A review on the pharmacological properties, toxicological characteristics, pathogenic mechanism and analytical methods of aristolochic acids

References

• Abdelgadir, A.A., et al., 2015. One-step preparative isolation of aristolochic acids by strong ion-exchange centrifugal partition chromatography. Separation and purification technology, 156, 444–449.
   Web of Science ®Google Scholar
• Agrawal, P., and Laddha, K., 2017. Development of validated high-performance thin layer chromatography for quantification of aristolochic acid in different species of the aristolochiaceae family. Journal of food and drug analysis, 25 (2), 425–429.
   PubMed Web of Science ®Google Scholar
• Arlt, V.M., Stiborova, M., and Schmeiser, H.H., 2002. Aristolochic acid as a probable human cancer hazard in herbal remedies: a review. Mutagenesis, 17 (4), 265–277.
   PubMed Web of Science ®Google Scholar
• Arlt, V.M., Wiessler, M., and Schmeiser, H.H., 2000. Using polymerase arrest to detect DNA binding specificity of aristolochic acid in the mouse H-ras gene. Carcinogenesis, 21 (2), 235–242.
   PubMed Web of Science ®Google Scholar
• Balachandran, P., et al., 2005. Structure activity relationships of aristolochic acid analogues: Toxicity in cultured renal epithelial cells. Kidney International, 67 (5), 1797–1805.
   PubMed Web of Science ®Google Scholar
• Bara, T., Jr., et al., 2017. A systematic review of the possible carcinogenic role of the aristolochic acid. Romanian journal of morphology and embryology = Revue roumaine de morphologie et Embryologie, 58 (1), 41–44.
   PubMed Web of Science ®Google Scholar
• Bastek, H., et al., 2019. Comparison of Aristolochic acid I derived DNA adduct levels in human renal toxicity models. Toxicology, 420, 29–38.
   PubMed Web of Science ®Google Scholar
• Chan, C.K.N., Pavlović, M., and Chan, W., 2019. Development of a novel liquid chromatography-tandem mass spectrometric method for aristolochic acids detection: application in food and agricultural soil analyses. Food Chemistry, 289, 673–679.
   PubMed Web of Science ®Google Scholar
• Chan, W., et al., 2008. Liquid chromatography/mass spectrometry for metabonomics investigation of the biochemical effects induced by aristolochic acid in rats: the use of information-dependent acquisition for biomarker identification. Rapid communications in mass spectrometry : RCM, 22 (6), 873–880.
   PubMed Web of Science ®Google Scholar
• Chan, W., et al., 2016. Quantitation of aristolochic acids in corn, wheat grain, and soil samples collected in Serbia: identifying a novel exposure pathway in the etiology of Balkan endemic nephropathy. Journal of agricultural and food chemistry, 64 (29), 5928–5934.
   PubMed Web of Science ®Google Scholar
• Chan, W., Zheng, Y.F., and Cai, Z.W., 2007. Liquid chromatography-tandem mass spectrometry analysis of the DNA adducts of aristolochic acids. Journal of the American society for mass spectrometry, 18 (4), 642–650.
   PubMed Web of Science ®Google Scholar
• Chang, H.R., et al., 2007. Aristolochic acid-induced cell cycle G1 arrest in human urothelium SV-HUC-1 cells. Food and chemical toxicology : an international journal published for the British industrial biological research association, 45 (3), 396–402.,
   PubMed Web of Science ®Google Scholar
• Chen, C.H., et al., 2013. Aristolochic acid-induced upper tract urothelial carcinoma in Taiwan: clinical characteristics and outcomes. International journal of cancer, 133 (1), 14–21.
   PubMed Web of Science ®Google Scholar
• Chen, M.J., et al., 2006. Metabonomic study of aristolochic acid-induced nephrotoxicity in rats. Journal of Proteome Research, 5 (4), 995–1002.
   PubMed Web of Science ®Google Scholar
• Cosyns, J.P., et al., 1999. Urothelial lesions in Chinese-herb nephropathy. American journal of kidney diseases : the official journal of the national kidney foundation, 33 (6), 1011–1017.
