title: Immunomodulatory constituents from an Ascomycete, Eupenicillium crustaceum, and revised absolute structure of macrophorin D.
abstract: 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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan. fujimoto@p.chiba-u.ac.jp
authors.forename: H
authors.initials: H
authors.lastname: Fujimoto
authors.forename: E
authors.initials: E
authors.lastname: Nakamura
authors.forename: Y P
authors.initials: YP
authors.lastname: Kim
authors.forename: E
authors.initials: E
authors.lastname: Okuyama
authors.forename: M
authors.initials: M
authors.lastname: Ishibashi
authors.forename: T
authors.initials: T
authors.lastname: Sassa
mesh_terms: 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
chemical_list: 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