title: Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy.
abstract: Naturally occurring spirostanol saponins bear a chacotriose, α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2' and/or 4' positions of chacotriose is described and the structure-activity relationships of the glycone part at 3-OH of chlorogenin investigated. These compounds were found to be weakly-cytotoxic toward leukemia cell lines CCRF and HL-20, indicating that the chacotriose moiety is important for anticancer activity.
authors.affiliation: School of Pharmacy, College of Medicine, National Taiwan University, Taipei 100, Taiwan.
authors.forename: Ying-Hsin
authors.initials: YH
authors.lastname: Wang
authors.forename: Hsien-Wei
authors.initials: HW
authors.lastname: Yeh
authors.forename: Hsiao-Wen
authors.initials: HW
authors.lastname: Wang
authors.forename: Chia-Chun
authors.initials: CC
authors.lastname: Yu
authors.forename: Jih-Hwa
authors.initials: JH
authors.lastname: Guh
authors.forename: Der-Zen
authors.initials: DZ
authors.lastname: Liu
authors.forename: Pi-Hui
authors.initials: PH
authors.lastname: Liang
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D008968:Molecular Conformation; D012503:Saponins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D006027:Glycosides; D012503:Saponins