Abstract
Definitive identification of original plant species is important for standardizing herbal medicine. Although only the dried roots of Cynanchum wilfordii (Asclepiadaceae) are prescribed as Cynanchi Wilfordii Radix in Korean Pharmacopoeia, the roots of C. wilfordii and C. auriculatum are often misused in the Korean herbal market due to their morphological similarity and similar name. Therefore, it would be very useful to discover an effective chemical marker for the identification of the two species. To this end, we carried out a phytochemical study on the roots of C. wilfordii. As a result, twenty compounds were isolated from the roots of C. wilfordii and their chemical structures were identified as β-sitosterol (1), wilfoside C1N (2), wilfoside C3N (3), wilfoside K1N (4), methyleugenol (5), wilfoside C1G (6), cynauriculoside A (7), daucosterol (8), 2,4-dihydroxyacetophenone (9), cynandione A (10), 2,5-dihydroxyacetophenone (11), acetovanillone (12), p-hydroxyacetophenone (13), sucrose (14), conduritol F (15), geniposide (16), succinic acid (17), 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione (18), bungeiside A (19), cynanoneside B (20). Among them, compounds 15, 16, 18, 19, and 20 were isolated for the first time from this species. Furthermore, conduritol F (15) was demonstrated to be contained only in C. wilfordii. Therefore, it may be useful as a chemical marker to identify the two species C. wilfordii and C. auriculatum.
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Akamanchi, K. G., Padmawar, P. A., Thatte, U. M., Rege, N. N., and Dahanukar, S. A., Synthesis and in-vitro evaluation of platelet aggregation inhibitory activity of paeonol and its analogues. Pharm. Pharmacol. Commun., 5, 323–329 (1999).
Chang, T. C. and Su, J. C., Starch phosphorylase and its inhibitor from sweet potato root. Kor. J. Pharmacogn., 17, 134–138 (1986).
Chwang, T. L., Wood, W. F., Parkhurst, J. R., Nesnow, S., Danenberg, P. V., and Heidelberger, C., 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dion, a new pyrimidine nucleoside analog related to uridine. J. Med. Chem., 19, 643 (1976).
Eknamkul, W. D. and Potduang, B., Biosynthesis of β-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry, 62, 389–398 (2003).
Faizi, S., Ali, M., Saleem, R., Irfanullah., and Bibi, S., Spectral assignments and reference data: complete 1H- and 13C-NMR assignments of stigma-5-en-3-O-β-glucoside and its acetylderivative. Magn. Reson. Chem., 39, 399–405 (2001).
Han, Y. N., Oh, H. K., Hwang, K. H., and Lee, M. S., Antioxidant components of gardenia fruit. Kor. J. Pharmacogn., 25, 226–232 (1994).
Heo, J. N., Holson, E. B., and Roush, W. R., Commonintermediate strategy for synthesis of conduritols and inositols via β-hydroxy cyclohexenylsilanes. Org. Lett., 5, 1697–1700 (2003).
Hoque, E., Isolation of p-hydroxyacetophenone from diseased shoots of Picea abies. Phytochemistry, 23, 923–925 (1984).
Junior, P., Acetophenonglucoside aus Penstemon pinifolius. Planta Med., 52, 218–220 (1986).
Kadota, K., Takeuchi, M., Taniguchi, T., and Ogasawara, K., A new convergent route to conduritols A-F from a common chiral building block. Org. Lett., 3, 1769–1772 (2001).
KFDA, The 9th Korean Herbal Pharmacopoeia. http://www.kfda.go.kr/index.kfda?mid=92&pageNo=4&seq=3534&cmd =v (2008).
Lee, P. J., Lee, J. S., Choi, S. Y., Lee, S. E., Lee, S. H., and Son, D. W., Geniposide from Gardenia jasminoides attenuates neuronal ell death in oxygen and glucose deprivation — exposed rat hippocampal slice culture. Biol. Pharm. Bull., 29, 174–176 (2006).
Li, J., Kawata, Y., Hattori, M., Xu, G. J., and Namba, T., Constituents of the roots of Cynanchum bungei DECNE. Isolation and structures of four new glucosides, bungeiside-A, -B, -C, and -D. Chem. Pharm. Bull. (Tokyo), 40, 3133–3137 (1992).
