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Coculture of Two Developmental Stages of a Marine-Derived Aspergillus alliaceus Results in the Production of the Cytotoxic Bianthrone Allianthrone A
journal contribution
posted on 2018-03-08, 14:50 authored by P. E. Mandelare, D. A. Adpressa, E. N. Kaweesa, L. N. Zakharov, S. LoesgenThe genetically encoded, small-molecule
chemical diversity of filamentous
fungi is still largely unexplored and represents an attractive source
for the discovery of new compounds. Here we report the production
of new chlorinated bianthrones from coculture of two different developmental
stages, or morphs, of a marine alga-derived Aspergillus alliaceus (teleomorph: Petromyces alliaceus) strain. The
vegetative stage (asexual morph) can be separated from the morph that
switched to sexual development (sclerotial morph); both produce distinct
secondary metabolite patterns. Ochratoxin (1) was mainly
found in the monoculture of the sclerotial morph, while the anthraquinone
pigment nalgiovensin (2) was produced by the asexual
morph. Surprisingly, combining cultures from both developmental stages
in a coculture experiment changed the metabolite profile drastically.
The chlorinated congener nalgiolaxin (3) was abundant,
and newly produced bianthrones were found. Allianthrone A (4) and its two diastereomers [allianthrones B (5) and
C (6)] were isolated, and the new structures were determined
by extensive NMR spectroscopic analysis, supported by optical properties
and X-ray crystallography. All metabolites were tested in antibiotic
and cytotoxicity assays, and allianthrone A (4) showed
weak cytotoxic activity against the HCT-116 colon cancer and SK-Mel-5
melanoma cell lines.
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HCT -116 colon cancerasexual morphmetaboliteNMR spectroscopic analysismelanoma cell linesCytotoxic Bianthrone Allianthronemarine alga-derived Aspergillus alliaceuschlorinated congener nalgiolaxinMarine-Derived Aspergillus alliaceus Resultsanthraquinone pigment nalgiovensinsmall-molecule chemical diversity
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