Optimization of solvent extraction and HPLC-DAD method parameters for determination of phenolic compounds in various Brazilian propolis

References

• Abd El-Hady, F. K., Souleman, A. M. A., Ibrahim, I. G., Abdel-Aziz, M. S., El-Shahid, Z. A., Ali, E. A., & Elsarrag, M. S. A. (2016). Cytotoxic, anti-acetylcholinesterase, antioxidant and antimicrobial activities of Sudanese propolis with correlation to its GC/MS and HPLC analysis. Der Pharmacia Lettre, 8(19), 339–350.
   Google Scholar
• Abu Shady, H. M., Mohamed, W. F., Sayed-Ahmed, E. F., & Amer, S. A. (2016). A comparative study on propolis and pollen extracts: Chemical profile analysis, antioxidant and anticancer activity, a comparative study on propolis and pollen extracts: chemical profile analysis, antioxidant and anticancer activity. International Journal of Current Microbiology and Applied Sciences, 5(3), 397–414. https://doi.org/10.20546/ijcmas.2016.503.047
   Google Scholar
• Andrade, J. K. S., Denadai, M., Oliveira, C. S., Nunes, M. L., & Narain, N. (2017). Evaluation of bioactive compounds potential and antioxidant activity of brown, green and red propolis from Brazilian northeast region. Food Research International (Ottawa, Ont.), 101, 129–138.
   PubMed Web of Science ®Google Scholar
• Beelders, T. (2011). HPLC method development for the characterisation of the flavonoid and phenolic acid composition of rooibos (Aspalathus linearis) infusions [Thesis]. Retreived January 4, 2020 from https://coreacuk/download/pdf/37344789pdf.
   Google Scholar
• Bruschi, M. L., Franco, S. L., & Gremiao, M. P. D. (2003). Application of an HPLC method for analysis of propolis extract. Journal of Liquid Chromatography Related Technology, 26, 2399–2409. https://doi.org/10.1081/JLC-120023254
   Web of Science ®Google Scholar
• Cai, R., Wang, S., Meng, Y., Meng, Q., & Zhao, W. (2012). Rapid quantification of flavonoids in propolis and previous study for classification of propolis from different origins by using near infrared spectroscopy. Analytical Methods, 4(8), 2388–2395. https://doi.org/10.1039/c2ay25184a
   Web of Science ®Google Scholar
• Cao, W., Fu, J., Suo, Z., Zheng, J., Song, J., & Wei, Y. (2007). HPLC analysis of chrysin and galangin in propolis. Chinese Journal of Analytical Chemistry, 27(4), 522–524.
   Google Scholar
• Chandrapala, J. (2015). Low intensity ultrasound applications on food systems. International Food Research Journal, 22(3), 888–895.
   Web of Science ®Google Scholar
• Chang, R., Piló-Veloso, D., Morais, S., & Nascimento, E. A. (2008). Analysis of a Brazilian green propolis from Baccharis dracunculifolia by HPLC-APCI-MS and GC-MS. The Revista Brasileira de Ciências Farmacêuticas, 18(4), 549–556.
   Google Scholar
• Chen, C. T., Chien, Y. H., Yu, Y. H., & Chen, Y. W. (2019). Extraction and analysis of Taiwanese green propolis. Journal of Visualized Experiments, 143, 58743.
   Google Scholar
• Coneaca, G., Gafiţanu, E., Hădărugă, D. I., Hădărugă, N. G., Riviş, A., Bandur, G. N., Pînzaru, I. A., Rusu, G., Urşica, L., Păunescu, V., Gruia, A., Sebeşan, M., Grozescu, I., Lazău, C., & Sfîrloagă, P. (2008). Propolis extract/β-cyclodextrin nanoparticles: synthesis, physico-chemical, and multivariate analyses. Journal of Agroalimentary Processes and Technologies, 14, 58–70.
   Google Scholar
• Croci, A. N., Cioroiu, B., Lazar, D., Corciova, A., Ivanescu, B., & Lazar, M. I. (2009). HPLC evaluation of phenolic and polyphenolic acids from propolis. Farmacia, 57(1), 52–57.
   Web of Science ®Google Scholar
• da Silva, J. L. D. C., Silva, F. F., Machado de Souza, T. F., Generoso, W. G., Souza Noronha, V., Reimar, R., Pereira, E. M., De Luca, M. P., Rago Abreu, S. L., & Santos, V. R. (2007). Synergic effect of associated green, red and brown Brazilian propolis extract onto Streptococcus mutans and Streptococcus sanguinis. African Journal of Pharmacy and Pharmacology, 7(29), 2006–2010.
