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Simultaneous determination of three naphthoquinones from Arnebia euchroma (Royle) Johnst in beagle plasma by UPLC-MS/MS and application for pharmacokinetics study

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A rapid, simple and efficient ultra-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (UPLC-ESI-MS/MS) method was established to simultaneous determination of shikonin, isobutyryl shikonin, β, βʹ-dimethylacryl alkanin in beagle plasma and evaluated by using esculetin as internal standard. The electrospray ionization (ESI) source was operated in negative ionization mode. Multi-reaction monitoring (MRM) was used to quantitatively analyzed shikonin m/z 287.0 → 217.9, isobutyryl shikonin m/z 357.0 → 268.9, β, βʹ-dimethylacryl alkanin m/z 370.0 → 270.1 and esculetin m/z 177.0 → 89.0, respectively. The method was validated for selectivity, linearity, lower limit of quantification, precision, accuracy, recovery, matrix effect and stability. All validation parameters met the acceptance criteria according to regulatory guidelines. This method was successfully applied for the pharmacokinetic study of shikonin, isobutyryl shikonin, β, βʹ-dimethylacryl alkanin in beagle dogs plasma after oral administration of A. euchroma extract.
Rocznik
Strony
403--411
Opis fizyczny
Bibliogr. 29 poz., tab., rys., wykr.
Twórcy
autor
  • Key Laboratory of Chinese Materia Medica (Ministry of Education), Heilongjiang University of Chinese Medicine, 24 Heping Road, Xiangfang District, Harbin, 150040, China
autor
  • Key Laboratory of Chinese Materia Medica (Ministry of Education), Heilongjiang University of Chinese Medicine, 24 Heping Road, Xiangfang District, Harbin, 150040, China
autor
  • Key Laboratory of Chinese Materia Medica (Ministry of Education), Heilongjiang University of Chinese Medicine, 24 Heping Road, Xiangfang District, Harbin, 150040, China
  • College of Pharmacy, Harbin Medical University, 157 Baojian Road, Nangang District, Harbin 150040, China
autor
  • Key Laboratory of Chinese Materia Medica (Ministry of Education), Heilongjiang University of Chinese Medicine, 24 Heping Road, Xiangfang District, Harbin, 150040, China
Bibliografia
  • 1. He, Y.; Li, Q.; Su, M.; Huang, W.; Zhu, B. Acetylshikonin from zicao exerts antifertility effects at high dose in rats by suppressing the secretion of GTH. Biochem. Biophysical Res. Commun. 2016, 476(4), 560–5.
  • 2. Bo, S.; Dan, M.; Li, W.; Zhang, P. Characterizations and immu- nostimulatory activities of a polysaccharide from Arnebia euchroma (Royle) Johnst. roots. Int. J. Biol. Macromolecules 2019, 125, 791–9.
  • 3. Wang, L.; Li, F.; Liu, X.; Chen, B.; Yu, K.; Wang, M.-K. Meroterpenoids and a naphthoquinone from Arnebia euchroma and their cytotoxic activity. Planta Med. 2015, 81(04), 320–6.
  • 4. Liu, H.; Jin, Y.-S.; Song, Y.; Yang, X.-N.; Yang, X.-W.; Geng, D.-S.; Chen, H.-S. Three new compounds from Arnebia euchroma. J. Asian Nat. Prod. Res. 2010, 12(4), 286–92.
  • 5. Zhu, M.; Gao, Y.; Wu, Z.; Zhao, Y. A rapid HPLC/ESI-MS/MS method for quantitative analysis of isovalerylshikonin in rat plasma. Biomed. Chromatogr. 2010, 24(4), 413–9.
  • 6. Wang, Y.; Zhu, Y.; Xiao, L.; Ge, L.; Wu, X. Meroterpenoids isolated from Arnebia euchroma (Royle) Johnst. And their cytotoxic activity in human hepatocellular carcinoma cells. Fitoterapia 2018.
  • 7. National Pharmacopoeia Commission. Pharmacopoeia of the People’s Republic of China (2015 Edition A); China Medical Science and Technology Press: Beijing, China, 2015.
  • 8. Singh, B.; Sharma, M. K.; Meghwal, P. R.; Sahu, P. M.; Singh, S. Anti-inflammatory activity of shikonin derivatives from Arnebia hispidissima. Phytomedicine 2003, 10(5), 375–80.
  • 9. Zhou, W.; Jiang, H.; Peng, Y.; Li, S. Comparative study on enantiomeric excess of main akannin/shikonin derivatives isolated from the roots of three endemic Boraginaceae plants in China. Biomed. Chromatogr. 2011, 25(10), 1067–75.
  • 10. Xiong, W.; Luo, G.; Zhou, L.; Zeng, Y.; Yang, W. In vitro and in vivo antitumor effects of acetylshikonin isolated from Arnebia euchroma (Royle) Johnst (Ruanzicao) cell suspension cultures. Chin. Med. 2009, 4(1), 14, 4, 1(2009-07-11).
  • 11. Sykłowska-Baranek, K.; Pietrosiuk, A.; Naliwajski, M. R.; Kawiak, A.; Jeziorek, M.; Wyderska, S.; Łojkowska, E.; Chinou, I. Effect of l-phenylalanine on PAL activity and production of naphthoquinone pigments in suspension cultures of Arnebia euchroma (Royle) Johnst. In Vitro Cell. Develop. Biol. - Plant, 2012.
