title: Glycosides from the stem bark of Fraxinus sieboldiana.
abstract: A norditerpene glucopyranoside with a novel carbon skeleton (1), eight new aromatic glycosides (2-9), and 25 known glycosides have been isolated from a H2O-soluble portion of an ethanolic extract of the stem bark of Fraxinus sieboldiana. Their structures were determined by spectroscopic and chemical methods. Based on analysis of the NMR data of threo- and erythro-arylglycerols in different solvents, an application of Delta delta C8-C7 values to distinguish threo-arylglycerol and erythro-arylglycerol isomers was proposed. In the in vitro assays, compound 5 displayed TNF-alpha secretion inhibitory activity with an IC50 value of 1.6 microM, compound 6 showed antioxidative activity inhibiting Fe+2-cystine-induced rat liver microsomal lipid peroxidation with an IC50 value of 0.9 microM, and plantasioside (10) showed selective activity against the human colon cancer cell line (HCT-8) with an IC50 value of 3.4 microM.
authors.affiliation: Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
authors.forename: Sheng
authors.initials: S
authors.lastname: Lin
authors.forename: Sujuan
authors.initials: S
authors.lastname: Wang
authors.forename: Mingtao
authors.initials: M
authors.lastname: Liu
authors.forename: Maoluo
authors.initials: M
authors.lastname: Gan
authors.forename: Shuai
authors.initials: S
authors.lastname: Li
authors.forename: Yongchun
authors.initials: Y
authors.lastname: Yang
authors.forename: Yinghong
authors.initials: Y
authors.lastname: Wang
authors.forename: Wenyi
authors.initials: W
authors.lastname: He
authors.forename: Jiangong
authors.initials: J
authors.lastname: Shi
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003553:Cystine / Q000494:pharmacology; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D031661:Fraxinus / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D015227:Lipid Peroxidation / Q000187:drug effects; D008099:Liver / Q000166:cytology; D008862:Microsomes, Liver / Q000187:drug effects; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D051381:Rats; D013237:Stereoisomerism; D014315:Triterpenes; D014409:Tumor Necrosis Factor-alpha / Q000187:drug effects
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D004224:Diterpenes; D006027:Glycosides; D014315:Triterpenes; D014409:Tumor Necrosis Factor-alpha; C521025:fraxinuacidoside; D003553:Cystine