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Comparison of three different protocols of alkaloid extraction from Glaucium corniculatum plant

Year 2022, Volume: 9 Issue: 1, 43 - 51, 10.03.2022
https://doi.org/10.21448/ijsm.980171

Abstract

Alkaloids, plant secondary metabolites, have a wide variety of biological effects. For this reason, the extraction of alkaloids from plants is of strategic importance. Different extraction protocols for the extraction of alkaloids from plants have been described by many authors. The objective of this study was to compare the efficacy of three different protocols for the extraction of alkaloids from Glaucium corniculatum. This article compares the Soxhlet and ultrasonication protocol, used in previous studies, to a modified Soxhlet protocol. While the alkaloid amount in the extract was determined by the spectrophotometric method, the qualitative estimation of the compounds in the extract was determined by Gas chromatograph-Mass spectrometer (GC-MS). The alkaloid amount and diversity in the extract, obtained through the recommended modified Soxhlet protocol, were higher than that of any extract obtained through other protocols. Thus, a new modified alkaloid extraction protocol was established, which is better than the other protocol.

Supporting Institution

Tübitak

Project Number

116S299

References

  • Almousawi, U.M.N., & Alwan, A.A. (2017). The significance of opium alkaloids in the classification of Papaveraceae in Iraq. Journal of Pharmacognosy and Phytochemistry, 6(1), 430-437.
  • Amirkia, V., & Heinrich, M. (2014). Alkaloids as drug leads A predictive structural and biodiversity based analysis. Phytochemistry Letters, 10. https://cyberleninka.org/article/n/1019139
  • Chaves, K.M.S., M. Feitosa, C., & da S. Araújo, L. (2016). Alkaloids Pharmacological Activities-Prospects for the Development of Phytopharmaceuticals for Neurodegenerative Diseases. Current Pharmaceutical Biotechnology, 17(7), 629-635.
  • Cushnie, T.P.T., Cushnie, B., & Lamb, A.J. (2014). Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities. International Journal of Antimicrobial Agents, 44(5), 377-386. https://doi.org/10.1016/j.ijantimicag.2014.06.001
  • Demaggio, A.E., & Lott, J.A. (1964). Application of Ultrasound for Increasing Alkaloid Yield from Datura Stramonium. Journal of Pharmaceutical Sciences, 53(8), 945-949. https://doi.org/10.1002/jps.2600530822
  • Desgrouas, C., Baghdikian, B., Mabrouki, F., Bory, S., Taudon, N., Parzy, D., & Ollivier, E. (2014). Rapid and green extraction, assisted by microwave and ultrasound of cepharanthine from Stephania rotunda Lour. Separation and Purification Technology, 123, 9-14. https://doi.org/10.1016/j.seppur.2013.12.016
  • Dittbrenner A. (2009). Morphologische, phytochemische und molekulare Untersuchungen zur intraspezifi schen Diversität von Schlafmohn (Papaver somniferum L.). [PhD Thesis, Martin Luther University]. Halle-Wittenberg, Germany. http://dx.doi.org/10.25673/502
  • Doncheva, T., Kostova, N., Yordanova, G., Saadi, H., Akrib, F., Dimitrov, D., & Philipov, S. (2014). Comparison of alkaloid profile from Glaucium corniculatum (Papaveraceae) of Algerian and Bulgarian origin. Biochemical Systematics and Ecology, 56, 278-280. https://www.cabdirect.org/cabdirect/abstract/20143390676
  • Hesse, M. (2002). Alkaloids: Nature’s Curse Or Blessing? John Wiley & Sons.
  • Järnberg, U., Asplund, L., & Jakobsson, E. (1994). Gas chromatographic retention behaviour of polychlorinated naphthalenes on non-polar, polarizable, polar and smectic capillary columns. Journal of Chromatography A, 683(2), 385-396. https://doi.org/10.1016/0021-9673(94)00515-X
  • Jimoh, F., Adedapo, A., Aliero, A., & Afolayan, A. (2010). Polyphenolic and biological activities of leaves extracts of Argemone subfusiformis (Papaveraceae) and Urtica urens (Urticaceae). Revista de Biología Tropical, 58(4), 1517-1531.
  • Kaya, G.I., Uzun, K., Bozkurt, B., Onur, M.A., Somer, N.U., Glatzel, D.K., & Fürst, R. (2017). Chemical characterization and biological activity of an endemic Amaryllidaceae species: Galanthus cilicicus. South African Journal of Botany, 108, 256 260. https://doi.org/10.1016/j.sajb.2016.11.008
