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Fractionation of Extract from Ligusticum chuanxiong (Apiaceae) by High Speed Counter Current Chromatography and Their Efficacy in Rice Against S-metolachlor Injury
Corresponding Author(s) : Lian-Yang Bai
Asian Journal of Chemistry,
Vol. 25 No. 3 (2013): Vol 25 Issue 3
Abstract
Herbicide S-metolachlor with the high efficacy toward the weed from Cyperaceae and Poaceae is never solely applied in rice field due to its grave inhibition to rice growth. This study was conducted to separate the active compound from Ligusticum chuanxiong Hort, which could protect rice from the injury of S-metolachlor. High speed counter current chromatography was applied to the separation of the crude extract of L. chuanxiong Hort. The crude extract obtained by supercritical fluid extraction was fractionated into four fractions after eluted in the head-to-tail pattern with a n-hexane/ethyl acetate/ethanol/water solvent system (5:4:3:2, v/v/v/v). Two components were successfully separated by high speed counter current chromatography and identified as Z-ligustilide and senkyunolide A by liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, proton nuclear magnetic resonance (1H NMR) and carbon nuclear magnetic resonance (13C NMR). The corresponding yields with the purity of over 96 % were 40 mg and 15 mg from 500 mg of crude extract in a single run, respectively. In bioassay experiments, results showed that the level of the growth recoveries conferred by Z-ligustilide and senkyunolide A were 100 % and 91 % of untreated control in plant height as well as 94 % and 83 % of untreated control in roots length, respectively. Z-ligustilide has the potential to be a safener with the capability of reversing the effects on rice caused by S-metolachlor.
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- I. Cummins, D.N. Bryant and R. Edwards, Plant Biotechnol. J., 7, 807 (2009).
- J.W. Gronwald and K.L. Plaisance, Plant Physiol., 117, 877 (1998).
- J. Davies and J.C. Caseley, Pestic. Sci., 55, 1043 (1999).
- B.P. DeRidder, D.P. Dixon, D.J. Beussman, R. Edwards and P.B. Goldsbrough, J. Plant Physiol., 130, 1497 (2002).
- F. Deng and K.K. Hatzios, Pestic. Biochem. Phys., 72, 24 (2002).
- J.R. Wu, C.L. Cramer and K.K. Hatzios, Physiol. Plant., 105, 102 (1999).
- I. Nagy, F. Compernolle, K. Ghys, J. Vanderleyden and M.R. De, Appl. Environ. Microbiol., 61, 2056 (1995).
- T. Yi, K.S.Y. Leung, G.H. Lu, H. Zhang and K. Chan, Chem. Pharm. Bull., 53, 1480 (2005).
- S.S. Chu, G.H. Jiang and Z.L. Liu, E.-J. Chem., 8, 300 (2011).
- Y. Tang, M. Zhu, S. Yu, Y. Hua, J.A. Duan, S. Su, X. Zhang, Y. Lu and A. Ding, Molecules, 15, 341 (2010).
- C. Zhang, M. Qi, Q. Shao, S. Zhou and R. Fu, J. Pharm. Biomed. Anal., 44, 464 (2007).
- S.S.K. Chan, A.O.K. Choi, R.L. Jones and G. Lin, Eur. J. Pharmacol., 537, 111 (2006).
- T. Yi, K.S.Y. Leung, G.H. Lu, K. Chan and H. Zhang, Chem. Pharm. Bull., 54, 255 (2006).
- L. Kong, Z. Yu, Y. Bao, X. Su, H. Zou and X. Li, Anal. Bioanal. Chem., 386, 264 (2006).
- L.S. Lim, P. Shen, Y.H. Gong and E.L. Yong, Phytochemistry, 67, 728 (2006).
- D. Zhang, H. Teng, G. Li, K. Liu and Z. Su, Sep. Sci. Technol., 41, 3397 (2006).
- Q. Chen, P. Li, B. Li, H. Yang, X. Li and F. Chen, Chromatographia, 7, 963 (2010).
- M. Miyazawa, T. Tsukamoto, J. Anzai and Y. Ishikawa, J. Agric. Food Chem., 52, 4401 (2004).
- Y. Sim and S. Shin, Arch. Pharm. Res., 31, 497 (2008).
- K.M. Meepagala, G. Sturtz, D.E. Wedge, K.K. Schrader and S.O. Duke, J. Chem. Ecol., 31, 1567 (2005).
- Y. Yu, J.R. Du, C.Y. Wang and Z.M. Qian, Exp. Brain Res., 184, 307 (2008).
