Planta Med 2012; 78 - PI86
DOI: 10.1055/s-0032-1320773

Two benzoquinones and one terphenyl compound from an unidentified fungus (MSX 47445)

T El-Elimat 1, M Figueroa 1, TN Graf 1, AF Adcock 2, DJ Kroll 2, MC Wani 3, CJ Pearce 4, 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
  • 3Natural Products Laboratory, Research Triangle Institute, Research Triangle Park, NC 27709
  • 4Mycosynthetix, Inc., Hillsborough, NC 27278

Three bioactive compounds were isolated from an organic extract of an unidentified fungus (MSX 47445) using bioactivity-directed fractionation methodology as part of a search for anticancer leads from filamentous fungi. Of these, two were benzoquinones [betulinan A (1) and betulinan C (3)] and the third was a terphenyl compound BTH-II0204–207:A (2). The structures of the isolated compounds were elucidated using a set of spectroscopic and spectrometric techniques; the structure of the new compound (3) was confirmed via X-ray crystallography. Compounds (1-3) were evaluated for cytotoxicity against a human cancer cell panel, for antimicrobial activity against an array of bacteria and fungi, and for phosphodiesterase (PDE4B2) inhibitory activities. The putative binding mode of 1-3 with PDE4B2 was examined using a validated docking protocol, and the binding and enzyme inhibitory activities correlated.