title: Graphiumins, new thiodiketopiperazines from the marine-derived fungus Graphium sp. OPMF00224.
abstract: Eight new thiodiketopiperazines, designated as graphiumins A to H (1-8), were isolated along with bisdethiobis(methylthio)-deacetylaranotin (9) and bisdethiobis(methylthio)-deacetylapoaranotin (10) from the culture broth of the marine-derived fungus Graphium sp. OPMF00224. The structures of the graphiumins were elucidated based on spectroscopic analyses (1D and 2D NMR data, ROESY correlations and CD data) and chemical methods. The absolute configuration of the common (3S)-3-hydroxy-octanoyl acid residue in 1, 3 and 4 was determined by hydrolysis, benzoyl derivatization and HPLC analysis using a chiral column. Five graphiumins moderately inhibited yellow pigment production by methicillin-resistant Staphylococcus aureus.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Fukuda
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
authors.forename: Minori
authors.initials: M
authors.lastname: Shinkai
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
authors.forename: Eri
authors.initials: E
authors.lastname: Sasaki
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
authors.forename: Kenichiro
authors.initials: K
authors.lastname: Nagai
authors.affiliation: OP BIO FACTORY Co., Ltd, Okinawa, Japan.
authors.forename: Yuko
authors.initials: Y
authors.lastname: Kurihara
authors.affiliation: OP BIO FACTORY Co., Ltd, Okinawa, Japan.
authors.forename: Akihiko
authors.initials: A
authors.lastname: Kanamoto
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tomoda
mesh_terms: D000900:Anti-Bacterial Agents / Q000302:isolation & purification / Q000494:pharmacology*; D001203:Ascomycota / Q000737:chemistry*; D005285:Fermentation; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D010879:Piperazines / Q000737:chemistry / Q000494:pharmacology*; D012623:Seawater / Q000382:microbiology; D021241:Spectrometry, Mass, Electrospray Ionization; D013438:Sulfhydryl Compounds / Q000737:chemistry / Q000494:pharmacology*; D014871:Water Microbiology
chemical_list: D000900:Anti-Bacterial Agents; D010879:Piperazines; D013438:Sulfhydryl Compounds; C000604591:graphiumins