Identification and determination of Aconitum alkaloids in Aconitum herbs and Xiaohuoluo Pill using UPLC-ESI-MS

Molecules

Volumn 17, Issue 9, 2012, Pages 10242-10257

  Cui, Ping ^a   Han, Han ^a   Wang, Rui ^a   Yang, Li ^a  

^a SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

Aconitum alkaloids; Multi component quantitative; Quality control; UPLC ESI MS; Xiaohuoluo pill

Indexed keywords

ACONITINE; ALKALOID; BENZOYLHYPACONINE; BENZOYLMESACONINE; DITERPENE; DRUG DERIVATIVE; HERBACEOUS AGENT; HYPACONITINE; MESACONITINE;

ACONITE; ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; PLANT ROOT; PRINCIPAL COMPONENT ANALYSIS;

ACONITINE; ACONITUM; ALKALOIDS; DITERPENES; DRUGS, CHINESE HERBAL; PLANT ROOTS; PRINCIPAL COMPONENT ANALYSIS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84866948334     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules170910242     Document Type: Article

References (49)

1. The State Pharmacopoeia Committee of People's Republic of China. Pharmacopoeia of People's Republic of China; Chemical Industry Press: Beijing, China, 2010; Volume 1, pp. 36-38, 220-221, 509.
2. Kita, Y.; Tto, M. Nuclear ribosomal ITS sequences and phylogeny in East Asian Aconitum subgenus Aconitum (Ranunculaceae), with special reference to extensive polymorphism in individual plants. Plant. Syst. Evol. 2000, 225, 1-13.
3. Wang, F.P. Chemical of Alkaloids; Chemical Industry Publishing: Beijing, China, 2008.
4. Chen, Y.; Chu, Y.L.; Chu, J.H. Alkaloids of the Chinese drugs, Aconitum Spp-IX. Alkaloids from Chuan-wu and Fu-zi, Aconitum Carmichaelidebx. Acta Phram. Sin. 1956, 12, 435-439.
5. Li, Z.B.; Lu, G.H.; Chen, D.L.; Wang, F.P. Chemical study on the alkaloids of "Cao Wu". Nat. Prod. Res. Dev. 1997, 1, 9-14.
6. Yun-Choi, H.S.; Park, K.M.; Chang, K.C.; Lee, D.H. Antithrombotic Effects of YS-49 and YS-51-1-Naphthylmethyl Analogs of Hi genamine. Thromb. Res. 2001, 104, 249-255.
7. Shim, S.H.; Kim, J.S.; Son, K.H.; Bae, K.H.; Kang, S.S. Alkaloids from the Roots of Aconitum pseudo-lave var. erectum. J. Nat. Prod. 2006, 69, 400-402.
8. Barbosa-Filho, J.M.; Piuvezam, M.R.; Moura, D.M.; Sliva, M.S. Anti-inflammatory activity of alkaloids: A twenty-century review. Rev. Bras. Farmacogn. 2006, 16, 109.
9. Li, H.Y.; Huang, C.Y.; Ye, Z.J. Experimental study on anti-inflammation and analgesia effect from Aconitum carmichaeli Debx. Chin. J. Curr. Prac. Med. 2006, 6, 27-29.
10. Zeng, J.; Luo, X. Study on tumor-inhibitory effect of Chuan Wu aqueous extract. J. Sichuan U. 2007, 16, 1345-1348.
11. De lnés, C.; Reina, M.; Gavín, J.A.; González- Coloma, A. In vitro cytotoxicity of norditerpenoid alkaloids. Z. Natllrforsch C. 2006, 61, 11-18.
12. Xu, T.H.; Zhao, H.F.; X, Y.J.; Xie, S.X. Cardiotonic constituents of Aconitum carmichaeli. Chin. Tradit. Herb. Drugs 2004, 9, 964.
13. Liu, W.H.; Zhou, Y.P.; Zeng, G.W. Effects of DL-Demethyloclaurine on experiment heart failure. Acta Phram. Sin. 1988, 2, 81-83.
14. Kimura, I.; Makino, M.; Honda, R.; Ma, J.; Kimura, M. Expression of major histocompatibility complex in mouse peritoneal macrophages increasingly depends on plasma corticosterone levels: Stimulation by aconitine. Biol. Pharm. Bull. 1995, 18, 1504-1508.
15. Yang, Q.E. Cytology of 12 species in Aconitum L. and of 8 species in Delphinium L. of tribe Delphineae (Ranunculaceae) from China. Acta Phram. Sin. 2001, 39, 502-514.
