Planta Med 2007; 73(4): 392-398
DOI: 10.1055/s-2007-967139
Original Paper
Analytical Methods
© Georg Thieme Verlag KG Stuttgart · New York

Comparative Analysis of Ligusticum chuanxiong and Related Umbelliferous Medicinal Plants by High Performance Liquid Chromatography-Electrospray Ionization Mass Spectrometry

Tao Yi1 , 2 , Kelvin Sze-Yin Leung3 , Guang-Hua Lu1 , 2 , Hao Zhang1
  • 1West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, P.R. China
  • 2Research and Development Division, School of Chinese Medicine, Hong Kong Baptist University, Kowloon Tong, Kowloon, Hong Kong Special Administrative Region, P.R.China
  • 3Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Kowloon, Hong Kong Special Administrative Region, P.R.China
Further Information

Publication History

Received: September 24, 2006

Accepted: February 10, 2007

Publication Date:
19 March 2007 (online)

Abstract

A highly precise and accurate method, based on high performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-ESI-MS), was developed for the qualitative and quantitative comparison of the main constituents in the rhizome of Ligusticum chuanxiong (LC) and three related umbelliferous medicinal plants. A comprehensive validation of the developed method was conducted, and the method was highly sensitive, reproducible and accurate. The unique properties of the present method were validated by analyzing 20 related herbal samples including 5 LC samples, 5 Cnidium officinale samples (CO), 5 Angelica sinensis samples (AS) and 5 Angelica acutiloba samples (AA). Twelve compounds including phenolic constituents, alkylphthalides and phthalide dimers were identified by online ESI-MS and by comparison with literature data and standard compounds, and six of them were quantified by HPLC-DAD simultaneously. The results demonstrated that identical compound types were identified as the main constituents of LC, CO, AS and AA herbs. The results also support the alternative application of these medicinal plants in Chinese and Japanese folk medicines. In the present study, it was found that the variation in the abundance of senkyunolide A was significant in these related herbs; it is therefore feasible to choose senkyunolide A as a characteristic compound for quality evaluation and chemical authentication of these herbs.

