Solvent Selection for Mitragynine Extraction by Hansen Solubility Parameter
Keywords:
Kratom, Mitragynine, Solubility Parameter, ProCAPE, GSK’s Solvent Selection GuideAbstract
Mitragyna speciosa (Korth.) Havil., commonly known as “Kratom” has a wide range of therapeutic benefits. In this research study the solvents that can be used to extract Mitragynine from kratom leaves. To predict solubility parameters, Hansen solubility parameters were employed. Then analyzing the solubility parameters using the ProCAPE application However, Mitragynine cannot directly determine the solubility. Instead, a method for evaluating the solubility from derivatives of Mitragynine was used in this study. A ternary graph shows the solubility of the derivatives and solvents. The solvents selected were considered for safety from the GSK’s Solvent Selection Guide. From the results, it was found that several types of solvents which that were dissolved derivatives of Mitragynine better than conventional solvents. Additionally, while using ProCAPE, the solubility parameters were predicted from extraction-related research was applied, and the results were shown as ternary graphs. The graphs were confirmed to be in accordance with the experimental data from the research that was collected.
References
Z. Hassan, M. Muzaimi, V. Navaratnam, N. H. M. Yusoff, F. W. Suhaimi, R. Vadivelu, B. K. Vicknasingam, D. Amato, S. Hörsten, N. I. W. Ismail et al., “From Kratom to mitragynine and its derivatives: Physiological and behavioural effects related to use, abuse, and addiction,” Neuroscience & Biobehavioral Reviews, vol. 37, no. 2, pp. 138–151, 2013, doi: 10.1016/j.neubiorev.2012.11.012.
K. S. Grewal, “the Effect of Mitragynine on Man,” British Journal of Medical Psychology, vol. 12, no. 1, pp. 41–58, 1932, doi: 10.1111/j.2044-8341.1932.tb01062
E. M. Mudge and P. N. Brown, “Determination of mitragynine in Mitragyna speciosa raw materials and finished products by liquid chromatography with UV detection: Single-laboratory validation,” Journal of AOAC International, vol. 100, no. 1, pp. 18–24, 2017, doi: 10.5740/jaoacint.16-0220.
S. Pine, P. Pine, D. C. Ritter and A. G. Campbell, “Supercritical Carbon Dioxide Extraction of Mitragyna speciosa,” Reader's Digest Asia, vol. 23, no. 532, pp. 157–162, 1989.
V. S. Kislik, “Modern (Classical) Fundamental Principles of Solvent Extraction,” in Solvent Extraction, Oxford, UK: Elsevier, 2012, ch. 1, pp. 3–67, doi: 10.1016/b978-0-444-53778-2.10001-9.
J. G. Huddleston, H. D. Willauer, R. P. Swatloski, A. E. Visser and R. D. Rogers, “Room temperature ionic liquids as novel media for ‘clean’ liquid-liquid extraction,” Chemical Communications, no. 16, pp. 1765–1766, 1998, doi: 10.1039/A803999B.
F. Pena-Pereira, I. Lavilla and C. Bendicho, “Miniaturized preconcentration methods based on liquid-liquid extraction and their application in inorganic ultratrace analysis and speciation: A review,” Spectrochimica Acta Part B: Atomic Spectroscopy, vol. 64, no. 1, pp. 1–15, 2009, doi: 10.1016/j.sab. 2008.10.042.
David T. Harvey, “7.7: Liquid-Liquid Extractions,” ANALYTICAL CHEMISTRY 2.1, 2.1th ed. San Francisco, California, United States: LibreTexts, 2020, ch. 7, sec. 7, pp. 7.7.1. [Online]. Available:https://batch.libretexts.org/print/Letter/Finished/chem-220642/Full.pdf
J. Burke, “Solubility Parameters: Theory and Application,” cool.culturalheritage.org. https://cool. culturalheritage .org/coolaic/sg/bpg/annual/v03/bp03-04.html (accessed Oct. 29, 2021).
E. J. Shellard. and M. D. Lees, “The anatomy of the leaves of Milragyna speciosa Korth.,” Planta Medica, vol. 13, no. 3, pp. 280–290, 1965, doi: 10.1055/s-0028-1100122.
