Copyright (c) 2013 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Structural Identification of Chemical Constituents from Scutellaria baicalensis by HPLC-ESI-MS/MS and NMR Spectroscopy
Corresponding Author(s) : Bin Wu
Asian Journal of Chemistry,
Vol. 25 No. 7 (2013): Vol 25 Issue 7
Abstract
Scutellariae Radix, the dried roots of Scutellaria baicalensis Georgi, which is one of the famous herb widely used in the treatment of pyrexia, jaundice and hypertension. To directly identify the compounds of the extract of the S. baicalensis was performed using HPLC-ESI-MS/MS. Chromatographic (analytical and preparative HPLC), chemical (hydrolysis) and spectroscopic (UV, 1H and 13C NMR, MS) techniques were applied for separation, isolation, purification and identification of new compounds. A systematic phytochemical investigantion of S. baicalensis led to the isolation of 7 new and 40 known chemical constituents. By HPLC-ESI-MS/MS and NMR spectral analyses, the new compounds were identified as 7-hydroxy-3,5,8-trimethoxy-3',4'-methylenedioxy flavone-7-O-b-glucopyranoside (1), 7-hydroxy-5,6,8-trimethoxy-3',4'-methylenedioxy flavone-7-O-b-glucopyranoside (2), patuletin-7-b-glucuronide (3), pinobankasin-6-C-glucopyranosyl-8-C-arabinopyranoside (4), chrysin-3-C-a-arabinopyranosyl-8-C-b-glucopyranoside (11), 6-sulfooxy-chrysin-7-glucoside (12) and 5-hydoxy-6,7,4'-trimethoxy-flavanone 5-sulfate (24).
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- National Commission of Chinese Pharmacopoeia, Pharmacopoeia of the People's Republic of China. China Medical Technology Press, Beiing (2010).
- Jiangsu New Medical College, Dictionary of Chinese Materia Medical, Science and Technology Press of ShangHai (1977).
- H.Z. Wen, S.Y. Xiao, Y.M. Wang and G.A. Luo, Nat. Prod. Res. Dev., 6, 575 (2004).
- G. Corinne, M. Frederic, B. Francoise, T. Francois, V. Jacqueline, S. Thierry and L. Marc, J. Nat. Prod., 62, 1188 (1999).
- W.L. Yang, H.F. Chen, B.J. Yu, P.Z. Zhang, Z.H. Yan, L. Jie and H. Xu, Zhong Yao Cai, 31, 1812 (2008).
- H. Tokunaru, S. Kenichi, Y. Kazuyo, K. Yasuhiko and T. Masao, Chem. Pharm. Bull., 45, 446 (1997).
- K. Masanori, Y. Yooko, F. Seigo, U. Akira, N. Tadataka and M. Toshio, Chem. Pharm. Bull., 30, 1602 (1982).
- D.W. Aksnes, A. Standnes and O.M. Anderson, Magn. Reson. Chem., 34, 820 (1996).
- H.J. Xia, F. Qiu, S. Zhu, T.Y. Zhang, G.X. Qu and X.S. Yao, Biol. Pharm. Bull., 30, 1308 (2007).
- E.A. Ali, M. Ibtissam, T. Rachida Chendid, B. Mohamed, E.A. Rachid, E.B. Brahim and L. Mohammed, Molecules, 9, 568 (2004).
- E. Wollenweber, V.H. Dietz, D. Schillo and G. Schilling, Zeitsch. Naturforschung, C: J. Biosci., 35, 685 (1980).
- D.K. Bhardwaj and R.M. Jain,Proc. Indian Nat. Sci. Acad., 49, 408 (1983).
- L.C. Dos Santos, C.M. Rodrigues, M.A. Silva, R.G. Coelho, M. Sannomiya and W. Vilegas, Biochem. System. Ecol., 33, 1159 (2005).
- C. Xie, N.C. Veitch, P.J. Houghton and S.J. Simmonds, Chem. Pharm. Bull., 51, 1204 (2003).
- L. Gobbo-Neto, M.D. Santos, A. Kanashiro, M.C. Almeida, Y.M. Lucisano-Valim, L.C. Lopes, E.P. Souza and N.P. Lopes, Planta Medica, 71, 3 (2005).
- S. Takagi, M. Yamaki and K. Inoue, Yakugaku Zasshi, 101, 899 (1981).
- Y. Yuan, W.L. Hou, M.H. Tang, H.D. Luo, L.J. Chen, Y.H. Guan and L.A. Sutherland, Chromatographia, 68, 885 (2008).
- G. Romussi, N. Fontana and N.D. Tommasi, Phytother. Res., 10, S84 (1996).
- Y.Y. Zhang, Y.Z. Guo, H. Ageta, Y. Harigaya, M. Onda, K. Hashimoto, Y. Ikeya, M. Okada and M. Maruno, J. Chin. Pharm. Sci., 6, 182 (1997).
