title: Penicacids A-C, three new mycophenolic acid derivatives and immunosuppressive activities from the marine-derived fungus Penicillium sp. SOF07.
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.
authors.affiliation: Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.
authors.forename: Ziming
authors.initials: Z
authors.lastname: Chen
authors.forename: Zhihui
authors.initials: Z
authors.lastname: Zheng
authors.forename: Hongbo
authors.initials: H
authors.lastname: Huang
authors.forename: Yongxiang
authors.initials: Y
authors.lastname: Song
authors.forename: Xuelian
authors.initials: X
authors.lastname: Zhang
authors.forename: Junying
authors.initials: J
authors.lastname: Ma
authors.forename: Bo
authors.initials: B
authors.lastname: Wang
authors.forename: Changsheng
authors.initials: C
authors.lastname: Zhang
authors.forename: Jianhua
authors.initials: J
authors.lastname: Ju
mesh_terms: D002681:China; D005960:Glucosides / Q000494:pharmacology; D006900:Hydroxylation; D007166:Immunosuppressive Agents / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009173:Mycophenolic Acid / Q000031:analogs & derivatives / Q000302:isolation & purification / Q000494:pharmacology*; D010407:Penicillium / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D005960:Glucosides; D007166:Immunosuppressive Agents; C575516:penicacid A; C575517:penicacid B; C575518:penicacid C; D009173:Mycophenolic Acid