H. Takayama, M. Kurihara, M. Kitajima, I. M. Said and N. Aimi, “New indole alkaloids from the leaves of malaysian: Mitragyna speciosa,” Tetrahedron, vol. 54, no. 29, pp. 8433–8440, 1998, doi: 10.1016/S0040-4020(98)00464-5.
H. Takayama, “Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa,” Chemical and Pharmaceutical Bulletin, vol. 52, no. 8, pp. 916–928, 2004, doi: 10.1248/cpb.52.916.
K. Matsumoto , S. Horie, H. Ishikawa, H. Takayama, N. Aimi, D. Ponglux and K. Watanabe, “Antinociceptive effect of 7-hydroxymitragynine in mice: Discovery of an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa,” Life Sciences, vol. 74, no. 17, pp. 2143–2155, 2004, doi:10.1016/j.lfs.2003.09.054.
K. Matsumoto, H. Takayama, M. Narita, A. Nakamura, M. Suzuki, T. Suzuki, T. Murayama, S. Wongseripipatana, K. Misawa, M. Kitajima et al., “MGM-9 [(E)-methyl 2-(3-ethyl-7a,12a-(epoxyethanoxy)-9-fluoro-1,2,3,4,6,7,12,12b-octahydro-8-methoxyindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate], a derivative of the indole alkaloid mitragynine: A novel dual-acting μ- and κ-opioid agonist with potent antinociceptive and weak rewarding effects in mice,” Neuropharmacology, vol. 55, no. 2, pp. 154–165, 2008, doi: 10.1016/j.neuropharm.2008.05.003.
A. Sabetghadam, V. Navaratnam and S. M. Mansor, “Dose–Response Relationship, Acute Toxicity, and Therapeutic Index between the Alkaloid Extract of Mitragyna speciosa and Its Main Active Compound Mitragynine in Mice,” Drug Development Research, vol. 74, no. 1, pp. 23–30, 2013, doi: 10.1002/ddr.21052.
W. Reanmongkol, N. Keawpradub and K. Sawangjaroen, “Effects of the extracts from Mitragyna speciosa Korth. leaves on analgesic and behavioral activities in experimental animals,” Songklanakarin Journal of Science and Technology, vol. 29, no. SUPPL. 1, pp. 39–48, 2007.
M. L. Warner, N. C. Kaufman and O. Grundmann, “The pharmacology and toxicology of kratom: from traditional herb to drug of abuse,” International Journal of Legal Medicine, vol. 130, pp. 127–138, 2016, doi: 10.1007/s00414-015-1279-y.
CRC Handbook of Chemistry and Physics, CRC Press, Boca Raton, FL, USA, 2007.
(-)-Mitragynine, National Center for Biotechnology Information, 2004. [Online]. Available: https://pubchem. ncbi.nlm.nih.gov/compound/Mitragynine.
D. Hooper, “The anti-opium leaf.,” Pharmaceutical Journal, vol. 78, p. 453, 1907.
E. Field, “Mitragynine and mitraversine, two new alkaloids from species of mitragyne,” Journal of the Chemical Society Transactions, vol. 119, pp. 887–891, 1921.
W. I. Taylor, B. S. Joshi and Raymond-Hamet., “Structure of Mitragynine (9-Methoxycorynan- theidine),” Chemistry and Industry, vol. 54, p. 573, 1963.
D. E. Zacharias, R. D. Rosenstein, and G. A. Jeffrey, “The structure of mitragynine hydroiodide,” Acta Crystallographica, vol. 18, no. 6, pp. 1039–1043, 1965, doi: 10.1107/S0365110X650024 99.
E. J. Shellard, “Ethnopharmacology of kratom and the Mitragyna alkaloids.,” Journal of Ethnopharmacology, vol. 25, no. 1, pp. 123–124, 1989, doi:10.1016/0378-8741(89)90053-6.
P. J. Houghton, A. Latiff and I. M. Said, “Alkaloids from Mitragyna speciosa,” Phytochemistry, vol. 30, no. 1, pp. 347–350, 1991, doi: 10.1016/0031-9422(91)84152-I.
H. Takayama, “Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa,” Chemical and Pharmaceutical Bulletin, vol. 52, no. 8, pp. 916–928, 2004, doi: 10.1248/cpb.52.916.
