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Planta Med 2014; 80(18): 1753-1762
DOI: 10.1055/s-0034-1383296
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Simultaneous Determination of Twenty-Two Components in Asari Radix et Rhizoma by Ultra Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Mass Spectrometry

Hao Wen
Department of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, China
,
Hui-yuan Gao
Department of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, China
,
Wen Qi
Department of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, China
,
Feng Xiao
Department of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, China
,
Li-li Wang
Department of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, China
,
Dong Wang
Department of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, China
,
Dan Yuan
Department of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, China
› Author Affiliations
Further Information

Publication History

received 21 June 2014
revised 14 October 2014

accepted 17 October 2014

Publication Date:
16 December 2014 (online)

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Abstract

Asari Radix et Rhizoma is a herbal medicine for the treatment of common cold, rhinitis, etc. An ultra performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry method has been established for the rapid analysis of 22 components in 27 samples from the raw materials of Asari Radix et Rhizoma and an adulterant. A total of 5 lignans, 5 essential oils, 3 aristolochic acids, 4 alkamides, and 5 flavanoids were identified by co-chromatography of samples extracts and comparison of the retention time, UV spectra, characteristic molecular ions, and fragment ions with those of authentic standards, or tentatively identified by MS/MS determination along with MassFragment software. Moreover, the method was validated for the simultaneous quantification and semi-quantification of 20 components. The samples from Asarum heterotropoides var. mandshuricum differed in the quantity of 2-methoxyl-4,5-methylenedioxypropiophenone and kakuol from those of Asarum sieboldii var. seoulense, and the chemical difference was supported by principal component analysis and orthogonal partial least squared discriminant analysis based on dataset obtained from UHPLC-QTOF/MS. In comparison with the samples from the two medicinal Asarum species mentioned above, those from A. himalaicum differed in the quality and quantity of major compounds and contained higher amounts of aristolochic acid I.

Key words

Asari Radix et Rhizoma - Aristolochiaceae - lignans - essential oils - aristolochic acids - UHPLC-QTOF/MS

Supporting Information

 