   PubMed Web of Science ®Google Scholar
• Cui, Y., et al., 2019. Untargeted LC-MS-based metabonomics revealed that aristolochic acid I induces testicular toxicity by inhibiting amino acids metabolism, glucose metabolism, β-oxidation of fatty acids and the TCA cycle in male mice. Toxicology and applied pharmacology, 373, 26–38.
   PubMed Web of Science ®Google Scholar
• Debelle, F.D., Vanherweghem, J.L., and Nortier, J.L., 2008. Aristolochic acid nephropathy: a worldwide problem. Kidney International, 74 (2), 158–169.
   PubMed Web of Science ®Google Scholar
• Dong, C. Z., et al., 2018. A potential green method for the separation and screening of aristolochic acid and its derivatives for effective control of Meloidogyne incognita. Chinese Patent Application 107604575 C, 2018-01-19.
   Google Scholar
• Fang, L.W., et al., 2019. Dual ionic liquid-immobilized silicas for multi-phase extraction of aristolochic acid from plants and herbal medicines. Journal of chromatography. A, 1592, 31–37.
   PubMed Web of Science ®Google Scholar
• Fernandes, C.A.H., et al., 2015. Structural basis for the inhibition of a phospholipase A2-like toxin by caffeic and aristolochic acids. Plos one, 10 (7), e0133370.
   PubMed Web of Science ®Google Scholar
• Filitis, L.N., and Massagetov, P.S., 1961. On the antineoplastic activity of aristolochic acid. Voprosy Onkol, 7 (8), 97–98.
   PubMedGoogle Scholar
• Ge, Y.H., et al., 2017. Selective analysis of aristolochic acid I in herbal medicines by dummy molecularly imprinted solid-phase extraction and HPLC . Journal of separation science, 40 (13), 2791–2799.,
   PubMed Web of Science ®Google Scholar
• Ge, Y.H., et al., 2019. Combined magnetic porous molecularly imprinted polymers and deep eutectic solvents for efficient and selective extraction of aristolochic acid I and II from rat urine. Materials science and engineering: C, 97, 650–657.
   PubMed Web of Science ®Google Scholar
• Girish, K.S., and Kemparaju, K., 2005. Inhibition of Naja naja venom hyaluronidase by plant-derived bioactive components and polysaccharides. Biochemistry. Biokhimiia, 70 (8), 948–952.
   PubMed Web of Science ®Google Scholar
• Heaton, J., et al., 2011. Evaluation of Chinese medicinal herbs fingerprinting by HPLC-DAD for the detection of toxic aristolochic acids. Journal of separation science, 34 (10), 1111–1115.
   PubMed Web of Science ®Google Scholar
• Hollstein, M., et al., 2013. Analysis of TP53 mutation spectra reveals the fingerprint of the potent environmental carcinogen, aristolochic acid. Mutation Research, 753 (1), 41–49.
   PubMed Web of Science ®Google Scholar
• Hu, Y., et al., 2017. Interference-free spectrofluorometric quantification of aristolochic acid I and aristololactam I in five Chinese herbal medicines using chemical derivatization enhancement and second-order calibration methods. Spectrochimica acta part A: molecular and biomolecular spectroscopy, 175, 229–238.
   PubMed Web of Science ®Google Scholar
• Huang, Y.T., et al., 2018. Aristolochic acid I interferes with the expression of BLCAP tumor suppressor gene in human cells. Toxicology Letters, 291, 129–137.
   PubMed Web of Science ®Google Scholar
• Jacob, S.S., Smith, N.W., and Legido-Quigley, C., 2007. Assessment of Chinese medicinal herb metabolite profiles by UPLC-MS-based methodology for the detection of aristolochic acids. Journal of separation science, 30 (8), 1200–1206.
   PubMed Web of Science ®Google Scholar
• Jelaković, B., et al., 2012. Aristolactam-DNA adducts are a biomarker of environmental exposure to aristolochic acid. Kidney International, 81 (6), 559–567.
