10.1021/acs.jnatprod.8b00024.s001
P. E. Mandelare
P. E.
Mandelare
D. A. Adpressa
D. A.
Adpressa
E. N. Kaweesa
E. N.
Kaweesa
L. N. Zakharov
L. N.
Zakharov
S. Loesgen
S.
Loesgen
Coculture of Two Developmental Stages of a Marine-Derived <i>Aspergillus alliaceus</i> Results in the Production of the Cytotoxic
Bianthrone Allianthrone A
American Chemical Society
2018
HCT -116 colon cancer
asexual morph
metabolite
NMR spectroscopic analysis
melanoma cell lines
Cytotoxic Bianthrone Allianthrone
marine alga-derived Aspergillus alliaceus
chlorinated congener nalgiolaxin
Marine-Derived Aspergillus alliaceus Results
anthraquinone pigment nalgiovensin
small-molecule chemical diversity
2018-03-08 14:50:09
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Coculture_of_Two_Developmental_Stages_of_a_Marine-Derived_i_Aspergillus_alliaceus_i_Results_in_the_Production_of_the_Cytotoxic_Bianthrone_Allianthrone_A/5962501
The 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 <i>Aspergillus alliaceus</i> (teleomorph: <i>Petromyces alliaceus</i>) 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 (<b>1</b>) was mainly
found in the monoculture of the sclerotial morph, while the anthraquinone
pigment nalgiovensin (<b>2</b>) 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 (<b>3</b>) was abundant,
and newly produced bianthrones were found. Allianthrone A (<b>4</b>) and its two diastereomers [allianthrones B (<b>5</b>) and
C (<b>6</b>)] 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 (<b>4</b>) showed
weak cytotoxic activity against the HCT-116 colon cancer and SK-Mel-5
melanoma cell lines.