基于UHPLC-Q/TOF-MS技术快速测定马兜铃科五种植物中8种马兜铃酸类物质的含量

doi:10.5246/jcps.2015.06.047

中国药学(英文版) ›› 2015, Vol. 24 ›› Issue (6): 364-375.DOI: 10.5246/jcps.2015.06.047

基于UHPLC-Q/TOF-MS技术快速测定马兜铃科五种植物中8种马兜铃酸类物质的含量

孔德强¹, 高慧媛¹, 李辛², 路金才¹, 袁丹^1*

1. 沈阳药科大学中药学院, 辽宁沈阳 110016
2. 沈阳药科大学医疗器械学院, 辽宁沈阳 110016

收稿日期:2014-11-03 修回日期:2015-02-07 出版日期:2015-06-26 发布日期:2015-03-02
通讯作者: Tel./Fax: 86-24-23986502
基金资助:
The National Science and Technology Support Program during the Twelfth Five-Year Plan of China (Grant No. 2011BAI03B05), the Distinguished Professor Foundation of Liaoning Province of China of 2011 and Innovative Drug Incubation Base Plan Project from Liaoning Province of China of 2013 (Grant No. 2013226027).

Rapid determination of eight aristolochic acid analogues in five Aristolochiaceae plants by ultra-high performance liquid chromatography quadrupole/time-of-flight mass spectrometry

Deqiang Kong¹, Huiyuan Gao¹, Xin Li², Jincai Lu¹, Dan Yuan^1*

1. School of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang 110016, China
2. School of Medical Devices Shenyang Pharmaceutical University, Shenyang 110016, China

Received:2014-11-03 Revised:2015-02-07 Online:2015-06-26 Published:2015-03-02
Contact: Tel./Fax: 86-24-23986502
Supported by:
The National Science and Technology Support Program during the Twelfth Five-Year Plan of China (Grant No. 2011BAI03B05), the Distinguished Professor Foundation of Liaoning Province of China of 2011 and Innovative Drug Incubation Base Plan Project from Liaoning Province of China of 2013 (Grant No. 2013226027).

摘要/Abstract

摘要：

马兜铃酸类物质普遍存在于马兜铃科植物中, 文献报道其具有肾毒性和致癌作用。本研究建立了一种高效、快速、灵敏的超高效液相串联飞行时间质谱的检测方法, 基于该方法能够对19份来源于五种马兜铃科植物(细辛、马兜铃、青木香、关木通和广防己) 的样品中8种马兜铃酸类物质(马兜铃酸I、马兜铃酸II、马兜铃酸IIIa、马兜铃酸IV、马兜铃酸IVa、马兜铃内酰胺I、马兜铃内酰胺II和马兜铃内酰胺III)进行快速鉴别及定量和半定量分析。马兜铃酸类物质在相应的线性范围内呈现良好的线性关系, 精密度及稳定性RDS<4.1%, 回收率在95.98%~98.67%之间。实验结果表明五种马兜铃科植物中马兜铃酸类物质的化学成分分布和含量存在显著差异, 这为马兜铃科中药材质量标准的建立奠定了基础。此外本研究对19个样品进行了主成分分析和正交偏最小二乘判别分析, 以期更加全面的阐明五种马兜铃科植物间的差异。

关键词: 马兜铃酸, 马兜铃内酰胺, 马兜铃科, UHPLC-Q/TOF-MS, 含量测定, 多元统计分析

Abstract:

Aristolochic acids (AAs) and aristololactams (ALs) are commonly found in some Aristolochiaceae plants, and they have been reported to be AA nephropathy (AAN), nephrotoxicity and carcinogenicity. In the present study, we established an ultra high performance liquid chromatography (UHPLC) coupled with quadrupole/time-of-flight mass spectrometry (Q/TOF-MS) method for the rapid analysis of eight AA analogues in 19 samples originated from the five Aristolochiaceae plants, the roots and rhizomes of Asarum sieboldii Miq. var. seoulense Nakai, the fruits of Aristolochia contorta Bunge or A. debilis Sieb. et Zucc., the roots of Aristolochia debilisSieb. et Zucc., the stems of Aristolochia manshuriensis Kom., and the roots of Aristolochia fangchi Y. C. Wu ex L. D. Chou et S. M. Hwang. A total of five AAs and three ALs were identified by co-chromatography of sample extract and comparing the retention time, UV spectra, and characteristic molecular ions and fragment ions with those of authentic standards, or tentatively identified by MS/MS determination along with Mass Fragment software. Moreover, the method was validated for the simultaneous quantification or semi-quantification of them. The samples significantly differed in the quality and quantity of AA analogues, which allowed the possibility of showing their chemical distinctness, and it might be helpful in their standardization and quality control. Furthermore, in order to holistically compare the difference between the five Aristolochiaceaeplants, dataset obtained from UHPLC-Q/TOF-MS was processed with principal component analysis (PCA) and orthogonal partial least squared discriminant analysis (OPLS-DA).

