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

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.