Antimicrobial Aromatic Polyketides from Gorgonian‐Associated Fungus, Penicillium commune 518

Seven new aromatic polyketides, communols A–G (1–7), were isolated and identified from the fermentation broth of Penicillium commune 518, a marine-derived fungus associated with the Gorgonian, Muricella abnormalis. The new structures of 1–7 were determined by spectroscopic analysis and X-ray single crystal diffraction. Among them, communol D (4) was the first example of a naturally occurring aromatic polyketide with a sulfoxide group from marine fungi. Compounds 1, 6, and 7 all showed moderate antimicrobial activities against Escherichia coli and Enterobacter aerogenes with MIC values of 4.1/16.4, 6.4/25.8, and 23.8/23.8 µmol·L−1, respectively.

[1]  Weiming Zhu,et al.  Cyclopeptides and polyketides from coral-associated fungus, Aspergillus versicolor LCJ-5-4 , 2011 .

[2]  M. Schindler,et al.  Asymmetric total synthesis of the indole alkaloid cyclopiazonic acid and first structure–activity data , 2011 .

[3]  Weiming Zhu,et al.  New quinazolinone alkaloids within rare amino acid residue from coral-associated fungus, Aspergillus versicolor LCJ-5-4. , 2011, Organic letters.

[4]  M. Rateb,et al.  Secondary metabolites of fungi from marine habitats. , 2011, Natural product reports.

[5]  C. Fæste,et al.  In vitro and in vivo hepatic metabolism of the fungal neurotoxin penitrem A , 2009, Drug and chemical toxicology (New York, N.Y. 1978).

[6]  P. Proksch,et al.  Bioactive metabolites from the endophytic fungus Ampelomyces sp. isolated from the medicinal plant Urospermum picroides. , 2008, Phytochemistry.

[7]  C. Kubicek,et al.  Clavatol and patulin formation as the antagonistic principle of Aspergillus clavatonanicus, an endophytic fungus of Taxus mairei , 2008, Applied Microbiology and Biotechnology.

[8]  L. Zaika,et al.  SPICES AND HERBS: THEIR ANTIMICROBIAL ACTIVITY AND ITS DETERMINATION , 2007 .

[9]  D. Gammon,et al.  An efficient synthesis of 7-hydroxy-2,6-dimethylchromeno[3,4-d]oxazol-4-one—a protected fragment of novenamine , 2005 .

[10]  E. Lacey,et al.  Roquefortine E, a diketopiperazine from an Australian isolate of Gymnoascus reessii. , 2005, Journal of natural products.

[11]  S. Ozerskaya,et al.  The Penicillium commune Thom and Penicillium clavigerum Demelius Fungi Producing Fumigaclavines A and B , 2003, Microbiology.

[12]  G. Gettinby,et al.  The production of cyclopiazonic acid by Penicillium commune and cyclopiazonic acid and aflatoxins by Aspergillus flavus as affected by water activity and temperature on maize grains , 1996, Mycopathologia.

[13]  J. Frisvad,et al.  Cell cytotoxicity and mycotoxin and secondary metabolite production by common penicillia on cheese agar. , 2002, Journal of agricultural and food chemistry.

[14]  G. Schmeda-Hirschmann,et al.  Acetophenone derivatives from Chilean isolate of Trichoderma pseudokoningii Rifai , 2000 .

[15]  N. Kagawa,et al.  TOTAL SYNTHESES OF NATURALLY OCCURRING BIS(METHYLTHIO)SILVATIN AND ITS THREE STEREOISOMERS , 1997 .

[16]  A. Srivastava,et al.  N-fatty acyl tryptamines from Annona reticulata , 1993 .

[17]  D. Scudiero,et al.  New colorimetric cytotoxicity assay for anticancer-drug screening. , 1990, Journal of the National Cancer Institute.

[18]  R. B. Fo,et al.  Synthesis of three natural 1,3-diarylpropanes: Two revised structures , 1989 .

[19]  T. Mosmann.  Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[20]  U. L. Diener,et al.  Penitrem A and Roquefortine Production by Penicillium commune , 1980, Applied and environmental microbiology.