  • References

  • 1 Drew AK, Whyte IM, Bensoussan A, Dawson AH, Zhu X, Myers SP. Chinese herbal medicine toxicology database: monograph on herba asari, “Xi Xin”. Clin Toxicol 2002; 40: 169-172
    CrossrefPubMedGoogle Scholar
  • 2 Kim SJ, Zhang CG, Lim JT. Mechanism of anti-nociceptive effects of Asarum sieboldii Miq. Radix: potential role of bradykinin, histamine and opioid receptor-mediated pathways. J Ethnopharmacol 2003; 88: 5-9
    CrossrefPubMedGoogle Scholar
  • 3 Chinese Pharmacopoeia Commission. Pharmacopoeia of the Peopleʼs Republic of China, Volume I. Beijing: Chemical Industry Press; 2010: 214-215
    Google Scholar
  • 4 Kosuge T, Yokota M, Nukaya H, Gotoh Y, Nagasawa M. Studies on antitussive principles of Asiasari radix. Chem Pharm Bull 1978; 26: 2284-2285
    CrossrefPubMedGoogle Scholar
  • 5 Dan Y, Liu HY, Gao WW, Chen SL. Activities of essential oils from Asarum heterotropoies var. mandshurium against five phytopathogens. Crop Prot 2010; 29: 295-299
    CrossrefPubMedGoogle Scholar
  • 6 Lee JY, Moon SS, Hwang BK. Isolation and antifungal activity of kakuol, a propiophenone derivative from Asarum sieboldii rhizome. Pest Manag Sci 2005; 61: 821-825
    CrossrefPubMedGoogle Scholar
  • 7 Baluchnejadmojarad T, Roghani M, Nadoushan MRJ, Mahdavi MRV, Kalalian-Moghaddam H, Roghani-Dehkordi F, Dariani S, Raoufi S. The sesame lignan sesamin attenuates vascular dysfunction in streptozotocin diabetic rats: Involvement of nitric oxide and oxidative stress. Eur J Pharmacol 2013; 698: 316-321
    CrossrefPubMedGoogle Scholar
  • 8 Quang TH, Ngan NTT, Minh CV, Kiem PV, Tai BH, Thao NP, Song SB, Kim YH. Anti-inflammatory and PPAR transactivational effects of secondary metabolites from the roots of Asarum sieboldii . Bioorg Med Chem Lett 2012; 22: 2527-2533
    CrossrefPubMedGoogle Scholar
  • 9 Li C, Xu F, Cao C, Shang MY, Zhang CY, Yu J, Liu GX, Wang X, Cai SQ. Comparative analysis of two species of Asari Radix et Rhizoma by electronic nose, head space GC–MS and chemometrics. J Pharmaceut Biomed 2013; 2: 231-238
    PubMedGoogle Scholar
  • 10 Yasuda I, Takeya K, Itokawa H. Structures of amides from Asiasarum heterotropoides Maek. var. mandshuricum Maek. Chem Pharm Bull 1981; 29: 564-566
    CrossrefPubMedGoogle Scholar
  • 11 Han AR, Kim HJ, Shin M, Hong M, Kim YS, Bae H. Constituents of Asarum sieboldii with inhibitory activity on lipopolysaccharide (LPS)-induced NO production in BV-2 microglial cells. Chem Biodivers 2008; 5: 346-351
    CrossrefPubMedGoogle Scholar
  • 12 Cai SQ, Wang X, Zhu S, Li JS, Lou ZQ, Namba T, Komatsu K. Studies on botanical origin of commercial samples of traditional Chinese drug Xixin (Herba Asari). Chin J Chin Mater Med 1996; 21: 712-717 760
    PubMedGoogle Scholar
  • 13 Li YL, Yu J, Cao C, Xie BB, Zhang CY, Liu Z, Shang MY, Wang X, Cai SQ. Survey on resources and varietie on Chinese markets of crude drug Xixin. Chin J Chin Mater Med 2010; 35: 3237-3241
    PubMedGoogle Scholar
  • 14 Cai SQ, Yu J, Wang X, Wang RQ, Ran FX, Shang MY, Cui JR, Komatsu K, Namba T. Cytotoxic activity of some Asarum plants. Fitoterapia 2008; 79: 293-297
    CrossrefPubMedGoogle Scholar
  • 15 Xie BB, Shang MY, Wang X, Cai SQ, Lee KH. A new aristolochic acid derivative from Asarum himalaicum . Acta Pharm Sin 2011; 46: 188-192
    PubMedGoogle Scholar
  • 16 Xie YY, Qu JL, Wang QL, Wang Y, Yoshikawa M, Yuan D. Comparative evaluation of cultivars of Chrysanthemum morifolium flowers by HPLC-DAD-ESI/MS analysis and antiallergic assay. J Agric Food Chem 2012; 60: 12574-12583
