title: Biosynthesis of Novel Glucosides Geldanamycin Analogs by Enzymatic Synthesis.
abstract: Two new glucosides (1 and 2) of geldanamycin (GA) analogs were obtained from in vitro glycosylation by UDP-glycosyltransferase (YjiC). Based on spectroscopic (HR-ESI-MS, 1D, and 2D-NMR) analyses, the glucosides were elucidated as 4,5-dihydro-7-O-descarbamoyl-7- hydroxyl GA-7-O-β-D-glucoside (1) and ACDL3172-18-O-β-D-glucoside (2). Furthermore, the water solubility of compounds 1 and 2 was about 215.2 and 90.7 times higher respectively, than that of the substrates. Among compounds 1-4, only 3 showed weak antiproliferative activity against four human tumor cell lines: MDA-MB-231, SMMC7721, HepG2, and SW480 (IC50: 13.6, 15.1, 31.8, and 22.7 micrometer, respectively).
authors.affiliation: Faculty of Pharmacy, Bengbu Medical College, Bengbu, Anhui 233030, P.R. China.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Huo
authors.affiliation: Faculty of Pharmacy, Bengbu Medical College, Bengbu, Anhui 233030, P.R. China.
authors.forename: Hong-Mei
authors.initials: HM
authors.lastname: Li
authors.affiliation: Chemical Biology Research Center, KRIBB, Cheongju 28116, Republic of Korea.
authors.forename: Jae Kyoung
authors.initials: JK
authors.lastname: Lee
authors.affiliation: Faculty of Pharmacy, Bengbu Medical College, Bengbu, Anhui 233030, P.R. China.
authors.forename: Jing
authors.initials: J
authors.lastname: Li
authors.affiliation: Faculty of Pharmacy, Bengbu Medical College, Bengbu, Anhui 233030, P.R. China.
authors.forename: Tao
authors.initials: T
authors.lastname: Ma
authors.affiliation: Faculty of Pharmacy, Bengbu Medical College, Bengbu, Anhui 233030, P.R. China.
authors.forename: Xinyu
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Faculty of Pharmacy, Bengbu Medical College, Bengbu, Anhui 233030, P.R. China.
authors.forename: Yiqun
authors.initials: Y
authors.lastname: Dai
authors.affiliation: Chemical Biology Research Center, KRIBB, Cheongju 28116, Republic of Korea.
authors.forename: Young-Soo
authors.initials: YS
authors.lastname: Hong
authors.affiliation: Faculty of Pharmacy, Bengbu Medical College, Bengbu, Anhui 233030, P.R. China.
authors.forename: Cheng-Zhu
authors.initials: CZ
authors.lastname: Wu
mesh_terms: D016227:Benzoquinones / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005960:Glucosides / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D016695:Glycosyltransferases / Q000378:metabolism*; D006801:Humans; D047029:Lactams, Macrocyclic / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D016227:Benzoquinones; D005960:Glucosides; D047029:Lactams, Macrocyclic; D016695:Glycosyltransferases; C001277:geldanamycin
keywords: Geldanamycin analogs; cytotoxicity; glycosyltransferase; water-solubility