Key words: Aristolochic acids, Aristololactams, Aristolochiaceae, UHPLC-Q/TOF-MS, Quantification, Multivariate statistical analysis

中图分类号:

R284

Supporting:

孔德强, 高慧媛, 李辛, 路金才, 袁丹. 基于UHPLC-Q/TOF-MS技术快速测定马兜铃科五种植物中8种马兜铃酸类物质的含量[J]. 中国药学(英文版), 2015, 24(6): 364-375.

Deqiang Kong, Huiyuan Gao, Xin Li, Jincai Lu, Dan Yuan. Rapid determination of eight aristolochic acid analogues in five Aristolochiaceae plants by ultra-high performance liquid chromatography quadrupole/time-of-flight mass spectrometry[J]. Journal of Chinese Pharmaceutical Sciences, 2015, 24(6): 364-375.

参考文献

[1] Vanherweghem, J.L.; Tielemans, C.; Abramowicz, D; Depierreux, M.; Fastre, R.V.; Vanhaelen, M.; Dratwa, M.; Richard, C.; Vandervelde, D.; Verbeelen, D.; Jadoul, M. Lancet. 1993, 341, 387-391.

[2] Jelaković, B.; Karanović, S.; Vuković-Lela, I.; Miller, F.; Edwards, K.L.; Nikolić, J.; Tomić, K.; Slade, N.; Brdar, B.; Turesky, R.J.; Stipančić, Ž.; Dittrich, D.; Grollman, A.P.; Dickman, K.G. Kidney Int. 2012, 81, 559-567.

[3] Lemy, A.; Wissing, K.M.; Rorive, S.; Zlotta, A.; Roumeguere, T.; Muniz Martinez, M.C.; Decaestecker, C.; Salmon, I.; Abramowicz, D.; Vanherweghem, J.L.; Nortier, J.L. Am. J. Kidney Dis. 2008, 51, 471-477.

[4] Nortier, J.L.; Vanherweghem, J.L. Toxicology. , 181-182, 577-580.2002

[5] Nortier, J.L.; Martinez, M.C.; Schmeiser, H.H.; Arlt, V.M.; Bieler, C.A.; Petein, M.; Depierreux, M.F.; De Pauw, L.; Abramowicz, D.; Vereerstraeten, P.; Vanherweghem, J.L. N. Engl. J. Med. 2000, 342, 1686-1692.

[6] Cheng, C.L.; Chen, K.J.; Shih, P.H.; Lu, L.Y.; Hung, C.F.; Lin, W.C.; Yesong, G.J. Cancer Lett. , 232, 236-2422006.

[7] Kohara, A.; Suzuki, T.; Honma, M.; Ohwada, T.; Hayashi, M. Mutat. Res. 2002, 515, 63-72.

[8] Stiborová, M.; Frei, E.; Arlt, V.M.; Schmeiser, H.H. Mutat. Res. 2008. 658, 55-67.

[9] Sato, N.; Takahashi, D.; Chen, S.M.; Tsuchiya, R.; Mukoyama, T.; Yamagata, S.; Ogawa, M.; Yoshida, M.; Satoh, N.; Ueda, S. J. Pharm. Pharmacol. , 56, 221-229.2004

[10] Xing, G.; Qi, X.; Chen, M.; Wu, Y.; Yao, J.; Gong, L.; Nohmi, T.; Luan, Y.; Ren, J. Mutat. Res. Genet. Toxicol. Environ. Mutagen. 2012, 743, 52-58.

[11] Zhang, L.; Li, J.; Jiang, Z.Z.; Bian, Y.; Yuan, D.P.; Long, J.; Zhang, L.Y. Tradit. Chin. Drug. Res. Clin. Pharmacol. 2011, 22, 359-364.

[12] Li, J.; Zhang, L.; Jiang, Z.Z.; Shu, B.; Li, F.; Bao, Q.L.; Zhang, L.Y. Toxicol. in Vitro. 2010, 24, 1092-1097.

[13] Yuan, J.B.; Nie, L.H.; Zeng, D.Y.; Luo, X.B.; Tang, F.; Ding, L.; Liu, Q.; Guo, M.L.; Yao, S.Z. Talanta. 2007, 73, 644-650.

[14] Yamasaki, K.; Tagami, T.; Kawaguchi, M.; Okihashi, M.; Takatori, S.; Sakagami, Y.; Sekita, S.; Satake, M. J. Nat. Med. 2009, 63, 451-458.

