Absolute configuration of keisslone, a new antimicrobial metabolite from Keissleriella sp. YS4108, a marine filamentous fungus.
In order to purify enough material for establishing the absolute stereochemistry of the new antifungal metabolite 3,6,8-trihydroxy-3-[3,5-dimethyl-2-oxo-3(E)-heptenyl]-2,3-dihydronaphthalen-1(4H)-one produced by Keissleriella sp., a marine filamentous fungus (strain number: YS 4108), a repeated growth and fractionation of the fungal culture was performed to give instead a new antimicrobial metabolite, keisslone (1), the structure of which was elucidated on the basis of spectral analyses including homo- and hetero-nuclear correlation NMR experiments (HMQC, COSY, NOESY and HMBC). The absolute configuration of metabolite 1 was determined mainly by its CD data and NOESY spectrum. The compound 1 was shown to be inhibitory against the human pathogenic fungi Candida albicans, Trichophyton rubrum and Aspergillus niger with MICs of 50, 70, 40 microg/mL, respectively. In order to purify enough material for establishing the absolute stereochemistry of the new antifungal metabolite 3,6,8-trihydroxy-3-[3,5-dimethyl-2-oxo-3(E)-heptenyl]-2,3-dihydronaphthalen-1(4 H)-one produced by Keissleriella sp., a marine filamentous fungus (strain number: YS 4108), a repeated growth and fractionation of the fungal culture was performed to give instead a new antimicrobial metabolite, keisslone (1), the structure of which was elucidated on the basis of spectral analyses including homo- and hetero-nuclear correlation NMR experiments (HMQC, COSY, NOESY and HMBC). The absolute configuration of metabolite 1 was determined mainly by its CD data and NOESY spectrum. The compound 1 was shown to be inhibitory against the human pathogenic fungi Candida albicans, Trichophyton rubrum and Aspergillus niger with MICs of 50, 70, 40 microg/mL, respectively.
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Huang
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D000935:Antifungal Agents / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology*; D001203:Ascomycota; D001234:Aspergillus niger / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006801:Humans; D008826:Microbial Sensitivity Tests; D003904:Mitosporic Fungi / Q000187:drug effects*; D009281:Naphthalenes / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology*; D008517:Phytotherapy; D014249:Trichophyton / Q000187:drug effects
C459631:3,6,8-trihydroxy-3-(3,5-dimethyl-2-oxo-3(E)-heptenyl)-2,3-dihydronaphthalen-1(4H)-one; D000935:Antifungal Agents; D009281:Naphthalenes