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Studies On The Chemical Constituents Of Euphorbia Nematocypha Hand.-Mazz

Posted on:2016-01-31Degree:MasterType:Thesis
Country:ChinaCandidate:H Y JiaFull Text:PDF
GTID:2284330503476318Subject:Chemical Engineering and Technology
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Euphorbia nematocypha Hand.-Mazz, which was a perennial herbaceous plant widely distributed in Yunnan, Taiwan and Sichuan Province, especially in the hillside grassland, shrub and sparse forest at altitudes between 200 and 3300 m, wasone of the species of genus Euphorbia. The roots of E. nematocypha had better effects for treating ascites, skin itching, scabies in Yunnan local, and it also had the functions of hemostasis, anti inflammation, detumescence, expelling wind. To ascertain its chemical constituent and medicinal value, the ethanolic extracts of the dried roots of E. nematocypha were investigated.Various separation materials such as silica gel, Sepahdes LH-20, MCI and RP-18 were used in column chromatography in this study. As a result, it resulted in the isolation of a new phenylpropanoid named 16-O-caffeoyl-16-hydroxylhexadecanoic acid (D7*) and a new P-amyrane type triterpenoid named trans,Trans-2’,4’-hexadienedioic acid-1’-β-amyrin ester (D40*), together with 38 known compounds from the ethanol extract of the dried roots of Euphorbia nematocypha. Their structures were elucidated on the basis of spectroscopic data. These compounds were as follows:ent-2-hydroxy-atis-1,16(17)-dien-3,14-dione (Dl), 17-hxdroxyjolkinolide A (D2), scopoletin (D3),3,3’-dimethoxy ellagic acid (D4), 2,2’-dimethoxy-3,3’-dihydroxy-5,5’-oxygen-6,6’-biphenyl formic anhydride (D5), jolkinolide A (D6),16-O-caffeoyl-16-hydroxylhexadecanoic acid (D7*), jolkinolide B (D8), P-sitosterol (D9), coffee acid octadecyl ester (D10),17-hxdroxyjolkinolide B (D11), catalpafurxin (D12), betulinic acid (D13), magdalenic acid (D14), lupeol (D15), ferulic acid hexacosyl ester (D16), gallic acid (D17), β-amyrin (D18), pseudo-taraxasterol (D19),3,3’,4-trimethoxy ellagic acid (D20),3,3’-di-O-methylellagic acid-4-O-β-D-glucopyranoside (D21), coffee acid arachidic ester (D22), pentadecanoic acid (D23), β-amyrin acetate (D24), brevifolin (D25), 3,3’-di-O-methyl ellagicacid-4’-O-a-D-arabinfuranoside (D26), ent-atisane-3β,16a,17-triol (D27), lupenyl acetat (D28),24-methylene cycloartanol (D29), β-daucostero (D30), a-amyrin acetate (D31), scopoletin-7-glucoside (D32), ellagic acid (D33),3(R)-3-hydroxy-atis-16-ene-2,14-dione(D34), jolkinolide E (D35), (-)-(5E,12E,2S,3S,4S,9S,11S,15R)-15-benzoyloxy-lathyra-5,12-dien-3-ol-14-one (D36), palmitic acid (D37), sucrose (D38), chiricanines A (D39) and trans,trans-2’,4’-hexadienedioic acid-1’-β-amyrin ester (D40*).These compounds contained several skeleton types of dieterpenoids and triterpenoids, steroids, phenylpropanoid, fatty acids, tannin and its derivatives. In particular, the new phenylpropanoid,16-O-caffeoyl-16-hydroxylhexadecanoic acid (D7*), was first to be isolated as a caffeic acyl long chain alkyl acid from the family Euphorbiaceae; magdalenic acid (D14), which was a more common diterpene of marine eunicellan carbon skeleton, was first found to be isolated from the family Euphorbiaceae and secondly reported from the terrestrial plant in our work. Among the 40 compounds, Dl, D5, D7*, D10, D12, D14, D15, D16, D18, D19, D20, D21, D22, D23, D24, D26, D28, D31, D32, D34, D36, D37, D39 and D40* were obtained from this plant for the first time.The in vitro cytotoxic activities of the new compound (D7*) against the MCF-7 and HeLa cell lines cells were tested. It showed cytotoxic activities against human breast cancer cell line MCF-7, with IC50 values in the range of 20.2 to 27.8 mol/L. Cytotoxic activities against the MCF-7 cells were higher than those against the HeLa cells.
Keywords/Search Tags:Euphorbia, Euphorbia nematocypha, Chemical constituents, dieterpenoids, eunicellane, triterpenoids, β-amyrane
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