title: Chlorocatechelins A and B from Streptomyces sp.: new siderophores containing chlorinated catecholate groups and an acylguanidine structure.
abstract: Two novel siderophores, chlorocatechelins A and B, were isolated from a culture broth of Streptomyces sp. Their structures were determined by spectroscopic analysis and degradation study. They contain chloro-substituted catecholate that has not been reported in natural products, whereas this group was conjugated to guanidine to form acylguanidine in chlorocatechelin A. This acylguanidine decomposed in weakly acidic solutions to furnish a less potent siderophore chlorocatechelin B. Chemical and biological insights into acylguanidine are also discussed.
authors.affiliation: †Department of System Chemotherapy and Molecular Sciences, Division of Bioinformatics and Chemical Genomics, Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Shinji
authors.initials: S
authors.lastname: Kishimoto
authors.affiliation: †Department of System Chemotherapy and Molecular Sciences, Division of Bioinformatics and Chemical Genomics, Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Shinichi
authors.initials: S
authors.lastname: Nishimura
authors.affiliation: †Department of System Chemotherapy and Molecular Sciences, Division of Bioinformatics and Chemical Genomics, Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Akira
authors.initials: A
authors.lastname: Hattori
authors.affiliation: ‡Faculty of Pharmaceutical Sciences, Teikyo-Heisei University, Nakano-ku, Tokyo 164-8530, Japan.
authors.forename: Masafumi
authors.initials: M
authors.lastname: Tsujimoto
authors.affiliation: §Institute of Microbial Chemistry, Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Masaki
authors.initials: M
authors.lastname: Hatano
authors.affiliation: §Institute of Microbial Chemistry, Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Igarashi
authors.affiliation: †Department of System Chemotherapy and Molecular Sciences, Division of Bioinformatics and Chemical Genomics, Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Hideaki
authors.initials: H
authors.lastname: Kakeya
mesh_terms: D004151:Dipeptides / Q000737:chemistry / Q000302:isolation & purification*; D004926:Escherichia coli / Q000378:metabolism; D019791:Guanidine / Q000737:chemistry*; D054879:Halogenation; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry / Q000302:isolation & purification*; D006877:Hydroxamic Acids / Q000737:chemistry; D007501:Iron / Q000378:metabolism; D015394:Molecular Structure; D017262:Siderophores / Q000737:chemistry / Q000302:isolation & purification*; D013302:Streptomyces / Q000378:metabolism
chemical_list: D004151:Dipeptides; D006843:Hydrocarbons, Chlorinated; D006877:Hydroxamic Acids; D017262:Siderophores; C000596578:chlorocatechelin A; C000596579:chlorocatechelin B; C573975:mirubactin; D007501:Iron; D019791:Guanidine