16. Zhang, Y.Y.; Zhang, Y.; Lin, R.C.; Sun, W.J. An expeditious HPLC method to distinguish Aconitum Kusnezoffi from related species. Fitoterapia 2009, 80, 333-338.
17. Chen, H.C.; Lee, C.Y.; Liau, B.C.; Lee, M.R.; Jong, T.T.; Chiang, S.T. Determination of aconitine-type alkaloids as makers in fuzi (Aconitum carmichaeli) by LC/(+) ESI /MS3. J. Pharm. Biomed. Anal. 2008, 48, 1105-1111.
18. Zhang, F.; Tang, M.H.; Chen, L.J.; Li, R.; Wang, X.H.; Duan, J.G.; Zhao, X.; Wei, Y.Q. Simultaneous quantitation of aconitine, mesaconitine, hypaconitine, benzolyaconitine, benzoylmesaconitine and benzoylhypaconitine in human plasma by liquid chromatography-tandem mass spectrometry and phramacokinetics evaluation of "SHEN-FU" injectable powder. J. Chromatogr. B 2008, 873, 173-179.
19. Lin, C.C.; Chan, T.Y.; Deng, J.F. Clinical features and management of herb-induced aconitine poisoning. Ann. Emerg. Med. 2004, 43, 574-579.
20. Zhang, H.S. Aconite toxicity and poisoning management. Adverse Drug Reac. J. 2005, 2, 114-115.
21. Csupor, D.; Wenziq, E.M.; Zupkó, I.; Wölkart, K.; Hohmann, J.; Bauer, R. Qualitative and quantitative analysis of aconitine-type and lipo-type alkaloids of Aconitum carmichaelli roots. J. Chromatogr. A 2009, 1216, 2079-2086.
22. Zhang, S.W.; Liu, Y.; Huang, G.Z.; Liu, L. Aconitine alters connexin43 phosphorylation status and [Ca2+] oscillation patterns in cultured neonatal rats. Toxicol. In Vitro 2007, 21, 1476-1485.
23. Liu, W.L.; Liu, Z.Q.; Song, F.R.; Liu, S.Y. Specific Conversion of Diester-diterpenoid Aconitum Alkaloids Components into Hydrolysis Monoester-diterpenoid Alkaloids Components and Lipo-alkaloids Components. Chem. J. Chin. U. 2007, 3, 717-720.
24. Zhou, Y.; Cui, Y.; Liu, Y.; Shen, G. Bioavailability study on xiaohuoluo pills. Chin. J. Chin. Mater. Med. 1995, 20, 159-161.
25. Liu, J.B.; Zhang, Y.J.; Chen, J.X. Pharmacodynamics study on Xiaohuoluo pills. Chin. Pharm. 2007, 18, 26-28.
26. Pan, J.Q.; Xiao, L.Y.; Zhang, D.; Han, C. Immunosuppresive, antioxidative, anti-inflammatory and analgesic effect of Xiaohuoluo pills. Chin. J. Clin. Rehabil. 2006, 47, 183-188.
27. Zhang, J.; Li, J.M.; Jiang, Y. Fast limit test of trace aconitine in Xiaohuoluo Pills. Chin. Trad. Pat. Med. 2009, 10, 1543-1546.
28. Zhu, Z.Y.; Wang, B.L.; Li, J.S. Quantitative Determination of Mesaconitine, Hypaconitine and Aconitine in Xiaohuoluo Pills by TLC-HPLC. J. Pharm. Anal. 1996, 3, 154-156.
29. Liu, X.X.; Chao, R.B. Determination of alkaloids in Radix Aconiti Lateralis Preparata by RP-ion-pair HPLC. Acta Phram. Sin. 2006, 4, 365-369.
30. Liu, F.; Yu, X.H.; Li, F.; Tan, Y.Y.; Qiao, Y.J. Determination of three kinds of diester diterpenoid alkaloids (DDAs) in Aconitum carmichaeli and its processed products by HPLC. Chin. J. Chin. Mater. Med. 2006, 14, 1160-1162.
31. Huang, Z.F.; Yi, J.H.; Chen, D.A.; Liu, Y.H. HPLC specific chromatogram of Radix Aconiti Praeparata and determination of six esteric alkaloids. J. Pharm. Anal. 2011, 2, 217-221.
32. Li, H.; Deng, G.H. HPLC fingerprint of Radix Aconiti. Chin. J. Exp. Tradit. Med. Form. 2011, 3, 3-6.
33. Yang, Z.F.; Liu, J.F.; Zhang, H. Study on the Quality Standards of Aconitum pendulum Busch. Chin. J. Chin. Mater. Med. 2005, 22, 1772-1773.
34. Yang, X.L.; Wen, Z.H. Study on Quality Standards of Aconitum vilmorinianum Komarov. Chin. J. Ethnomed. and Ethnopharm. 2005, 72, 54-57.
