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.
MeSH terms
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Adjuvants, Immunologic / chemistry
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Adjuvants, Immunologic / isolation & purification*
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Adjuvants, Immunologic / pharmacology
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Animals
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Ascomycota / chemistry*
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Azathioprine / pharmacology
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B-Lymphocytes / drug effects
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B-Lymphocytes / metabolism
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Chromatography, High Pressure Liquid
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Circular Dichroism
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Concanavalin A / pharmacology
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Cyclosporine / pharmacology
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Drug Screening Assays, Antitumor
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Immunosuppressive Agents / chemistry
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Immunosuppressive Agents / isolation & purification*
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Immunosuppressive Agents / pharmacology
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Inhibitory Concentration 50
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Japan
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Lipopolysaccharides / pharmacology
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Magnetic Resonance Spectroscopy
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Mice
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Molecular Structure
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Sesquiterpenes / chemistry
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Sesquiterpenes / isolation & purification*
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Sesquiterpenes / pharmacology
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Spectrophotometry, Infrared
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Spectrophotometry, Ultraviolet
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Spleen / cytology
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Spleen / drug effects
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Stereoisomerism
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Structure-Activity Relationship
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T-Lymphocytes / drug effects
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T-Lymphocytes / metabolism
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Tacrolimus / pharmacology
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Tumor Cells, Cultured / drug effects
Substances
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4'-oxomacrophorin A
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4'-oxomacrophorin D
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Adjuvants, Immunologic
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Immunosuppressive Agents
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Lipopolysaccharides
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Sesquiterpenes
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macrophorin D
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Concanavalin A
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Cyclosporine
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Azathioprine
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Tacrolimus