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Optimization of a Reverse-Phase High Performance Liquid Chromatography (RP-HPLC) Method for Simultaneous Separation of Aloe-Emodin, Rhein, Emodin, Chrysophanol and Physcion

Year 2021, Issue: 27, 972 - 984, 30.11.2021
https://doi.org/10.31590/ejosat.987628

Abstract

In this study, a reverse-phase high performance liquid chromatography (RP-HPLC) method with high separation efficiency, high detection sensitivity and excellent selectivity was successfully developed for the simultaneous quantitative determination of the aloe-emodin, rhein, emodin, chrysophanol, and physcion compounds. These optimum method conditions were determined by studying various columns, mobile phases and compositions, flow rates and column temperatures. The successful separation was carried out with a Supelcosil LC-18 column (250 × 4.6 mm, 5 µm) and a gradient program. The procedure was carried out at 20 °C with the flow rate of 1.0 mL/min and the injection volume of 20 μL utilizing an RP-HPLC method with DAD detector at 225 nm. Deionized water containing 0.5% orthophosphoric acid and methanol was used as the mobile phases A and B. This study showed an optimized analytical method can be effectively utilized to identify and measure anthraquinone compounds.

References

  • Agarwal, S.K., Singh, S.S., Verma, S., & Kumar, S., (2000). Antifungal activity of anthraquinone derivatives from Rheum emodi. Journal of Ethnopharmacology, 72 (1-2), 43-46. doi: 10.1016/s0378-8741(00)00195-1
  • Ahmad, W., Zaidi, S.M.A., Mujeeb, M., Ansari, S.H., & Ahmad, S., (2014). HPLC and HPTLC Methods by Design for Quantitative Characterization and in vitro Anti-oxidant Activity of Polyherbal Formulation Containing Rheum emodi. Journal of Chromatographic Science, 52 (8), 911-918. doi: 10.1093/chromsci/bmt123
  • Aichner, D., & Ganzera, M., (2015). Analysis of anthraquinones in rhubarb (Rheum palmatum and Rheum officinale) by supercritical fluid chromatography. Talanta, 144, 1239-1244. doi: 10.1016/j.talanta.2015.08.011
  • Chen, C., Fu, Z., Zhou, W., Chen, Q., Wang, C., Xu, L., Wang, Z. and Zhang, H., (2020). Ionic liquid-immobilized NaY zeolite-based matrix solid phase dispersion for the extraction of active constituents in Rheum palmatum L. Microchemical Journal, 152, 104245. doi: 10.1016/j.microc.2019.104245
  • Chen, S.H., Lin, K.Y., Chang, C.C., Fang, C.L., & Lin, C.P., (2007). Aloe-emodin-induced apoptosis in human gastric carcinoma cells. Food and Chemical Toxicology, 45 (11), 2296-2303. doi: 10.1016/j.fct.2007.06.005
  • Chien, S.C., Wu, Y.C., Chen, Z.W., & Yang, W.C., (2015). Naturally occurring anthraquinones: chemistry and therapeutic potential in autoimmune diabetes. Evidence-Based Complementary and Alternative Medicine, Article ID 357357. doi: 10.1155/2015/357357
  • ElSohly, M.A., Gul, W., & Murphy, T.P., (2004). Analysis of the anthraquinones aloe-emodin and aloin by gas chromatography/mass spectrometry. International Immunopharmacology, 4 (14), 1739-1744. doi: 10.1016/j.intimp.2004.07.005
  • Farooq, U., Pandith, S.A., Singh, Saggoo, M.I., & Lattoo, S.K., (2013). Altitudinal variability in anthraquinone constituents from novel cytotypes of Rumex nepalensis Spreng—a high value medicinal herb of North Western Himalayas. Industrial Crops and Products, 50, 112-117. doi: 10.1016/j.indcrop.2013.06.044
