title: Isolation of a novel paxilline analog pyrapaxilline from fungus that inhibits LPS-induced NO production.
abstract: We have screened microbial culture filtrates for nitrogen monoxide (NO) production inhibitors using mouse macrophage cell line RAW264.7. As a result, paxilline, 21-isopentenylpaxilline and a novel analog of paxilline have been isolated from the culture filtrate of fungus Eupenicillium shearii. The novel analog possesses an additional dihydropyran ring, and was named as pyrapaxilline. This compound inhibited the NO production with lower toxicity than paxilline.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
authors.forename: Chino
authors.initials: C
authors.lastname: Matsui
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
authors.forename: Yoko
authors.initials: Y
authors.lastname: Ikeda
authors.affiliation: Bioscience Associates, Tokyo, Japan.
authors.forename: Hironobu
authors.initials: H
authors.lastname: Iinuma
authors.affiliation: Meiji Seika Pharma Co. Ltd, Tokyo, Japan.
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Kushida
authors.affiliation: Meiji Seika Pharma Co. Ltd, Tokyo, Japan.
authors.forename: Takao
authors.initials: T
authors.lastname: Kunisada
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
authors.forename: Siro
authors.initials: S
authors.lastname: Simizu
authors.affiliation: Department of Molecular Target Medicine Screening, Aichi Medical University School of Medicine, Nagakute, Japan.
authors.forename: Kazuo
authors.initials: K
authors.lastname: Umezawa
mesh_terms: D000818:Animals; D002460:Cell Line; D055324:Eupenicillium / Q000378:metabolism*; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects* / Q000378:metabolism; D051379:Mice; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000096:biosynthesis
chemical_list: C475533:21-isopentenylpaxilline; D026121:Indole Alkaloids; D007211:Indoles; D008070:Lipopolysaccharides; C000594661:pyrapaxilline; D009569:Nitric Oxide; C048220:paxilline