[15] Zhang, C.Y.; Wang, X.; Shang, M.Y.; Yu, J.; Xu, Y.Q.; Li, Z.G.; Lei, L.C.; Li, X.M.; Cai, S.Q. Biomed. Chromatogr. , 20, 309-318.2006

[16] Ioset, J.R.; Raoelison, G.E.; Hostettmann, K. Food Chem. Toxicol. 2003, 41, 29-36.

[17] Dolma, P.; Yang, D.H.; Yu, J.; Wang, X.; Cai, S.Q. J. Chin. Pharm. Sci. 2009, 18, 79-83.

[18] Chinese Pharmacopeia Commission. Chinese Pharmacopoeia, Vol. 1. Beijing. Chinese Medical Science and Technology Press. 2010, 214-215.

[19] The Ministry of Health, Labour and Welfare of Japan. English Edition. Japanese pharmacopoeia, 16th edn. Tokyo. Pharmaceutical and Medical Devices Agency. 2011. 1602-1603.

[20] Zhao, Z.Z.; Liang, Z.T.; Jiang, Z.H.; Leung, K.S.; Chan, C.L.; Chan, H.Y.; Sin, J.; Man, T.O.; Law, K.W. Phytomedicine. 2008, 15, 741-748.

[21] Chen, M,J,; Su, M.M.; Zhao, L.P.; Jiang, J.; Liu, P.; Cheng, J.Y.; Lai, Y.J.; Liu, Y.M.; Jia, W. J. Proteome Res. 2006, 5, 995-1002.

[22] Chan, W.; Lee, K.C.; Liu, N.; Cai, Z.W. J. Chromatogr. A. 2007, 1164, 113-119.

[23] Yuan, J.B.; Liu, Q.; Zhu, W.F.; Ding, L.; Tang, F.; Yao, S.Z. J. Chromatogr. A. 2008, 1182, 85-92.

[24] Zhang, Y.T.; Jiang, J.Q. Helv. Chim. Acta. 2006, 89, 2665-2670.

[25] Sime, K.R.; Feeny, P.P.; Haribal, M.M. Chemoecology. 2000, 10, 169-178.

[26] Priestap, H.A.; Velandia, A.E.; Johnson, J.V.; Barbieri, M.A. Biochem. Syst. Ecol. 2012, 40, 126-137.

[27] Yuan, J.B.; Liu, Q.; Wei, G.B.; Tang, F.; Ding, L.; Yao, S.Z. Rapid Commun. Mass Spectrom. , 21, 2332-23422007.

[28] Chan, W.; Cui, L.; Xu, G.W.; Cai, Z.W. Rapid Commun. Mass Spectrom. 2006, 20, 1755-1760.

[29] Wei, F.; Cheng, X.L.; Ma, L.Y.; Jin, W.T.; Schaneberg, B.T.; Khan, I.A.; Lin, R.C. Phytochem. Anal. 2005, 16, 222-230.

[30] Dong, S.W.; Shang, M.Y.; Wang, X.; Zhang, S.X.; Li, C.; Cai, S.Q. J. Chin. Pharm. Sci. 2009, 18, 146-150.

[31] Liu, Q.F.; Shi, Y.; Wang, Y.; Lu, J.; Cong, W.J.; Luo, G.A.; Wang, Y.M. Talanta. 2009, 80, 84-91.

[32] Lee, M.C.; Tsao, C.H.; Iou, S.C.; Chuang, W.C.; Sheu, S.J. J. Sep. Sci. 2003, 26, 818-822.

[33] Heaton, J.; Whiley, L.; Hong, Y.; Sebastian, C.M.; Smith, N.W.; Quigley, C.L. J. Sep. Sci. 2011, 34, 1111-1115.

[34] Tagami, T.; Takeda, A.; Asada, A.; Aoyama, A.; Doi, T.; Kawaguchi, M.; Kajimura, K.; Sawabe, Y.; Obana, H.; Yamasaki, K. J. Nat. Med. , 67, 838-843.2013

[35] Guo, L.; Yue, H.; Cai, Z.W. J. Pharm. Biomed. Anal. 2010, 53, 37-42.

[36] Kuo, C.H.; Lee, C.W.; Lin, S.C.; Tsai, I.L.; Lee, S.S.; Tseng, Y.J.; Kang, J.J.; Peng, F.C.; Chu, L.W. Talanta. 2010, 80, 1672-1680.

[37] Debelle, F.D.; Nortier, J.L.; De Prez, E.G.; Garbar, C.H.; Vienne, A.R.; Salmon, I.J.; Deschodt-Lanckman, M.M.; Vanherweghem, J.L. J. Am. Soc. Nephrol. 2002, 13, 431-436.

基于UHPLC-Q/TOF-MS技术快速测定马兜铃科五种植物中8种马兜铃酸类物质的含量

Rapid determination of eight aristolochic acid analogues in five Aristolochiaceae plants by ultra-high performance liquid chromatography quadrupole/time-of-flight mass spectrometry

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