title: Nonthmicin, a Polyether Polyketide Bearing a Halogen-Modified Tetronate with Neuroprotective and Antiinvasive Activity from Actinomadura sp.
abstract: Nonthmicin (1), a new polyether polyketide bearing a chlorinated tetronic acid, was isolated from the culture extract of a soil-derived Actinomadura strain. The structure of 1 was elucidated by interpretation of NMR and MS spectroscopic data, and the absolute configuration of 1 was proposed on the basis of the crystal structure of its dechloro congener ecteinamycin (2) also isolated from the same strain. Tetronic acids modified by halogenation have never been reported from natural products. Compounds 1 and 2 were found to have neuroprotective activity and antimetastatic properties at submicromolar concentrations in addition to antibacterial activity.
authors.affiliation: Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University , Imizu, Toyama 939-0398, Japan.
authors.forename: Yasuhiro
authors.identifier: 0000-0001-5114-1389
authors.initials: Y
authors.lastname: Igarashi
authors.affiliation: Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University , Imizu, Toyama 939-0398, Japan.
authors.forename: Noriaki
authors.initials: N
authors.lastname: Matsuoka
authors.affiliation: Department of Physical Chemistry, Osaka University of Pharmaceutical Sciences , Takatsuki, Osaka 569-1041, Japan.
authors.forename: Yasuko
authors.initials: Y
authors.lastname: In
authors.affiliation: Bioscience and Informatics, Keio University , Yokohama, Kanagawa 223-8522, Japan.
authors.forename: Tetsushi
authors.initials: T
authors.lastname: Kataura
authors.affiliation: Bioscience and Informatics, Keio University , Yokohama, Kanagawa 223-8522, Japan.
authors.forename: Etsu
authors.initials: E
authors.lastname: Tashiro
authors.affiliation: Department of Bioscience, Institute of Natural Medicine, Toyama University , 2630 Sugitani, Toyama 930-0194, Japan.
authors.forename: Ikuo
authors.initials: I
authors.lastname: Saiki
authors.affiliation: Hyphagenesis, Inc. , 2-18-28 Tamagawa Gakuen, Machida, Tokyo 194-0041, Japan.
authors.forename: Yuri
authors.initials: Y
authors.lastname: Sudoh
authors.forename: Kannika
authors.initials: K
authors.lastname: Duangmal
authors.forename: Arinthip
authors.initials: A
authors.lastname: Thamchaipenet
mesh_terms: D000192:Actinomycetales / Q000737:chemistry*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001343:Autophagy; D002470:Cell Survival / Q000187:drug effects; D004987:Ethers / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D009361:Neoplasm Invasiveness; D018696:Neuroprotective Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D016716:PC12 Cells; D061065:Polyketides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D051381:Rats; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D004987:Ethers; D005663:Furans; D018696:Neuroprotective Agents; D061065:Polyketides; C003422:tetronic acid