HomeVolumesJMA, vol. XIV, iss. 2, 2011Systematic identification of active ingredients of Silybum marianum seed

Systematic identification of active ingredients of Silybum marianum seed

March 31, 2012

Systematic identification of active ingredients of Silybum marianum seed

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Title: Systematic identification of active ingredients of Silybum marianum seed
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Article_Title: Systematic identification of active ingredients of Silybum marianum seed
Authors: Lajos Nagy, Ákos Kuki, Gyögy Deák, Bernadett Biri, Miklós Nagy, Miklós Zsuga, Sándor Kéki*
Affiliation: Department of Applied Chemistry, University of Debrecen
Abstract: Silybum Marianum seed and its extract Silymarin are widely used to treat and prevent many liver diseases such as
cirrhosis. Due to other biological effects (antitumor, antioxidant, cytotoxic activities) numerous Silymarin content
drugs (Silegon, Legalon etc.) are commercially available worldwide. Thus the development of applicable extraction
and separation methods has become sorely needed as well as the improvement of analytical methods (HPLC,
UPLC, HPLC-, UPLC-MS and MS/MS) for these flavonolignans in order to realize a unified quality control. This
paper reviews some extraction and separation methods as well as the fragmentation patterns of different active
components of Silymarin under MS/MS conditions.
Keywords:
References: Y.M. Zhao, C.Y. Wang, X.D. Liu Application of Statistics
and Management 2000; 20, 1.
V. Křen, D. Walterová, Biomed. Papers 2005; 29, 149.
Y. Yanaida, H. Kohno, K. Yoshida, Y. Hiroshe, Y. Yamada,
H. Mori, Tanaka T. Carcinogenesis 2002; 23, 787.
R.P. Singh, R. Agarwal Cancer Mutat. Res. 2004; 21,
555.
S.C. Pradhan, C. Girish Indian J. Med. Res. 2006; 124,
491.
A. Valenzuela, A. Garrido Biol. Res. 1994; 27, 105.
G. Scambia, R. De Vincenso, F. Raneletti, P. Panici,
Ferrandina G., G. D’Agostino, A. Fattorossi, E.
Bombardelei, S. Manausco Eur. J. Cancer 1996;
32A, 877.
F. Lirussi, L. Okolicsanyi Acta Physiol. Hung. 1992; 80,
363.
D.I. Hadaruga, N.G. Hadaruga Chem. Bull.
“POLITEHNICA” Univ. 2009; 54(68), 2.
Z. Asghar, Z. Masood Pak. J. Pharm. Sci. 2008; 21, 249.
F. Kvasnicka, B. Biba, R. Sevcik, M. Voldrich, J. Kratka
J. Chromatogr. 2003; A 990, 239.
