Skip to main content

Advertisement

SpringerLink
Log in

Comparative study of the contents of analogues of aristolochic acid in two kinds of Aristolochiae Fructus by high-performance liquid chromatography

  • Original Paper
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

Aristolochiae Fructus (“Madouling”) is derived from the fruits of Aristolochia contorta and A. debilis (Aristolochiaceae). These two species contain potentially nephrotoxic constituents, but are officially used in China. Distinction of constituents and toxicity between these two species remains unclear. A high-performance liquid chromatography method was developed and validated for the simultaneous determination of seven analogues of aristolochic acid (aristolochic acids I, II, IIIa, IVa and VIIa), as well as aristololactams I and II in Aristolochiae Fructus. Chromatographic separation was achieved on a Zorbax SB-C18 column with a gradient mobile phase comprising acetonitrile and 1 % acetic acid–30 mM triethylamine (20:1, v/v) buffer. Analytes were detected with a diode array detector at 250 and 260 nm. The contents of seven constituents in samples (11 batches of A. contorta fruits, 15 batches of A. debilis fruits and 33 commercial samples of Madouling) were determined. The content of aristolochic acid IVa was higher than that of aristolochic acid VIIa in A. contorta fruits, whereas the opposite was true in A. debilis fruits. This feature can be used to distinguish the two species from each other and identify the resource plant of Madouling. Through a morphological method and a newly found principle based on the ratio AA-IVa/AA-VIIa, we found that the 33 commercial samples collected from 12 provinces in China were all derived from the fruits of A. contorta.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Dong LS, Shang MY, Cai SQ (2003) Study of species, origin, and processing history of Madouling (Aristolochiae Fructus). China J Chin Mater Med 28:927–931

    Google Scholar 

  2. Tang SW (1982) Classified materia medica (Chongxiu Zhenghe Jingshi Zhenglei Beiyong Bencao). People’s Medical Publishing House, Beijing, p 272

    Google Scholar 

  3. Chinese Pharmacopoeia Committee (2010) Pharmacopoeia of the People’s Republic of China, 2010 edn, p 48

  4. Vanherweghem JL, Depierreux M, Tielemans C, Abramowicz D, Dratwa M, Jadoul M, Richard C, Vandervelde D, Verbeelen D, Fastre RV, Vanhaelen M (1993) Rapidly progressive interstitial renal fibrosis in young women: association with slimming regimen including Chinese herbs. Lancet 341:387–391

    Article  PubMed  CAS  Google Scholar 

  5. China State Food and Drug Administration (2004) Affiche about tightening supervision of six crude drug and related medicinal preparation such as Guangfangji. http://www.sfda.gov.cn/WS01/CL0055/10242.html

  6. Wang BQ, Gao WY (2007) Measurement of content of aristolochic acid A of Aristolochia debilis with the method of high performance liquid chromatography. For By-Product Spec China 88:23–24

    Google Scholar 

  7. Lee TY, Wu ML, Deng JF, Hwang DF (2001) High-performance liquid chromatographic determination for aristolochic acid in medicinal plants and slimming products. J Chromatogr B 766:169–174

    Article  Google Scholar 

  8. Yuan JB, Liu Q, Wei GB, Tang F, Ding L, Yao SZ (2007) Characterization and determination of six aristolochic acids and three aristololactams in medicinal plants and their preparations by high-performance liquid chromatography–photodiode array detection/electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom 21:2332–2342

    Article  PubMed  CAS  Google Scholar 

  9. Zhang CY, Wang X, Shang MY, Yu J, Xu YQ, Li ZG, Lei LC, Li XM, Cai SQ, Namba T (2006) Simultaneous determination of five aristolochic acids and two aristololactams in Aristolochia plants by high-performance liquid chromatography. Biomed Chromatogr 20:309–318

    Article  PubMed  CAS  Google Scholar 

  10. Wei F, Cheng XL, Ma LY, Jin WT, Schaneberg BT, Khan IA, Lin RC (2005) Analysis of aristolochic acids and analogues in medicinal plants and their commercial products by HPLC–PAD–ESI/MS. Phytochem Anal 16:222–230

    Article  PubMed  CAS  Google Scholar 

  11. Yuan JB, Liu Q, Zhu WF, Ding L, Tang F, Yao SZ (2008) 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 1182:85–92

    Article  PubMed  CAS  Google Scholar 

  12. Yuan JB, Nie LH, Zeng DY, Luo XB, Tang F, Ding L, Liu Q, Guo ML, Yao SZ (2007) Simultaneous determination of nine aristolochic acid analogues in medicinal plants and preparations by high-performance liquid chromatography. Talanta 73:644–650

    Article  PubMed  CAS  Google Scholar 

  13. Lee MC, Tsao CH, Iou SC, Chuang WC, Sheu SJ (2003) Analysis of aristolochic acids in herbal medicines by LC/UV and LC/MS. J Sep Sci 26:818–822

    Article  CAS  Google Scholar 

  14. Zhang WJ, Jiang QB, Zeng JC, Xia TL (2008) Measurement of aristolochic acid A of Aristolochia debilis with the method of high performance liquid chromatography. Life Sci Instrum 6:40–41

    Google Scholar 

  15. Zhou XG, Zheng CY, Sun JY, You TY (2006) Analysis of nephrotoxic and carcinogenic aristolochic acids in Aristolochia plants by capillary electrophoresis with electrochemical detection at a carbon fiber microdisk electrode. J Chromatogr A 1109:152–159

