Planta Med 2013; 79 - PL13
DOI: 10.1055/s-0033-1348654

Cytotoxic Polyketides from an Unidentified Fungus (MSX 45109)

T El-Elimat 1, M Figueroa 1, AF Adcock 2, DJ Kroll 2, SM Swanson 3, MC Wani 4, CJ Pearce 5, NH Oberlies 1
  • 1Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402
  • 2Department of Pharmaceutical Sciences, BRITE, North Carolina Central University, Durham, NC 27707
  • 3Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago
  • 4Natural Products Laboratory, Research Triangle Institute, Research Triangle Park, NC 27709
  • 5Mycosynthetix, Inc., 505 Meadowland Dr., Suite 103, Hillsborough, NC 27278

Sixteen polyketides were isolated from an organic extract of an unidentified fungus (MSX 45109) using bioactivity-directed fractionation as part of a search for anticancer leads from filamentous fungi. Of these, six were new: paecilin D (1), blennolide I (2), blennolide J (3), ent-blennolide G (4), penicillixanthone B (5), and 6,8-dihydroxy-3-(1-hydroxypropyl)isochroman-1-one (6). The known compounds were: aigialomycin (7), hypothemycin (8), dihydrohypothemycin (9), nidulalin B (10), paecilin B (11), pyrenochaetic acid C (12), penicillixanthone A (13), and secalonic acids A (14), E (15), and G (16). The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configurations were determined using CD spectroscopy combined with time-dependent density functional theory (TDDFT) calculations. Compounds (1 – 16) were evaluated for cytotoxicity against a human cancer cell panel, and for antimicrobial activity against an array of bacteria and fungi.