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

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Citation

Chen Z, Zheng Z, Huang H, Song Y, Zhang X, Ma J, Wang B, Zhang C, Ju J

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.

PubMed ID
22464133 [ View in PubMed
]
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.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
Mycophenolic acidInosine-5'-monophosphate dehydrogenase 2IC 50 (nM)630N/AN/ADetails