35. Koji, W.; Hideo, B.; Norio, K. Determination and Quantitative Analysis of aconitum Alkaloids in Plants by Liquid Chromatography Atmospheric Pressure Chemical Ionization Mass Spectrometry. J. Chromatogr. A 1993, 644, 43-48.
36. Ohta, H.; Seto, Y.; Tsunoda, N.; Takahashi, Y.; Matsuura, K.; Oqasawara, K. Determination of Aconitum alkaloids in blood and urine samples II. Capillary liquid chromatographic-frit fast atom bombardment mass spectrometric analysis. J. Chromatogr. B Biomed. Sci. Appl. 1998, 714, 215-221.
37. Feng, H.T.; Li, S.F. Determination of five toxic alkaloids in two common herbal medicines with capillary electrophoresis. J. Chromatogr. A 2002, 973, 243-248.
38. Zhou, D.; Pan, G.M. Detection of Aconitine and Mesaconitine and Hypaconitine in Biology Samples by LC/MS/MS. Mod. Sci. Ins. 2005, 4, 64-67.
39. Qiao, Y.L; Zhang, Y.H.; Zhang, W.; Zhang, J.L. A rapid resolution liquid chromatographic method for fingerprint analysis of raw and processed Caowu (Aconitum kusnezoffii). J. AOAC Int. 2009, 92, 653-662.
40. Zhou, S.S.; Ma, Z.C.; Liang, Q.D.; Wang, Y.G.; Tan, H.L.; Xiao, C.R.; Zhang, B.L.; Gao, Y. UPLC/Q-TOF-MS based chemical profiling approach to evaluate chemical composition of augmentation toxicity in combination of Radix Aconiti and Pinellia Praeparata. Acta Chim. Sin. 2010, 70, 284-290.
41. Chen, X.G.; Lai, Y.Q.; Cai, Z.W. Simultaneous analysis aconitine and its metabolites by liquid chromatography-electrospray ion trap mass spectrometry. J. Chin. Mass Spectrom. Soc. 2012, 2, 65-73.
42. Zhang, H.G.; Sun, Y.; Duan, M.Y.; Chen, Y.J.; Zhong, D.F.; Zhang, H.Q. Separation and identification of Aconitum alkaloids and their metabolites in human urine. Toxicon 2005, 46, 500-506.
43. Xiang, P.; Shen, M.; Shen, B.H.; Zhuo, X.Y. Simultaneous Screening for 59 Drugs of Abuse in Biological Samples by LC-MS/MS-MRM. J. Chin. Mass Spectrom. Soc. 2006, 4, 237-241.
44. Trygg, J.; Wold, S. Orthogonal projections to latent structures (O-PLS). J. Chemometr. 2002, 16, 119-128.
45. Qi, M.; Xiong, A.Z.; Geng, F.; Yang, L.; Wang, Z.T. A novel strategy for target profiling analysis of bioactive phenylethanoid glycosides in Plantago meidicine plants using ultra-performace liquid chromatography coupled with tandem quadrupole mass spectrometry. J. Sep. Sci. 2012, 35, 1470-1478.
46. Xiong, A.Z.; Yang, L.; Ji, L.L.; Wang, Z.Y.; Yang, X.J.; Chen, Y.; Wang, X.L.; Wang, C.H.; Wang, Z.T. UPLC-MS based metabolomices study on Senecio scandens and S. vulgaris: An approach for the differentiation of two Senecio herbs with similar morphology but different toxicity. Metabolomics 2012, 8, 614-623.
47. Wiklund, S.; Johansson, E.; Sjöström, L.; Mellerowicz, E. J.; Edlund, U.; Shochcor, J. P.; Gottfries, J.; Moritz, T.; Trygg, J. Visualization of GC/TOF-MS-based metabolomics data for identification of biochemically interesting compounds using OPLS class models. Anal. Chem. 2008, 80, 115-122.
48. Xie, G. X.; Ni, Y.; Su, M. M.; Zhang, Y. Y.; Zhao, A. H.; Gao, X. F.; Liu, Z.; Xiao, P. G.; Jia, W. Application of Ultra-performance LC-TOF MS metabolite profiling techniques to the analysis of medicinal Panax herbs. Metabolomics 2008, 4, 248-260.
49. Kobayashi, S.; Putri, S.P.; Yamamoto, Y.; Donghyo, K.; Bamba, T.; Fukusaki, E. Gas chromatography-mass spectrometry based metabolic profiling for the identification of discrimination markers of Angelicae Radix and its application to gas cheomatography-flame ionization detector system. J. Biosci. Bioeng. 2012, 114, 232-236.