L. Mollison, L. Totten, J. Flexman, M. Beaman, R. Batey
J. Gastroenterol. Hepatol. 2006; 21 1184.
Y.P. Pei, J. Chen, W.L. Li Medicinal Aromatic Plant Sci.
Biotech. 2009; 3(1), 1.
P.R. Rao, R.K. Viswanath Exp Clin Cardiol. 2007; 12(4),
179.
S. Giacomelli, D. Gallo, P. Apollonio, C. Ferlini, M.
Distefano, P. Morazzoni, A. Riva, E. Bombardelli,
S. Mancuso, G. Scambia Life Sci. 2002;70, 1447.
S. Dhanalakshmi, P. Agarwal, L.M. Glode, R. Agarwal
Int. J. Cancer 2003; 106, 699.
M. Bialecka, Ann. Acad. Med. Stetin. 1997; 43, 41.
Gu M., Singh R.P., Dhanalakshmi S., Agarwal C.,
Agarwal R. Cancer Res. 2007;67, 3483.
H. Wagner, P. Diesel, M. Seitz Arzneilmittelforschung
1974; 24, 466.
Y.Q. Chen, C.M. Wang, W.H. Zhang Acta Agriculturae
Boreali-Occidentalis Sinica 1997; 6, 91.
S.N. Wallace, D.J. Carrier, E.C. Clausen Appl. Biochem.
Biotechnol. 2003; 108, 891.
A.P. Kahol, K.L. Singh, S. Tandon, S. Kumar US patent
2001; patent no.: US 6,309,678 B1.
W. Li, J. Han, Z. Li, X. Li, S. Zhou, C. Liu J. Chromatogr.
B 2008; 862, 51.
M. Shibano, A.S. Lin, H. Itokawa, K.H. Lee J. Nat. Prod.
2007; 70, 1424.
K. Wang, H. Zhang, L. Shen, Q. Du, J. Li J. Pharm.
Biomed. Anal. 2010; 53, 1053.
F. Kvasnička, B. Bíba, R. Ševčik, M. Voldřich, J. Krátká
J. Chromatogr. A 2003; 990, 239.
J.I. Lee, B.H. Hsu, D. Wu, J.S. Barrett J. Chromatogr. A
2006; 1116, 57.
H. Ling, Y.P. Xiao, Y. Huang, J. Li Hunan Journal of
Traditional Chinese Medicine 2004; 20, 72.
T.M. Ding, S.J. Tian, Z.X. Zhang, D.Z. Gu, Y.F. Chen,
Y.H. Shi, Z.P. Shun J. Pharm. Biomed. Anal. 2001;
26, 155.
D. Yuan, G.F. Zhang, R.J. Wang Journal of Shenyang
Pharmaceutical University 2003; 20, 119.
D.Y.W. Lee, Y. Liu ACS Symposium Series, American
Chemical Society, Washington DC, 2005; Ch. 3, 19.
A. Pelter, R. Hänsel, R. Chem. Ber. 1975; 108, 790.
E. Benfenati, R. Frassinito, N. Di Toro, R. Fanelli, A.
Brandt, M. DiRella, L. Cecchetelli Nat. Prod. Lett.
1994; 4, 247.
N.A. Khan, H. Wu Rapid Commun. Mass Spectrom.
2004, 18, 2960.
S. Keki, K. Tóth, M. Zsuga, R. Ferenczi, S. Antus Rapid
Commun. Mass Spectrom. 2007; 21, 2255.
P.R. Davis-Searles, Y. Nakanishi, N.C. Kim, T.N. Graf,
N.H. Oberlies, M.C. Wani, M.E. Wall, R. Agarwal,
D.J. Kroll Cancer Res. 2005; 65(10), 4448.
Read_full_article: pdf/vol14/iss2/JMA14-2-2011-Nagy.pdf
Correspondence:

