Immunomodulatory constituents from an Ascomycete, Eupenicillium crustaceum, and revised absolute structure of macrophorin D.
Fractionation guided by immunomodulatory activity of the EtOAc extract of the Ascomycete Eupenicillium crustaceum has afforded two new naturally occurring products, 4'-oxomacrophorin D (1) and 4'-oxomacrophorin A (2), as the immunosuppressive components of this fungus [1: 3-hydroxy-3-methylglutaryl (HMG) conjugate of 2]. The structures including the absolute configurations of 1 and 2 have been determined on the basis of chemical correlation of 1 with macrophorin D (3). The absolute configuration of the HMG moiety in 3 has been revised from 3R to 3S.
Fujimoto
H
H
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan. fujimoto@p.chiba-u.ac.jp
Nakamura
E
E
Kim
Y P
YP
Okuyama
E
E
Ishibashi
M
M
Sassa
T
T
D000276:Adjuvants, Immunologic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D001203:Ascomycota / Q000737:chemistry*; D001379:Azathioprine / Q000494:pharmacology; D001402:B-Lymphocytes / Q000187:drug effects / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D003208:Concanavalin A / Q000494:pharmacology; D016572:Cyclosporine / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D007166:Immunosuppressive Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007564:Japan; D008070:Lipopolysaccharides / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013154:Spleen / Q000166:cytology / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013601:T-Lymphocytes / Q000187:drug effects / Q000378:metabolism; D016559:Tacrolimus / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
C438425:4'-oxomacrophorin A; C438423:4'-oxomacrophorin D; D000276:Adjuvants, Immunologic; D007166:Immunosuppressive Agents; D008070:Lipopolysaccharides; D012717:Sesquiterpenes; C438424:macrophorin D; D003208:Concanavalin A; D016572:Cyclosporine; D001379:Azathioprine; D016559:Tacrolimus