   PubMed Web of Science ®Google Scholar
• Jenkins, R.H., et al., 2014. miR-192 induces G2/M growth arrest in aristolochic acid nephropathy. The American journal of Pathology, 184 (4), 996–1009.
   PubMed Web of Science ®Google Scholar
• Jin, M. H., 2013. Composition containing aristolochic acid C for improving an anti-wrinkling effect and skin elasticity. Korean Patent Application 1020130083776 A, 2013-07-23.
   Google Scholar
• Kathuria, P., et al., 2015. Conformational preferences of DNA following damage by aristolochic acids: structural and energetic insights into the different mutagenic potential of the ALI and ALII-N(6)-dA adducts . Biochemistry, 54 (15), 2414–2428.
   PubMed Web of Science ®Google Scholar
• Kim, J.S., and Southard, J.H., 2000. Effect of phospholipase A2 inhibitors on the release of arachidonic acid and cell viability in cold-stored hepatocytes. Cryobiology, 40 (1), 27–35.
   PubMed Web of Science ®Google Scholar
• Kite, G.C., et al., 2002. Detecting aristolochic acids in herbal remedies by liquid chromatography/serial mass spectrometry. Rapid communications in mass spectrometry : RCM, 16 (6), 585–590.
   PubMed Web of Science ®Google Scholar
• Kong, X. S., Liu, Y., and Kong, X., 2014. Application of aristolochic acid in the preparation of drugs to treat rheumatoid arthritis. Chinese Patent Application 103989670 A, 2014-08-20.
   Google Scholar
• Kwak, D.H., et al., 2014. Aristolochic acid I induces ovarian toxicity by inhibition of Akt phosphorylation. Chemical research in toxicology, 27 (12), 2128–2135.
   PubMed Web of Science ®Google Scholar
• Kwak, D.H., and Lee, S., 2016. Aristolochic Acid I causes testis toxicity by inhibiting Akt and ERK1/2 phosphorylation. Chemical research in toxicology, 29 (1), 117–124.
   PubMed Web of Science ®Google Scholar
• Lai, M.N., et al., 2010. Population-based case–control study of Chinese herbal products containing aristolochic acid and urinary tract cancer risk. JNCI Journal of the national cancer institute, 102 (3), 179–186.
   PubMedGoogle Scholar
• Leung, E.M.K., and Chan, W., 2014. Noninvasive measurement of aristolochic acid-DNA adducts in urine samples from aristolochic acid-treated rats by liquid chromatography coupled tandem mass spectrometry: evidence for DNA repair by nucleotide-excision repair mechanisms. Mutation Research, 766–767, 1–6.
   PubMed Web of Science ®Google Scholar
• Li, C.Y., et al., 2012. Development of gastric precancerous lesion animal model. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 37 (1), 89–93.
   PubMedGoogle Scholar
• Li, P., 2016. A pharmaceutical composition for treating atherosclerosis and application thereof. Chinese Patent Application 105998044 A, 2016-10-12.
   Google Scholar
• Li, W., et al., 2006. Study on separation of aristolochic acid I and II by micellar electrokinetic capillary chromatography and competition mechanism between SDS and beta-cyclodextrin. Electrophoresis, 27 (4), 837–841.
   PubMed Web of Science ®Google Scholar
• Li, X.W., et al., 2013. Development of an eastern blotting technique for the visual detection of aristolochic acids in Aristolochia and Asarum species by using a monoclonal antibody against aristolochic acids I and II. Phytochemical analysis : PCA, 24 (6), 645–653.
   PubMed Web of Science ®Google Scholar
• Liao, Y., 2009. A Chinese herbal medicine preparation for treating ascitic type liver cancer. Chinese Patent Application 101385788 A, 2009-03-18.
   Google Scholar
• Lin, S.H., et al., 2010. Liquid chromatography/mass spectrometry for investigating the biochemical effects induced by aristolochic acid in rats: the plasma metabolome. Rapid communications in mass spectrometry : RCM, 24 (9), 1312–1318.
