The Effect of Acids on Alkaloid Yield in Pressurized Water Extraction of Narcissus Pseudonarcissus

Authors

  • Orchidea Rachmaniah Chemical Engineering Department, Institut Teknologi Sepuluh Nopember, Sukolilo, Surabaya 60111,
  • Jaap van Spronsen Biotechnology Department, Faculty of Applied Science, Delft University of Technology, Julianalaan 67, 2628 BC, Delft, The Netherlands
  • Robert Verpoorte Natural Products Laboratory, Institute of Biology Leiden, Leiden University, Sylviusweg 72, 2333 BE, Leiden, The Netherlands
  • Geert Jan Witkamp Biological and Environmental Science and Engineering, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia

DOI:

https://doi.org/10.5614/j.eng.technol.sci.2021.53.6.8

Abstract

Pressurized water (PW) extraction of galanthamine from Narcissus pseudonarcissus bulbs was performed. The obtained yield was compared with the yield from conventional acidified water extraction and methanolic Soxhlet extraction. Both PW and conventional acidified water extraction were followed by a subsequent purification step for the alkaloids. The PW extraction (70C, 150 bar, 45 min) yielded as much galanthamine as methanolic-Soxhlet extraction (ca. 3.50 mg/g). Meanwhile, acid-base extraction with 1% of HBr (v/v) at 65C for 3 h gave a lower yield (ca. 2.65 mg/g). A higher PW temperature did not significantly increase the galanthamine yield. Pressure increase is not necessary since more water-soluble compounds such as proteins and polysaccharides are co-extracted, resulting in high viscosity of the water extract solution, which hampers the filtration process. Hence, the acidity of the solution is highly important both in the case of PW extraction and acidified water extraction. Besides galanthamine, the total alkaloid profile following Narcissus alkaloids was also obtained. Lycoramine, O-methyloduline, norgalanthamine, epi-norgalanthamine, narwedine, oduline, haemanthamine, O-methyllycorenine, and a haemanthamine derivate were identified. Although a high yield was obtained from PW extraction, the further purification needs to be improved to obtain an economically feasible industrial extraction process.

References

Bastida, J. & Viladomat, F., Alkaloids of Narcissus, Narcissus and Daffodil: The Genus Narcissus, Gordon R. Hanks, Taylor & Francis, pp. 141-214, 2002.

Kreh, M., Matusch, R. & Witte, L., Capillary Gas Chromatography-mass Spectrometry of Amaryllidaceae Alkaloids, Phytochemistry, 38(3), pp. 773-776, Feb. 1995.

Gotti, R., Fiori, J., Bartolini, M. & Cavrini, V., Analysis of Amaryllidaceae Alkaloids from Narcissus by GC-MS and capillary Electrophoresis, Journal of Pharmaceutical and Biomedical Analysis, 42(1), pp. 17-24, Sep. 2006.

Kreh, M., Matusch, R. & Witte, L., Acetylated Alkaloids from Narcissus pseudonarcissus, Phytochemistry, 40(4), pp. 1303-1306, Nov. 1995.

Bastida, J., Viladomat, F., Labres, J.M., Quiroga, S., Codina, C. & Rubiralta, M., Nacissus nivalis: A New Source of Galanthamine, Planta Medica, 56(1), pp. 123-124, Dec. 1990.

Kreh, M. & Matusch, R., O-methyloduline and N-demethylmasonine, Alkaloids from Narcissus pseudonarcissus, Phytochemistry, 38(6), pp. 1533-1535, April. 1995.

Piozzi, F., Marino, M.L., Fuganti, C. & Di Martino, A., Occurrence of Non-basic Metabolites in Amaryllidaceae, Phytochemistry, 8(9), pp. 1745-1748, Sep. 1969.

Bastida, J., Rodolfo, L. & Viladomat, F., Chemical and Biological Aspects of Narcissus Alkaloids, The Alkaloids, Geoffrey A. Cordell, Academic Press, Elsevier, pp. 87-179, 2006.

Cronnin, J.R., The Plant Alkaloid Galanthamine. Approved as a Drug; Sold as a Supplement, Alternative & Complementary Therapies, 7(6), pp. 380-383, July. 2001.

Heinrich, M. & Lee Teoh, H., Galanthamine from Snowdrop ? The Development of a Modern Drug Against Alzheimer?s Disease from Local Caucasian Knowledge, Journal of Ethnopharmacology, 92, pp. 147-162, 2004.

