Penicacids A-C, three new mycophenolic acid derivatives and immunosuppressive activities from the marine-derived fungus Penicillium sp. SOF07

Bioorg Med Chem Lett. 2012 May 1;22(9):3332-5. doi: 10.1016/j.bmcl.2012.02.106. Epub 2012 Mar 11.

Abstract

Three new mycophenolic acid derivatives, penicacids A-C (1-3), together with two known analogues, mycophenolic acid (MPA, 4) and 4'-hydroxy-MPA (5), were isolated from a fungus Penicillium sp. SOF07 derived from a South China Sea marine sediment. The structures of compounds 1-3 were elucidated on the basis of MS and NMR ((1)H, (13)C, HSQC and HMBC) data analyses and comparisons with the known compounds. Structure-activity relationship studies of compounds 1-5 focused on inosine-monophosphate dehydrogenase inhibition revealed that hydroxylation at C-4', methylation at C-7-OH, dual hydroxylation at C-2'/C-3' double bond of MPA diminished bioactivity whereas glucosyl hydroxylation at C-4' correlated to bioactivity comparable to that observed for MPA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • China
  • Glucosides / pharmacology
  • Hydroxylation
  • Immunosuppressive Agents / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Mycophenolic Acid / analogs & derivatives
  • Mycophenolic Acid / isolation & purification
  • Mycophenolic Acid / pharmacology*
  • Penicillium / chemistry*
  • Structure-Activity Relationship

Substances

  • Glucosides
  • Immunosuppressive Agents
  • penicacid A
  • penicacid B
  • penicacid C
  • Mycophenolic Acid