   PubMed Web of Science ®Google Scholar
• Liu, J.L., et al., 2019. Developed a novel sensor based on fluorescent graft conjugated polymer for the determination of aristolochic acid in traditional Chinese medicine. Spectrochimica acta. Part A, molecular and biomolecular spectroscopy, 222, 117239
   PubMed Web of Science ®Google Scholar
• Liu, Y.M., et al., 2010. A liquid chromatography/tandem mass spectrometry method for determination of aristolochic acid-I in rat plasma. Biomedical chromatography : BMC, 24 (2), 174–179.
   PubMed Web of Science ®Google Scholar
• Liu, Y.S., et al., 2019. Quantitation of DNA adducts in target and nontarget organs of Aristolochic acid I-exposed rats: correlating DNA adduct levels with organotropic activities. Chemical research in toxicology, 32 (3), 397–399.
   PubMed Web of Science ®Google Scholar
• Mao, W.W., et al., 2017. Characterization and quantitation of aristolochic acid analogs in different parts of Aristolochiae Fructus, using UHPLC-Q/TOF-MS and UHPLC-QqQ-MS. Chinese journal of natural medicines, 15 (5), 392–400.
   PubMed Web of Science ®Google Scholar
• Martinez, M.C.M., et al., 2002. Progression rate of Chinese herb nephropathy: impact of Aristolochia fangchi ingested dose. Nephrology, dialysis, transplantation : official publication of the European dialysis and transplant association - European Renal Association, 17 (3), 408–412.
   PubMed Web of Science ®Google Scholar
• Mengs, U., 1983. On the histopathogenesis of rat forestomach carcinoma caused by aristolochic acid. Archives of toxicology, 52 (3), 209–220.
   PubMed Web of Science ®Google Scholar
• Mengs, U., Lang, W., and Poch, J.A., 1982. The carcinogenic action of aristolochic acid in rats. Archives of toxicology, 51 (2), 107–119.
   Web of Science ®Google Scholar
• Mengs, U., and Stotzem, C.D., 1993. Renal toxicity of aristolochic acid in rats as an example of nephrotoxicity testing in routine toxicology. Archives of toxicology, 67 (5), 307–311.
   PubMed Web of Science ®Google Scholar
• Michl, J., et al., 2016. LC-MS-and 1H NMR-based metabolomic analysis and in vitro toxicological assessment of 43 aristolochia species. Journal of natural products, 79 (1), 30–37.
   PubMed Web of Science ®Google Scholar
• Ni, Y., et al., 2007. Metabolic profiling using combined GC-MS and LC-MS provides a systems understanding of aristolochic acid-induced nephrotoxicity in rat . FEBS letters, 581 (4), 707–711.
   PubMed Web of Science ®Google Scholar
• Noetzel, C., et al., 2002. Enzymatic activity and inhibition of the neurotoxic complex vipoxin from the venom of vipera ammodytes meridionalis. Zeitschrift fur Naturforschung. C, journal of biosciences, 57 (11–12), 1078–1083.,
   PubMedGoogle Scholar
• Nortier, J.L., et al., 2000. Urothelial carcinoma associated with the use of a Chinese Herb (Aristolochia Fangchi). The New England journal of medicine, 342 (23), 1686–1692.
   PubMed Web of Science ®Google Scholar
• Ouyang, L., et al., 2019. New dual-spectroscopic strategy for the direct detection of aristolochic acids in blood and tissue. Analytical chemistry, 91 (13), 8154–8161.,
   PubMed Web of Science ®Google Scholar
• Pfau, W., Schmeiser, H.H., and Wiessler, M., 1990. Aristolochic acid binds covalently to the exocyclic amino group of purine nucleotides in DNA. Carcinogenesis, 11 (2), 313–319.
   PubMed Web of Science ®Google Scholar
• Pfau, W., Schmeiser, H.H., and Wiessler, M., 1990. 32P-postlabelling analysis of the DNA adducts formed by aristolochic acid I and II. Carcinogenesis, 11 (9), 1627–1633.
   PubMed Web of Science ®Google Scholar
• Poon, S.L., et al., 2014. Genome-wide mutational signatures of aristolochic acid in urothelial cancer. European Urology Supplements, 13 (1), e41–e41a.
