title: Acyclic congeners from Actinoalloteichus cyanogriseus provide insights into cyclic bipyridine glycoside formation.
abstract: Inactivation of the O-methyltransferase gene crmM of Actinoalloteichus cyanogriseus WH1-2216-6 led to a mutant that produced three new acyclic bipyridine glycosides, cyanogrisides E-G (1-3). Further chemical analysis of the wild strain yielded 1 and another new analogue, cyanogriside H (4). Compounds 1-4 possess a skeleton consisting of a 2,2'-bipyridine and a d-quinovose or l-rhamnose sugar moiety. Cyanogriside G (3) was considered to be a key biosynthetic intermediate of the cyclic bipyridine glycosides cyanogrisides A-D. Compounds 2 and 3 showed cytotoxicities against HCT116 and HL-60 cells, and compounds 1 and 4 were cytotoxic on K562 cells.
authors.affiliation: Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, China.
authors.forename: Peng
authors.initials: P
authors.lastname: Fu
authors.forename: Yiguang
authors.initials: Y
authors.lastname: Zhu
authors.forename: Xiangui
authors.initials: X
authors.lastname: Mei
authors.forename: Yi
authors.initials: Y
authors.lastname: Wang
authors.forename: Haijian
authors.initials: H
authors.lastname: Jia
authors.forename: Changsheng
authors.initials: C
authors.lastname: Zhang
authors.forename: Weiming
authors.initials: W
authors.lastname: Zhu
mesh_terms: D015082:2,2'-Dipyridyl / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000192:Actinomycetales / Q000737:chemistry / Q000201:enzymology / Q000235:genetics; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045325:HCT116 Cells; D018922:HL-60 Cells; D006801:Humans; D020014:K562 Cells; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D006027:Glycosides; D015082:2,2'-Dipyridyl