定量核磁共振氢谱法对徐长卿中丹皮酚含量的快速提取和含量测定

doi:10.5246/jcps.2020.06.040

中国药学(英文版) ›› 2020, Vol. 29 ›› Issue (6): 422-430.DOI: 10.5246/jcps.2020.06.040

定量核磁共振氢谱法对徐长卿中丹皮酚含量的快速提取和含量测定

李雪娇¹, 董建伟^1*, 高秀^2*, 李贵军¹, 史俊友¹, 张艳清¹

1. 曲靖师范学院化学与环境科学学院, 云南曲靖 655011
2. 曲靖师范学院生物资源与食品工程学院, 云南曲靖 655011

收稿日期:2019-12-14 修回日期:2020-03-24 出版日期:2020-06-30 发布日期:2020-03-30
通讯作者: Tel.: +86-874-8998658; +86-874-8998620, E-mail: jwdongyn@mail.qjnu.edu.cn; appleartgao@163.com
基金资助:
Science and Technology Project of Yunnan Provincial Department of Science and Technology (Grant No. 2018FD081), Yunnan Local Colleges Applied Basic Research Projects [Grant Nos. 2019FH001(-109), 2017FH001-092, 2017FH001-094 and 2018FH001-019], and Youth Research Foundation of Qujing Normal University in 2019 (Grant No. 2019QN004).

Application of a quantitative 1H NMR method for rapid extraction and determination of the content of paeonol in Cynanchum paniculatum

Xuejiao Li¹, Jianwei Dong^1*, Xiu Gao^2*, Guijun Li¹, Junyou Shi¹, Yanqing Zhang¹

1. College of Chemistry and Environmental Science, Qujing Normal University, Qujing 655011, China
2. College of Biological Resources and Food Engineering, Qujing Normal University, Qujing 655011, China

Received:2019-12-14 Revised:2020-03-24 Online:2020-06-30 Published:2020-03-30
Contact: Tel.: +86-874-8998658; +86-874-8998620, E-mail: jwdongyn@mail.qjnu.edu.cn; appleartgao@163.com
Supported by:
Science and Technology Project of Yunnan Provincial Department of Science and Technology (Grant No. 2018FD081), Yunnan Local Colleges Applied Basic Research Projects [Grant Nos. 2019FH001(-109), 2017FH001-092, 2017FH001-094 and 2018FH001-019], and Youth Research Foundation of Qujing Normal University in 2019 (Grant No. 2019QN004).

摘要/Abstract

摘要：

徐长卿是一种治疗多种疾病的中药材。丹皮酚是徐长卿的主要活性成分, 也是质量控制的关键指标物。本文以核磁共振氢谱建立了一种徐长卿中丹皮酚含量的快速、准确、精密的检测方法。结果表明, 氘代甲醇作溶剂可以很好的实现核磁共振氢谱中信号的分离, H-6 (δ 7.78) 可用作定量分析特征信号, 均苯三甲酸用作内标。所建立的方法经线性范围、专属性、重复性和稳定性进行了确证。本文首次采用定量核磁共振氢谱检测徐长卿中丹皮酚的含量, 线性范围较其他药材中丹皮酚的含量检测更宽。采用单次提取方式对丹皮酚进行提取, 方法快速, 更利于应用于质量控制中。本文研究表明相对现有基于高效液相色谱检测方法, 定量核磁共振氢谱法是一种适合徐长卿质量控制可行的替代方法。

关键词: 徐长卿, 定量核磁共振氢谱, 丹皮酚, 含量检测

Abstract:

