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A New Acetylenic Compound and Other Bioactive Metabolites from a Shark Gill-derived Penicillium Strain

Yi Zhang, Yan Feng, Markus Kramer, Frank Essmann and Stephanie Grond

College of Food Science and Technology, Guangdong Ocean University (GDOU), Guangdong Provincial Key Laboratory of Aquatic Product Processing and Safety, Zhanjiang Key Laboratory of Brain Health Related Marine Drugs and Nutritions, Analytical and Testing Center of GDOU, 524088 Zhanjiang, China

School of Life Science and Technology, Dalian University of Technology, 116024 Dalian, China;

Institute of Organic Chemistry, University of Tübingen, 72076 Tübingen, Germany

Abstract: Nine chiral compounds (1−9) were isolated from the static fermentation culture of a shark gill-derived fungus Penicillium polonicum AP2T1. These compounds include a new acetylenic aromatic ether (1 , (-)-WA ), four alkaloids ( a urantiomide C ( 2 ), fructigenine A (3), cyclopenin (4) and cyclopenol (5)) and four oxygenated compounds ((R)-penipratynolene (6), (3S,4S)-3,4-dihydro-3,4,8-trihydroxyl-naphthalenone (7), verrucosidin (8) and norverrucosidin (9)). Their structures were elucidated by MS, NMR , optical rotation and circular dichroism (CD) . In antimicrobial tests , compounds 1–4, 6 and 8–9 showed weak antibacterial activity against Staphylococcus aureus, Bacillus subtilis, and/or Escherichia coli.Compounds 3, 8 and 9 also exhibited moderate toxicity against Artemia salina larva , and showed cytotoxicity against human colon cancer cell line HCT116.

Keywords: Secondary metabolites ; shark; Penicillium polonicum ; bioactivity . © 2017 ACG Publications. All rights reserved.