title: Epi-trichosetin, a new undecaprenyl pyrophosphate synthase inhibitor, produced by Fusarium oxysporum FKI-4553.
abstract: A new compound, designated epi-trichosetin (1), was isolated along with the known compound trichosetin (2) from the culture broth of Fusarium oxysporum FKI-4553 by solvent extraction, silica gel column chromatography and reversed-phase HPLC. The structure of 1 was elucidated by comparing various spectral data with those of 2, revealing that 1 was a stereoisomer of 2. Compounds 1 and 2 inhibited the undecaprenyl pyrophosphate synthase activity of Staphylococcus aureus with IC50 values of 83 and 30 μM, respectively, and showed antimicrobial activity, particularly against Gram-positive bacteria, including methicillin-sensitive and -resistant S. aureus.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
authors.forename: Junji
authors.initials: J
authors.lastname: Inokoshi
authors.forename: Naoki
authors.initials: N
authors.lastname: Shigeta
authors.forename: Takashi
authors.initials: T
authors.lastname: Fukuda
authors.forename: Ryuji
authors.initials: R
authors.lastname: Uchida
authors.forename: Kenichi
authors.initials: K
authors.lastname: Nonaka
authors.forename: Rokurou
authors.initials: R
authors.lastname: Masuma
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tomoda
mesh_terms: D019883:Alkyl and Aryl Transferases / Q000037:antagonists & inhibitors*; D005591:Chemical Fractionation; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D004271:DNA, Fungal / Q000737:chemistry / Q000235:genetics; D021903:DNA, Ribosomal Spacer / Q000737:chemistry / Q000235:genetics; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005670:Fusarium / Q000737:chemistry* / Q000145:classification / Q000235:genetics / Q000302:isolation & purification; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D017422:Sequence Analysis, DNA; D013057:Spectrum Analysis; D013211:Staphylococcus aureus / Q000187:drug effects / Q000201:enzymology
chemical_list: D004271:DNA, Fungal; D021903:DNA, Ribosomal Spacer; D004791:Enzyme Inhibitors; D011760:Pyrrolidinones; C465303:trichosetin; D019883:Alkyl and Aryl Transferases; C023266:undecaprenyl pyrophosphate synthetase