  • Khamtache-Abderrahim, S., Lequart-Pillon, M., Gontier, E., Gaillard, I., Pilard, S., Mathiron, D., Djoudad-Kadji, H., & Maiza-Benabdesselam, F. (2016). Isoquinoline alkaloid fractions of Fumaria officinalis: Characterization and evaluation of their antioxidant and antibacterial activities. Industrial Crops and Products, 94, 1001 1008. https://doi.org/10.1016/j.indcrop.2016.09.016
  • Kintsurashvili, L.G., & Vachnadze, V. Yu. (2000). Alkaloids ofGlaucium corniculatum andG. flavum growing in Georgia. Chemistry of Natural Compounds, 36(2), 225-226. https://doi.org/10.1007/BF02236441
  • Kutchan, T. M. (1995). Alkaloid Biosynthesis[mdash]The Basis for Metabolic Engineering of Medicinal Plants. The Plant Cell, 7(7), 1059. https://doi.org/10.1105/tpc.7.7.1059
  • Luque de Castro, M.D., & Garcı́a-Ayuso, L.E. (1998). Soxhlet extraction of solid materials: An outdated technique with a promising innovative future. Analytica Chimica Acta, 369(1), 1-10. https://doi.org/10.1016/S0003-2670(98)00233-5
  • Nigdelioglu Dolanbay, S., Kocanci, F. G., & Aslim, B. (2021). Neuroprotective effects of allocryptopine-rich alkaloid extracts against oxidative stress-induced neuronal damage. Biomedicine & Pharmacotherapy, 140, 111690. https://doi.org/10.1016/j.biopha.2021.111690
  • Novelli, S., Lorena, C., & Antonella, C. (2014). Identification of Alkaloid’s Profile in Ficus benjamina L. Extracts with Higher Antioxidant Power. American Journal of Plant Sciences, 05(26), 4029. https://doi.org/10.4236/ajps.2014.526421
  • Petruczynik, A. (2012). Analysis of alkaloids from different chemical groups by different liquid chromatography methods. Open Chemistry, 10(3), 802-835. https://doi.org/10.2478/s11532-012-0037-y
  • Phillipson, J.D., Gray, A.I., Askari, A.A.R., & Khalil, A.A. (1981). Alkaloids From Iraqi Species of Papaveraceae. Journal of Natural Products, 44(3), 296-307. https://doi.org/10.1021/np50015a011
  • Preininger, V. (1985). Chemotaxonomy of the Papaveraceae Alkaloids. Içinde J. D. Phillipson, M. F. Roberts, & M. H. Zenk (Ed.), The Chemistry and Biology of Isoquinoline Alkaloids (ss. 23-37). Springer Berlin Heidelberg.
  • Sarikaya, B.B., Somer, N.U., Kaya, G.I., Onur, M.A., Bastida, J., & Berkov, S. (2014). GC-MS Investigation and Acetylcholinesterase Inhibitory Activity of Galanthus rizehensis. Zeitschrift für Naturforschung C, 68(3-4), 118-124. https://doi.org/10.1515/znc-2013-3-407
  • Schmeck, T., & Wenclawiak, B.W. (2005). Sediment Matrix Induced Response Enhancement in the Gas Chromatographic–Mass Spectrometric Quantification of Insecticides in Four Different Solvent Extracts from Ultrasonic and Soxhlet Extraction. Chromatographia, 62(3), 159-165. https://doi.org/10.1365/s10337-005-0589-5
  • Shafiee, A., Ghanbarpour, A., & Akhlaghi, S. (1985). Alkaloids of Papaveraceae, XII. Alkaloids of Glaucium corniculatum subspecies Refractum, Population Pol-Dokhtar. Journal of Natural Products, 48(5), 855-856. https://doi.org/10.1021/np50041a037
  • Slavík, J., & Šantavý, F. (1972). Alkaloids of the Papaveraceae. XLVII. Identity of bocconine with chelirubine. Collection of Czechoslovak Chemical Communications, 37(8), 2804-2806. https://doi.org/10.1135/cccc19722804
  • Villas‐Bôas, S.G., Mas, S., Åkesson, M., Smedsgaard, J., & Nielsen, J. (2005). Mass spectrometry in metabolome analysis. Mass Spectrometry Reviews, 24(5), 613-646. https://doi.org/10.1002/mas.20032
  • Webster, G.R.B. (2006). Soxhlet and Ultrasonic Extraction of Organics in Solids. Içinde Encyclopedia of Analytical Chemistry. American Cancer Society. https://doi.org/10.1002/9780470027318.a0864
  • Yu, H.-H., Kim, K.-J., Cha, J.-D., Kim, H.-K., Lee, Y.-E., Choi, N.-Y., & You, Y.-O. (2005). Antimicrobial Activity of Berberine Alone and in Combination with Ampicillin or Oxacillin Against Methicillin-Resistant Staphylococcus aureus. Journal of Medicinal Food, 8(4), 454-461. https://doi.org/10.1089/jmf.2005.8.454
  • Yu, X., Gao, X., Zhu, Z., Cao, Y., Zhang, Q., Tu, P., & Chai, X. (2014). Alkaloids from the tribe Bocconieae (papaveraceae): A chemical and biological review. Molecules (Basel, Switzerland), 19(9), 13042-13060. https://doi.org/10.3390/molecules190913042