   Google Scholar
• El-Hady, A. F. K., Souleman, A., Hawary, S. E., Salah, N., & El-Shahid, Z. A. (2015). Egyptian propolis bioassay guided fractionation and GC/MS, HPLC analysis of highly anti-acetylcholinesterase sub-fractions A Research. International Journal of Pharmaceutical Sciences Review and Research, 35, 53–62.
   Google Scholar
• El-Mawla, A. A., & Osman, H. (2011). HPLC analysis and role of the Saudi Arabian propolis in improving the pathological changes of kidney treated with monosodium glutamate. Spatula DD, 1, 119–127.
   Google Scholar
• Falcão, S. I., Tomás, A., Vale, N., Gomes, P., Freire, C., & Vilas-Boas, M. (2013). Phenolic quantification and botanical origin of Portuguese própolis. Industrial Crops and Products, 49, 805–812.
   Web of Science ®Google Scholar
• Falcão, S., Vilas-Boast, M., Freire, C., Domingues, M. R. M., Cardoso, S. M. (2009). Characterization of new phenolic derivatives in Portuguese propolis by Electrospray, Mass Spectrometry. In Euro food chem XV, food for the future—Proceeding-2, Copenhagen, 64–67. Retreived March 3, 2019 from http://hdl.handle.net/10198/5265.
   Google Scholar
• García-Viguera, C., Ferreres, F., & Tomás-Barberán, F. A. (1993). Study of Canadian propolis by GC-MS and HPLC. Zeitschrift Für Naturforschung, 48c(9), 731–735.
   Google Scholar
• Gardana, C., Scaglianti, M., Pietta, P., & Simonetti, P. (2007). Analysis of the polyphenolic fraction of propolis from different sources by liquid chromatography tandem mass spectrometry. Journal Pharmaceutical Biomedical Analysis, 45(3), 390–399.
   PubMed Web of Science ®Google Scholar
• Hakimah, N., Salim, N. H. M., Omar, E. A., Omar, W. A. W., & Mohamed, R. (2018). Chemical constituents and antioxidant activity of ethanolic extract of propolis from Malaysian stingless bee Geniotrigona thoracica species. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 9(6), 646–651.
   Google Scholar
• Hamasaka, T., Kumazawa, S., Fujimoto, T., & Nakayama, T. (2004). Antioxidant activity and constituents of propolis collected in various areas of Japan. Food Science and Technology Research, 10(1), 86–92. https://doi.org/10.3136/fstr.10.86
   Web of Science ®Google Scholar
• Heidorn, M. (2016). The role of temperature and column thermostatting in liquid chromatograph, White Paper. WP71499-EN 09/16S. Thermo Scientific. Retreived February 14, 2020 from http://tools.thermofisher.com/content/sfs/brochures/WP-71499-LC-TemperatureColumn-Thermostatting-WP71499-EN.pdf.
   Google Scholar
• Hernández Zarate, M. S., Abraham Juárez, M. R., Cerón-García, A., Ozuna López, C., Gutiérrez Chávez, A. J., Segoviano Garfias, J. J. N., & Avila Ramos, F. (2018). Flavonoids, phenolic content, and antioxidant activity of Propolis from various areas of Guanajuato, Mexico. Food Science Technology, 38(2), 210–215.
   Web of Science ®Google Scholar
• Hrobonova, K., Lehotay, J., Skacani, I., & Čižmárik, J. (2005). HPLC Determination and MS-identification of dehydroabietic acid and abietic acid in propolis. Journal of Liquid Chromatography Related Technologies, 28(11), 1725–1735.
   Web of Science ®Google Scholar
• ICH. (2005). Validation of analytical procedures-PA/PH/OMCL(05) 47 DEF elaborated by OMCL Network/EDQM of the council of Europe. Retreived March 13, 2020 from https://wwwedqmeu/medias/fichiers/validation_of_analytical_procedures_paphomcl_13_82_2rpdf.
   Google Scholar
• Kasiotis, K. M., Anastasiadou, P., Papadopoulos, A., & Machera, K. (2017). Revisiting Greek Propolis: chromatographic analysis and antioxidant activity study. PLoS One, 12(1), e0170077. https://doi.org/10.1371/journal.pone.0170077
   PubMed Web of Science ®Google Scholar
• Kongkiatpaiboon, S., Vongsak, B., Machana, S., Weerakul, T., & Pattarapanich, C. (2015). Simultaneous HPLC quantitative analysis of mangostin derivatives in Tetragonula pagdeni propolis extracts. Journal of King Saud University Science, 28(2), 131–135.