Moraes, R.M., Galanthamine Production from Narcissus: Agronomic and Related Considerations, Narcissus and Daffodil: The genus Narcissus, Gordon R. Hanks, Taylor & Francis, pp. 273-285, 2002.

Rossing, W.A., Jansma, J.E., Ruijter, F.J.D. & Schans, J., Operationalizing Sustainability: Exploring Options for Environmentally Friendly Flower Bulb Production Systems, European Journal of Plant Pathology, 103, pp. 217-234, 1997.

Palma, M., Barbero, G.F., Pineiro, Z., Liazid, A., Barroso, C.G., Rostagno, M.A., Prado, J.M. & Meireles, M.A.A., Extraction of Natural Products: Principles and Fundamental Aspects, Natural Product Extraction: principles and applications, Mauricio A. Rostagno & Juliana M. Prado, RSC Publishing, pp. 59-85, 2013.

Rachmaniah, O., Choi, Y.H., Arruabarrena, I., Vermeulen, B., Verpoorte, R. & Witkamp, G.J., Environmentally Benign Super Critical CO2 Extractionn of Galanthamine from Floricultural Crop Waste of Narcissus pseudonarcissus, The Journal of Supercritical Fluids, 93, pp. 7-19, 2014.

Bastos, J.K., Xu, L., Nanayakkara, N.P.D., Burandt, C.L., Moraes-Cerdeira, R.M. & Mcchesney, J.D., A Rapid Quantitative Method for the Analysis of Galanthamine and Other Amaryllidaceae Alkaloids by Capillary Column Gas Chromatography, Journal of Natural Product , 59, pp. 638-640, 1996.

Berkov, S., Bastida, J., Nikolova, M., Viladomat, F. & Codina, C., Rapid TLC/GC-MS Identification of Acetylcholinesterase Inhibitors in Alkaloid Extracts, Phytochemical Analysis, 19, pp. 411-419, 2008.

Ptak, A., El Tahchy, A., Dupire, F.O., Boisbrun, M. & Henry, M., Chapleur Y, Mos M, Laurain-Mattar D., LCMS and GCMS for the Screening of Alkaloids in Natural and in Vitro Extracts of Leucojum aestivum, Journal of Natural Products, 72, pp. 142-147, 2008.

Sagdullaev, S.S., Preparation of Galantamine Hydrobromide from Leaves of Ungerniya Victoris by Aqueous Alcohol Extraction, Chemistry of Natural Compounds, 41, pp. 239-239, 2005.

Hille, T., Hoffmann, H.R., Kreh, M. & Matusch, R., Process for The Isolation of Galanthamine, DE patent application 09/986792, 2002.

Andrade, J.P. de, Pigni, N.B., Torras, C.L., Berkov, S., Codina, C., Viladomat, F. & Bastida, J., Bioactive Alkaloid Extracts from Narcissus broussonetii: Mass Spectral Studies. Journal of Pharmaceutical and Biomedical Analysis, 70, pp. 13-25, 2012.

Mustafa, N.R., Rhee, I.K. & Verpoorte, R., Rapid Method for Determination of Galanthamine in Amaryllidaceae Plants Using HPLC. Journal of Liquid Chromatography & Related Technologies, 26, pp. 3217-3233, 2003.

Luque de Castro, M.D. & Garcia-ayuso, L.E., Soxhlet Extraction of Solid Materials: an Out-Dated Technique with a Promising Innovative Future, Analytica Chimica Acta, 369, pp. 1-10, 1998.

Li, H.Y., Ma, G.E., Xu, Y. & Hong, S.H., Alkaloids of Lycoris guangxiensis, Planta Medica, 53, pp. 259-261, 1987.

Codina, C., Bastida, J, Viladomat, F., Fernandez, J.M., Bergonon, S., Rubiralta, M. & Quirion, J.C., Alkaloids from Narcissus muzii-garmendiae, Phytochemistry, 32, pp. 1354-1356, 1993.

Araujo, P., Key aspects of Analytical Method Validation and Linearity Evaluation, Journal of Chromatography B, 877, pp. 2224-2234, 2009.

Narayan De, D., Plant Cell Vacuoles: An Introduction, Collingwood, CSIRO Publishing, 2000.