  • Feng, S.X., Li, M.M., Zhao, D., Li, X.H., Zhang, L., Wang, Z., & Gao, N.N., (2017). Simultaneous Determination of 10 Anthraquinones in Rhubarb Based on HPLC-Q-HR/MS. Chinese Herbal Medicines, 9 (4), 388-395. doi: 10.1016/S1674-6384(17)60120-5
  • Gao, X.Y., Jiang, Y., Lu, J., & Tu, P-.F., (2009). One single standard substance for the determination of multiple anthraquinone derivatives in rhubarb using high-performance liquid chromatography-diode array detection. Journal of Chromatography A, 1216 (11), 2118-2123. doi: 10.1016/j.chroma.2008.11.104
  • Gautam, R., Srivastava, A., & Jachak, S.M., (2011). Simultaneous Determination of Naphthalene and Anthraquinone Derivatives in Rumex nepalensis Spreng. Roots by HPLC: Comparison of Different Extraction Methods and Validation. Phytochemical Analysis, 22 (2), 153-157. doi: 10.1002/pca.1261
  • Guo, S., Feng, B., Zhu, R., Ma, J., & Wang, W., (2011). Preparative Isolation of Three Anthraquinones from Rumex japonicus by High-Speed Counter-Current Chromatography. Molecules, 16 (2), 1201–1210. doi: 10.3390/molecules16021201
  • He, D., Chen, B., Tian, Q., & Yao, S., (2009). Simultaneous determination of five anthraquinones in medicinal plants and pharmaceutical preparations by HPLC with fluorescence detection. Journal of Pharmaceutical and Biomedical Analysis, 49 (4), 1123-1127. doi: 10.1016/j.jpba.2009.02.014
  • Hu, S.S., Cao, W., Dai, H.B., Da, J.H., Ye, L.H., Cao, J., & Li, X.Y., (2014). Ionic-liquid-micelle-functionalized mesoporous Fe3O4 microspheres for ultraperformance liquid chromatography determination of anthraquinones in dietary supplements. Journal of Agricultural and Food Chemistry, 62 (35), 8822-8829. doi: 10.1021/jf502323f
  • Iizuka, A., Iijima, O.T., Kondo, K., Itakura, H., Yoshie, F., Miyamoto, H., Kubo, M., Higuchi, M., Takeda, H., & Matsumiya, R., (2004). Evaluation of Rhubarb using antioxidative activity as an index of pharmacological usefulness. Journal of Ethnopharmacology, 91 (1), 89-94. doi: 10.1016/j.jep.2003.11.021
  • Koyama, J., Morita, I., & Kobayashi, N., (2007). Simultaneous determination of anthraquinones in rhubarb by high-performance liquid chromatography and capillary electrophoresis. Journal of Chromatography A, 1145 (1-2), 183-189. doi: 10.1016/j.chroma.2007.01.076
  • Koyama, J., Morita, I., Tagahara, K., Nobukuni, Y., Mukainaka, T., Kuchide, M., Tokuda, H., & Nishino, H., (2002). Chemopreventive effects of emodin and cassiamin B in mouse skin carcinogenesis. Cancer Letters, 182 (2), 135-139. doi: 10.1016/S0304-3835(02)00100-3
  • Kuo, C.H., & Sun, S.W., (2003). Analysis of nine rhubarb anthraquinones and bianthrones by micellar electrokinetic chromatography using experimental design. Analytica Chimica Acta, 482 (1), 47-58. doi: 10.1016/S0003-2670(03)00169-7
  • Liu, S.Y., Sporer, F., Wink, M., Jourdane, J., Henning, R., Li, Y.L., & Ruppel, A., (1997). Anthraquinones in Rheum palmatum and Rumex dentatus (Polygonaceae), and phorbol esters in Jatropha curcas (Euphorbiaceae) with molluscicidal activity against the schistosome vector snails Oncomelania, Biomphalaria, and Bulinus. Tropical Medicine and International Health, 2 (2): 179-188. doi: 10.1046/j.1365-3156.1997.d01-242.x