S. N. Harizal, S. M. Mansor, J. Hasnan, J. K. J. Tharakan and J. Abdullah, “Acute toxicity study of the standardized methanolic extract of Mitragyna speciosa Korth in Rodent,” Journal of Ethnopharmacology, vol. 131, no. 2, pp. 404–409, 2010, doi: 10.1016/j.jep.2010.07.013.
S. Mansor, A. Sabetghadam and S. Ramanathan, “The evaluation of antinociceptive activity of alkaloid, methanolic, and aqueous extracts of Malaysian Mitragyna speciosa Korth leaves in rats,” Pharmacognosy Research, vol. 2, no. 3, p. 181, 2010, doi: 10.4103/0974-8490.65514.
A. R. Shamima, S. Fakurazi, M. T. Hidayat, I. Hairuszah, M. A. M. Moklas and P. Arulselvan, “Antinociceptive Action of Isolated Mitragynine from Mitragyna Speciosa through Activation of Opioid Receptor System,” International Journal of Molecular Sciences, vol. 13, no. 9, pp. 11427–11442, 2012, doi:10.3390/ijms130911427.
L. Orio, L. Alexandru, G. Cravotto, S. Mantegna and A. Barge, “UAE, MAE, SFE-CO2 and classical methods for the extraction of Mitragyna speciosa leaves,” Ultrasonics Sonochemistry, vol. 19, no. 3, pp. 591–595, 2012, doi:10.1016/j.ultsonch.2011.10.001.
J. Lara, D. Drolet, C. Hansen, A. Chollot, and N. Monta, “The use of the Hansen solubility parameters in the selection of protective polymeric materials resistant to chemicals.,” International Journal of Current Research, vol. 9, no. 3, pp. 47860–47867, 2017.
S. Parthasarathy, S. Ramanathan, V. Murugaiyah, M. R. Hamdan, M. I. M. Said, C. Lai and S. M. Mansor, “A simple HPLC–DAD method for the detection and quantification of psychotropic mitragynine in Mitragyna speciosa (ketum) and its products for the application in forensic investigation,” Forensic Science International, vol. 226, no. 1–3, pp. 183–187, Mar. 2013, doi:10.1016/j.forsciint.2013.01.014.
A. Pandey, S. Tripathi and C. A. Pandey, “Concept of standardization, extraction and pre phytochemical screening strategies for herbal drug,” Journal of Pharmacognosy and Phytochemistry, vol. 2, no. 5, pp. 115–119, 2014.
L. Boffa, C. Ghè, A. Barge, G. Muccioli and G. Cravotto, “Alkaloid Profiles and Activity in Different Mitragyna speciosa Strains,” Natural Product Communications, vol. 13, no. 9, pp. 1111–1116, 2018, doi:10.1177/1934578X1801300904.
A. Sharma, S. H. Kamble, F. León, N. J. -Y. Chear, T. I. King, E. C. Berthold, S. Ramanathan, C. R. McCurdy and B. A. Avery, “Simultaneous quantification of ten key Kratom alkaloids in Mitragyna speciosa leaf extracts and commercial products by ultra‐performance liquid chromatography−tandem mass spectrometry,” Drug Testing and Analysis, vol. 11, no. 8, pp. 1162–1171, Aug. 2019, doi: 10.1002/dta.2604.
R. R. Mustafa, R. Sukor, S. M. Mohd Nor, N. Saari, and F. A. Azri, “Enhancing extraction yield and purity of mitragynine from mitragyna speciosa through sequential solvent extraction and characterisation using nmr technique,” International Journal of Scientific & Technology Research., vol. 9, no. 3, pp. 3846–3854, 2020.
L. Flores-Bocanegra, H. A. Raja, T. N. Graf, M. Augustinović, E. D. Wallace, S. Hematian, J. J. Kellogg, D. A. Todd, N. B. Cech and N. H. Oberlies, “The Chemistry of Kratom [ Mitragyna speciosa ]: Updated Characterization Data and Methods to Elucidate Indole and Oxindole Alkaloids,” Journal of Natural Products, vol. 83, no. 7, pp. 2165–2177, 2020, doi: 10.1021/acs.jnatprod.0c00257.
