<strong>Several</strong> <strong>flavonoids</strong> <strong>from</strong> <strong>Capsella</strong> <strong>bursa</strong>-<strong>pastoris</strong> (L.) <strong>Medic</strong>./ Asian Journal of Traditional <strong>Medic</strong>ines, 2007, 2 ( 5 )of kaempferol-3-O-rutinoside [16] .Results and discussionNine <strong>flavonoids</strong> were isolated and identified bydetermining their physicochemical properties andspectral analysis. All the compounds were obtained<strong>from</strong> this genus for the first time.Compound 6 was isolated as a yellow, amorphouspowder <strong>from</strong> methanol. Three proton signals δ6.89(1H, d, J = 8.1 Hz), δ 7.39 (1H, dd, J = 8.1, 2.5 Hz)and δ 7.42 (1H, d, J = 2.5 Hz) indicated the presenceof an ABX coupling system. This showed that 3′, 4′ or 4′, 5′ were disubstituted on the B-ring. The 13 CNMR data showed that there were 21 carbon signals,15 of which were typical for a flavone skeleton, andthe others were assigned to a glycoside. There wereno anomeric carbon signals for sugar observed near100, which indicated that it was not an O-glycoside,but maybe a C-glyciside. Moreover, 1 H and 13 CNMR data were consistent with quercetin-6-C-β-D-glucopyranoside. Therefore, it was identified asquercetin-6-C-β-D-gluco- pyranoside.Compound 8 was isolated as a yellow, amorphouspowder <strong>from</strong> methanol. Three proton signals δ 6.85(1H, d, J = 8.5 Hz), δ 7.60 (1H, dd, J = 8.5, 2.5 Hz)and δ 7.62 (1H, d, J = 2.5 Hz) showed the presenceof an ABX coupling system. It was also found that3′, 4′ or 4′, 5′ were disubstituted on the B-ring. The13C NMR data indicated that there were 27 carbons inthis structure, 15 of which were typical for a flavoneskeleton, and the others were assigned to glycosides.Compound 8 was identified as quercetin-3-O-β-Dglucopyranosyl-7-O-α-L–rhamno-pyranoside bycomparing 1 H and 13 C NMR data with the literature.Compounds 7 and 9 were isolated as yellow,amorphous powders <strong>from</strong> methanol. Two sets ofsymmetric proton signals δ 8.08 (2H, d, J = 8.8 Hz),δ 6.90 (2H, d, J = 8.8 Hz) for compound 7 and δ7.98 (2H, d, J = 8.7 Hz), δ 6.88 (2H, d, J = 8.7 Hz)for compound 9 showed the presence of an AA′BB′ coupling system, which indicated that 4′ wassubstituted on the B-ring. Also, 27 carbons werefound in the 13 C NMR spectra, 15 of which weretypical of a flavone skeleton, and the others wereassigned to a glycoside. At the same time, glucose andrhamnose were found after acid hydrolysis confirmingthe 13 C NMR resonances. Also, 3, 7 shifting tothe upfield for 2.2, 4.3 and 2, 4, 6, 8 shifting to thedownfield for 10, 1.9, 0.7, 0.3, indicated that 3 and 7were substituted by a glycoside in compound 7, while,2, 4 shifting to the downfield for 9.7, 1.4, indicatedthat 3 was substituted by a glycoside in compound 9.1H and 13 C NMR data were consistent with compound7 and 9 being kaempferol-3-O-β-D-glucopyranosyl-7-O-α-L-rhamno- pyranoside and kaempferol-3-Orutinosideby comparison of the spectroscopic datawith the literature values.References[1] Health Department of Jiangsu Province. Standard ofChinese crude drug of Jiangsu Province, 1989: 161-163.[2] Jiangsu New <strong>Medic</strong>al College. The Dictionary of Chinese<strong>Medic</strong>ine, Shanghai. Shanghai Peoples′ Publishing House,1977: 1606.[3] Jurisson S. Flavonoid substances of <strong>Capsella</strong> <strong>bursa</strong><strong>pastoris</strong>.Farmatsiya (Moscow), 1973, 22: 34-35.[4] Wohlfart R, Gademann R, Kirchner CP. Physiologicalchemicalobservationas changes in the flavonoid patternof <strong>Capsella</strong> <strong>bursa</strong>-<strong>pastoris</strong>. Deut. Apoth.-Ztg, 1972, 112:1158-1160.[5] Al-khalil S, Abu ZM, Zeitoun N, et al. Chemicalconstituents of <strong>Capsella</strong> <strong>bursa</strong>-<strong>pastoris</strong>. Alexandria J.Pharm. Sci., 2000, 14: 91-94.[6] Nazmi SN, Sarg T, Seif-El DA. A Phytochemicalinvestigation of <strong>Capsella</strong> <strong>bursa</strong>-<strong>pastoris</strong> (L.) <strong>Medic</strong>.growing in Egypt. Egypt. J. Pharm. Sci, 1975, 16:521-522.[7] Kimiko N. Studies on <strong>Capsella</strong> <strong>bursa</strong>-<strong>pastoris</strong>, I.Carboxylic acids, amino acids, Carbohydrates, alcohols,and inorganic, components in C.<strong>bursa</strong>-<strong>pastoris</strong>. YakugakuKenkyu, 1960, 32: 617-626.[8] Zheng W, Zhou CX, Zhang SL, et al. Studies on thechemical constituents of Ranunculus japonicus Thunb.China J. Chin. Mater. Med, 2006, 31: 892-893.[9] Wang Z, He ZS. Studies on Chemical Constituents ofCuscuta chinensis Lam. Chin. Tradit. Herb Drugs, 1998,29: 577-579.[10] Liu XQ, Chen FK, Wu LJ, et al. Studies on the chemical221
<strong>Several</strong> <strong>flavonoids</strong> <strong>from</strong> <strong>Capsella</strong> <strong>bursa</strong>-<strong>pastoris</strong> (L.) <strong>Medic</strong>./ Asian Journal of Traditional <strong>Medic</strong>ines, 2007, 2 ( 5 )constituents of Polygonum bistorta L. Journal ofShenyang Pharmaceutical University, 2003, 21:187-189.[11] Tang BS, Zuo CX. Studies on the chemical constituentsof Hylotelephium mingjinianum (S. H. Fu)H. Ohba. ActaPharm. Sinica, 1994, 29: 519-525.[12] Chen L, Du LJ, Ding Y., et al. Studies on chemicalconstituents <strong>from</strong> flowers of Apocynum venetum. ChinaJournal of Chinese Materia <strong>Medic</strong>a, 2005, 30: 1340-1342.[13] Li YL, Ding CX, Wang HL, et al. Glycosides ofLomatogonium rotatum. Acta Botanica Boreali-Occidentalia Sinica, 2006, 26: 197-200.[14] Ouyang MA. Studies on lignans and flavonoid glycosidesof Ligustrum sinense.Chin. Tradit. Herb Drugs, 2003, 34:196-198.[15] Chen QB, Yang JX, Cheng ZQ, et al. Separation,Purificationand Identification of Flavonol Glycoside <strong>from</strong> Momordicagrosvenori Leafs. Guangxi Sciences, 2006, 13: 25-36, 42.[16] Bao TN, Peng SL, Zhou ZZ, et al. Chemical Constituentsof Buckwheat. Natural Product Research andDevelopment, 2003, 15: 24-26.222
Change language