Comparison of three different protocols of alkaloid extraction from Glaucium corniculatum plant

Year 2022, Volume: 9 Issue: 1, 43 - 51, 10.03.2022
https://doi.org/10.21448/ijsm.980171

Abstract

Alkaloids, plant secondary metabolites, have a wide variety of biological effects. For this reason, the extraction of alkaloids from plants is of strategic importance. Different extraction protocols for the extraction of alkaloids from plants have been described by many authors. The objective of this study was to compare the efficacy of three different protocols for the extraction of alkaloids from Glaucium corniculatum. This article compares the Soxhlet and ultrasonication protocol, used in previous studies, to a modified Soxhlet protocol. While the alkaloid amount in the extract was determined by the spectrophotometric method, the qualitative estimation of the compounds in the extract was determined by Gas chromatograph-Mass spectrometer (GC-MS). The alkaloid amount and diversity in the extract, obtained through the recommended modified Soxhlet protocol, were higher than that of any extract obtained through other protocols. Thus, a new modified alkaloid extraction protocol was established, which is better than the other protocol.

Project Number

116S299

References

  • Almousawi, U.M.N., & Alwan, A.A. (2017). The significance of opium alkaloids in the classification of Papaveraceae in Iraq. Journal of Pharmacognosy and Phytochemistry, 6(1), 430-437.
  • Amirkia, V., & Heinrich, M. (2014). Alkaloids as drug leads A predictive structural and biodiversity based analysis. Phytochemistry Letters, 10. https://cyberleninka.org/article/n/1019139
  • Chaves, K.M.S., M. Feitosa, C., & da S. Araújo, L. (2016). Alkaloids Pharmacological Activities-Prospects for the Development of Phytopharmaceuticals for Neurodegenerative Diseases. Current Pharmaceutical Biotechnology, 17(7), 629-635.
  • Cushnie, T.P.T., Cushnie, B., & Lamb, A.J. (2014). Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities. International Journal of Antimicrobial Agents, 44(5), 377-386. https://doi.org/10.1016/j.ijantimicag.2014.06.001
  • Demaggio, A.E., & Lott, J.A. (1964). Application of Ultrasound for Increasing Alkaloid Yield from Datura Stramonium. Journal of Pharmaceutical Sciences, 53(8), 945-949. https://doi.org/10.1002/jps.2600530822
  • Desgrouas, C., Baghdikian, B., Mabrouki, F., Bory, S., Taudon, N., Parzy, D., & Ollivier, E. (2014). Rapid and green extraction, assisted by microwave and ultrasound of cepharanthine from Stephania rotunda Lour. Separation and Purification Technology, 123, 9-14. https://doi.org/10.1016/j.seppur.2013.12.016
  • Dittbrenner A. (2009). Morphologische, phytochemische und molekulare Untersuchungen zur intraspezifi schen Diversität von Schlafmohn (Papaver somniferum L.). [PhD Thesis, Martin Luther University]. Halle-Wittenberg, Germany. http://dx.doi.org/10.25673/502
