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Studies On Chemical Constituents And Pharmacological Activities Of Lannea Coromandelica

Posted on:2013-05-20Degree:MasterType:Thesis
Country:ChinaCandidate:X J YunFull Text:PDF
GTID:2234330374474794Subject:Organic Chemistry
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Lannea coromandelica (Anacardiaceae) is a deciduous tropical tree widely distributedin Bangladesh,India and some other tropical countries.There are only one species found inHainan,Guangdong,Guangxi and Yunnan provinces in China.Plants belonging to thisgenusare used in folk medicine for treatment of elephantiasis,leprosy,ulcers,toothache,oraldiseases,bedsore,heart disease,dysentery,gout,rheumatism,vaginal worry and impotence,etc.InChina,the bark of L. coromandelica was used for bone fractures and detoxification.In Wuzhishan area,it was used for gastritis,enteritis,leukorrhagia.Scholars at home and abroadreported the isolation of steroids,flavonoids,anthraquinones,ketone,phenols,olefinic alcoholfrom Lannea genus.In this paper,the chemical components and activities of the L.coromandelica were further studied,it is very useful for searching active components andaccumulating natural chemical information.The air dried L. coromandelica are crushed,and then extracted by78%ethanol (involume fraction).After evaporation under reduced pressure a dark ethanol extract wasobtained. The extract was mixed with water, extracted by petroleum ether, chloroform, ethylacetate and n-BuOH,respectively.The four fractions were subjected to columnchromatography over macroporous resin, normal and reversed-phase silica gel,sephadexLH-20,preparation thin-layer chromatography and recrystallization,respectively.Twenty sixcompounds were isolated,and their structures were established on the basis of extensivespectroscopic (IR,1D-NMR,2D-NMR,MS) data analysis and by the comparison withspectroscopic data reported in the literature.Then tests on anti-oxidation and cytotoxicactivities of different fractions and some compounds had been taken.Bioassay-guided isolation studies on the stem extract of L. coromandelica led to theisolation of twenty six compounds:quercetin-3-O-rutinoside(1),quercetin(2),5,5′-dibuthoxy-2,2′-bifuran(3),taraxerone(4),taraxerol(5),taraxeryl acetate(6),myricadiol(7),lupenol(8),stigmastane-3,6-dione(9),stigmast-4-en-6β-ol-3-one(10),daucosterol(11),β-sitosteryl-3β-glucopyranoside-6′-O-palmitate(12),β-sitosterol palmitate(13),β-sitosterol(14),(2S,3S,4R,10E)-2-[(2′R)-2′-hydroxytetracosanoyl amino]-10-octadecene-1,3,4-triol(15),aralia cerebroside(16),nicotinic acid(17),protocatechuic acid(18),4-hydroxy-3-methoxybenzaldehyde(19),2- hydroxy-3-methoxybenzaldehyde(20),benzoic acid(21),p-hydroxybenzoic acid ethyl ester(22),trans-cinnamic acid(23),citric acid(24),palmitic acid(25),stearic acid(26). In additionto compound2and14,other compounds were isolated from this plant for the first time.The types of ceramide,heterocycles and triterpene compound,which were unpreviouslyreported in Lannea genus,improvedthe chemical structures of L. coromandelica.The anti-oxidation activity of the extract was evaluated by using methods of DPPH.and.OH with Vc as reference substance.The study showed that the anti-oxidation activity ofpetroleum ether fraction and ethyl acetate fraction were stronger than that of Vc on.OH, IC50were65.17μg/mL and117.79μg/mL.The anti-oxidation activity of chloroform fraction andethyl acetate fraction were stronger than that of Vc on DPPH., IC50were124.84μg/mL and0.011μg/mL。The petroleum ether,chloroform,ethyl acetate,and n-BuOH fractions,and somecompounds were evaluated in vitro for cytotoxic activities against the SPCA-1(human lungcancer),BEL-7402(human hepatocellular carcinoma),SGC-7901(human gastric cancer)andK-562(human myelogenous leukaemia) cancer cell lines using the MTT assay method. Thepetroleum ether fraction showed cytotoxic activities towards all the four cancer celllines,especially towards SGC-7901and SPCA-1,with IC50values of8.05μg/mL and11.27μg/mL,respectively.The chloroform fraction only showed cytotoxic activities towardsSGC-7901,IC50value was21.8μg/mL.Compound25showed cytotoxic activities towardsSPCA-1and SGC-7901,IC50value were26.28μg/mL and70.42μg/mL, respectively.
Keywords/Search Tags:Lannea coromandelica, chemical constituents, cytotoxic activity
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