Cynanchum paniculatum (Bunge) Kitagawa is usually used as an herbal medicine for treating many diseases. Paeonol is the main active component, and its content is the key indicator for quality control of C. paniculatum. In the present study, we developed a rapid, accurate and precise method for quantitation of paeonol in C. paniculatum using ¹H NMR spectra. The deuteratedsolvent of methanol-d₄ enabled satisfactory separation of the signals to be integrated in ¹H NMR spectrum. H-6 (δ 7.78) of¹H NMR spectrum of C. paniculatum was selected as the feature signal for quantitation, and trimesic acid (TMA) was selected as an internal standard. Validation of the quantitative method was performed in terms of linearity, specificity, repeatability and stability. This is the first time to report quantitative ¹H NMR(qHNMR) applied to determine the content of paeonol in C. paniculatum and showed a wider linearity range than the reported quantitation of paeonol in others. The simple extraction of paeonol from C. paniculatum was rapid and will prompt the application of the developed method. This work implied that qHNMR represented a feasible alternative to HPLC-based methods for quantitation of paeonol in C. paniculatum, and it was suitable for the quality control of C. paniculatum.

Key words: Cynanchum paniculatum, Quantitative 1H NMR, Paeonol, Quantitative determination

中图分类号:

R917

Supporting:

李雪娇, 董建伟, 高秀, 李贵军, 史俊友, 张艳清. 定量核磁共振氢谱法对徐长卿中丹皮酚含量的快速提取和含量测定[J]. 中国药学(英文版), 2020, 29(6): 422-430.

Xuejiao Li, Jianwei Dong, Xiu Gao, Guijun Li, Junyou Shi, Yanqing Zhang. Application of a quantitative 1H NMR method for rapid extraction and determination of the content of paeonol in Cynanchum paniculatum[J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(6): 422-430.

参考文献

[1] Flora of China Editorial Committee. Flora Reipublicae Popularis Sinicae. Beijing: Science Press, 2004.

[2] Chinese Pharmacopoeia Committee. Chinese pharmacopoeia. Beijing: China Medical Science and Technology Press, 2015.

[3] Dou, J.; Li, P.; Bi, Z.M.; Zhou, J.L. New C21 steroidal glycoside from Cynanchum paniculatum. Chin. Chem. Lett. 2007, 18, 300-302.

[4] Huang, X.; Tan, A.M.; Yang, S.B.; Zhang, A.Y.; Zhang, H. Two new C21Steroidal glycosides from the stems of Cynanchum paniculatum Kitag. Helvetica Chimica Acta 2009, 92, 937-943.

[5] Kim, C.S.; Oh, J.Y.; Choi, S.U.; Lee, K.R. Chemical constituents from the roots of Cynanchum paniculatum and their cytotoxic activity. Carbohydr. Res. 2013, 381, 1-5.

[6] Li, S.L.; Tan, H.; Shen, Y.M.; Kawazoe, K.; Hao, X.J. A pair of new C-21 steroidal glycoside epimers from the roots of Cynanchum paniculatum. J. Nat. Prod. 2004, 67, 82-84.

[7] Yu, H.L.; Long, Q.; Yi, W.F.; Yang, B.J.; Song, Y.; Ding, X.; Li, S.L.; Hao, X.J. Two new C21 steroidal glycosides from the roots of Cynanchum paniculatum. Nat. Prod. Bioprospect. 2019, 9, 209-214.

[8] Zhao, D.; Feng, B.M.; Chen, S.F.; Chen, G.; Li, Z.F.; Lu, X.J.; Sang, X.N.; An, X.; Wang, H.F.; Pei, Y.H. C21 steroidal glycosides from the roots of Cynanchum paniculatum. Fitoterapia. 2016, 113, 51-57.

[9] Zhao, D.; Wang, H.F.; Chen, G.; Li, Y.P.; Hua, H.M.; Pei, Y.H. Two new 13,14:14,15-disecopregnane-type compounds from the roots of Cynanchum paniculatum. J. Asian Nat. Prod. Res. 2016, 18, 339-343.

[10] Lee, S.K.; Nam, K.A.; Heo, Y.H. Cytotoxic activity and G2/M cell cycle arrest mediated by antofine, a phenanthroindolizidine alkaloid isolated from Cynanchum paniculatum. Planta Med. 2003, 69, 21-25.