- Z.H. Zhou and C.R. Yang, Yunnan Zhiwu Yanjiu, 22, 475 (2000).
- T. Tomimori, Y. Miyaichi, Y. Imoto, H. Kizu and Y. Tanabe, Yakugaku Zasshi, 103, 607 (1983).
- J. Han, M. Ye, M. Xu, J.H. Sun, B.R. Wang and D. Guo, J. Chromatogr. B, 848, 355 (2007).
- T .Hase, K. Ohtani, R. Kasai, K. Yamasaki and C. Picheansoonthon, Phytochemistry, 40, 287 (1995).
- Y.Q. Wang, K. Matsuzaki, K. Takahashi, T. Okuyama and S. Shibata, Chem. Pharmaceut. Bull., 36, 3206 (1988).
- R. Kunde and O. Isaac, Planta Medica, 37, 124 (1979).
- K. Abe, O. Inoue and E. Yumioka, Chem. Pharm. Bull., 38, 208 (1990).
- W.H. Huang, A.R. Lee and C.H. Yang, Biosci. Biotechnol. Biochem., 70, 2371 (2006).
- W.L. Mei, W. Ni, Y. Hua and C.X. Chen, Nat. Prod. Res. Dev., 14, 26 (2002).
- Y.Y. Zhang and Y.Z. Guo, Shenyang Yaoxueyuan Xuebao, 8, 137 (1991).
- S. Takagi, M. Yamaki and K. Inoue, Phytochemistry, 20, 2443 (1981).
- H.Y. Wang, L.H. Xiao, L. Liu and S.X. Xu, Shenyang Yaoke Daxue Xuebao, 20, 339, 348 (2003).
- M.L. Liu, M.L. Li, X.T. Liang, X.Y. Lin, Q.T. Zheng, S.D. Zhang and F.L. Shen, Zhongcaoyao, 17, 438 (1986).
- T. Tomimori, Y. Miyaichi and H. Kizu, Yakugaku Zasshi, 102, 388 (1982).
- M. Inuma, S. Matsuura and K. Kusuda, Chem. Pharm. Bull., 28, 708 (1980).
- R.R. Biekofsky, C.A. Buschi and A.B. Pomilio, Magn Reson. Chem., 29, 569 (1991).
- L.H. Qin, X.Y. Guo, M. Fan, A.S. Din, N.L. Wang and X.S. Yao, Shenyang Yaoke Daxue Xuebao, 23, 633 (2006).
- J.Y. Peng, G.R. Fan and Y.T. Wu, China J .Chin. Mater. Medica, 31, 128 (2006).
- W.H. Huang, Y.B. Li and J.Q. Jiang, Zhongguo Zhongyao Zazhi, 34, 712 (2009).
- S.G. Yu, N.B. Fang and T.J. Mabry, Phytochemistry, 27, 171 (1988).
- X. Li, J.H. Wang, X. Li and D.L. Liang, Shenyang Yaoke Daxue Xuebao, 19, 178 (2002).
- C.N. He, W.W. Gao, W.Y. Xu and J.M. Tong, Zhong Cao Yao, 39, 1783 (2008).
- Z.T. Ma and X.W. Yang, Zhongguo Zhongyao Zazhi, 33, 2080 (2008).
- N.Y. Yang, J.H. Duang, P. Li, S.H. Qian and W.C. Hu, Zhongguo Tianran Yaowu, 4, 98 (2006).
References
National Commission of Chinese Pharmacopoeia, Pharmacopoeia of the People's Republic of China. China Medical Technology Press, Beiing (2010).
Jiangsu New Medical College, Dictionary of Chinese Materia Medical, Science and Technology Press of ShangHai (1977).
H.Z. Wen, S.Y. Xiao, Y.M. Wang and G.A. Luo, Nat. Prod. Res. Dev., 6, 575 (2004).
G. Corinne, M. Frederic, B. Francoise, T. Francois, V. Jacqueline, S. Thierry and L. Marc, J. Nat. Prod., 62, 1188 (1999).
W.L. Yang, H.F. Chen, B.J. Yu, P.Z. Zhang, Z.H. Yan, L. Jie and H. Xu, Zhong Yao Cai, 31, 1812 (2008).
H. Tokunaru, S. Kenichi, Y. Kazuyo, K. Yasuhiko and T. Masao, Chem. Pharm. Bull., 45, 446 (1997).
K. Masanori, Y. Yooko, F. Seigo, U. Akira, N. Tadataka and M. Toshio, Chem. Pharm. Bull., 30, 1602 (1982).
D.W. Aksnes, A. Standnes and O.M. Anderson, Magn. Reson. Chem., 34, 820 (1996).
H.J. Xia, F. Qiu, S. Zhu, T.Y. Zhang, G.X. Qu and X.S. Yao, Biol. Pharm. Bull., 30, 1308 (2007).
E.A. Ali, M. Ibtissam, T. Rachida Chendid, B. Mohamed, E.A. Rachid, E.B. Brahim and L. Mohammed, Molecules, 9, 568 (2004).
