| This thesis is written by through sorting out,summarizing and elaborating the research content and work results during the period of master’s degree.This thesis is composed of three parts,the chemical constituents of the aerial parts of Ternstroemia gymnanthera is elaborated in chapter one;the analgesic activity of the aerial parts of T.gymnanthera is elaborated in chapter two;the research progress of chemical constituents and analgesic activities of the Theaceae is elaborated in chapter three.Objective:To study the chemical constituents of the aerial parts of T.gymnanthera and fully understand the basis of analgesic activity of some related substances.Methods:The major constituents of T.gymnanthera were isolated and purified by column chromatography padded with positive and reverse phase silica gel,Sephadex LH-20,HPLC,MCI and macroporous resin respectively,as well as preparative high performance liquid chromatography.Structures of the compounds were determined by the comprehensive analyses of the physicochemical properties and spectral data(1D NMR,2D NMR,and MS).The analgesic activity test in mice was determined at each extraction site of the plant and the chemical constituents separated from the plant.The structure-activity relationship of the analgesic activity of the separated compounds was studied by the activity test of individual compounds and the method of combination of drugs.Results:1.Chemical constituents of the aerial part of T.gymnanthera: Thirty compounds were isolated from the 95% ethanol extract of the aerial part of T.gymnanthera and identified as terngymnin A(1),terngymnin B(2),terngymnin C(3),terngymnin D(4),6′-O-coumaroyl-1′-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside(5),ternstroside A(6),ternstroside D(7),2-(3,4-dihydroxyphenyl)ethanol glucoside(8),scopoletin(9),4-hydroxy-3-(methoxycarbonyl)benzoic acid(10),protocatechualdehyde(11),methyl 2-(3,4-dihydroxyphenyl)-2-methoxyacetate(12),3,4-dihydroxyphenylethanol(13),methyl 2-(3,4-dihydroxyphenyl)acetate(14),4-hydroxybenzaldehyde(15),3,4-dihydroxyphenylaceticacid(16),ursolic acid(17),oleanolic acid(18),kajiichigoside F1(19),α-spinasterol(20),daucosterol(21),β-sitosterol(22),rosmarinic acid(23),1,6-caprolactam(24),jacaranone(25),α-tocopherol(26),stearic acid(27),oleic acid(28),linoleic acid(29),and hexacosane(30)respectively.2.(1).The result of analgesic activity of extracts from the aerial parts of T.gymnanthera: According to the bioactive experiment,comparing with the data of blank control group,ethanol extract of T.gymnanthera(i.g.1000 mg/kg)and every extracting parts(i.g.1000 mg/kg)of it can effectively inhibit the writhing times of mice which were induced by acetic acid,while(aspirin,i.g.200 mg/kg: inhibition rate: 55.27%)and The writhing inhibition rate of different extracting parts were as followed: ethyl acetate part(50.63%)> petroleum ether part(46.84%)> n-butanol part(35.02%)> water part(31.65%)> ethanol extract of T.gymnanthera(23.21%).(2).Analgesic activity of monomer compounds(i.g.50 mg/kg)isolated from T.gymnanthera.Compounds 1～12,14,26 and 25 could effectively reduce the times of writhing in mice(inhibition rates: >30%).(3).Results of the structure-activity relationship of analgesic activities of phenylethanoid glycosides from T.gymnanthera.The combination of(1,5)(62.66%),(1,2,4)(62.03%),(1,6,8)(63.71%),(8,25)(64.56%),and(9,10,11)(48.52%),can reduce the times of writhing more effectively than single compound more effectively.Compound 16(-8.23%)even increased the times of writhing in mice compared with blank control group.(i)The evidence is showed as following: compound 8(56.21%)> compound 6(49.37%),compound 8(56.21%)> compound 7(48.73%),compound 6(49.37%)> compound 4(34.18%),compound 7(48.73%)> compound 4(34.18%)and compound 3(65.40%)> compound 1(60.34%).Compared with the former,the latter has a lower activity,and the latter has a 16-group structure.(ii)The results of group compound 6(49.37%)and 7(48.73%)showed that they had the same inhibition rate of writhing induced by acetic acid in mice.(iii)The rsults can be listed as following group compound 3(65.40%)> group 7(48.73%)and group compound 1(60.34%)> group compound 4(34.18%).The structural difference between the former and the latter is that the position six substituents of the former are compound 25,while the latter is compound 16.(iv)The results of group compound 8,25 and group compound 3 are 64.56% and 65.40%.The comparison between the two groups shows that the analgesic activity of the two groups is almost similar,but the structure of compound 3 can be changed into compound 8,25 after hydrolysis.Conclusion: 1.Chemical constituents of aerial parts of T.gymnanthera: Compounds 1-4 are new compounds(Phenylethanoid glycoside derivatives of glucose).Compounds 8～11,13～16,21 and 25～30 were firstly obtained from this plant,and compounds 8～11,13,15～16 and 25～ 30 were isolated from Ternstroemia genus for the first time.2.Analgesic activity of the aerial part of T.gymnanthera:(1)Comparing with the data of blank control group,the ethanol extracts of T.gymnanthera and every extracting parts of it have analgesic activity,and the ethyl acetate extracts(i.g.1000 mg/kg,50.63%)have the strongest activity.(2)Compounds 1～12,14,25 and 27 showed some peripheral analgesic activity.(3)The combination of(1,2,4),(1,6,8),(8,25)and(9,10,11)can reduce the times of writhing more effectively than single drug.(4)Compound 16 had no analgesic activity,and even increased the times of writhing in mice.(5)Substitution of compound 16 at 6 or 2 sites of glucose in compound 8 has little effect on analgesic activity.(6)Compound 25(49.37%)inhibited the torsion induced by acetic acid in mice much more than compound 16.(7)Glucose derivatives of phenylethanol may be hydrolyzed in vivo,which plays a crucial role in peripheral analgesia.In summary,this is the first systematic study on the chemical constituents of the palnt T.gymnanthera and its analgesic activity,as well as the structure-activity relationship of phenylethanol compounds which played an analgesic role in mice in T.gymnanthera.This study has enriched the understanding of analgesic compounds from T.gymnanthera,and provided the data foundation for exploiting more analgesic components from the plants of the genus Ternstroemia. |
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