   Google Scholar
• Poon, W.T., Lai, C.K., and Chan, A.Y.W., 2007. Aristolochic acid nephropathy: the Hong Kong perspective. Hong Kong journal of nephrology, 9 (1), 7–14.
   Google Scholar
• Pu, X.Y., et al., 2016. Oral exposure to aristolochic acid I induces gastric histological lesions with non-specific renal injury in rat. Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische , 68 (6), 315–320.
   PubMedGoogle Scholar
• Ren, G., et al., 2014. Cloud point extraction-HPLC method for the determination and pharmacokinetic study of aristolochic acids in rat plasma after oral administration of Aristolochiae Fructus. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 953–954 (1), 73–79.
   PubMedGoogle Scholar
• Rosenthal, M.D., Vishwanath, B.S., and Franson, R.C., 1989. Effects of aristolochic acid on phospholipase A2 activity and arachidonate metabolism of human neutrophils. Biochimica et biophysica acta, 1001 (1), 1–8.
   PubMedGoogle Scholar
• Sati, H., et al., 2011. Phytochemical and pharmacological potential of aristolochia indica: a review. Research journal of pharmaceutical, biological and chemical ences, 2 (4), 647–654.
   Google Scholar
• Sato, N.T., et al., 2004. Acute nephrotoxicity of aristolochic acids in mice. The journal of pharmacy and pharmacology, 56 (2), 221–229.
   PubMed Web of Science ®Google Scholar
• Schmeiser, H.H.J., et al., 1990. Aristolochic acid activates ras genes in rat tumors at deoxyadenosine residues. Cancer research, 50 (17), 5464–5469.
   PubMed Web of Science ®Google Scholar
• Shu, H., et al., 2018. Hybrid-type carbon microcoil-chitosan composite for selective extraction of aristolochic acid I from Aristolochiaceae medicinal plants. Journal of chromatography. A, 1561, 13–19.
   PubMed Web of Science ®Google Scholar
• Song, R.J., et al., 2014. Three-phase hollow fiber liquid-phase microextraction based on a magnetofluid for the analysis of aristolochic acids in plasma by high-performance liquid chromatography. Journal of separation science, 37 (13), 1622–1631.
   PubMed Web of Science ®Google Scholar
• Stiborová, M., et al., 1994. Characterization of DNA adducts formed by aristolochic acids in the target organ (forestomach) of rats by 32P-postlabelling analysis using different chromatographic procedures. Carcinogenesis, 15 (6), 1187–1192.
   PubMed Web of Science ®Google Scholar
• Sun, R. L., 2018. A pharmaceutical composition for treating Alzheimer’s syndrome and application thereof. Chinese Patent Application 107802634 A, 2018-03-16.
   Google Scholar
• Tankeu, S., et al., 2016. Differentiation between two “fang ji” herbal medicines, Stephania tetrandra and the nephrotoxic Aristolochia fangchi, using hyperspectral imaging. Phytochemistry, 122, 213–222.
   PubMed Web of Science ®Google Scholar
• Vanherweghem, J.L., et al., 1993. Rapidly progressive interstitial renal fibrosis in young women: association with slimming regimen including Chinese herbs. The Lancet, 341 (8842), 387–391.
   PubMed Web of Science ®Google Scholar
• Vishwanath, B.S., Fawzy, A.A., and Franson, R.C., 1988. Edema-inducing activity of phospholipase A2 purified from human synovial fluid and inhibition by aristolochic acid. Inflammation, 12 (6), 549–561.
   PubMed Web of Science ®Google Scholar
• Vishwanath, B.S., and Gowda, T.V., 1987. Interaction of aristolochic acid with Vipera russelli phospholipase A2: its effect on enzymatic and pathological activities. Toxicon : official journal of the international society on toxinology, 25 (9), 929–937.
   PubMed Web of Science ®Google Scholar
• Vishwanath, B.S., Kini, R.M., and Gowda, T.V., 1987. Characterization of three edema-inducing phospholipase A2 enzymes from habu (Trimeresurus flavoviridis) venom and their interaction with the alkaloid aristolochic acid. Toxicon : official journal of the international society on toxinology, 25 (5), 501–515.