    CrossrefPubMedGoogle Scholar
  • 17 Wang GF, Zhang SR, Zhu SQ. Determination of L-sesamin and L-asarinin in Asarum heterotropoides Fr. Schmidt var. mandshuricum (Maxim.) Kitag. by HPLC. Chin J Pharm Anal 1999; 19: 251-253
    PubMedGoogle Scholar
  • 18 Zhang L, Chen XH, Liu YL, Zhang J, Bi KS. Simultaneous determination of L-asarinin, L-sesamin and kakuol in Asarum heterotropoides by RP-HPLC. Chin Tradit Herbal Drugs 2008; 39: 1098-1100
    PubMedGoogle Scholar
  • 19 Liu YH, Yi JH, Huang J, Huang ZF, Liu YH. RP-HPLC simultaneous determination of methyleugenol, safrole and asarinin in Asari Radix et Rhizoma. Chin J Pharm Anal 2012; 32: 822-825
    PubMedGoogle Scholar
  • 20 Zhao ZZ, Liang ZT, Jiang ZH, Leung KSY, Chan CL, Chan HY, Sin J, Man TO, Law KW. Comparative study on the aristolochic acid I content of Herba Asari for safe use. Phytomedicine 2008; 15: 741-748
    CrossrefPubMedGoogle Scholar
  • 21 The Ministry of Health, Labour and Welfare. Japanese Pharmacopeia, 16th edition. Tokyo: The Ministry of Health, Labour and Welfare; 2011: 1602-1603
    Google Scholar
  • 22 Hashimoto K, Higuchi M, Makino B, Sakakibara I, Kubo M, Komatsu Y, Maruno M, Okada M. Quantitative analysis of aristolochic acids, toxic compounds, contained in some medicinal plants. J Ethnopharmacol 1999; 64: 185-189
    CrossrefPubMedGoogle Scholar
  • 23 Jong TT, Lee MR, Hsiao SS, Hsai JL, Wu TS, Chiang ST, Cai SQ. Analysis of aristolochic acid in nine sources of Xixin, a traditional Chinese medicine, by liquid chromatography/atmospheric pressure chemical ionization/tandem mass spectrometry. J Pharmaceut Biomed 2003; 33: 831-837
    CrossrefPubMedGoogle Scholar
  • 24 Yuan J, Liu Q, Zhu W, Ding L, Tang F, Yao S. Simultaneous analysis of six aristolochic acids and five aristolactams in herbal plants and their preparations by high-performance liquid chromatography-diode array detection-fluorescence detection. J Chromatogr A 2008; 1182: 85-92
    CrossrefPubMedGoogle Scholar
  • 25 Li J, Zhang L, Jiang ZZ, Shu B, Li F, Bao Q, Zhang LY. Toxicities of aristolochic acid I and aristololactam I in cultured renal epithelial cells. Toxicol In Vitro 2012; 24: 1092-1097
    PubMedGoogle Scholar
  • 26 Balachandran P, Wei F, Lin RC, Khan IA, Pasco DS. Structure activity relationships of aristolochic acid analogues: Toxicity in cultured renal epithelial cells. Kidney Int 2005; 67: 1797-1805
    CrossrefPubMedGoogle Scholar
  • 27 Sato N, Takahashi D, Chen SM, Tsuchiya R, Mukoyama T, Yamagata SI, Ogawa M, Yoshida M, Kondo S, Satoh N, Ueda S. Acute nephrotoxicity of aristolochic acids in mice. J Pharm Pharmacol 2004; 56: 221-229
    CrossrefPubMedGoogle Scholar
  • 28 Tistaert C, Dajaegher B, Heyden YV. Chromatographic separation techniques and handing methods for herbal fingerprints: A review. Anal Chim Acta 2011; 902: 148-161
    PubMedGoogle Scholar
  • 29 Zhang A, Sun H, Wang P, Han Y, Wang X. Modern analytical techniques in metabolomics analysis. Analyst 2012; 137: 293-300
    CrossrefPubMedGoogle Scholar
  • 30 Yamamoto H, Kuribayashi H, Seshima Y, Zhao P, Kouno I, Taguchi G, Shimomura K. Metabolism of administered (2RS)-naringenin in flavonoid-producing cultured cells of Sophora flavescens . Plant Biotechnol 2004; 21: 355-359
    CrossrefPubMedGoogle Scholar