Toews, K.L., Shroll, R.M., Wai, C.M. & Smart, N.G., pH-Defining Equilibrium between Water and Supercritical CO2. Influence on SFE of Organics and Metal Chelates, Analytical Chemistry, 67, pp. 4040-4043, 1995.

Kreh, M., Studies on Galanthamine Extraction from Narcissus and other Amaryllidaceae, Narcissus and Daffodil: The genus Narcissus, Gordon R. Hanks, Taylor & Francis, pp. 256-272, 2002.

Alfonsi, K., Colberg, J., Dunn, P.J., Fevig, T., Jennings, S., Johnson, T.A., Kleine, H.P., Knight, C., Nagy, M.A. & Perry, D.A., Green Chemistry Tools to Influence a Medicinal Chemistry and Research Chemistry Based Organisation, Green Chemistry, 10, pp. 31-36, 2008.

Nanayakkara, N.P.D. & Bastos, J.K., Extraction and Quantitative Analysis of Amaryllidaceae alkaloids, Narcissus and Daffodil: The genus Narcissus, Gordon R. Hanks, Taylor & Francis, pp. 286-303, 2002.

Sramek, J.J., Frackiewicz, E.J. & Cutler, N.R., Review of the Acethylcholinesterase Inhibitor Galanthamine, Expert Opinion Investigation of Drugs, 9, pp. 2393-2402, 2000.

Berkov, S., Bastida, J., Viladomat, F. & Codina, C., Development and validation of a GC-MS method for Rapid Determination of Galanthamine in Leucojum aestivum and Narcissus ssp.: A Metabolomic Approach, Talanta, 83, pp. 1455-1465, 2011.

Rakhimov, D.A. & Zhauynbaeva, K.S., Plant polysaccharides. V. Carbohydrates of Narcissus poeticus, Chemistry of Natural Compounds, 33, pp. 208-208, 1997.

Zhauynbaeva, K.S., Malikova, M.K., Rakhimov, D.A. & Khushbaktova, Z.A., Water-soluble Polysaccharides from Narcissus poeticus and Their Biological Activity, Chemistry of Natural Compounds, 39, pp. 520-522, 2003.

Opute, F.I. & Osagie, A.U., Fatty Acid Composition of Total Lipids from Some Tropical Storage Organs, Journal of the Science of Food and Agriculture, 29, pp. 959-962, 1978.

Lubbe, A., Gude, H., Verpoorte, R. & Choi, Y.H., Seasonal Accumulation of Major Alkaloids in Organs of Pharmaceutical Crop Narcissus Carlton, Phytochemistry, 88, pp. 43-53, 2013.

Bastida, J., Berkov, J., Berkov, S., Torras, L., Pigni, N.B., Andrade, J.P. de, Martinez, J., Codina, C. & Viladomat, F., Chemical and Biological Aspects of Amaryllidaceaea Alkaloids, in Muz-Torrero, D. (ed.), Recent Advances in Pharmaceutical Sciences, Barcelona: Transworld Research Network, 2011.

Duffield, A.M., Aplin, R.T., Budzikiewicz, H., Djerassi, C., Murphy, C.F. & Wildman, W.C., Mass Spectrometry in Structural and Stereochemical Problems, LXXXII.1 A Study of the Fragmentation of Some Amaryllidaceae Alkaloids, Journal of the American Chemical Society, 87, pp. 4902-4912, 1965.

Bastida, J., Viladomat, F., Bergonon, S., Fernandez, J.M., Codina, C., Rubiralta, M. & Quirion, J.C., Alkaloids from Narcissus leonensis, Phytochemistry, 34, pp. 1656-1658, 1993.

Sun, S., Wei, Y., Cao, Y., & Deng, B., Simultaneous Electrochemiluminescence Determination of Galanthamine, Homolycorine, Lycorenine, and Tazettine in Lycoris Radiata by Capillary Electrophoresis with Ultrasonic-Assisted Extraction, Jounal of Chromatography B, 1055-1056, pp.15-19, 2017.

Tian, C.L., Wang, P., Qin, J.X., Liu, X.P., Song, K. & Xiao, Z.B., Enzyme-Assisted Extraction and Enrichment of Galanthamine from Lycoris aurea, Chinese Herbal Medicines, 8, pp. 182-188, 2016.

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2021-12-29

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