Cytotoxic terpenoid and immunosuppressive phenolic glycosides from the root bark of Dictamnus dasycarpus.
Five new compounds, two degraded terpene glycosides, dasycarpusides A and B (1, 2), and three phenolic glycosides, 2-methoxy-4-hydroxymethylphenol 1-O-alpha-rhamnopyranosyl-(1"-->6')- beta-glucopyranoside ( 3), 2-methoxy-4-acetylphenol 1-O-alpha-rhamnopyranosyl-(1"-->6')-beta-glucopyranoside (4), and 2-methoxy-4-(8-hydroxyethyl)-phenol 1-O-alpha-rhamnopyranosyl-(1"-->6')-beta-glucopyranoside (5), were isolated from the water-soluble constituents of the root bark of Dictamnus dasycarpus Turcz.(Rutaceae). Their structures were elucidated by spectroscopic analysis and chemical evidence. Moreover, it was found that dasycarpuside A (1) showed weak cytotoxic activity against A-549 (human lung adenocarcinoma) cell line, while 4 and 5 showed more remarkable activity of inhibiting the proliferation of T-cells in vitro.
Chang
Jun
J
Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai, People's Republic of China.
Xuan
Li-Jiang
LJ
Xu
Ya-Ming
YM
Zhang
Jin-Sheng
JS
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000302:isolation & purification / Q000494:pharmacology*; D002247:Carbon Isotopes; D004187:Disaccharides / Q000302:isolation & purification / Q000494:pharmacology*; D005663:Furans / Q000302:isolation & purification / Q000494:pharmacology*; D005960:Glucosides / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000494:pharmacology*; D006801:Humans; D007166:Immunosuppressive Agents / Q000494:pharmacology*; D008175:Lung Neoplasms / Q000188:drug therapy / Q000473:pathology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry*; D018517:Plant Roots / Q000737:chemistry*; D027821:Rutaceae; D013729:Terpenes / Q000494:pharmacology*; D014407:Tumor Cells, Cultured / Q000187:drug effects
C462029:2-methoxy-4-(1-hydroxyethyl)phenol 1-O-rhamnopyranosyl-1''-6'-glucopyranoside; C462028:2-methoxy-4-acetylphenol 1-O-rhamnopyranosyl-1''-6'-glucopyranoside; C462027:2-methoxy-4-hydroxymethylphenol 1-O-rhamnopyranosyl-1''-6'-glucopyranoside; D002247:Carbon Isotopes; D004187:Disaccharides; D005663:Furans; D005960:Glucosides; D006027:Glycosides; D007166:Immunosuppressive Agents; D013729:Terpenes; C462025:dasycarpuside A; C462026:dasycarpuside B; D015107:4-Butyrolactone