References

  • 1 The State Pharmacopoeia Commission of P.R.China. The Pharmacopoeia of the People's Republic of China, Vol. 1. Beijing; Chemical Industry Publishing Press 2005: 28 and 89.
  • 2 The Society of Japanese Pharmacopoeia. Japanese Pharmacopoeia (English version), 14th edition. Tokyo; Junkudo Book Shop 2001: 899 and 956.
  • 3 Chen K J, Chen K. Ischemic stroke treated with Ligusticum chuanxiong .  Chin Med J. 1992;  105 870-3.
  • 4 Naito T, Kubota K, Shimoda Y, Sato T, Ikeya Y, Okada M. et al . Effects of constituents of a Chinese crude drug, Ligustici chuanxiong Rhizoma, on vasoconstriction and blood viscosity.  Nat Med. 1995;  49 288-92.
  • 5 Hou Y Z, Zhao G R, Yang J, Yuan Y J, Zhu G G, Hiltunen R. Protective effect of Ligusticum chuanxiong and Angelica sinensis on endothelial cell damage induced by hydrogen peroxide.  Life Sci. 2004;  75 1775-86.
  • 6 Yi T, Leung K SY, Lu G H, Zhang H, Chan K. Identification and comparative determination of senkyunolide A in traditional Chinese medicinal plants Ligusticum chuanxiong and Angelica sinensis by HPLC coupled with DAD and ESI-MS.  Chem Pharm Bull. 2005;  53 1480-3.
  • 7 Tsai P L, Tsai T H. HPLC determination of berberine in medicinal herbs and a related traditional Chinese medicine.  Anal Lett. 2002;  35 2459-70.
  • 8 Liu L F, Liu T, Li G X, Wang Q, Ng T. Isolation and determination of p-hydroxybenzoylcholine in traditional Chinese medicine Semen sinapis Albae.  Anal Bioanal Chem. 2003;  376 854-8.
  • 9 Lu G H, Chan K, Chan C L, Leung K, Jiang Z H, Zhao Z Z. Quantification of ligustilides in the roots of Angelica sinensis and related umbelliferous medicinal plants by high-performance liquid chromatography and liquid chromatography-mass spectrometry.  J Chromatogr A. 2004;  1046 101-7.
  • 10 Schilter B, Andersson C, Anton R, Constable A, Kleiner J, Brien J O. et al . Guidance for the safety assessment of botanicals and botanical preparations for use in food and food supplements.  Food Chem Toxicol. 2003;  41 1625-49.
  • 11 Lee K H. Research and future trends in the pharmaceutical development of medicinal herbs from Chinese medicine.  Public Health Nutr. 2000;  3 515-22.
  • 12 Zhang H J, Shen P, Cheng Y Y. Identification and determination of the major constituents in traditional Chinese medicine Si-Wu-Tang by HPLC coupled with DAD and ESI-MS.  J Pharm Biomed Anal. 2004;  34 705-13.
  • 13 Zschocke S, Classen-Houben D, Bauer R. Radix angelicae sinensis (Danggui).  In: Chinese drug monographs and analysis, Vol. 3 (14). Wagner H, Bauer R, Xiao PG, Chen JM, editors Beijing; Chinese drug monographs and analysis 2001: 5-8.
  • 14 Zschocke S, Classen-Houben D, Bauer R. Radix ligustici chuanxiong (Chuanxiong).  In: Chinese drug monographs and analysis, Vol. 3 (16). Wagner H, Bauer R, Xiao PG, Chen JM, editors Beijing; Chinese drug monographs and analysis 2001: 5-8.
  • 15 Li S L, Lin G, Chung H S, Tam Y K. Study on fingerprint of Rhizoma Chuanxiong by HPLC-DAD-MS.  Yao Xue Xue Bao. 2004;  39 621-6.
  • 16 Zschocke S, Klaiber I, Bauer R, Vogler B. HPLC-coupled spectroscopic techniques (UV, MS, NMR) for the structure elucidation of phthalides in Ligusticum chuanxiong .  Mol Divers. 2005;  9 33-9.
  • 17 Yan R, Li S L, Chung H S, Tam Y K, Lin G. Simultaneous quantification of 12 bioactive components of Ligusticum chuanxiong Hort. by high-performance liquid chromatography.  J Pharm Biomed Anal. 2005;  37 87-95.
  • 18 Li S L, Chan S S, Lin G, Ling L, Yan R, Chung H S. et al . Simultaneous analysis of seventeen chemical ingredients of Ligusticum chuanxiong by on-line high performance liquid chromatography-diode array detector-mass spectrometry.  Planta Med. 2003;  69 445-51.
  • 19 Zschocke S, Liu J H, Stuppner H, Bauer R. Comparative study of roots from Angelica sinensis and related umbelliferous drugs by thin layer chromatography, high-performance liquid chromatography, and liquid chromatography - mass spectrometry.  Phytochem Anal. 1998;  9 283-90.
  • 20 Li Y H, Peng S L, Zhou Y, Yu K B, Ding L S. Two new phthalides from Ligusticum chuanxiong .  Planta Med. 2006;  72 652-6.
  • 21 Yi T, Leung K SY, Lu G H, Chan K, Zhang H. Simultaneous qualitative and quantitative analyses of the major constituents in the rhizome of Ligusticum chuanxiong using HPLC-DAD-MS.  Chem Pharm Bull. 2006;  54 255-9.
  • 22 Naito T, Katsuhara T, Niitsu K, Ikeya Y, Okada M, Mitsuhashi H. Phthalide dimers from Ligusticum chuangxiong hort.  Heterocycles. 1991;  32 2433-42.
  • 23 Fischer F C, Gijbels M JM. cis- and trans-neocnidilide; 1H- and 13C-NMR data of some phthalides.  Planta Med. 1987;  53 77-80.
  • 24 Zhang X, Xiao H, Xu Q, Li X, Wang J, Liang X. Characterization of phthalides in Ligusticum chuanxiong by liquid chromatographic-atmospheric pressure chemical ionization-mass spectrometry.  J Chromatogr Sci. 2003;  41 428-33.
  • 25 Lin L Z, He X G, Lian L Z, King W, Elliott J. Liquid chromatographic-electrospray mass spectrometric study of the phthalides of Angelica sinensis and chemical changes of Z-ligustilide.  J Chromatogr A. 1998;  810 71-9.
  • 26 Lu G H, Chan K, Leung Y Z, Leung K, Chan C L, Jiang Z H. et al . Development of high-performance liquid chromatographic fingerprints for distinguishing Chinese Angelica from related umberlliferae herbs.  J Chromatogr A. 2005;  1073 383-92.
  • 27 Li H X, Ding M Y, Yu J Y. Separation and identification of the phthalic anhydride derivatives of Ligusticum chuanxiong Hort by GC-MS, TLC, HPLC-DAD, and HPLC-MS.  J Chromatogr Sci. 2002;  40 156-61.

Prof. Hao Zhang

West China School of Pharmacy

Sichuan University

No. 17, Section 3, Ren-Min-Nan-Lu Road

Chengdu

Sichuan 610041

People's Republic of China

Phone: +86-28-8550-3037

Fax: +86-28-8550-3037

Email: zhanghhx@vip.sina.com

>