[11] Niu, Y.L.; Chen, X.; Wu, Y.; Jiang, H.Q.; Zhang, X.L.; Li, E.T.; Li, Y.Y.; Zhou, H.L.; Liu, J.G.; Wang, D.Y. Chemical constituents from Cynanchum paniculatum (bunge) kitag. Biochem. Syst. Ecol. 2015, 61, 139-142.

[12] Jin, R.H.; Fan, L.; An, X.N. Ionic liquid-assisted extraction of paeonol from Cynanchum paniculatum. Chromatographia 2011, 73, 787-792.

[13] Weon, J.B.; Lee, B.; Yun, B.R.; Lee, J.; Ma, C.J. Simultaneous determination of ten bioactive compaounds from the roots of Cynanchum paniculatum by using high performance liquid chromatography coupled-diode array detector. Pharmacogn. Mag. 2012, 8, 231-236.

[14] Gai, Z.H.; Wang, Z.X.; Zhang, L.; Ma, J.; Zhu, Q. Paeonol protects against hypertension in spontaneously hypertensive rats by restoring vascular endothelium. Biosci. Biotechnol. Biochem. 2019, 83, 1992-1999.

[15] Zhang, X.X.; Shi, Q.Q.; Ji, D.; Niu, L.X.; Zhang, Y.L. Determination of the phenolic content, profile, and antioxidant activity of seeds from nine tree peony (Paeonia section Moutan DC.) species native to China. Food Res. Int. 2017, 97, 141-148.

[16] Fuentes Campo, A.; Sancho, M.I.; Melo, G.; Dávila, Y.A.; Gasull, E. In vitro and in vivo inhibition of Hass avocado polyphenol oxidase enzymatic Browning by paeonol, β-cyclodextrin, and paeonol: β-cyclodextrin inclusion complex. J. Biosci. Bioeng. 2019, 127, 703-709.

[17] Kim, S.H.; Kim, S.A.; Park, M.K.; Kim, S.H.; Park, Y.D.; Na, H.J.; Kim, H.M.; Shin, M.K.; Ahn, K.S. Paeonol inhibits anaphylactic reaction by regulating histamine and TNF-alpha. Int. Immunopharmacol. 2004, 4, 279-287.

[18] Hafez, H.M.; Morsy, M.A.; Mohamed, M.Z.; Zenhom, N.M. Mechanisms underlying gastroprotective effect of paeonol against indomethacin-induced ulcer in rats. Hum. Exp. Toxicol. 2019, 38, 510-518.

[19] Li, X.F.; Guo, Y.J.; Zhang, D.M.; Chen, Z.; Wei, X.; Li, Y.H.; Zhang, S.L.; Tao, J.Y.; Dong, J.H.; Mei, Y.W.; Li, L.L.; Zhao, L. Protective activity of the ethanol extract of Cynanchum paniculatum (BUNGE) Kitagawa on treating Herpes simplex encephalitis. Int. J. Immunopathol. Pharmacol. 2012, 25, 259-266.

[20] Ramachandhiran, D.; Vinothkumar, V.; Babukumar, S. Paeonol exhibits anti-tumor effects by apoptotic and anti-inflammatory activities in 7, 12-dimethylbenz(a)anthracene induced oral carcinogenesis. Biotech. Histochem. 2019, 94, 10-25.

[21] Liu, D.H.; Agbo, E.; Zhang, S.H.; Zhu, J.L. Anticonvulsant and neuroprotective effects of paeonol in epileptic rats. Neurochem. Res. 2019, 44, 2556-2565.

[22] Chen, S.M.; Zhou, S.Q. Proceedings of the International Conference on Advances in Energy, Environment and Chemical Engineering. Vol 23. Paris: Atlantis Press. 2015, 715-718.

[23] Bai, X.M.; Liu, D.L.; Wei, Y.J. Content determination of paeonol in Cynanchum paniculatum by three-dimensional fluorescence coupled with ATLD algorithm. China Pharm. 2017, 28, 2089-2092.

