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Trigeminal Cents Dishes, Multi-barrel Algae And Stinking Hot Tree Chemical Composition And Biological Activity Study

Posted on:2006-04-21Degree:DoctorType:Dissertation
Country:ChinaCandidate:Q W LiuFull Text:PDF
GTID:1110360152485958Subject:Marine Chemistry
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The dissertation has three parts which deals mainly with chemical and bioactive investigation on two marine red algae, Ceramium rubrum and Polysiphonia urceolata, and one traditional Chinese medicinal plants Evodia fargesu. In order to discover bioactive compounds or lead compounds, we have successively investigated two marine red algae and one plant. 31 compounds were isolated by repeatedly chromatography on normal and reversed-phase silica gel columns, Sephadex LH-20, and final purification by C-18 HPLC. Their structures were elucidated by detailed analysis of their spectral data and chemical methods. Among these compounds, 5 were identified to be new compounds, 1 new natural compound , and 25 were isolated from the corresponding plants for the first time. Some compounds were found to show significant bioactivities on specific bioassay models. 1. Ceramium rubrum, belonging to red algae, has not been researched priviously on its secondly metablites. In this dissertation, we collected enough sample from Qingdao coast, Shandong Provence and studied its constituents. Utilizing 1H NMR. 13CNMR. MS 2D NMR technique, more than ten compounds were isolated, four of which were elucidated as 3,7,11,15-tetramethyl-hexadec-2-en-1-ol (CR01), cholest-5-en-3β-ol (CR02), 3-palm itoyloxy-propane-1,2-diol (CR06), adenosine (CR09). This is the first report on secondary metablites of Ceramium rubrum. 2.Polysiphonia urceolata, belonging to the family Rhodomeceae, which was known to produce many bromophenols as its secondary metablites. Howerever, this red algae in the coast of China has not been reported previously on its constituents. In order to systematicly study the constituents of P. urceolata, screen new lead compounds, we collected enough sample of P. urceolata from Qingdao coast, Shandong provence. By chromatograph for many times and purification, our phytochemical research experiments on P. urceolata yielded eleven bromophenols. By 1H NMR,13C NMR,LREIMS,HREIMS and 2D NMR(HHCOSY,HSQC,HMBC,NOESY) and X-ray diffraction technique, they were determined to be four new compounds, 3-bromo-4-[3-bromo-4,5-dihydroxyphenyl]methyl-5-(ethoxymethyl)-1,2-benzenediol,(5R, 10R)-2,7-dibromo-3,8-dihydroxy-5,10-dimethoxyl-5,10-dihydro-chromeno [5,4,3-cde]chromene , 2,7-dibromo-3,8-dihydroxy-5,10-dimethoxyl-5,10-dihydro- chromeno[5,4,3-cde]chromene , 2,7-dibromo-3,8-dihydroxy-10-dimethoxyl-5,10- dihydro-chromeno[5,4,3-cde]chromene, one new natural product, 3-bromo-4,5-dihydroxy-α-ethoxy-toluol, together with six known compounds, 3-bromo-4-[2,3-dibromo-4,5-dihydroxyphenyl]methyl-5-(methoxymethyl)-1,2-benzenediol , 3-bromo-4,5-dihydroxy-benzaldehyde , 3,4-dibromo-5-(methoxymethyl)- 1,2-benzenediol , 3,4-dibromo-5 (methoxymethyl)-1,2-benzenediol , 3-bromo-4,5- dihydroxybenzyl alcohol,2,3-dibromo-4,5-didroxybenzyl alcohol。 3. Evodia fargesii, belonging to the family Rutaceae, was a Chinese herbal drug and used for the treatment of hepatitis in Jiangxi Provence. In this dissertation, in order to find its bioactive principles, the chemical constituents were investigated by normal and reversed phase chromatography sytematically. 16 compounds were isolated from this plant, their chemical structure type include alkaloids, flovoids, triterpenoids, etc. Their chemical structures had been elucidated based on spectral evidences and chemical studies. They are 6-Hydroxy-N-methyl-1,2,3,4-tetrahydro-β-carboline (LE1) , N,N-Dimethyltryptamine (LE2) ,N-p-coumaroyltyramine (LE3),Dictamnine (LE4),Robustine (LE5),Haplophine (LE6),Limonin (LE7),Rutaevine (LE8),Evodol (LE9),Quercetin (LE10),(+)-Dihydroquercetin (LE11),β-sitosterol (LE12) , Daucosterol (LE13) , Syringic acid (LE14) ,1,2,3,4-tetrahydro-2-methyl-β-carboline(LE15),5-hydroxy-N,N-dimethyltryptamine (LE16). LE1 was a new compound, 2-16 was first obtained from E. fargesii. 4 Concurrent with the spread of the western lifestyle, the prevalence of all types of diabetes is on the rise in the world's population. 90% of diabetics is Type 2 diabetes subjects. Traditional oral anti...
Keywords/Search Tags:Ceramium rubrum, Polysiphonia urceolata Evodia fargesii, chemical constituents, biological activity
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