  • 12. Yang, Y.; Zhao, D.; Yuan, K.; Zhou, G.; Wang, Y.; Xiao, Y.; Wang, C.; Xu, J.; Yang, W. Two new dimeric naphthoquinones with neuraminidase inhibitory activity from Lithospermum erythrorhizon. Nat. Product. Res. 2015, 29(10), 908–13.
  • 13. Yao, X.; Wang, Y.; Gao, S.; Rui, Z.; Ren, R.; Li, N.; Zhang, H. Determination of the active constituents in Arnebia euchroma (Royle) Johnst. by ionic liquid-based ultrasonic-assisted extraction high-performance liquid chromatography. J. Chromatogr. B Anal. Tech. Biomed. Life Sci. 2011, 879(20), 1833–8.
  • 14. Kumar, P.; Saini, M.; Bhushan, S.; Warghat, A. R.; Pal, T.; Malhotra, N.; Sood, A. Effect of salicylic acid on the activity of PAL and PHB geranyltransferase and shikonin derivatives production in cell suspension cultures of arnebia euchroma (Royle) Johnst—a medicinally important plant species. Appl. Biochemistry & Biotechnology 2014.
  • 15. Fan, H.; Yang, M.; Che, X.; Zhang, Z.; Xu, H.; Liu, K.; Meng, Q. Activity study of a hydroxynaphthoquinone fraction from Arnebia euchroma in experimental arthritis - ScienceDirect. Fitoterapia 2012, 83(7), 1226–37.
  • 16. Wang, X. C.; Feng, J.; Huang, F.; Sheng, F. Y.; Wang, Y. Y.; Cao, L. Y.; Wen, C. P. Effects of shikonin isolated from zicao on lupus nephritis in NZB/W F1 mice. Biol. Pharm. Bull. 2009, 32.
  • 17. Chen, X. Shikonin, a component of Chinese herbal medicine, inhibits chemokine receptor function and suppresses human immunodeficiency virus type 1. Antimicrob. Agents Chemother. 2003, 47(9), 2810–6.
  • 18. Guan, L.; Qiang, L.; Shi, J.; Wei, Y. Application of ionic-liquid-magnetized stirring bar liquid-phase microextraction coupled with HPLC for the determination of naphthoquinones in zicao. J. Separation Sci. 2018, 41.
  • 19. Hu, Y.; Jiang, Z.; Leung, S. Y.; Zhao, Z. Simultaneous determination of naphthoquinone derivatives in Boraginaceous herbs by high-performance liquid chromatography. Analytica Chim. Acta 2006, 577(1), 26–31.
  • 20. Su, M.; Huang, W.; Zhu, B.; Anna, A. Acetylshikonin from zicao prevents obesity in rats on a high-fat diet by inhibiting lipid accumulation and inducing lipolysis. Plos One 2016, 11(1), e0146884.
  • 21. Papageorgiou, V. P.; Assimopoulou, A. N.; Samanidou, V. F.; Papadoyannis, I. N. Recent advances in chemistry, biology and biotechnology of alkannins and shikonins. Curr. Org. Chem. 2006, 10(16), 2123–42.
  • 22. He, G.; He, G.; Zhou, R.; Pi, Z.; Zhu, T.; Jiang, L.; Xie, Y. Enhancement of cisplatin-induced colon cancer cells apoptosis by shikonin, a natural inducer of ROS in?vitro and in?vivo. Biochem. Biophysical Res. Commun. 2015, S0006291X15311050.
  • 23. Esmaeilzadeh, E.; Gardaneh, M.; Gharib, E.; Sabouni, F. Shikonin protects dopaminergic cell line PC12 against 6-hydroxydopamine-mediated neurotoxicity via both glutathione-dependent and independent pathways and by inhibiting apoptosis. Neurochem. Res. 2013, 38(8), 1590–604.
  • 24. Lu, L.; Qin, A.; Huang, H.; Zhou, P.; Zhang, C.; Liu, N.; Li, S.; Wen, G.; Zhang, C.; Dong, W. Shikonin extracted from medicinal Chinese herbs exerts anti-inflammatory effect via proteasome inhibition. Eur. J. Pharmacol. 2011, 658(2-3), 242–7.
  • 25. Chen, H. M.; Wang, P. H.; Chen, S. S.; Wen, C. C.; Chen, Y. H.; Yang, W. C.; Yang, N. S. Shikonin induces immunogenic cell death in tumor cells and enhances dendritic cell-based cancer vaccine. Cancer Immunol. Immunother. 2012, 61(11), 1989–2002.
  • 26. Yao, Y.; Zhou, Q. A novel antiestrogen agent Shikonin inhibits estrogen-dependent gene transcription in human breast cancer cells. Breast Cancer Res. Treat. 2010, 121(1), 233–40.
  • 27. Preeti, K.; Shalika, R.; Dinesh, K.; Shiv, K.; Shashi, B. Concurrent NP-HPTLC determination of shikonin and b,b-dimethylacryl shikonin in arnebia benthamii. J. Chromatogr. 2016(8), 8.
  • 28. U.S. Department of Health and Human Services; Food and Drug Administration; Center for Drug Evaluation and Research (CDER); Center for Veterinary Medicine (CVM). Bioanalytical Method Validation Guidance for Industry USA. 2018.
  • 29. Huang, S.; Yu, L.; Shen, P. Simultaneous quantitative analysis of shikonin and deoxyshikonin in rat plasma by rapid LC–ESI–MS–MS. Chromatographia 2010, 72(1–2), 63–9.
Uwagi
Opracowanie rekordu ze środków MEiN, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2022-2023).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-ccd71f6e-4291-4fbb-92d5-3621069812b7
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