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Mycophenolic acid (MPA) is a potent inosine-5&amp;prime;-monophosphate dehydrogenase (IMPDH) inhibitor for immunosuppressive chemotherapy. Most importantly, as the 2-morpholinoethyl ester prodrug of MPA, mycophenolate mofetil (MMF) is a well-known immunosuppressant used to prevent rejection in organ transplantations. Nevertheless, due to its frequently occurred side effects, searching for new therapeutic agents is ongoing. In our current work, by virtue of efficient bioassay-guided fractionation and purification, eleven mycophenolic acid derivatives, including five previously unreported metabolites ( 3 ⁻ 7 ) and six known compounds ( 1 , 2 , and 8 ⁻ 11 ), were obtained from the coral-derived fungus Penicillium bialowiezense . Their structures were elucidated by means of extensive spectroscopic analyses (including 1D and 2D NMR and HRESIMS data) and comparison of the NMR and other physical data with those reported in the literature in the case of the known compounds. All the isolates 1 ⁻ 11 were evaluated for the immunosuppressive activity, and 1 ⁻ 3 showed potent IMPDH2 inhibitory potency with IC 50 values of 0.84⁻0.95 &amp;mu;M, which were comparable to that of MPA (the positive control), while 4 ⁻ 10 showed significant inhibitory potency with IC 50 values of 3.27⁻24.68 &amp;mu;M. All the MPA derivatives showed promising immunosuppressive activity, endowing them as potential drug leads for organ transplantations and autoimmune related diseases.

Mycophenolic Acid Derivatives with Immunosuppressive Activity from the Coral-Derived Fungus Penicillium bialowiezense