[24] Geng, T.; Wang, G.; Ma, X.; Zhang, Z.; Liu, T.; Ge, Y.; Jin, J.; Sun, X.; Zhang, Y.; Yang, D.; Ma, M. Discovery of tryptamine derivatives from Bacillus sp. PKU-TA00001. J. Chin. Pharm. Sci. 2019, 28, 527-536.

[25] Yang, X.L.; Xue, X.; Lin, Y.; Huang, Q.; Mo, M.; Wang, S.; Meng, J. Chemical constituents from the Moutan Cortex charcoal and their potential coagulation activities. J. Chin. Pharm. Sci. 2018, 27, 608-616.

[26] Gottstein, V.; Müller, M.; Günther, J.; Kuballa, T.; Vetter, W. Direct 1H NMR quantitation of valuable furan fatty acids in fish oils and fish oil fractions. J. Agric. Food Chem. 2019, 67, 11788-11795.

[27] Tanaka, R.; Inagaki, R.; Sugimoto, N.; Akiyama, H.; Nagatsu, A. Application of a quantitative 1H-NMR (1H-qNMR) method for the determination of geniposidic acid and acteoside in Plantaginis Semen. J. Nat. Med. 2017, 71, 315-320.

[28] Dong, J.W.; Li, X.J.; Cai, L.; Shi, J.Y.; Li, Y.F.; Yang, C.; Li, Z.J. Simultaneous determination of alkaloids dicentrine and sinomenine in Stephania epigeae by 1H NMR spectroscopy. J. Pharm. Biomed. Anal. 2018, 160, 330-335.

[29] Dong, J.W.; Li, X.J.; Shi, J.Y.; Liu, K.Q. Application of a proton quantitative nuclear magnetic resonance spectroscopy method for the determination of actinodaphnine in Illigera aromatica and Illigera henryi. J. Nat. Med. 2019, 73, 312-317.

[30] Dona, A.C.; Kyriakides, M.; Scott, F.; Shephard, E.A.; Varshavi, D.; Veselkov, K.; Everett, J.R. A guide to the identification of metabolites in NMR-based metabonomics/metabolomics experiments. Comput. Struct. Biotechnol. J. 2016, 14, 135-153.

[31] Zhou, J.T.; Yin, Y.X. Strategies for large-scale targeted metabolomics quantification by liquid chromatography-mass spectrometry. Analyst. 2016, 141, 6362-6373.

[32] Beyer, T.; Schollmayer, C.; Holzgrabe, U. The role of solvents in the signal separation for quantitative (1)H NMR spectroscopy. J. Pharm. Biomed. Anal. 2010, 52, 51-58.

[33] Tanaka, R.; Shibata, H.; Sugimoto, N.; Akiyama, H.; Nagatsu, A. Application of a quantitative (1)H-NMR method for the determination of paeonol in Moutan cortex, Hachimijiogan and Keishibukuryogan. J. Nat. Med. 2016, 70, 797-802.

定量核磁共振氢谱法对徐长卿中丹皮酚含量的快速提取和含量测定

Application of a quantitative 1H NMR method for rapid extraction and determination of the content of paeonol in Cynanchum paniculatum

RichHTML

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 3

编辑推荐

Metrics

本文评价

[1]	欧阳怡, 张敬, 吴鸿飞, 戴敏. 丹皮酚纳米乳在肠细胞模型中吸收机制研究[J]. 中国药学(英文版), 2019, 28(3): 174-185.
[2]	宋爱伟, 吴鸿飞, 戴敏. 丹皮酚减缓动脉粥样硬化病变的形成及发展涉及脂质调节, 抗炎和抗氧化活性[J]. 中国药学(英文版), 2018, 27(8): 565-575.
[3]	梁云爱. 二阶导数差示脉冲极谱法用于中草药有效成分的定量研究[J]. , 1997, 6(3): 154-159.