title: 19-[(1'S,4'R)-4'-Hydroxy-1'-methoxy-2'-oxopentyl]geldanamycin, a natural geldanamycin analogue from Streptomyces hygroscopicus 17997.
abstract: A novel natural geldanamycin analogue was discovered in Streptomyces hygroscopicus 17997. Its 4,5-dihydro form was also identified in the gdmP gene disruption mutant of Streptomyces hygroscopicus 17997. The structures of the two compounds were determined to be 19-[(1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl]geldanamycin (1) and 19-[(1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl]-4,5-dihydrogeldanamycin (2), respectively, by extensive spectroscopic data analysis, including 2D NMR, modified Mosher's method, and electronic circular dichroism. Compared to geldanamycin, 1 and 2 showed increased water solubility and decreased cytotoxicity against HepG2 cells.
authors: Key Laboratory of Biotechnology of Antibiotics of Ministry of Health, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, People's Republic of China.
authors: Shufen
authors: S
authors: Li
authors: Siyang
authors: S
authors: Ni
authors: Linzhuan
authors: L
authors: Wu
authors: Li
authors: L
authors: Li
authors: Bingya
authors: B
authors: Jiang
authors: Hongyuan
authors: H
authors: Wang
authors: Guizhi
authors: G
authors: Sun
authors: Maoluo
authors: M
authors: Gan
authors: Jingyan
authors: J
authors: Li
authors: Weiqing
authors: W
authors: He
authors: Ling
authors: L
authors: Lin
authors: Yiguang
authors: Y
authors: Wang
authors: Shuoke
authors: S
authors: Bai
authors: Shuyi
authors: S
authors: Si
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D056945:Hep G2 Cells; D006801:Humans; D047029:Lactams, Macrocyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012995:Solubility; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry* / Q000235:genetics; D014867:Water
chemical_list: C582869:19-((1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl)-4,5-dihydrogeldanamycin; C582870:19-((1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl)geldanamycin; D000970:Antineoplastic Agents; D016227:Benzoquinones; D047029:Lactams, Macrocyclic; D014867:Water; C001277:geldanamycin