Extraction Of Indole Alkaloids From Tabernaemontana Catharinensis Using Supercritical Co2+ethanol: An Evaluation Of The Process Variables And The Raw Material Origin

Indole alkaloids from Tabernaemontana catharinensis, collected from different places, were extracted using a mixture of supercritical CO2 plus ethanol. The effects of the process variables: temperature, pressure, solvent flow rate, and percentage of cosolvent on the total yield, chemical composition of the extract, and extraction kinetics were determined. The extracts were solvent-partitioned and their composition analyzed by TLC, GC-MS and 1H and 13C NMR. Voacangine and coronaridine were identified as the major compounds in the extracts; the individual alkaloids were quantified by GC-FID using external standard. At 250 bar and 45°C the largest yield (1.29%) and the faster extraction rate were obtained; increasing the percentage of cosolvent improved the extraction rate as well as the yield. Employing an intermittent process consisting in six pressurization- depressurization steps appreciably reduced the total extraction time. © 2003 Elsevier B.V. All rights reserved.3015161Mc Hugh, M., Krukonis, V., (1994) Appendix A: Patent Reviews. in Supercritical Fluid Extraction: Principles and Pratice 2nd Edition, p. 503. , Boston, MA: ButterworthLopez-Avila, B., Robaugh, D., Supercritical fluid extraction of oxindoles alkaloids from Uncaria tomentosa (1997) J. High Resolution Chromatogr., 20, p. 231Spitzer, V., Rates, M.K., Henriques, A.T., Marx, F., The fatty acid composition of the seed oil of Peschiera australis (1995) Fett (Germany), 97, p. 334Rates, S.M.K., Schapoval, E.E.S., Souza, I.A., Henriques, A.T., Chemical constituents and pharmacological activities of Peschiera australis (1993) Int. J. Pharmacogn., 31, p. 288Van Beek, T.A., Veerpoorte, R., Svendsen, A.B., Leeuwenberg, A.J.M., Bisset, N.G., Tabernaemontana L.: A review of its taxonomy, phytochemistry, ethnobotany and pharmacology (1984) J. Ethnopharmacol., 10, p. 1Delorenzi, J.C.M.O.B., (1998) Estudo Farmacológico de Peschiera Australis e Sua Ação Sobre Leishmania Amazonensis (Pharmacological Study of Peschiera Australis and Its Action over Leishmania Amazonensis), , M.Sc. thesis, Instituto de Biofísica Carlos Chagas Filho-Universidade Federal do Rio de Janeiro, Rio de Janeiro, BrazilGiamarellou, H., AIDS and skin: Parasitic diseases (2000) Clin. Dermatol., 18, p. 433Buzcek, B., Geldart, D., Determination of density of porous particles using very fine dense powders (1986) Powder Technol., 45, p. 173Jacobs, M.B., (1973) The Chemical Analysis of Food and Products, , New York, USA: Robert KriegerHoisington, D., Khairallah, M., Gonzalez-De-Lion, D., (1994) Laboratory Protocols: CIMMYT Applied Molecular Genetics Laboratory 2nd Edition, , Mexico, DF: CIMMYTColombo, C., Second, G., Charrier, A., Diversity within American cassava germ plasm based on RAPD markers (2000) Genet. Mol. Biol., 23, p. 189Rohl, F.J., (1995) NTSYS-pc Numerical Taxonomy and Multivariate Analysis System, , Setauket, NY: Exeter SoftwarePasquel, A., Meireles, M.A.A., Marques, M.O.M., Petenate, A.J., Extraction of stevia glycosides with CO2+water, CO 2+ethanol, and CO2+water+ethanol (2000) Braz. J. Chem. Eng., 17, p. 271Gunasekera, S.P., Cordell, G.A., Farnswor, T.H., Anticancer indole alkaloids of Ervatamia heyneana (1980) Phytochemistry, 19, p. 1213Van Beek, T.A., Verpoorte, R., Svendsen, A.B., Antimicrobially active alkaloids from Tabernaemontana chippi (1985) J. Nat. Prod., 48, p. 401Cardoso, C.A.L., Vilegas, W., Pozetti, G.L., Gas chromatographic analysis of indole alkaloids from Tabernaemontana hilariana (1997) J. Chromatogr. a, 788, p. 204Van Beek, T.A., Veerpoorte, R., Svendsen, A.B., Identification of Tabernaemontana alkaloids by mean of thin-layer chromatography and chromogenic reactions (1984) J. Chromatogr., 298, p. 289Moeller, D.A., Schaal, B.A., Genetic relationships among native American maize accessions of the Great Plains assessed by RAPDs (1999) Theor. Appl. Genet., 99, p. 1061Toledo, A., Martin-Sanchez, J., Pesson, B., Sanchiz-Marin, C., Morillas-Marquez, F., Genetic variability within the species Leishmania infantum by RAPD (2002) Mol. Biochem. Parasitol, 119, p. 257Pelletier, S.W., Alkaloids of Tabernaemontana species (1988) Alkaloids: Chemical and Biological Perspectives, 6, p. 542. , Pelletier S.W. New York, NY: Institute for Natural Products Research, Wiley-Interscience PublicationPereira, P.S., (1999) Estudo Fitoquímico e Biotecnológico de Tabernaemontana Catharinensis A.DC. (Apocynaceae), , Ph.D. thesis, Faculdade de Filosofia, Ciências e Letras-Ribeirão Preto, Universidade do Estado de São Paulo, São Paulo, BrazilAngus, S., Armstrong, B., De Reuck, K.M., (1976) International Thermodynamic Tables of the Fluid State - Carbon Dioxide, p. 385. , Pergamon Press, Oxford, UKHoyer, G.C., Extraction with supercritical fluids: Why, how and so what (1985) Chemtech., 7, p. 440Schaeffer, S., Zalkow, L.H., Teja, A.S., Extraction and isolation of chemotherapeutic pyrrolizidine alkaloids from plant substrates (1989) Supercritical Fluid Science and Technology, ACS Symposium Series, p. 550. , Washington, DC: ACSSaldaña, M.D.A., Mohamed, R.S., Baer, M.G., Mazzafera, P., Extraction of purine alkaloids from Maté (Ilx paraguarinensis) using supercritical CO2 (1999) J. Agric. Food Chem., 47, p. 3804Montgomery, D.C., (2001) Design and Analysis of Experiments 5th Edition, p. 247. , New York, NY: WileySmith Jr., R.L., Malaluan, R.M., Setianto, W.B., Inomata, H., Arai, K., Separation of cashew (Anacardium occidentale L.) nut shell liquid with supercritical carbone dioxide (2003) Bioresource Technol., 88, p.