   Web of Science ®Google Scholar
• Kosalec, M., Bakmaz, S., & Pepeljnjak, S. (2003). Analysis of propolis from the continental and Adriatic regions of Croatia. Acta Pharmaceutica, 53(4), 275–285.
   PubMedGoogle Scholar
• Kwon, Y. I. I., Vattem, D. A., & Shetty, K. (2006). Evaluation of clonal herbs of Laminaceae species against diabetes and hypertension. Asian Pacific Journal of Clinical Nutrition, 15(1), 107–118.
   PubMed Web of Science ®Google Scholar
• Lee, Y.-N., Chen, C.-R., Yang, H.-L., Lin, C.-C., & Chang, C.-M J. (2007). Isolation and purification of 3,5-diprenyl-4-hydroxycinnamic acid (Artepillin C) in Brazilian propolis by supercritical fluid extractions. Separation and Purification Technology, 54(1), 130–138. https://doi.org/10.1016/j.seppur.2006.08.028
   Web of Science ®Google Scholar
• Machado, B. A. S., Silva, R. P. D., Barreto, G. d A., Costa, S. S., Silva, D. F. d., Brandão, H. N., Machado, C. S., Mokochinski, J. B., de Lira, T. O., de Oliveira, F. C., Cardoso, M. V., Ferreira, R. G., Sawaya, A. C., Ferreira, A. G., Pessoa, C., Cuesta-Rubio, O., Monteiro, M. C., de Campos, M. S., & Torres, Y. R. (2016). Comparative study of chemical composition and biological activity of yellow, green, brown and red Brazilian propolis. Evidence Based Complementary Alternative Medicine, 6057650, 1–11.
   Web of Science ®Google Scholar
• Meda, A., Lamien, C. E., Romito, M., Millogo, J., & Nacoulma, O. G. (2005). Determination of the total phenolic, flavonoid and proline contents in Burkina Fasan honey, as well as their radical scavenging activity. Food Chemistry, 91(3), 571–577. https://doi.org/10.1016/j.foodchem.2004.10.006
   Web of Science ®Google Scholar
• Medic-Saric, M., Boji, M., Rastija, V., & Cvek, J. (2013). Polyphenolic profiling of croatian propolis and wine. Food Technology and Biotechnology, 51(2), 159–170.
   Web of Science ®Google Scholar
• Midorikawa, K., Banskota, A. H., Tezuka, Y., Nagaoka, T., Matsushige, K., Message, D., Huertas, A. A., & Kadota, S. (2001). Liquid chromatography–mass spectrometry analysis of propolis. Phytochemical Analysis : PCA, 12(6), 366–373.
   PubMed Web of Science ®Google Scholar
• Murugan, R., Arunachalam, K., & Parimelazhagan, T. (2012). Antioxidant, anti-inflammatory activity, and phytochemical constituents of Ficus (Ficus amplissima Smith) Bark. Food Science and Biotechnology, 21, 59–67.
   Web of Science ®Google Scholar
• Murugan, R., Chandran, R., & Parimelazhagan, T. (2016). Effect of in vitro simulated gastrointestinal digestion of Phoenix loureirii on polyphenolics, antioxidant and acetylcholinesterase inhibitory activities. LWT-Food Science and Technology, 7, 363–370.
   Web of Science ®Google Scholar
• Murugan, R., Saravanan, S., & Parimelazhagan, T. (2017). Study of intestinal anti-inflammatory activity of Phoenix loureiroi Kunth (Arecaceae) fruit. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 93, 156–164.
   PubMed Web of Science ®Google Scholar
• Nunes, C. F., Finger, P. F., Fischer, G., Castro, C. C., Hübner, S. O., Paulino, N., Marcucci, M. C., Vieira, O., Martes, P. E., & Vargas, G. D. (2012). Standardization of an ethanolic sample of Green Propolis. Phytochemistry, 7, 67–72.
   Google Scholar
• Park, Y. K., Alencar, S. M., & Aguiar, C. L. (2002). Botanical origin and chemical composition of Brazilian propolis. Journal of Agricultural and Food Chemistry, 50(9), 2502–2506.