Liede, S. and Tauber, A., Circumscription of the genus Cynanchum (Apocynaceae-Asclepiadoideae). Syst. Bot., 27, 789–800 (2002).
Lin, C. N., Huang, P. L., Lu, C. M., Yen, M. H., and Wu, R. R., Revised structure for five acetophenones from Cynanchum taiwanianum. Phytochemistry, 44, 1359–1363 (1997).
Lin, Y. L., Lin, T. C., and Kuo, Y. H., Two Acetophenone glucosides, cynanonesides A and B, from Cynanchum taiwanianum and revision of the structure for cynandione A. J. Nat. Prod., 60, 368–370 (1997).
Meepagala, K. M., Sturtz, G., and Wedge, D. E., Antifungal constituents of the essential oil fraction of Artemisia dracunculus L. Var. dracunculus. J. Argic. Food Chem., 50, 6989–6992 (2002).
Nord, L. I., Vaag, A., and Duus, J. O., Quantification of organic and amino acids in beer by 1H-NMR spectroscopy. Anal. Chem., 76, 47901–4798 (2004).
Patti, A., Sanfilippo, C., Piattelli, M., and Nicolosi, G., Enantioselective synthesis of (-)- and (+)-conduritol F via enzymatic asymmetrization of cis-cyclohexa-3,5-diene-1,2-diol. J. Org. Chem., 61, 6458–6461 (1996).
Shan, L., Liu, R. H., Shen, Y. H., Zhang, W. D., Zhang, C., Wu, D. W., Min, L., Su, J., and Xu, X. K., Gastroprotective effect of a traditional Chinese herbal drug “Baishouwu” on experimental gastric lesions in rats. J. Ethnopharmacol., 107, 389–394 (2006).
Shan, L., Studies of chemical constituents and bioactivities of Cynanchum auriculatum royle ex wight. Excellent doctor and master’s degree thesis full-text database of China, (2008).
Song, K. S., Shin, C. G., and Ju, Y. S., External and internal morphological standard of original plants and herbal states in Polygoni multiflori and Cynanchi wilfordii Radix. Kor. J. Herbol., 19, 55–66 (2004).
Sun, Y. S., Liu, Z. B., Wang, J. H., Lan, X., and Zhu, L. X., Separation and purification of Baishouwubenzophenone, 4-hydroxyacetophenone and 2,4-dihydroxyacetophenone from Cynanchum auriculatum Royle ex wight by HSCCC. Chromatographia, 70, 1–6 (2009).
The Chinese Traditional Medicine State Administration, Shanghai science technology publication, Shanghai, China, (1999).
Tsiang, Y. and Li, P. T., Flora of China. China, 63, 309 (1977a).
Tsiang, Y. and Li, P. T. Flora Popularis Sinicae. China, 63, 249–575 (1977b).
Tsukamoto, S., Hayashi, K., and Mitsuhashi, H., The structures of six glycosides, wilfoside C1N, C2N, C3N, C1G, C2G and C3G, with novel sugar chain containing a pair of optically isomeric sugars. Tetrahedron, 41, 927–934 (1985a).
Tsukamoto, S., Hayashi, K., and Mitsuhashi, H., Studies on the constituents of Asclepiadaceae. LX. Further studies on glycosides with a novel sugar chain containing a pair of optically isomeric sugars, D- and L-cymarose, from Cynanchum wilfordii. Chem. Pharm. Bull. (Tokyo), 33, 2294–2304 (1985b).
Zhang, J. F., Li, Y. B., Qian, S. H., Li, C. L., and Jiang, J. Q., Studies on chemical constituents in root tuber of Cynanchum auriculatum. Zhongguo Zhong Yao Za Zhi, 31, 814–816 (2006).
Zhou, X. Q., Bi, Z. M., Li, P., Tang, D., and Cai, H. X., A new iridoid glycoside from Gardenia jasminoides. Chin. Chem. Lett., 18, 1221–1223 (2007).
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Jiang, Y., Choi, H.G., Li, Y. et al. Chemical constituents of Cynanchum wilfordii and the chemotaxonomy of two species of the family Asclepiadacease, C. wilfordii and C. auriculatum . Arch. Pharm. Res. 34, 2021–2027 (2011). https://doi.org/10.1007/s12272-011-1203-z
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DOI: https://doi.org/10.1007/s12272-011-1203-z