E. Wollenweber, V.H. Dietz, D. Schillo and G. Schilling, Zeitsch. Naturforschung, C: J. Biosci., 35, 685 (1980).
D.K. Bhardwaj and R.M. Jain,Proc. Indian Nat. Sci. Acad., 49, 408 (1983).
L.C. Dos Santos, C.M. Rodrigues, M.A. Silva, R.G. Coelho, M. Sannomiya and W. Vilegas, Biochem. System. Ecol., 33, 1159 (2005).
C. Xie, N.C. Veitch, P.J. Houghton and S.J. Simmonds, Chem. Pharm. Bull., 51, 1204 (2003).
L. Gobbo-Neto, M.D. Santos, A. Kanashiro, M.C. Almeida, Y.M. Lucisano-Valim, L.C. Lopes, E.P. Souza and N.P. Lopes, Planta Medica, 71, 3 (2005).
S. Takagi, M. Yamaki and K. Inoue, Yakugaku Zasshi, 101, 899 (1981).
Y. Yuan, W.L. Hou, M.H. Tang, H.D. Luo, L.J. Chen, Y.H. Guan and L.A. Sutherland, Chromatographia, 68, 885 (2008).
G. Romussi, N. Fontana and N.D. Tommasi, Phytother. Res., 10, S84 (1996).
Y.Y. Zhang, Y.Z. Guo, H. Ageta, Y. Harigaya, M. Onda, K. Hashimoto, Y. Ikeya, M. Okada and M. Maruno, J. Chin. Pharm. Sci., 6, 182 (1997).
Z.H. Zhou and C.R. Yang, Yunnan Zhiwu Yanjiu, 22, 475 (2000).
T. Tomimori, Y. Miyaichi, Y. Imoto, H. Kizu and Y. Tanabe, Yakugaku Zasshi, 103, 607 (1983).
J. Han, M. Ye, M. Xu, J.H. Sun, B.R. Wang and D. Guo, J. Chromatogr. B, 848, 355 (2007).
T .Hase, K. Ohtani, R. Kasai, K. Yamasaki and C. Picheansoonthon, Phytochemistry, 40, 287 (1995).
Y.Q. Wang, K. Matsuzaki, K. Takahashi, T. Okuyama and S. Shibata, Chem. Pharmaceut. Bull., 36, 3206 (1988).
R. Kunde and O. Isaac, Planta Medica, 37, 124 (1979).
K. Abe, O. Inoue and E. Yumioka, Chem. Pharm. Bull., 38, 208 (1990).
W.H. Huang, A.R. Lee and C.H. Yang, Biosci. Biotechnol. Biochem., 70, 2371 (2006).
W.L. Mei, W. Ni, Y. Hua and C.X. Chen, Nat. Prod. Res. Dev., 14, 26 (2002).
Y.Y. Zhang and Y.Z. Guo, Shenyang Yaoxueyuan Xuebao, 8, 137 (1991).
S. Takagi, M. Yamaki and K. Inoue, Phytochemistry, 20, 2443 (1981).
H.Y. Wang, L.H. Xiao, L. Liu and S.X. Xu, Shenyang Yaoke Daxue Xuebao, 20, 339, 348 (2003).
M.L. Liu, M.L. Li, X.T. Liang, X.Y. Lin, Q.T. Zheng, S.D. Zhang and F.L. Shen, Zhongcaoyao, 17, 438 (1986).
T. Tomimori, Y. Miyaichi and H. Kizu, Yakugaku Zasshi, 102, 388 (1982).
M. Inuma, S. Matsuura and K. Kusuda, Chem. Pharm. Bull., 28, 708 (1980).
R.R. Biekofsky, C.A. Buschi and A.B. Pomilio, Magn Reson. Chem., 29, 569 (1991).
L.H. Qin, X.Y. Guo, M. Fan, A.S. Din, N.L. Wang and X.S. Yao, Shenyang Yaoke Daxue Xuebao, 23, 633 (2006).
J.Y. Peng, G.R. Fan and Y.T. Wu, China J .Chin. Mater. Medica, 31, 128 (2006).
W.H. Huang, Y.B. Li and J.Q. Jiang, Zhongguo Zhongyao Zazhi, 34, 712 (2009).
S.G. Yu, N.B. Fang and T.J. Mabry, Phytochemistry, 27, 171 (1988).
X. Li, J.H. Wang, X. Li and D.L. Liang, Shenyang Yaoke Daxue Xuebao, 19, 178 (2002).
C.N. He, W.W. Gao, W.Y. Xu and J.M. Tong, Zhong Cao Yao, 39, 1783 (2008).
Z.T. Ma and X.W. Yang, Zhongguo Zhongyao Zazhi, 33, 2080 (2008).
N.Y. Yang, J.H. Duang, P. Li, S.H. Qian and W.C. Hu, Zhongguo Tianran Yaowu, 4, 98 (2006).