Glycosides from the stem bark of Fraxinus sieboldiana.
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.
Lin
Sheng
S
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
Wang
Sujuan
S
Liu
Mingtao
M
Gan
Maoluo
M
Li
Shuai
S
Yang
Yongchun
Y
Wang
Yinghong
Y
He
Wenyi
W
Shi
Jiangong
J
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
D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D004224:Diterpenes; D006027:Glycosides; D014315:Triterpenes; D014409:Tumor Necrosis Factor-alpha; C521025:fraxinuacidoside; D003553:Cystine