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Studies On The Chemical Constituents And Bioactivities Of Morus Australis And Morus Cathayana

Posted on:2008-08-24Degree:DoctorType:Dissertation
Country:ChinaCandidate:Q J ZhangFull Text:PDF
GTID:1114360272981940Subject:Medicinal chemistry
Abstract/Summary:PDF Full Text Request
Morus australis and Morus cathayana,which belongs to the genus Morus of Moraceae,grow in many provinces of China.The root bark of them was a substitute of 'Sang-Bai-Pi'--the root bark of M.alba,which was an important medicinal material in traditional Chinese medicine.Many novel bioactive compounds were isolated from the plants of Morus.Phenol compounds,which were the main composition of the alcohol soluble part,showed antihypertension,antivirus, antibacterial,antifungi,antioxidation,antiinflammation,and anticancer activities.The water soluble compounds are mostly amino acids and polyhydroxyalkaloids which have antiglycemia activity.Morus australis and Morus cathayana were collected in Jiangxi province and identified by Professor Ce-ming Tan,the Jiujiang Botany Institute of Forest,Jiangxi province.By means of chromatographic and spectroscopic technologies as well as chemical methods,Morus australis and Morus cathayana were studied systemically in chemistry and related bioassays.Ninteen compounds were isolated,purified and identified from 95%ethanol extract of the stem of Morus australis.They were identified as follows:australisine A(1), austrafuran A(2),5,7,2',4'-tetrahydroxy-3-methoxyflavane(3),albanol B(4), sanggenon C(5),oxyresveratrol(6),3,4,3',5'-tetrahydroxystilbene(7),resveratrol(8), 2,4,3'-trihydroxybibenzyl(9),dihydromorin(10),quercetin(11),isolicoflavonol(12), kaempferol(13),sitosteryl 3β-glucoside 6'-O-palmitate(14),5,7-dihydroxycoumarin (15),3,5-dihydroxybenzaldehyde(16),vanillic acid(17),2,4- dihydroxybenzaldehyde (18),β-daucosterol(19).Forty compounds,including six compounds that had been isolated from the stem of Morus australis,were obtained from 95%ethanol extract of the stem bark of Morus australis.They were identified as follows:australisine B(20),australisine C(21), Austrafuran B-C(22-23),mulberrofuran F(24),mulberrofuran G(25),mulberrofuran J(26),mulberrofuran E(27),chalcomoracin(28),mongolicin C(29),kuwanon G(30), mulberrofuran C(31),albafuran C(32),kuwanol A(33),kuwanon X(34),kuwanon P (35),mulberrofuran Q(36),kuwanon Z(37),moracin M(38),moracin G(39), albafuran A(40),mulberroside C(41),macrourin B(42),macrourin D(43),morusin (44),kuwanon C(45),albanin E(46),betulinic acid(47),mulberroside A(48), oxyresveratrol 2-O-β-D-glucopyranoside(49),mulberroside B(50),xeroboside(51), scopolin(52),cichoriin(53).Among the fifty three compounds,there were three new Diels-Alder type adducts (compounds 1,20 and 21),three new oligostilbenes(compounds 2,22 and 23) and a new flavonol(compound 3).Among the known compounds,fourteen compounds(7-9, 12-18,49,51-53) were isolated from the genus Morus and the plant for the first time, and other twenty seven compounds(4-6,10,24-29,31-43,45,46,48,50) were isolated from Morus australis for the first time.Thirteen compounds were obtained from 95%ethanol extract of the stem bark of Morus cathayana.They were identified as follows:cathayanon C(MC-1), cathayanon D(MC-2),cathayanon E(MC-3),sanggenon C(MC-4),mulberrofuran Q(MC-5),mulberrofuran K(MC-6),albanol B(MC-7),moracin M(MC-8), austrafuran A(MC-9),moracin P(MC-10),oxyresveratrol(MC-11),resveratrol (MC-12),β-daucosterol(MC-13).Among them,there were three new compounds (MC-1,MC-2 and MC-3),and other five compounds(MC-5,MC-6,MC-7,MC-9 and MC-12) were isolated from Morus cathayana for the first time.The negative HRESI-FTMS/MSn spectra of ninteen Diels-Alder adducts(1,4,5,20, 21,24-28,30-35,MC-1,MC-2) were studied.Based on the data,some fragmentation partern was found.On the negative ESI-MS/MS2 spectrum,one or two phenol molecules were broken away the anion[M-H]- of cis-trans and all-trans Diels-Alder type adducts through Mclafferty rearrangement,which produced several diagnostic ion peaks;the ketalized Diels-Alder type adducts tended to loss a phenol molecule or a molecule of cyclohexa-2,5-dienone derivatives,and gave two kinds of diagnostic ion peaks.The bigger was larger 12 daltons than the other.These regulation and diagnostic ion peaks,which were found for the first time in this thesis,could be used to identify Diels-Alder type adducts quickly. The results of bioassays displayed:(1) compounds 1,4,8,11,12,13,20,21,24,25, 27-29,33,40,44,47,which were obtained from the 95%ethanol extract of Morus australis,showed moderate anticancer activity to five human cancer cell lines(A549, Bel-7402,BGC-823,HCT-8,A2780) with IC50 ranging from 3.9-9.5μg/mL.(2) Twenty one compounds(2,4,6-8,11,12,24-29,31-36,39,40),isolated from the EtOAc soluble part of Morus australis,inhibited the production of the lipid peroxide induced by Fe2+-Cys system in the liver microsomal obviously,with inhibitory rates more than 50%at a concentrate of 10-5mol/L.Compound MC-2,obtained from the ethanol extract of Morus cathayana,displayed 88%inhibitory rate at 10-6mol/L,far more than its analogue MC-1.(3) On the pharmacological model of release ofβ-glucuronidase from rat PMNs induced by PAF,twelve compounds(6,7,8,12,13, 17,18,27,29,31,34,36),isolated from Morus australis,were revealed the antiinflammation activity with the inhibitory rates more than 50%at a concentration of 10-5 mol/L.On the same pharmacological model,the inhibitory rates of compounds MC-1 and MC-2 were 53.8%and 85.8%,respectively.Compared with MC-1,the better activity of MC-2 in antioxidant and antiinflammatory assays was worthy to study continuously.(4) In other bioassays,compounds 26 and 31 improved the survival rates of the Eahy926 cells in an anoxic situation and compound 39 inhibited the duplication of HIV virus with 94.5%inhibitory rate at a concentration of 10-5 mol/L.
Keywords/Search Tags:Bioactivities
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