  • Li-Weber M., (2013). Targeting apoptosis pathways in cancer by Chinese medicine. Cancer Letters, 332 (2), 304-312. doi: 10.1016/j.canlet.2010.07.015
  • Locatelli M., (2011). Anthraquinones: analytical techniques as a novel tool to investigate on the triggering of biological targets. Current Drug Targets, 12 (3) 366-380. doi: 10.2174/138945011794815338
  • Lü, H., Wang, J., Wang, X., Lin, X., Wu, X., & Xie Z., (2007). Rapid separation and determination of structurally related anthraquinones in Rhubarb by pressurized capillary electrochromatography. Journal of Pharmaceutical and Biomedical Analysis, 43 (1), 352-357. doi: 10.1016/j.jpba.2006.06.023
  • Mandrioli, R., Mercolini, L., Ferranti, A., Fanali, S., & Raggi, M.A., (2011). Determination of aloe emodin in Aloe vera extracts and commercial formulations by HPLC with tandem UV absorption and fluorescence detection. Food Chemistry, 126 (1), 387-393. doi: 10.1016/j.foodchem.2010.10.112
  • Mehta, J., (2012). Separation and characterization of anthraquinone derivatives from Cassia fistula using chromatographic and spectral techniques. International Journal of Chemical Sciences, 10(1), 306-316.
  • Rafaelly, L., Heron, S., Nowik, W., & Tchapla, A., (2008). Optimisation of ESI-MS detection for the HPLC of anthraquinone dyes. Dyes and Pigments, 77 (1), 191-203. doi: 10.1016/j.dyepig.2007.05.007
  • Reynolds T., (2004). Aloes: The genus Aloe (Medicinal and Aromatic Plants − Industrial Profiles). CRC Press. Rong, F., Xi, H., Yang, W., Ping, R., Feng, Q., Chunhu, Z., Lan, F., Lichen, G., Zhaoqian, L., & Honghao, Z., (2011). Determination of anthraquinones by UPLC method in patient with craniocerebral injuries after oral administration of rhubarb. Word Science and Technology, 13, 676-680.
  • Shang, X., & Yuan, Z., (2003). Determination of hydroxyanthraquinoids in Rhubarb by cyclodextrin-modified micellar electrokinetic chromatography using a mixed micellar system of sodium dodecyl sulfate and sodium cholate. Journal of Pharmaceutical and Biomedical Analysis, 31 (1), 75-81. doi: 10.1016/s0731-7085(02)00596-4
  • Sharma, N., Kumar, R., Sinha, A.K., Reddy, P.B., Nayeem, S.M., & Deep, S., (2012). Anthraquinone derivatives based natural dye from Rheum emodi as a probe for thermal stability of proteins: Spectroscopic and chromatographic studies. Journal of Pharmaceutical and Biomedical Analysis, 62, 96-104. doi: 10.1016/j.jpba.2011.12.017
  • Shi, Y.B., Li, H.L., Wang, H.Q., Yang, Y.B., Zhang, X.Y., Wang, H., Zhu, Z.J., Zhang, Z.Y., & Zhang, C.A., (2014). Simultaneous determination of five anthraquinones in a Chinese traditional preparation by RP-HPLC using an improved extraction procedure. Journal of Integrative Medicine 12 (5), 455-462. doi: 10.1016/S2095-4964(14)60037-6
  • Singh, N.P., Gupta, A.P., Sinha, A.K., & Ahuja, P.S., (2005). High-performance thin layer chromatography method for quantitative determination of four major anthraquinone derivatives in Rheum emodi. Journal of Chromatography A, 1077 (2), 202-206. doi: 10.1016/j.chroma.2005.03.130
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Optimization of a Reverse-Phase High Performance Liquid Chromatography (RP-HPLC) Method for Simultaneous Separation of Aloe-Emodin, Rhein, Emodin, Chrysophanol and Physcion

