| Eupatorium odoratum L.(alias Chromolaena odorata) is a perennial herb belonging to the Eupatorium L. genus of Compositae family. It is origin from Central America, and widely distributed in Guangdong, Guangxi, Hainan, Yunnan, Guizhou(the Southwestern) in China. It is one of the first published malignant invasion plants by our government. This plant is provided with the effects of eliminating swelling, detoxication and hemostasis, so it is used for bruises, swelling, sores, dermatitis and traumatic bleeding in our folk. In recent years, study on this plant increasing day by day, and compounds isolated from this plant are proved to have antibacterial, antitumor and hypoglycemic activities. In order to effectively develop the medicinal values of Eupatorium odoratum L. and turn waste into treasure, we studied the constituents of CH2Cl2 and n-butanol extractions from Eupatorium odoratum L. and their activities.Objective: The study of the chemical constituents of E. odoratum L.. Methods of silica gel column chromatography, preparative thin layer chromatography and preparative high-performance liquid chromatography were used to separate the chemical constituents in the plants. All the compounds were identified by 1H-NMR, 13C-NMR, 1H-1H COSY, NOESY and other spectroscopic techniques. Then screen of some constituents for their antitumor activities.Methods: Dry herbal of Eupatorium odoratum L.(about 15 Kg) were extracted with 95% ethanol. The extract(about 2330.8 g) then was scattered the residue in water, and extracted with petroleum ether(60~90℃), CH2Cl2, Et OAc and n-butanol, respectively. The extracts of CH2Cl2 and n-butanol were isolated and purified by methods of silica gel column chromatography, Sephadex LH-20, preparative thin layer chromatography and preparative high-performance liquid chromatography. The structures of compounds were deduced with UV, MS, 1H-NMR, 13C-NMR, 1H-1H COSY, HMQC, HMBC, NOESY, et al. Then the anti-tumor activity of these compounds was tested by MTT.Results: Forty-four compounds were isolated from the herb of E. odoratum L., including thirty-seven flavonoids(among them, seventeen flavonoids, fifteen flavanones, four chalcone and one biflavone), one sterol, one amide alcohol ester, two phenylpropanoid, two fatty acid and one styrene-acrylic acid derivatives. The results of identification as follows:Ombuin(1), ?-sitosterol(2), isosakuranetin(3), 4, 2′-dihydroxy-4′, 5′, 6′-trimethoxychalcone(4), 6′-hydroxy-2′, 3′, 4, 4′-tetramethoxychalcone(5), odoratin(6), rhamnocitrin(7), 5, 6, 7, 4′-tetramethoxyflavanone(8), pectolinarigenin(9), kaempferide(10), persicogenin(11), 5, 6, 7, 8-tetrahydroxy-4′-methoxyflavanone(12), acacetin(13), dillenetin(14), fatty alcohol(15), fatty acid(16), dihydrokaempferide(17), blumeatin B(18), naringenine(19), 7-O-methylaromadenrin(20), folerogenin(21), N-benzoylphenylalaninyl-N-benzoylphenylalaninate(22), tamarixetin(23), 2′-hydroxy-3, 4, 4′, 5′, 6′-pentamethoxychalcone(24), 5, 6, 7, 3′, 4′-pentamethoxyflavanone(25), eupatilin(26), 5, 7-dihydroxy-3′, 4′-dimethoxyflavone(27), 4′-hydroxy-5, 6, 7-trimethoxyflavanone(28), marionol(29), chrysoeriol(30), diosmetin(31), 3, 4′-dihydroxy-5, 6,7-trimethoxyflavone(32), 6, 6-methylenebis(5, 7-dihydroxy-4′-methoxyl dihydroflavanone)(33), rhamnetin(34), padmatin(35), 4′, 5, 6, 7-tetramethoxyflavone(36), 4′, 6-dihydroxy-5, 7-dimethoxyflavanone(37), isovanillic acid(38), rutin(39), 5-p-transcoumaroylquinic acid(40), hesperidin(41), kaempferol 3-rutinoside(42), eugenyl-?-D-glucopyranoside(43), 5, 6, 4′-trihydroxy-7, 3′-dimethoxyflavanone-4′-?-D-glucoside(44).Among these compounds, 4′, 5, 6, 7-tetramethoxyflavone(36) exhibited significant antitumor activity against He La, Sn12-PM6 and K562 cancer cells; in addition, tamarixetin(23), 4′-hydroxy-5, 6, 7-trimethoxyflavanone(28), diosmetin(31) exhibited good activities against K562 cancer cells.Conclusion: Forty-four compounds were isolated and identified from the CH2Cl2 and n-butanol extracts of the herb of E. odoratum. Among these compounds, three are new compounds, including 5, 6, 7, 8- tetrahydroxy-4′-methoxyflavanone(12), 6-methylenebis(5, 7-dihydroxy-4′- methoxyldihydroflavanone)(33) and 5, 6, 4′-trihydroxy-7, 3′-dimethoxyflava none-4′-glucoside(44); Seven are isolated for the first time from Eupatorium genus, including naringenine(19), folerogenin(21), eupatilin(26), chrysoeriol(30), 4′, 6-dihydroxy-5, 7-dimethoxyflavanone(37), hesperidin(41) and eugenyl-?-D-glucopyranoside(43), among them 4′, 6-dihydroxy-5, 7-dimethoxyflavanone(37) was first found in the natural products; Kaempferol 3-rutinoside(42) are isolated for the first time from the plant of E. odoratum.Compounds tamarixetin(23), 4′-hydroxy-5, 6, 7-trimethoxyflavanone(28), diosmetin(31), 4′, 5, 6, 7-tetramethoxyflavone(36) showed good anti-tumor activities, but others exhibited weak activities. |
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