title: Three oxygenated cyclohexenone derivatives produced by an endophytic fungus.
abstract: Three cyclohexenone derivatives, (4S,5S,6S)-5,6-epoxy-4-hydroxy-3-methoxy-5-methyl-cyclohex-2-en-1-one (1), (4R,5R)-4,5-dihydroxy-3-methoxy-5-methyl-cyclohex-2-en-1-one (2), and (4R,5S,6R)-4,5,6-trihydroxy-3-methoxy-5-methyl-cyclohex-2-en-1-one (3), were isolated from unpolished rice fermented with an xylariaceous endophytic fungus (strain YUA-026). The structures of three compounds were established on the basis of spectroscopic analyses and chemical conversion. The minimum inhibitory concentrations of 1 and 3 were 100 microg/ml and 400 microg/ml against Staphylococcus aureus, 100 microg/ml and 200 microg/ml against Pseudomonas aeruginosa, and 200 microg/ml and >400 microg/ml against Candida albicans, respectively. In addition, 1 and 3 exhibited phytotoxic activity against lettuce.
authors.affiliation: Department of Bioresource Engineering, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata, Japan. yshiono@tds1.tr.yamagata-u.ac.jp
authors.forename: Yoshihito
authors.initials: Y
authors.lastname: Shiono
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Murayama
authors.forename: Koetsu
authors.initials: K
authors.lastname: Takahashi
authors.forename: Katsuhide
authors.initials: K
authors.lastname: Okada
authors.forename: Shigeyoshi
authors.initials: S
authors.lastname: Katohda
authors.forename: Michimasa
authors.initials: M
authors.lastname: Ikeda
mesh_terms: D000890:Anti-Infective Agents / Q000302:isolation & purification* / Q000494:pharmacology; D001487:Basidiomycota / Q000737:chemistry*; D002176:Candida albicans / Q000187:drug effects; D003512:Cyclohexanones / Q000302:isolation & purification* / Q000494:pharmacology; D018525:Germination / Q000187:drug effects; D018545:Lactuca / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D012639:Seeds / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: C502046:4,5,6-trihydroxy-3-methoxy-5-methylcyclohex-2-en-1-one; C502045:4,5-dihydroxy-3-methoxy-5-methylcyclohex-2-en-1-one; C502044:5,6-epoxy-4-hydroxy-3-methoxy-5-methylcyclohex-2-en-1-one; D000890:Anti-Infective Agents; D003512:Cyclohexanones