Year 2021, Issue: 27, 972 - 984, 30.11.2021
https://doi.org/10.31590/ejosat.987628

Abstract

In this study, a reverse-phase high performance liquid chromatography (RP-HPLC) method with high separation efficiency, high detection sensitivity and excellent selectivity was successfully developed for the simultaneous quantitative determination of the aloe-emodin, rhein, emodin, chrysophanol, and physcion compounds. These optimum method conditions were determined by studying various columns, mobile phases and compositions, flow rates and column temperatures. The successful separation was carried out with a Supelcosil LC-18 column (250 × 4.6 mm, 5 µm) and a gradient program. The procedure was carried out at 20 °C with the flow rate of 1.0 mL/min and the injection volume of 20 μL utilizing an RP-HPLC method with DAD detector at 225 nm. Deionized water containing 0.5% orthophosphoric acid and methanol was used as the mobile phases A and B. This study showed an optimized analytical method can be effectively utilized to identify and measure anthraquinone compounds.

References

  • Agarwal, S.K., Singh, S.S., Verma, S., & Kumar, S., (2000). Antifungal activity of anthraquinone derivatives from Rheum emodi. Journal of Ethnopharmacology, 72 (1-2), 43-46. doi: 10.1016/s0378-8741(00)00195-1
  • Ahmad, W., Zaidi, S.M.A., Mujeeb, M., Ansari, S.H., & Ahmad, S., (2014). HPLC and HPTLC Methods by Design for Quantitative Characterization and in vitro Anti-oxidant Activity of Polyherbal Formulation Containing Rheum emodi. Journal of Chromatographic Science, 52 (8), 911-918. doi: 10.1093/chromsci/bmt123
  • Aichner, D., & Ganzera, M., (2015). Analysis of anthraquinones in rhubarb (Rheum palmatum and Rheum officinale) by supercritical fluid chromatography. Talanta, 144, 1239-1244. doi: 10.1016/j.talanta.2015.08.011
  • Chen, C., Fu, Z., Zhou, W., Chen, Q., Wang, C., Xu, L., Wang, Z. and Zhang, H., (2020). Ionic liquid-immobilized NaY zeolite-based matrix solid phase dispersion for the extraction of active constituents in Rheum palmatum L. Microchemical Journal, 152, 104245. doi: 10.1016/j.microc.2019.104245
  • Chen, S.H., Lin, K.Y., Chang, C.C., Fang, C.L., & Lin, C.P., (2007). Aloe-emodin-induced apoptosis in human gastric carcinoma cells. Food and Chemical Toxicology, 45 (11), 2296-2303. doi: 10.1016/j.fct.2007.06.005
  • Chien, S.C., Wu, Y.C., Chen, Z.W., & Yang, W.C., (2015). Naturally occurring anthraquinones: chemistry and therapeutic potential in autoimmune diabetes. Evidence-Based Complementary and Alternative Medicine, Article ID 357357. doi: 10.1155/2015/357357
  • ElSohly, M.A., Gul, W., & Murphy, T.P., (2004). Analysis of the anthraquinones aloe-emodin and aloin by gas chromatography/mass spectrometry. International Immunopharmacology, 4 (14), 1739-1744. doi: 10.1016/j.intimp.2004.07.005
  • Farooq, U., Pandith, S.A., Singh, Saggoo, M.I., & Lattoo, S.K., (2013). Altitudinal variability in anthraquinone constituents from novel cytotypes of Rumex nepalensis Spreng—a high value medicinal herb of North Western Himalayas. Industrial Crops and Products, 50, 112-117. doi: 10.1016/j.indcrop.2013.06.044
  • Feng, S.X., Li, M.M., Zhao, D., Li, X.H., Zhang, L., Wang, Z., & Gao, N.N., (2017). Simultaneous Determination of 10 Anthraquinones in Rhubarb Based on HPLC-Q-HR/MS. Chinese Herbal Medicines, 9 (4), 388-395. doi: 10.1016/S1674-6384(17)60120-5
  • Gao, X.Y., Jiang, Y., Lu, J., & Tu, P-.F., (2009). One single standard substance for the determination of multiple anthraquinone derivatives in rhubarb using high-performance liquid chromatography-diode array detection. Journal of Chromatography A, 1216 (11), 2118-2123. doi: 10.1016/j.chroma.2008.11.104
  • Gautam, R., Srivastava, A., & Jachak, S.M., (2011). Simultaneous Determination of Naphthalene and Anthraquinone Derivatives in Rumex nepalensis Spreng. Roots by HPLC: Comparison of Different Extraction Methods and Validation. Phytochemical Analysis, 22 (2), 153-157. doi: 10.1002/pca.1261
  • Guo, S., Feng, B., Zhu, R., Ma, J., & Wang, W., (2011). Preparative Isolation of Three Anthraquinones from Rumex japonicus by High-Speed Counter-Current Chromatography. Molecules, 16 (2), 1201–1210. doi: 10.3390/molecules16021201
  • He, D., Chen, B., Tian, Q., & Yao, S., (2009). Simultaneous determination of five anthraquinones in medicinal plants and pharmaceutical preparations by HPLC with fluorescence detection. Journal of Pharmaceutical and Biomedical Analysis, 49 (4), 1123-1127. doi: 10.1016/j.jpba.2009.02.014
  • Hu, S.S., Cao, W., Dai, H.B., Da, J.H., Ye, L.H., Cao, J., & Li, X.Y., (2014). Ionic-liquid-micelle-functionalized mesoporous Fe3O4 microspheres for ultraperformance liquid chromatography determination of anthraquinones in dietary supplements. Journal of Agricultural and Food Chemistry, 62 (35), 8822-8829. doi: 10.1021/jf502323f