    Article  PubMed  CAS  Google Scholar 

  16. Zhao ZZ, Liang ZT, Jiang ZH, Leung KSY, Chan CL, Chan HY, Sin J, Man TO, Law KW (2008) Comparative study on the aristolochic acid I content of Herba Asari for safe use. Phytomedicine 15:741–748

    Article  PubMed  CAS  Google Scholar 

  17. Hashimoto K, Higuchi M, Makino B, Sakakibara I, Kubo M, Komatsu Y, Maruno M, Okada M (1999) Quantitative analysis of aristolochic acids, toxic compounds, contained in some medicinal plants. J Ethnopharmacol 64:185–189

    Article  PubMed  CAS  Google Scholar 

  18. Chan W, Lee KC, Liu N, Cai ZW (2007) A sensitivity enhanced high-performance liquid chromatography fluorescence method for the detection of nephrotoxic and carcinogenic aristolochic acid in herbal medicines. J Chromatogr A 1164:113–119

    Article  PubMed  Google Scholar 

  19. Chan W, Hui KM, Poon WT, Lee KC, Cai ZW (2006) Differentiation of herbs linked to “Chinese herb nephropathy” from the liquid chromatographic determination of aristolochic acids. Anal Chim Acta 576:112–116

    Article  PubMed  Google Scholar 

  20. Yu FY, Lin YH, Su CC (2006) A sensitive enzyme-linked immunosorbent assay for detecting carcinogenic aristolochic acid in herbal remedies. J Agric Food Chem 54:2496–2501

    Article  PubMed  CAS  Google Scholar 

  21. Peng GP, Lou FC, Zhao SX (1995) Chemical studies on Aristolochia tubiflora Dunn. Acta Pharma Sin 30:521–525

    CAS  Google Scholar 

  22. Priestap HA (1987) Minor aristolochic acids from Aristolochia argentina and mass spectral analysis of aristolochic acids. Phytochemistry 26:519–529

    Article  CAS  Google Scholar 

  23. Shibutani S, Dong H, Suzuki N, Ueda S, Miller F, Grollman AP (2007) Selective toxicity of aristolochic acids I and II. Drug Metab Dispos 35:1217–1222

    Article  PubMed  CAS  Google Scholar 

  24. Stiborová M, Frei E, Schmeiser HH (2008) Biotransformation enzymes in development of renal injury and urothelial cancer caused by aristolochic acid. Kidney Int 73:1209–1211

    Article  PubMed  Google Scholar 

  25. Stiborová M, Frei E, Breuer A, Bieler CA, Schmeiser HH (1999) Aristolactam I a metabolite of aristolochic acid I upon activation forms an adduct found in DNA of patients with Chinese herbs nephropathy. Exp Toxicol Pathol 51:421–427

    Article  PubMed  Google Scholar 

  26. Stiborová M, Frei E, Schmeiser HH, Wiessler M (1995) Cytochrome P-450 and peroxidase oxidize detoxication products of carcinogenic aristolochic acids (aristolactams) to reactive metabolites binding to DNA in vitro. Collect Czech Chem Commun 60:2189–2199

    Article  Google Scholar 

  27. Dong H, Suzuki N, Torres MC, Bonala RR, Johnson F, Grollman AP, Shibutani S (2006) Quantitative determination of aristolochic acid-derived DNA adducts in rats using 32P-postlabeling/polyacrylamide gel electrophoresis analysis. Drug Metab Dispos 34:1122–1127

    Article  PubMed  CAS  Google Scholar 

  28. Li B, Li XM, Zhang CY, Wang X, Cai SQ (2004) Injury in renal proximal tubular epithelial cells induced by aristololactam I. China J Chin Mater Med 29:78–83

    CAS  Google Scholar 

  29. Wen YJ, Su T, Tang JW, Zhang CY, Wang X, Cai SQ, Li XM (2006) Cytotoxicity of phenanthrenes extracted from Aristolochia contorta in human proximal tubular epithelial cell line. Nephron Exp Nephrol 103:95–102

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported financially by the State Administration of Traditional Chinese Medicine of the People’s Republic of China (Grant number 2001BA701A11-07), the National Natural Science Foundation of China (30873466) and the National Eleventh Five-year Key Technologies R&D Program of China (2006BAI14B01). The authors thank Mr. Ce-Ming Tan, Mr. De-Qun Wang, Mr. Guo-Ping Peng and Mr. Min-Jian Qin for helpful support during plant collections.

Author information

Authors and Affiliations

  1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, People’s Republic of China

    Yu-Qiong Xu, Xiao-Wei Li, Guang-Xue Liu, Ming-Ying Shang & Shao-Qing Cai

  2. Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, People’s Republic of China

    Xiao-Wei Li & Xuan Wang

  3. West China of Pharmacy, Sichuan University, Sichuan, 610041, China

    Yu-Qiong Xu

  4. Renal Division, First Hospital, Peking University, Beijing, 100034, People’s Republic of China

    Xiao-Mei Li

  5. Division of Pharmacognosy, School of Pharmaceutical Sciences, Peking University, Beijing, 100191, People’s Republic of China

    Shao-Qing Cai

Authors
  1. Yu-Qiong Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xiao-Wei Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Guang-Xue Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xuan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ming-Ying Shang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Xiao-Mei Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Shao-Qing Cai
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Xuan Wang or Shao-Qing Cai.

Additional information

Y.-Q. Xu and X.-W. Li contributed equally to this work.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Xu, YQ., Li, XW., Liu, GX. et al. Comparative study of the contents of analogues of aristolochic acid in two kinds of Aristolochiae Fructus by high-performance liquid chromatography. J Nat Med 67, 113–122 (2013). https://doi.org/10.1007/s11418-012-0664-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-012-0664-9

Keywords

Search

Navigation