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Studies On Chemical Constituents And Bioactivities Of Scorzonera Mongolica Maxim. And Tamarix Chinensis Lour. From Coastal Wetland Of Yellow River Delta

Posted on:2008-09-16Degree:DoctorType:Dissertation
Country:ChinaCandidate:B WangFull Text:PDF
GTID:1104360242955490Subject:Medicinal chemistry
Abstract/Summary:PDF Full Text Request
Organisms of coastal wetlands, effected by oceanic and terrestrial environment, likely produce more unique secondary metabolites with various biological activities. At present, a lot of structurally novel and bioactive secondary metabolities, including sesquiterpenes, diterpenes, triterpenes, steroids, ceramides and somon, have been isolated from them. These constituents exhibited potential bioactivities such as antiflammation, antitumor, antifouling and cytotoxic activities. All these will provide more opportunities to find lead compounds.Yellow River Delta wetland is the youngest, broadest and the most integrated wetland ecosystem in the warm-temperate zone of the world. It posseses the rich and diverse biological resource. Among them, the family Compositae plant Scorzonera mongolica Maxim. and the family Tamaricaceae plant Tamarix chinensis Lour. were used as Traditional Chinese Medicine(TCM) or folk herbal drug the past time. However, no reports have been found about the chemical research on these plant to date. In order to find bioactive components, we systematically investigated the constituents of S. mongolica Maxim. and T. chinensis Lour. collected from Dongying, Shandong Province of China, including amino acids, organic elements, volatile oils and other organic compounds.The MeOH extracts of two species showed significant cytotoxic activities against selected tumor lines, mouse leukemia cell (P388), human hepatic carcinoma cell (BEL-7402), human lung cancer cells (NCI-H460), Breast Carcinoma Cell Line (MCF7), human glioma cell line (SF-268) and Human lung adenocarcinoma epithelial cell line (A-549), respectively. Bioassay-guided isolation resulted in 50 components, 4 new ones as well as 46 known ones. Their structures and stereochemistry were determined on the basis of MS, IR, 1H-NMR, 13C-NMR (DEPT), extensive 2DNMR (1H-1HCOSY, HMQC, HMBC, NOESY) spectroscopic analysis and comparison with the literatures.(1) The inorganic element of the sample from S. mongolica Maxim. and T. chinensis Lour. were measured by ICP-MS. 27 elements were detected in the two species. The main inorganic elements were Ce, K, Al, Ca and Fe and the main trace elements were Ce, Ga, Mn, Zn and Cu. in S. mongolica Maxim. respectively. While in T. chinensis Lour., the main inorganic elements were K, Na, Ca and Mg, the main trace elements were Ce, Fe, Mn and Zn.(2) The determination of Volatile oils was finished by GC-MS. The results showed that the plant S. mongolica Maxim. was composition of 13 ones, and 2 main components that Hentriacontane (34.75%) and A? - neogammacer - 22(29) - en - 3β- ol(21.47%) account for 93.43% in total Volatile oils. The Volatile oils of T. chinensis Lour. contains 26 components, among them, 4 ones including Hexadecanoic acid methyl ester (29.20%), 11,14-Octadecadienoic acid methyl ester (20.88%), 9-Octadecenoic acid methyl ester (12.31%) andβ-Tocopherol (7.65%) account for 70.0% in total Volatile oils.(3) The amino acid analysis was determined on the auto-aminoacid analyzer. 16 kinds of amino (5.7318%) were identified, the main components were Cys(0.8839%), Asp(0.0.88001%) and Arg(0.7883%) in S. mongolica Maxim., respectively. The species T. chinensis Lour. also contained 16 kinds of amino acids(6.3336%), the main components were Glu(0.7197%), Arg(0.5866%) and Cys (0.9457%).(4) Guided by cytotoxic activities, 23 Compounds, 3β–teradecanoyloxy-28– hydroxyl–olean–18–ene (SM-1), 3β–dodecanoyl–28–hydroxyl–olean–18–ene (SM-2), lupeol (SM-3), betulin (SM-4), betulinic acid (SM-5), lupeo acetate (SM-6), 23Z–3β–acetoxyeupha–7, 23–diene–25–ol (SM-7), Dammar–20-ene-3β-ol, 24– methylene–acetate (SM-8),β–pulcherryl acetate (SM-9), taraxasterol (SM-10), Taraxasterol acetate (SM-11),ψ–taraxasterol (SM-12),ψ–taraxasteryl acetate (SM-13),α–Amyrin acetate (SM-14), Dammar–24–ene-3, 20–diol (SM-15), 3β–tetradecanoate, butyrospermol acetate (SM-16), Dehydrocostus lactone (SM-17),β-sitosterol (SM-18), cholesterol (SM-19), 5α. 8α-epidioxy-(22E, 24R)-stigmaster- 6, 22- dien-3β-ol (SM-20), multiflorenyl acetate (SM-21), 3β–teradecanoyloxy-28–hydroxyl–olean–12–ene (SM-22) and 3β– dodecanoyl–28–hydroxyl–olean–12–ene (SM-23),were obtained from S. mongolica Maxim. Among them, SM-1, SM-2, SM-22 and SM-23 were new triterpenes; SM-4, SM-5, SM-7, SM-8, SM-10, SM-11, SM-12, SM-13, SM-14, SM-15, SM-16, SM-17, SM-20 and SM-21 were isolated from the genus Scorzonera for the first time. All components were isolated firstly from the species S. mongolica Maxim.(5) 27 Compounds were obtained from T. chinensis Lour. Based on spectroscopic analysis and comparison with the literatures, their sructures were identified asβ–sitosterol (TC-1), stigmast–4–ene-3, 6–dione (TC-2), Ergosta–4, 24(28)–diene–3–one (TC-3), stigmast–4–ene-3, 6-dione (TC-4), sitoste rone (TC-5), cholesterol (TC-6), lupeol (TC-7), betulin (TC-8), myricadiol (TC-9), isomyricadiol (TC-10), isoaleuritolic acid (TC-11), isoaleuritolic acid 3-p-hydroxy cinnamate (TC-12), maslinic acid (TC-13), 24–methylenecycoartanol (TC-14), Phyto (TC-15), 5-hydroxy–7, 4?–dime–thoxyflavone (TC-16), Kaempferol (TC-17), 4′- methylkaempfero (TC-18), 7-methylkaempfero (TC-19), 4′,7–dimethyl– kaempfero (TC-20), diiso–butyl–O–phthalate (TC-21), dibutyl phthalate (TC-22), 4-Hydroxy -benzoic acid (TC-23), Quercetin (TC-24), 3',4'-dimethylquercetin (TC-25), ferulic acid (TC-26) and methyl-P-hydrobenzoate (TC-27). Among them, TC-2, TC-3, TC-4, TC-5, TC-11, TC-13, TC-14, TC-16 and TC-27 were isolated from the genus Tamarix for the first time. TC-7,TC-8, TC-9, TC-10, TC-15, TC-21, TC-22, TC-23 and TC-26 were isolated firstly from T. chinensis Lour.(6) The anti-tumor activities of 23 compounds were tested by MTT and SRB methods. SM-4,SM-5,SM-6,SM-7,TC-2,TC-12,TC-13and TC-15 showed potential anti-tumor activities.
Keywords/Search Tags:Scorzonera mongolica Maxim., Tamarix chinensis Lour., Constituents, Bioactivities
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