mass spectra measurements. This study was supported by the Israel Science Foundation grant ( ISF 996/06 ).

Keywords

  • Aspergillus insuetus
  • Drimane sesquiterpens
  • Marine-derived fungi
  • Meroteroenoids
  • Psammocinia sp
  • Sponge

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