Studies on the Chemical Constituents of Caesalpinia Sappan and Bridelia Tomentosa

Abstract: Sappan Lignum, the dried heartwood of Caesalpinia sappan L., is used intraditional Chinese medicine as an emmenagogue, hemoststic and anti-inflammatoryagent. It is used for treatment of contusion and thrombosis. The pharmacologicalscreens disclosed that the 95% alcohol and water extract of Caesalpinia sappan bothshowed anti-tumor activities. To investigate the chemical constituents and discovernew active compounds, a detailed phytochemical investigation was carried out on theheartwood of Caesalpinia sappan.By means of chromatography methods and spectral technologies, twenty-fourcompounds were isolated. Among them, twenty-one were identified. They are: twonew compounds: Neocaesalpin A(1), Neocaesalpin B(2); three brazilin derivatives:Brazilein (3), Brazilin (4), brazilide A (5); two dibenzoxocins: Protosappanin A (6),Protosappanin C (7); two lignans: (±)-Lyoniresinol (8), (-)-Syringaresinol (9); twochalcones: 3-deoxysappanchalcone (10), Sappanchalcone (11); one homoisoflavonoid:3-deoxysappanone B (12); two flavonoids: Rhamnetin (13), 3,8-dihydroxy-4,10-dimethoxy-7-oxo-[2]benzopyrano[4,3-b]benzopyran(14); one stilbene: (E)-3,Y-dime-thoxy-4,4'-dihydroxystilbene (15); one chroman: 3,7-dihydroxy-chroman-4-one (16);three sterols: Stigrnasterol (17),β-sitosterol (18), Daucosterin (19); two fatty acid:Dimethyl adipate (20), Stearic (21). Compounds 1, 2, 14 are new. 8, 15, 20 wereisolated from the Caesalpinia genus for the first time. 9 was obtained fromCaesalpinia sappan for the first time.The preliminary pharmacological screening has been established on the isolatedcompounds in related to anti-tumor. Compounds 1, 3, 4, 11 exhibited moderatecytotoxicity against seven tumor cell lines (HCT-8, Bel-7402, A549, BGC-823,BGC-803, A2780 and MDA-MB-468). In addition, we also explored thepharmacological activities about antiinflammmatory, hepatoprotectiv effect,antithrombase, hypoglycemic effect, et al. Compound 1 exhibited the strongestinhibitory effects on TNF-αproduction, where 2, 11, 12 showed less potent action. Compounds 15 displayed pronounced hepatoprotective activities against D-GaIN-induced toxicity in WB-F344 cells (at the concentration of 1×10~(-4) mol/L, cell survivalrate is 70%, P<0.001, compared to model group), and compounds 3, 5, 6 showedslightly antithrombase effect.A ~1H NMR method was established for the finger-print of Caesalpinia sappanfor the first time and 5 crude marerials from different regions were analyzed. Thecharacteristic signals of the ~1H NMR finger-print were assigned through analyzing the~1H NMR signals of every compound and comparing them with the CSPD. The resultsshowed the ~1H NMR finger-print of Caesalpinia sappan we Studied had highlycharacteristic features and reproducibility. The same species from different regionshad wonderful consistency.Bridelia tomentosa B1., a small shrub in the Euphorbiaceae family, is widelydistributed in Taiwan, Guangdong, Guangxi and Yunnan Provinces of south China.As a traditional medicine, it is used for curing neurasthenic, turbulence of emmenia,bite of dog, tumefaction and so on. Eleven compounds were obtained from the 95%alcohol extract of the leaves of Bridetia tomentosa (EtOAc, n-BuOH). From which,the structures of ten were determined by the spectroscopic analysis and chemicalmethods as Tamarixetin 3-O-β-D-xylopyranosyl-(1-2)-α-D-ribopyranoside (1),Tamarixetin 3-O-α-D-ribopyranoside (2), Tamarixetin (3), Tricin (4), CapparilosideA(5), Friedelin(6), Friedelanol (7), Stigmasterol 3-O-β-D-glucoside(8),β-sitosterol(9) and palmitin oic acid glyceride (10). Compounds 1, 2 are new ones. Compounds3, 4, 5, 10 were isolated from the Bridelia genus for the first time. Thepharmacological screening on 95% alcohol extract, every extraction part and isolatedcompounds showed only compound 5 had slightly antithrombase effect…
Key words: Caesalpinia sappan; finger-print; ~1H NMR; Bridelia tomentosa

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