  • Iizuka, A., Iijima, O.T., Kondo, K., Itakura, H., Yoshie, F., Miyamoto, H., Kubo, M., Higuchi, M., Takeda, H., & Matsumiya, R., (2004). Evaluation of Rhubarb using antioxidative activity as an index of pharmacological usefulness. Journal of Ethnopharmacology, 91 (1), 89-94. doi: 10.1016/j.jep.2003.11.021
  • Koyama, J., Morita, I., & Kobayashi, N., (2007). Simultaneous determination of anthraquinones in rhubarb by high-performance liquid chromatography and capillary electrophoresis. Journal of Chromatography A, 1145 (1-2), 183-189. doi: 10.1016/j.chroma.2007.01.076
  • Koyama, J., Morita, I., Tagahara, K., Nobukuni, Y., Mukainaka, T., Kuchide, M., Tokuda, H., & Nishino, H., (2002). Chemopreventive effects of emodin and cassiamin B in mouse skin carcinogenesis. Cancer Letters, 182 (2), 135-139. doi: 10.1016/S0304-3835(02)00100-3
  • Kuo, C.H., & Sun, S.W., (2003). Analysis of nine rhubarb anthraquinones and bianthrones by micellar electrokinetic chromatography using experimental design. Analytica Chimica Acta, 482 (1), 47-58. doi: 10.1016/S0003-2670(03)00169-7
  • Liu, S.Y., Sporer, F., Wink, M., Jourdane, J., Henning, R., Li, Y.L., & Ruppel, A., (1997). Anthraquinones in Rheum palmatum and Rumex dentatus (Polygonaceae), and phorbol esters in Jatropha curcas (Euphorbiaceae) with molluscicidal activity against the schistosome vector snails Oncomelania, Biomphalaria, and Bulinus. Tropical Medicine and International Health, 2 (2): 179-188. doi: 10.1046/j.1365-3156.1997.d01-242.x
  • Li-Weber M., (2013). Targeting apoptosis pathways in cancer by Chinese medicine. Cancer Letters, 332 (2), 304-312. doi: 10.1016/j.canlet.2010.07.015
  • Locatelli M., (2011). Anthraquinones: analytical techniques as a novel tool to investigate on the triggering of biological targets. Current Drug Targets, 12 (3) 366-380. doi: 10.2174/138945011794815338
  • Lü, H., Wang, J., Wang, X., Lin, X., Wu, X., & Xie Z., (2007). Rapid separation and determination of structurally related anthraquinones in Rhubarb by pressurized capillary electrochromatography. Journal of Pharmaceutical and Biomedical Analysis, 43 (1), 352-357. doi: 10.1016/j.jpba.2006.06.023
  • Mandrioli, R., Mercolini, L., Ferranti, A., Fanali, S., & Raggi, M.A., (2011). Determination of aloe emodin in Aloe vera extracts and commercial formulations by HPLC with tandem UV absorption and fluorescence detection. Food Chemistry, 126 (1), 387-393. doi: 10.1016/j.foodchem.2010.10.112
  • Mehta, J., (2012). Separation and characterization of anthraquinone derivatives from Cassia fistula using chromatographic and spectral techniques. International Journal of Chemical Sciences, 10(1), 306-316.
  • Rafaelly, L., Heron, S., Nowik, W., & Tchapla, A., (2008). Optimisation of ESI-MS detection for the HPLC of anthraquinone dyes. Dyes and Pigments, 77 (1), 191-203. doi: 10.1016/j.dyepig.2007.05.007
  • Reynolds T., (2004). Aloes: The genus Aloe (Medicinal and Aromatic Plants − Industrial Profiles). CRC Press. Rong, F., Xi, H., Yang, W., Ping, R., Feng, Q., Chunhu, Z., Lan, F., Lichen, G., Zhaoqian, L., & Honghao, Z., (2011). Determination of anthraquinones by UPLC method in patient with craniocerebral injuries after oral administration of rhubarb. Word Science and Technology, 13, 676-680.
  • Shang, X., & Yuan, Z., (2003). Determination of hydroxyanthraquinoids in Rhubarb by cyclodextrin-modified micellar electrokinetic chromatography using a mixed micellar system of sodium dodecyl sulfate and sodium cholate. Journal of Pharmaceutical and Biomedical Analysis, 31 (1), 75-81. doi: 10.1016/s0731-7085(02)00596-4
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  • Shi, Y.B., Li, H.L., Wang, H.Q., Yang, Y.B., Zhang, X.Y., Wang, H., Zhu, Z.J., Zhang, Z.Y., & Zhang, C.A., (2014). Simultaneous determination of five anthraquinones in a Chinese traditional preparation by RP-HPLC using an improved extraction procedure. Journal of Integrative Medicine 12 (5), 455-462. doi: 10.1016/S2095-4964(14)60037-6
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There are 55 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Gizem Yıldırım Baştemur 0000-0002-4634-4525

Reyhan Akpınar This is me 0000-0001-5910-4160

Sabriye Perçin Özkorucuklu 0000-0001-9778-2034

Esengül Kır 0000-0002-6641-3444

Early Pub Date July 29, 2021
Publication Date November 30, 2021
Published in Issue Year 2021 Issue: 27

Cite

APA Yıldırım Baştemur, G., Akpınar, R., Perçin Özkorucuklu, S., Kır, E. (2021). Optimization of a Reverse-Phase High Performance Liquid Chromatography (RP-HPLC) Method for Simultaneous Separation of Aloe-Emodin, Rhein, Emodin, Chrysophanol and Physcion. Avrupa Bilim Ve Teknoloji Dergisi(27), 972-984. https://doi.org/10.31590/ejosat.987628