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Article Title: Systematic identification of active ingredients of Silybum marianum seed
Authors: Lajos Nagy, Ákos Kuki, Gyögy Deák, Bernadett Biri, Miklós Nagy, Miklós Zsuga, Sándor Kéki*
Affiliation: Department of Applied Chemistry, University of Debrecen
Abstract: Silybum Marianum seed and its extract Silymarin are widely used to treat and prevent many liver diseases such as
cirrhosis. Due to other biological effects (antitumor, antioxidant, cytotoxic activities) numerous Silymarin content
drugs (Silegon, Legalon etc.) are commercially available worldwide. Thus the development of applicable extraction
and separation methods has become sorely needed as well as the improvement of analytical methods (HPLC,
UPLC, HPLC-, UPLC-MS and MS/MS) for these flavonolignans in order to realize a unified quality control. This
paper reviews some extraction and separation methods as well as the fragmentation patterns of different active
components of Silymarin under MS/MS conditions.
Keywords:
References: Y.M. Zhao, C.Y. Wang, X.D. Liu Application of Statistics
and Management 2000; 20, 1.
V. Křen, D. Walterová, Biomed. Papers 2005; 29, 149.
Y. Yanaida, H. Kohno, K. Yoshida, Y. Hiroshe, Y. Yamada,
H. Mori, Tanaka T. Carcinogenesis 2002; 23, 787.
R.P. Singh, R. Agarwal Cancer Mutat. Res. 2004; 21,
555.
S.C. Pradhan, C. Girish Indian J. Med. Res. 2006; 124,
491.
A. Valenzuela, A. Garrido Biol. Res. 1994; 27, 105.
G. Scambia, R. De Vincenso, F. Raneletti, P. Panici,
Ferrandina G., G. D’Agostino, A. Fattorossi, E.
Bombardelei, S. Manausco Eur. J. Cancer 1996;
32A, 877.
F. Lirussi, L. Okolicsanyi Acta Physiol. Hung. 1992; 80,
363.
D.I. Hadaruga, N.G. Hadaruga Chem. Bull.
“POLITEHNICA” Univ. 2009; 54(68), 2.
Z. Asghar, Z. Masood Pak. J. Pharm. Sci. 2008; 21, 249.
F. Kvasnicka, B. Biba, R. Sevcik, M. Voldrich, J. Kratka
J. Chromatogr. 2003; A 990, 239.
L. Mollison, L. Totten, J. Flexman, M. Beaman, R. Batey
J. Gastroenterol. Hepatol. 2006; 21 1184.
Y.P. Pei, J. Chen, W.L. Li Medicinal Aromatic Plant Sci.
Biotech. 2009; 3(1), 1.
P.R. Rao, R.K. Viswanath Exp Clin Cardiol. 2007; 12(4),
179.
S. Giacomelli, D. Gallo, P. Apollonio, C. Ferlini, M.
Distefano, P. Morazzoni, A. Riva, E. Bombardelli,
S. Mancuso, G. Scambia Life Sci. 2002;70, 1447.
S. Dhanalakshmi, P. Agarwal, L.M. Glode, R. Agarwal
Int. J. Cancer 2003; 106, 699.
M. Bialecka, Ann. Acad. Med. Stetin. 1997; 43, 41.
Gu M., Singh R.P., Dhanalakshmi S., Agarwal C.,
Agarwal R. Cancer Res. 2007;67, 3483.
H. Wagner, P. Diesel, M. Seitz Arzneilmittelforschung
1974; 24, 466.
Y.Q. Chen, C.M. Wang, W.H. Zhang Acta Agriculturae
Boreali-Occidentalis Sinica 1997; 6, 91.
S.N. Wallace, D.J. Carrier, E.C. Clausen Appl. Biochem.
Biotechnol. 2003; 108, 891.
A.P. Kahol, K.L. Singh, S. Tandon, S. Kumar US patent
2001; patent no.: US 6,309,678 B1.
W. Li, J. Han, Z. Li, X. Li, S. Zhou, C. Liu J. Chromatogr.
B 2008; 862, 51.
M. Shibano, A.S. Lin, H. Itokawa, K.H. Lee J. Nat. Prod.
2007; 70, 1424.
K. Wang, H. Zhang, L. Shen, Q. Du, J. Li J. Pharm.
Biomed. Anal. 2010; 53, 1053.
F. Kvasnička, B. Bíba, R. Ševčik, M. Voldřich, J. Krátká
J. Chromatogr. A 2003; 990, 239.
J.I. Lee, B.H. Hsu, D. Wu, J.S. Barrett J. Chromatogr. A
2006; 1116, 57.
H. Ling, Y.P. Xiao, Y. Huang, J. Li Hunan Journal of
Traditional Chinese Medicine 2004; 20, 72.
T.M. Ding, S.J. Tian, Z.X. Zhang, D.Z. Gu, Y.F. Chen,
Y.H. Shi, Z.P. Shun J. Pharm. Biomed. Anal. 2001;
26, 155.
D. Yuan, G.F. Zhang, R.J. Wang Journal of Shenyang
Pharmaceutical University 2003; 20, 119.
D.Y.W. Lee, Y. Liu ACS Symposium Series, American
Chemical Society, Washington DC, 2005; Ch. 3, 19.
A. Pelter, R. Hänsel, R. Chem. Ber. 1975; 108, 790.
E. Benfenati, R. Frassinito, N. Di Toro, R. Fanelli, A.
Brandt, M. DiRella, L. Cecchetelli Nat. Prod. Lett.
1994; 4, 247.
N.A. Khan, H. Wu Rapid Commun. Mass Spectrom.
2004, 18, 2960.
S. Keki, K. Tóth, M. Zsuga, R. Ferenczi, S. Antus Rapid
Commun. Mass Spectrom. 2007; 21, 2255.
P.R. Davis-Searles, Y. Nakanishi, N.C. Kim, T.N. Graf,
N.H. Oberlies, M.C. Wani, M.E. Wall, R. Agarwal,
D.J. Kroll Cancer Res. 2005; 65(10), 4448.
*Correspondence:

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