  • 31 Chen JW, Wu LL, Li X, Zhou HY, Wu TZ. GC-MS analysis of volatile components in supercritical fluid extracts of the root and rhizome of Asarum heterotropoides Fr. var. mandshuricum . Nat Prod Res Dev 2012; 24: 195-198
    PubMedGoogle Scholar
  • 32 Bijak M, Saluk J, Tsirigotis-Maniecka M, Komorowska H, Wachowicz B, Zacynska E, Czarny A, Czechowski F, Nowak P, Pawlaczyk I. The influence of conjugates isolated from Matricaria chamomilla L. on platelets activity and cytotoxicity. Int J Biol Macromol 2013; 61: 218-229
    CrossrefPubMedGoogle Scholar
  • 33 Luo XB, Chen B, Yao SZ, Zeng JG. Simultaneous analysis of caffeic acid derivatives and alkamides in roots and extracts of Echinacea purpurea by high-performance liquid chromatography-photodiode array detection-electrospray mass spectrometry. J Chromatogr A 2003; 986: 73-81
    CrossrefPubMedGoogle Scholar
  • 34 Zhang Y, Shi W, Xi T, Zhang Y, Zhou W. Synthesis and antifungal activity of 1-(2-acyloxy-4, 5-methylenedioxy)phenyl-2-methyl propylene ketones. Chin J Pestic Sci 2012; 14: 95-98
    PubMedGoogle Scholar
  • 35 Jiang Y, Liu GQ, Ma JR, Xie L, Wu HQ. The pharmacological studies on methyleugenol. Acta Pharm Sin 1982; 17: 87-92
    PubMedGoogle Scholar
  • 36 Zhou HQ, Yu B, Qiao WH, Wang DY, Zhang WR, Bai Y, Su YM. Research on pharmacological activities of methyleugenol. Acta Chin Med Pharm 2000; 28: 79-80
    PubMedGoogle Scholar
  • 37 Sun Q, Wu Y, Jia L. Quantitative Determination of Aristolochic Acid in Asarum heterotropoides Fr. Schmidt var. mandshuricum (Maxim.) Kitag. Asian J Tradit Med 2006; 1: 5-13
    PubMedGoogle Scholar
  • 38 Chen J, Sun BH, Huang J, Gao HY, Wang JQ, Wu LJ. Determination of aristolochic acid IVA in the different part of Asarum heterotropoides Fr. Schmidt var. mandshuricum (Maxim.) Kitag. by HPLC. J Shenyang Pharm Univ 2011; 28: 797-800
    PubMedGoogle Scholar
  • 39 Goey AKL, Rosing H, Meijerman I, Sparidans RW, Schellens JHM, Beijnen JH. The bioanalysis of the major Echinacea purpurea constituents dodeca-2E,4E,8Z,10E/Z-tetraenoic acid isobutylamides in human plasma using LC-MS/MS. J Chromatogr B 2012; 902: 151-156
    CrossrefPubMedGoogle Scholar
  • 40 Gallo M, Ferracane R, Naviglio D. Antioxidant addition to prevent lipid and protein oxidation in chicken meat mixed with supercritical extracts of Echinacea angustifolia . J Supercrit Fluid 2012; 72: 198-204
    CrossrefPubMedGoogle Scholar
  • 41 Lv S, Xu L, Huang J, Gao HY, Wu LJ. Chemical constituents of the root of Asarum heterotropoides Fr. Schmidt var. mandshuricum (Maxim.) Kitag. J Shenyang Pharm Univ 2008; 25: 702-704
    PubMedGoogle Scholar
  • 42 Qi W, Wang LL, Wen H, Zhang L, Yuan D. Isolation and identification of chemical constituents in roots and rhizomes of Asarum heterotropoides Fr. Schmidt var. mandshuricum (Maxim.) Kitag. J Shenyang Pharm Univ 2014; 31: 681-686
    PubMedGoogle Scholar
  • 43 Kong L. Studies on quality evaluation of Chinese Echinacea purpurea [master]. Shenyang: Shenyang Pharmaceutical University; 2006
    Google Scholar
  • 44 Delectis Florae Reipublicae Popularis Sinicae Agendae Academiae Sinicae Edita. Flora Reipublicae Popularis Sinicae, Tomus 24. Beijing: Science Press; 1988: 176-177
    Google Scholar
  • 45 Liu Q, Shi Y, Wang Y, Lu J, Cong W, Luo G, Wang Y. Metabolism profile of scutellarin in urine following oral administration to rats by ultra performance liquid chromatography coupled to time-of-flight mass spectrometry. Talanta 2009; 80: 84-91
    CrossrefPubMedGoogle Scholar