  • Doncheva, T., Kostova, N., Yordanova, G., Saadi, H., Akrib, F., Dimitrov, D., & Philipov, S. (2014). Comparison of alkaloid profile from Glaucium corniculatum (Papaveraceae) of Algerian and Bulgarian origin. Biochemical Systematics and Ecology, 56, 278-280. https://www.cabdirect.org/cabdirect/abstract/20143390676
  • Hesse, M. (2002). Alkaloids: Nature’s Curse Or Blessing? John Wiley & Sons.
  • Järnberg, U., Asplund, L., & Jakobsson, E. (1994). Gas chromatographic retention behaviour of polychlorinated naphthalenes on non-polar, polarizable, polar and smectic capillary columns. Journal of Chromatography A, 683(2), 385-396. https://doi.org/10.1016/0021-9673(94)00515-X
  • Jimoh, F., Adedapo, A., Aliero, A., & Afolayan, A. (2010). Polyphenolic and biological activities of leaves extracts of Argemone subfusiformis (Papaveraceae) and Urtica urens (Urticaceae). Revista de Biología Tropical, 58(4), 1517-1531.
  • Kaya, G.I., Uzun, K., Bozkurt, B., Onur, M.A., Somer, N.U., Glatzel, D.K., & Fürst, R. (2017). Chemical characterization and biological activity of an endemic Amaryllidaceae species: Galanthus cilicicus. South African Journal of Botany, 108, 256 260. https://doi.org/10.1016/j.sajb.2016.11.008
  • Khamtache-Abderrahim, S., Lequart-Pillon, M., Gontier, E., Gaillard, I., Pilard, S., Mathiron, D., Djoudad-Kadji, H., & Maiza-Benabdesselam, F. (2016). Isoquinoline alkaloid fractions of Fumaria officinalis: Characterization and evaluation of their antioxidant and antibacterial activities. Industrial Crops and Products, 94, 1001 1008. https://doi.org/10.1016/j.indcrop.2016.09.016
  • Kintsurashvili, L.G., & Vachnadze, V. Yu. (2000). Alkaloids ofGlaucium corniculatum andG. flavum growing in Georgia. Chemistry of Natural Compounds, 36(2), 225-226. https://doi.org/10.1007/BF02236441
  • Kutchan, T. M. (1995). Alkaloid Biosynthesis[mdash]The Basis for Metabolic Engineering of Medicinal Plants. The Plant Cell, 7(7), 1059. https://doi.org/10.1105/tpc.7.7.1059
  • Luque de Castro, M.D., & Garcı́a-Ayuso, L.E. (1998). Soxhlet extraction of solid materials: An outdated technique with a promising innovative future. Analytica Chimica Acta, 369(1), 1-10. https://doi.org/10.1016/S0003-2670(98)00233-5
  • Nigdelioglu Dolanbay, S., Kocanci, F. G., & Aslim, B. (2021). Neuroprotective effects of allocryptopine-rich alkaloid extracts against oxidative stress-induced neuronal damage. Biomedicine & Pharmacotherapy, 140, 111690. https://doi.org/10.1016/j.biopha.2021.111690
  • Novelli, S., Lorena, C., & Antonella, C. (2014). Identification of Alkaloid’s Profile in Ficus benjamina L. Extracts with Higher Antioxidant Power. American Journal of Plant Sciences, 05(26), 4029. https://doi.org/10.4236/ajps.2014.526421
  • Petruczynik, A. (2012). Analysis of alkaloids from different chemical groups by different liquid chromatography methods. Open Chemistry, 10(3), 802-835. https://doi.org/10.2478/s11532-012-0037-y
  • Phillipson, J.D., Gray, A.I., Askari, A.A.R., & Khalil, A.A. (1981). Alkaloids From Iraqi Species of Papaveraceae. Journal of Natural Products, 44(3), 296-307. https://doi.org/10.1021/np50015a011