   PubMed Web of Science ®Google Scholar
• Wang, D.P., and Mao, X.C., 2014. Research progress of aristolochic acid. Journal of north pharmacy, 11 (11), 97–98.
   Google Scholar
• Wang, L.M., et al., 2018. Oral administration of Aristolochia manshuriensis Kom in rats induces tumors in multiple organs. Journal of Ethnopharmacology, 225, 81–89.
   PubMed Web of Science ®Google Scholar
• Wang, Q. L., 2016. A tablet for treating tuberculous pericarditis and preparation method thereof. Chinese Patent Application 105770867 A, 2016-07-20.
   Google Scholar
• Wang, Y.N., and Chan, W., 2014. Determination of aristolochic acids by high-performance liquid chromatography with fluorescence detection. Journal of agricultural and food chemistry, 62 (25), 5859–5864.
   PubMed Web of Science ®Google Scholar
• Wu, S.H., 1964. Two cases of acute renal failure caused by Akebia stem. Jiangsu journal of traditional Chinese medicine, 10, 12–14.
   Google Scholar
• Wu, T.S., et al., 2005. Chemical constituents and pharmacology of aristolochia species. Studies in natural products chemistry, 32 (05), 855–1018.
   Google Scholar
• Xiao, Y.H., et al., 2017. Preparation and adsorption properties of molecularly imprinted polymer via RAFT precipitation polymerization for selective removal of aristolochic acid II. Talanta, 162, 415–422.
   PubMed Web of Science ®Google Scholar
• Yang, Y., Chen, J., and Shi, Y.P., 2010. Determination of aristolochic acid in urine using hollow fiber liquid-phase microextraction combined with high-performance liquid chromatography. Biomedical chromatography : BMC, 24 (12), 1350–1355.
   PubMed Web of Science ®Google Scholar
• Ye, J., et al., 2019. Aristolochic acid I aggravates renal injury by activating the C3a/C3aR complement system. Toxicology letters, 312, 118–124.
   PubMed Web of Science ®Google Scholar
• Yu, F.Y., Lin, Y.H., and Su, C.C., 2006. A sensitive enzyme-linked immunosorbent assay for detecting carcinogenic aristolochic acid in herbal remedies. Journal of agricultural and food chemistry, 54 (7), 2496–2501.
   PubMed Web of Science ®Google Scholar
• Yu, J., et al., 2016. Analysis of aristolochic acids, aristololactams and their analogues using liquid chromatography tandem mass spectrometry. Chinese journal of natural medicines, 14 (8), 626–640.
   PubMed Web of Science ®Google Scholar
• Yuan, J.B., et al., 2007. Simultaneous determination of nine aristolochic acid analogues in medicinal plants and preparations by high-performance liquid chromatography. Talanta, 73 (4), 644–650.
   PubMed Web of Science ®Google Scholar
• Yun, B.H., et al., 2012. Biomonitoring of Aristolactam-DNA adducts in human tissues using ultra-performance liquid chromatography/ion-trap mass spectrometry. Chemical research in toxicology, 25 (5), 1119–1131.
   PubMed Web of Science ®Google Scholar
• Zhang, J.F., and Zhao, H., 2003. Structure analysis and feature research of aristolochic acid. Journal of Zhoukou teachers college, 20 (2), 34–35.
   Google Scholar
• Zhang, W. Q., 2016. Oral granules for treating mumps and preparation method thereof. Chinese Patent Application 105769867 A, 2016-07-20.
   Google Scholar
• Zhang, Y., et al., 2019. Exposure to aristolochic acid I compromises the maturational competency of porcine oocytes via oxidative stress-induced DNA damage. Aging, 11 (8), 2241–2252.
   PubMedGoogle Scholar
• Zhou, T., et al., 2012. Evaluation of microwave-assisted extraction for aristolochic acid from Aristolochiae Fructus by chromatographic analysis coupled with nephrotoxicity studies. Biomedical Chromatography : BMC, 26 (2), 166–171.
   PubMed Web of Science ®Google Scholar