   PubMed Web of Science ®Google Scholar
• Paviani, L. C., Fiorito, G., Sacoda, P., & Cabral, F. A. (2013). Different solvents for extraction of Brazilian Green propolis: Composition and extraction yield of phenolic compounds, III Iberoamerican Conference on Supercritical Fluids, Cartagena de Indias, Colombia, 1–5.
   Google Scholar
• Pellati, F., Orlandinia, G., Pinetti, D., & Benvenutia, S. (2011). HPLC-DAD and HPLC-ESI-MS/MS methods for metabolite profiling of propolis extracts. Journal of Pharmaceutical and Biomedical Analysis, 55(5), 934–948. https://doi.org/10.1016/j.jpba.2011.03.024
   PubMed Web of Science ®Google Scholar
• Pereira, A. S., Seixas, F. R. M. S., & Neto, F. R. A. (2002). Própolis: 100 anos de pesquisa e suas perspectivas futuras. Quím Nova, 25(2), 321–326.
   Web of Science ®Google Scholar
• Pisarev, D. I., Novikov, O. O., Malyutina, A. Y., Lupina, E. V., Zhilyakova, E. T., & Boyko, N. N. (2017). Development of a technique for assessing the quality of propolis by the content of caffeic acid phenethyl ester by high-performance liquid chromatography with a diodematrix detector. Drug Invention Today, 9, 53–58.
   Google Scholar
• Rajan, M., Barbosa, P. F., Gualberto, N. C., Santos de Oliveira, C., Leite Neta, M. T. S., & Narain, N. (2019). Optimization and method validation of determining polyphenolic compounds by UFLC-DAD system using two biphenyl and pentafluorophenyl propyl columns. Journal of Liquid Chromatography Related Technology, 42(11-12), 351–357.
   Web of Science ®Google Scholar
• Rajan, M., Rajkumar, G., Guedes, T. J. F. L., Barros, R. G. C., & Narain, N. (2020). Performance of different solvents on extraction of bioactive compounds, antioxidant and cytotoxic activities in Phoenix loureiroi Kunth leaves. Journal of Applied Research on Medicinal and Aromatic Plants, 17, 100247.
   Web of Science ®Google Scholar
• Regueira Neto, M. S., Tintino, S. R., Pereira da Silva, A. R., Costa, M. d S., Boligon, A. A., Matias, E. F. F., Balbino, V. d Q., Menezes, I. R. A., & Melo Coutinho, H. D. (2017). Seasonal variation of Brazilian red propolis: Antibacterial activity, synergistic effect and phytochemical screening. Food Chemical and Toxicology, 107, 572–580.
   PubMed Web of Science ®Google Scholar
• Riani, L. R., Silva, L. M., Filhoa, A. A. D. S. (2019). Validation of UHPLC-MS method for Artepillin C quantification on green própolis. 6th BCNP Brazilian Conference on Natural Products, Federal University of Espirito Santo Vitoria. Retreived July 17, 2020 from https://proceedingsscience/bcnp/papers/validation-of-uhplc-ms-method-for-artepillin-c-quantification-on-green-propolis?lang=en.
   Google Scholar
• Rice-Evans, C. A., & Miller, N. J. (1996). Antioxidant activities of flavonoids as bioactive components of food. Biochemical Society Transactions, 24(3), 790–795. https://doi.org/10.1042/bst0240790
   PubMed Web of Science ®Google Scholar
• Rocha, B. A., Bueno, P. C. P., Vaz, M. M. O. L. L., Nascimento, A. P., Ferreira, N. U., Moreno, G. P., Rodrigues, M. R., Costa-Machado, A. R. M., Barizon, E. A., Campos, J. C., de Oliveira, P. F., Acésio, N. O., Martins, S. P. L., Tavares, D. C., & Berretta, A. A. (2013). Evaluation of a Propolis water extract using a reliable RP-HPLC methodology and in vitro and in vivo efficacy and safety characterization. Evidence Based Complementary Alternative Medicine, 670451, 1–11.
   Google Scholar
• Salatino, A., Teixeira, E. W., Negri, G., & Message, D. (2005). Origin and chemical variation of Brazilian propolis. Evidence Based Complementary Alternative Medicine, 2, 33–38.
   PubMed Web of Science ®Google Scholar
• Sawaya, A. C. H. F., Cunha, I. B. S., & Marcucci, M. C. (2011). Analytical methods applied to diverse types of Brazilian propolis. Chemistry Central Journal, 5, 1–27.