  • Preininger, V. (1985). Chemotaxonomy of the Papaveraceae Alkaloids. Içinde J. D. Phillipson, M. F. Roberts, & M. H. Zenk (Ed.), The Chemistry and Biology of Isoquinoline Alkaloids (ss. 23-37). Springer Berlin Heidelberg.
  • Sarikaya, B.B., Somer, N.U., Kaya, G.I., Onur, M.A., Bastida, J., & Berkov, S. (2014). GC-MS Investigation and Acetylcholinesterase Inhibitory Activity of Galanthus rizehensis. Zeitschrift für Naturforschung C, 68(3-4), 118-124. https://doi.org/10.1515/znc-2013-3-407
  • Schmeck, T., & Wenclawiak, B.W. (2005). Sediment Matrix Induced Response Enhancement in the Gas Chromatographic–Mass Spectrometric Quantification of Insecticides in Four Different Solvent Extracts from Ultrasonic and Soxhlet Extraction. Chromatographia, 62(3), 159-165. https://doi.org/10.1365/s10337-005-0589-5
  • Shafiee, A., Ghanbarpour, A., & Akhlaghi, S. (1985). Alkaloids of Papaveraceae, XII. Alkaloids of Glaucium corniculatum subspecies Refractum, Population Pol-Dokhtar. Journal of Natural Products, 48(5), 855-856. https://doi.org/10.1021/np50041a037
  • Slavík, J., & Šantavý, F. (1972). Alkaloids of the Papaveraceae. XLVII. Identity of bocconine with chelirubine. Collection of Czechoslovak Chemical Communications, 37(8), 2804-2806. https://doi.org/10.1135/cccc19722804
  • Villas‐Bôas, S.G., Mas, S., Åkesson, M., Smedsgaard, J., & Nielsen, J. (2005). Mass spectrometry in metabolome analysis. Mass Spectrometry Reviews, 24(5), 613-646. https://doi.org/10.1002/mas.20032
  • Webster, G.R.B. (2006). Soxhlet and Ultrasonic Extraction of Organics in Solids. Içinde Encyclopedia of Analytical Chemistry. American Cancer Society. https://doi.org/10.1002/9780470027318.a0864
  • Yu, H.-H., Kim, K.-J., Cha, J.-D., Kim, H.-K., Lee, Y.-E., Choi, N.-Y., & You, Y.-O. (2005). Antimicrobial Activity of Berberine Alone and in Combination with Ampicillin or Oxacillin Against Methicillin-Resistant Staphylococcus aureus. Journal of Medicinal Food, 8(4), 454-461. https://doi.org/10.1089/jmf.2005.8.454
  • Yu, X., Gao, X., Zhu, Z., Cao, Y., Zhang, Q., Tu, P., & Chai, X. (2014). Alkaloids from the tribe Bocconieae (papaveraceae): A chemical and biological review. Molecules (Basel, Switzerland), 19(9), 13042-13060. https://doi.org/10.3390/molecules190913042
There are 29 citations in total.

Details

Primary Language English
Subjects Structural Biology
Journal Section Articles
Authors

Fatma Gonca Koçancı 0000-0002-7248-7933

Serap Niğdelioğlu Dolanbay 0000-0002-1238-0894

Belma Aslım 0000-0002-0595-7237

Project Number 116S299
Publication Date March 10, 2022
Submission Date August 8, 2021
Published in Issue Year 2022 Volume: 9 Issue: 1

Cite

APA Koçancı, F. G., Niğdelioğlu Dolanbay, S., & Aslım, B. (2022). Comparison of three different protocols of alkaloid extraction from Glaucium corniculatum plant. International Journal of Secondary Metabolite, 9(1), 43-51. https://doi.org/10.21448/ijsm.980171
International Journal of Secondary Metabolite

e-ISSN: 2148-6905