- C.C. Ho, A. Kumaran and L.S. Hwang, Food Chem., 114, 246 (2009).
- M. Kaouadji, F.D. Pachtere, C. Pouget, A.J. Chulia and S. Lavaitte, J. Nat. Prod., 49, 872 (1986).
- H. Wang, H. Zou, J. Ni and B. Guo, Chromatographia, 52, 459 (2000).
- Y. Ito, J. Chromatogr A., 1065, 145 (2005).
- H.B. Li and F. Chen, J. Chromatogr A., 1047, 249 (2004).
- Q. Duanmu, A. Li, A. Sun, R. Liu and X. Li, J. Sep. Sci., 33, 1746 (2010).
- S. Han and K.K. Hatzios, Pestic. Biochem. Physiol., 39, 270 (1991).
References
I. Cummins, D.N. Bryant and R. Edwards, Plant Biotechnol. J., 7, 807 (2009).
J.W. Gronwald and K.L. Plaisance, Plant Physiol., 117, 877 (1998).
J. Davies and J.C. Caseley, Pestic. Sci., 55, 1043 (1999).
B.P. DeRidder, D.P. Dixon, D.J. Beussman, R. Edwards and P.B. Goldsbrough, J. Plant Physiol., 130, 1497 (2002).
F. Deng and K.K. Hatzios, Pestic. Biochem. Phys., 72, 24 (2002).
J.R. Wu, C.L. Cramer and K.K. Hatzios, Physiol. Plant., 105, 102 (1999).
I. Nagy, F. Compernolle, K. Ghys, J. Vanderleyden and M.R. De, Appl. Environ. Microbiol., 61, 2056 (1995).
T. Yi, K.S.Y. Leung, G.H. Lu, H. Zhang and K. Chan, Chem. Pharm. Bull., 53, 1480 (2005).
S.S. Chu, G.H. Jiang and Z.L. Liu, E.-J. Chem., 8, 300 (2011).
Y. Tang, M. Zhu, S. Yu, Y. Hua, J.A. Duan, S. Su, X. Zhang, Y. Lu and A. Ding, Molecules, 15, 341 (2010).
C. Zhang, M. Qi, Q. Shao, S. Zhou and R. Fu, J. Pharm. Biomed. Anal., 44, 464 (2007).
S.S.K. Chan, A.O.K. Choi, R.L. Jones and G. Lin, Eur. J. Pharmacol., 537, 111 (2006).
T. Yi, K.S.Y. Leung, G.H. Lu, K. Chan and H. Zhang, Chem. Pharm. Bull., 54, 255 (2006).
L. Kong, Z. Yu, Y. Bao, X. Su, H. Zou and X. Li, Anal. Bioanal. Chem., 386, 264 (2006).
L.S. Lim, P. Shen, Y.H. Gong and E.L. Yong, Phytochemistry, 67, 728 (2006).
D. Zhang, H. Teng, G. Li, K. Liu and Z. Su, Sep. Sci. Technol., 41, 3397 (2006).
Q. Chen, P. Li, B. Li, H. Yang, X. Li and F. Chen, Chromatographia, 7, 963 (2010).
M. Miyazawa, T. Tsukamoto, J. Anzai and Y. Ishikawa, J. Agric. Food Chem., 52, 4401 (2004).
Y. Sim and S. Shin, Arch. Pharm. Res., 31, 497 (2008).
K.M. Meepagala, G. Sturtz, D.E. Wedge, K.K. Schrader and S.O. Duke, J. Chem. Ecol., 31, 1567 (2005).
Y. Yu, J.R. Du, C.Y. Wang and Z.M. Qian, Exp. Brain Res., 184, 307 (2008).
C.C. Ho, A. Kumaran and L.S. Hwang, Food Chem., 114, 246 (2009).
M. Kaouadji, F.D. Pachtere, C. Pouget, A.J. Chulia and S. Lavaitte, J. Nat. Prod., 49, 872 (1986).
H. Wang, H. Zou, J. Ni and B. Guo, Chromatographia, 52, 459 (2000).
Y. Ito, J. Chromatogr A., 1065, 145 (2005).
H.B. Li and F. Chen, J. Chromatogr A., 1047, 249 (2004).
Q. Duanmu, A. Li, A. Sun, R. Liu and X. Li, J. Sep. Sci., 33, 1746 (2010).
S. Han and K.K. Hatzios, Pestic. Biochem. Physiol., 39, 270 (1991).