   PubMedGoogle Scholar
• Sha, N., Huang, H.-L., Zhang, J.-Q., Chen, G.-T., Tao, S.-J., Yang, M., Li, X.-N., Li, P., & Guo, D.-A. (2009). Simultaneous quantification of eight major bioactive phenolic compounds in Chinese propolis by high-performance liquid chromatography. Natural Product Communications, 4(6), 813–818.
   PubMed Web of Science ®Google Scholar
• Shanmugam, S., Thangaraj, P., Lima, B. S., Trindade, G. G. G., Narain, N., Mara de Oliveira e Silva, A., Santin, J. R., Broering, M. F., Serafini, M. R., Quintans-Júnior, L. J., & Antunes de Souza Araújo, A. (2020). Protective effects of flavonoid composition rich P. subpeltata Ortega. on indomethacin induced experimental ulcerative colitis in rat models of inflammatory bowel diseases. Journal of Ethnopharmacology, 248, 112350. https://doi.org/10.1016/j.jep.2019.112350
   PubMed Web of Science ®Google Scholar
• Shetty, K., Curtis, O. F., Levin, R. E., Witkowsky, R., & Ang, W. (1995). Prevention of vitrification Aßociated with in vitro shoot culture of Oregano. (Origanum vulgare) by Pseudomonas spp. Journal of Plant Physiology, 147(3-4), 447–451.
   Web of Science ®Google Scholar
• Spulber, R., Colța, T., Băbeanu, N., & Popa, O. (2017). Chemical diversity of polyphenols from bee pollen and propolis. AgroLife Science Journal, 6, 183–194.
   Web of Science ®Google Scholar
• Stalikas, C. D. (2007). Extraction, separation, and detection methods for phenolic acids and flavonoids. Journal of Separation Science, 30(18), 3268–3295. https://doi.org/10.1002/jssc.200700261
   PubMed Web of Science ®Google Scholar
• Sulaiman, G. M., Al Sammarrae, K. W., Ad’hiah, A. H., Zucchetti, M., Frapolli, R., Bello, E., Erba, E., D’Incalci, M., & Bagnati, R. (2011). Chemical characterization of Iraqi propolis samples and assessing their antioxidant potentials. Food and Chemical Toxicology : An International Journal Published for the British Industrial Biological Research Association, 49(9), 2415–2421.
   PubMed Web of Science ®Google Scholar
• Thaipong, K., Boonprakob, U., Crosby, K., Cisneros-Zevallos, L., & Byrne, D. H. (2006). Comparison of ABTS, DPPH, FRAP, and ORAC assays for estimating antioxidant activity from guava fruit extracts. Journal of Food Composition Analysis, 19(6-7), 669–675.
   Web of Science ®Google Scholar
• Tlak Gajger, I. T., Pavlović, I., Bojić, M., Kosalec, I., Srečec, S., Vlai Nić, T., & Vlainić, J. (2017). Components responsible for the antimicrobial activity of propolis from continental and mediterranean regions in Croatian. Czech Journal of Food Science, 35, 376–385.
   Web of Science ®Google Scholar
• Vega Arroy, D. J., Ruiz-Espinosa, H., Luna-gueVara, J. J., Luna-Guevara, M. L., Hernández-Carranza, P., Avila-Sosa, R., & Ochoa-Velasco, C. E. (2017). Effect of solvents and extraction methods on total anthocyanins, phenolic compounds and antioxidant capacity of Renealmia alpinia (Rottb) Maas peel. Czech Journal of Food Science, 35(5), 456–465.
   Web of Science ®Google Scholar
• Volpi, N., & Bergonzini, G. (2006). Analysis of flavonoids from propolis by on-line HPLC–electrospray mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis, 42(3), 354–361.
   PubMed Web of Science ®Google Scholar
• Yang, L., Yan, Q.-H., Ma, J.-Y., Wang, Q., Zhang, J.-W., & Xi, G.-X. (2013). High performance liquid chromatographic determination of phenolic compounds in propolis. Tropical Journal of Pharmaceutical Research, 12(5), 771–776.
   Web of Science ®Google Scholar
• Zhang, A., Wan, L., Wu, C., Fang, Y., Han, G., Li, H., Zhang, Z., & Wang, H. (2013). Simultaneous determination of 14 phenolic compounds in grape canes by HPLC-DAD-UV using wavelength switching detection. Molecules, 18(11), 14241–14257.
   PubMed Web of Science ®Google Scholar