J. H. Hildebrand, R. L. Scott, “Book Reviews,” in Regular Solutions Englewood Cliffs, NJ, USA: Prentice-Hall International Series in Chemistry, 1962, pp. 431.
J. K. Fink, “Terpene Resins,” in Reactive Polymers Fundamentals and Applications, Oxford, UK: William Andrew, 2013, ch. 12, pp. 303–315, doi: 10.1016/b978-1-4557-3149-7.00012-7.
B. C. Roughton, J. White, K. V. Camarda and R. Gani, “Simultaneous Design of Ionic Liquids and Azeotropic Separation Processes,” Computer Aided Chemical Engineering, vol. 29, pp. 1578–1582, 2011, doi: 10.1016/B978-0-444-54298-4.50094-5.
H. J. Vandenburg, A. A. Clifford, K. D. Bartle, R. E. Carlson, J. Carroll and I. D. Newton, “A simple solvent selection method for accelerated solvent extraction of additives from polymers,” Analyst, vol. 124, no. 11, pp. 1707–1710, 1999, doi: 10.1039/a904631c.
C. M. Hansen, “Hansen Solubility Parameters of Asphalt, Bitumen, and Crude Oils,” in Hansen solubility parameters: A user’s handbook, 2nd ed., Boca Raton, FL, USA: CRC Press,2007, ch. 9, sec. 1, pp. 158.
C. M. Hansen, “The Three Dimensional Solubility Parameter and Solvent Diffusion Coefficient. Their Importance in Surface Coating Formulation,” Journal Paint Technology, vol. 39, pp. 104, 1967.
E. Stefanis and C. Panayiotou, “Prediction of Hansen Solubility Parameters with a New Group-Contribution Method,” International Journal of Thermophysics, vol. 29, pp. 568–585, 2008, doi: 10.1007/s10765-008-0415-z.
L. Constantinou and R. Gani, “New group contribution method for estimating properties of pure compounds,” AIChE Journal, vol. 40, no. 10, pp. 1697–1710, 1994, doi: 10.1002/aic.690401011.
R. K. Henderson, C. Jiménez-González, D. J. C. Constable, S. R. Alston, G. G. A. Inglis, G. Fisher, J. Sherwood, S. P. Binks and A. D. Curzons, “Expanding GSK’s solvent selection guide –embedding sustainability into solvent selection starting at medicinal chemistry,” Green Chemistry, vol. 13, no. 4, pp. 854–862, 2011, doi: 10.1039/c0gc00918k.
R. Gani, “PROCAPE Computer-aided Tool for Property Estimation,” pseforspeed.com. https://www.pseforspeed.com/cpt_product/procape (accessed Oct. 27, 2022).
R. Kikura-Hanajiri, M. Kawamura, T. Maruyama, M. Kitajima, H. Takayama and Y. Goda, “Simultaneous analysis of mitragynine, 7-hydroxymitragynine, and other alkaloids in the psychotropic plant ‘kratom’ (Mitragyna speciosa) by LC-ESI-MS,” Forensic Toxicology, vol. 27, pp. 67–74, 2009, doi: 10.1007/s11419-009-0070-5.
G. T. Beng, M. R. Hamdan, M. J. Siddiqui, M. N. Mordi and S. M. Mansor, “A simple and cost effective isolation and purification protocol of mitragynine from mitragyna speciosa korth (ketum) leaves,” The Malaysian Journal of Analytical Sciences, vol. 15, no. 1, pp. 54–60, 2011.
Y. S. Goh, T. Karunakaran, V. Murugaiyah, R. Santhanam, M. H. Abu Bakar and S. Ramanathan, “Accelerated Solvent Extractions (ASE) of Mitragyna speciosa Korth. (Kratom) Leaves: Evaluation of Its Cytotoxicity and Antinociceptive Activity,” Molecules, vol. 26, no. 12, 2021, Art. no. 3704, doi:10.3390/molecules26123704.
D. Xie, J. Jin, J. Sun, L. Liang, X. Wang, W. Zhang, X. Wang and Q. Jin, “Comparison of solvents for extraction of krill oil from krill meal: Lipid yield, phospholipids content, fatty acids composition and minor components,” Food Chemistry, vol. 233, pp. 434–441, 2017, doi: 10.1016/j.foodchem.2017.04.138.
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