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Chemical Constituents, Bioactivities And Its Application Of The Extract Of Two Genus Of Marine Algae

Posted on:2007-09-27Degree:DoctorType:Dissertation
Country:ChinaCandidate:J SunFull Text:PDF
GTID:1100360182493855Subject:Marine Chemistry
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The paper are made up of two parts. The first part is bioactivities of the extractof Laminaria japonica and the effluence to vegetables and the machnism of function.The second part of the paper is the bioactive screening of ethanol extract andchemical constituents of the red alge Laurencia tristicha. The bioactivities of somepurify compounds were also carried out.The extract of Laminaria japonica, which was cultured was prepared withadvanced technique combided with seaweed amylose. To offer the foundation ofproducing seaweed fertilizer, the extract was applied to vegetables to find the effectand machinery of it to the anti-drought, nitrate accumulation, quality and anti-virusof crop. The relative water content was 92~94%. The rate of the prevention and cureto mosaic virus was 91%. The quality of vegetables were improved a lot. The nitratecontent was reduced. All of these were proved by farm experiment.The innovation of the research include two aspects. One is the extractingtechnique combined with seawed amylose, which not only decrease the cost ofextracting but also a rational utilization of seaweed. The other is the conclusion thatseawed amylose has bioactivies with cytokinins, betaines and auxins.Algae, as favorite sources of marine secondary metabolites, contain rich kindsof bioactive compounds. The study on marine algae chemical constituents and itsbioactivities was carried out to search for bioactive leading compounds from marineorganisms.The literatures regarding the chemical investigation of the red algae Laurenciain nearly 20 years in CA have been searched and summarized.The bioactive screening of ethanol extract of the algae Laurencia tristicha,which were collected from Naozhou Island, south sea of China, was designed tosearching for bioactive compounds. Standard MTT method was used for testingcytotoxicity of ethanol extracts against human cancer cell lines KB, Bel-7402,PC-3M, Ketr3 and MCF-7. The inhibitory activity of extracts againstNa+,K+-ATPase was carried out on enzyme mode. The inhibitory activity of extractsagainst dog vascular smooth muscle cell proliferation was also screened by MTTmethod. The results showed that the ethanol extract of the algae Laurencia tristichawas active against Na+,K+-ATPase and dog vascular smooth muscle cell proliferation.To study the chemical constituents of the red algae Laurencia tristicha aimingat searching for bioactive natural products. 33 compounds were isolated by variouschromatographic techniques including column chromatography over normal phasesilica gel and Sephadex LH-20 gel and reverse phase HPLC as well asrecrystallization. Their structures were determined by spectroscopic methodsincluding IR, MS, 1D, 2D NMR and X-ray techniques. Compounds L1~L8 werenew compounds;compound L5 possessed unusual novel carbon skeleton;compounds L9~L13 were new natural products;compounds L18 and L22 werefirstly obtained from marine organisms;All compounds were firstly isolated fromLaurencia genus. All the new compounds were sesquiterpenes and their names weredesignated as: (1R,3R)-(-)-3-(3-hydroxy-4-methylphenyl)-1,3-dimethyl–2-methylidenecyclo-pentanol(L1),(1R,3R)-(-)-3-(4-methylphenyl)-1,3-dimethyl-2-methylid-enecyclopentanol (L2),(1R,3R)-(-)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl–2–methylidenecyclopentanol (L3),(+)-(1S,2R)–2-(3–hydroxy–4–methylphenyl)-1,2-[3.1.0]bicyclohexane (L4),(?)-(1′S, 2′R)-5-hydroxy–6–methyl-spiro-dihydrobenzofuran-2(3H),2′-{1′-methyl-[3.1.0]bicyclohexane}(L5),(+)-6-methyl-2-(p-tolyl)hept-4-en-2,6-diol (L6),(3R,3aS,8bS)-(-)-2,3,3a,8b–tetrahydro –7-bromo–3a–hydroxy-methyl -3,6,8b -trimethyl-1H-cyclopenta[b] benzofuran (L7 ),(3R,3aS,8bS) -(-) -2, 3, 3a, 8b– tetrahydro –3 a– hydroxymethyl -3, 6, 8b -trimethyl -1H–cyclopenta[b]benzofu ran(L8). By comparing with corresponding literature data, 25 known compounds were readlyidentified as: (+)-(1R,2R)-4-bromo-1,5,9–trimethyl–12–methylidene–8–oxa-tricyclo [7.2.1.02]dodeca-2,4,6-triene(L9),(3S,3aR,8bS)-(-)-2,3,3a,8b–tetrahydro–7-bromo–3– hydroxy-3,3a,6,8b-tetramethyl -1H-cyclopenta [b] benzofuran (L10 ),(3R,3aR,8bS) -(-) -2, 3, 3a, 8b – tetrahydro–7-bromo–3 – hydroxy -3,3a,6,8b-tetramethyl -1H -cyclopenta[b]benzofuran (L11 ),(3S, 3aR,8bS) -(-)-2, 3, 3a, 8b – tetrahydro – 3 – hydroxy -3, 3a, 6, 8b-tetramethyl-1H-cyclopenta[b]benzofuran (L12 ), ( 3aR,8bS) -(-) -3a, 8b – dihydro–7-bromo– 3, 3a, 6, 8b -tetramethyl -1H-cyclopenta [b]benzofuran (L13 ),aplysinol (L14 ) ,aplysin (L15 ),laurebiphenyl (L16 ),johnstonol (L17),gossonorol (L18 ),7,10-epoxy-ar-bisabol-11-ol (L19 ),10-epi-7,10-epoxyarbisabol-11-ol (L20 ) 3β-hydroxy-5α, 6α-epoxy-β-ionone (L21 ),3β-hydroxy-5β,6β-epoxy-β-ionone (L22 ),cholesterol (L23 ),cholesta-5-en-3β,7α-diol (L24 ),β-sitosterol(L25 ),phytol (L26 ),zeaxanthin (L27 ),4-hydroxybenzaldehyde (L28 ),indolyl-3-carbaldehyde (L29 ) , 1-O-hexadecanoyl-3-O-β-D-galactopyranosyl-glycerol(L30 ),1-O-Octadecanoyl-3 -O-β-D-galactopyranosyl-glycerol (L31),glycerol-1-hexade canoate (L32),hexade-canoic acid (L33 )。Cytotoxicity against human cancer cell lines BGC-823, Bel-7402, A549, A2870,HCT-8 and HELA of 23 compounds and inhibitory activity of 13 compounds againstdog vascular smooth muscle cell proliferation were screened by MTT method. Somepurify compounds showed bioactive.
Keywords/Search Tags:The extract of alga, Bioactivity, Chemical constituents, Laminaria japonica, Laurencia tristicha
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