Separation of xanthone and vitamin E from Calophyllum inophyllum leaf
Keywords:C. inophyllum leaf, polarity, recovery, soxhlet solvent extraction, vitamin E
Calophyllum inophyllum (nyamplung) has many advantages start from stems, leaves, roots, to seeds. Indonesian society generally only know that seeds can produce biodiesel. Nyamplung leaves have bioactive compounds, such as xanthone that can be used for medical purposed. Recently, quantification of xanthone and vitamin E in the nyamplung leaf still doesn’t exist. This research aims to isolate and quantify the content of xanthone and vitamin E from the crude nyamplung leaf. The separation is done through liquid-liquid extraction with methanol and petroleum ether (PE) to obtain two layers namely non-polar fraction (PE fraction) and polar fraction (methanol fraction). The mass ratio of solvent mixture-to-crude extract (10,30, 50 and 70) and the mass ratio of PE-to-methanol (1 and 3) were applied and analyzed by TLC, GC-MS, and UV-Vis. Xanthones (0.150 equilibrium constant, 15.16% purity and 94.43% recovery) were obtained in the methanol fraction based on the mass ratio of solvent mixture-to-crude extract of 70 and mass ratio of PE-to-methanol at 1.From GC-MS, Xanthones were detected in the methanol fraction with quality of 94% and Vitamin E was detected in the petroleum ether fraction with quality of 99%.
Aparamarta, H. W., Saputra, T., Claratika, A., Ju, Y. H., Gunawan, S. 2016. Separation and purification of triacylglycerols from Nyamplung (Calophyllum inophyllum) oil by batchwise solvent extraction. Ind. Eng. Chem. Re. 55, 3113–3119.
Aparamarta, H. W., Qadariyah, L., Ju, Y. H., Gunawan, S. 2018. Separation and identification of fatty acid in triacylglycerols isolated from Calophyllum inophyllum Oil. JEAS. 3, 442-451.
Ali, M. S., Mahmud, S., Perveen, S., Ahmad, V. U., Rizwani, G. H. 1999. Epimers from the leaves of Calophyllum inophyllum. Phytochem. 50, 1385-1389.
Atabani, A. E., Cesar, A. D. 2014. Calophyllum Inopyllum L. – A prospective non-edible biodiesel feedstock. Study of Biodiesel production, properties, fatty acid composition, blending and engine performance. Renew. Sust. Energ Rev. 37, 644–655.
Crane, S., Aurore, G., Joseph, H., Mouloungui, Z., Bourgeois, P. 2005. Composition of fatty acids triacylglycerols and unsaponifiable matter in Calophyllum calaba L. oil from Guadeloupe. Phytochem. 66, 1825-1831.
Forestry Department. 2008. Nyamplung (Callophyllum Inophyllum L.). Potential source of biofuel energy. The center information of forest (Indonesia).
Fylaktakidou, K. C., Hadipavlou-Litina, D. J., Litinas , K.E., Nicolaides, D. N. 2004. Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities. Curr. Pharm. 10, 3813-3833.
Goli, A. H., Barzegar, M., Sahari, M. A. 2004. Antioxidant activity and total phenolic compounds of pistachio (Pistachia vera) hull extracts. Food Chem. 92, 521–525.
Gunawan, S., Fabian, C., Ju, Y. H. 2008. Isolation and purification of fatty acid steryl esters from soybean oil deodorizer distillate. Ind. Eng. Chem. Res. 47, 7013-7018.
Hathurusingha, S., Ashwath, N., Midmore, D. 2011. Periodic variation in Kernel oil content and fatty acid profiles of Callophyllum Inophyllum L.: A potential biodiesel feedstock in Australia. Biomass. Bioenerg. 35, 3448-3452.
Heyne, K. 1987. The useful plant in Indonesia. Badan Litbang Kehutanan (Indonesia), 3, 1375-1378.
Iinuma, M., Tosa, H., Tanaka, T., Yonemori, S. 1994. Two Xanthones from root bark of Calophyllum inophyllum. Phytochem. 35, 527-532.
Itoigawa, M., Ito, C., Tan, H. T. W., Kuchide, M., Tokuda, H., Nishino, H., Furukawa, H. 2001. Cancer chemopreventive agents, 4-phenylcoumarins from Calophyllum inophyllum. Cancer Lett. 169, 15-19.
Ito, C., Itoigawa, M., Miyamoto, Y., Rao, K. S., Takayusu, J., Okuda, Y., Mukainaka, T., Tokuda, H., Nishino, H., Furukawa, H. A. 1999. New biflavonoid from Calophyllum panciflrorum with Antitumor-Promoting Activity. J. Nat. Prod. 62 , 1668-1671.
Jung, J., Kin, J., Park, O. S. A. 2001. Convenient one-pot synthesis of 4-hydroxycoumarin, and 4-hydroxyquinolin-2(1H)-one. Synth. Commun. 31, 1195-1200.
Khan, N. U., Parveen, N., Singh, M. P., Singh, R., Achari, B. 1996. Two isomeric benzodipyranone derivatives from Calophyllum inophyllum. Phytochem. 42, 1181-1183.
Kondo, M., Zhang, L., Ji, H., Kou, Y., Ou, B. 2009. Bioavailability and antioxidant effects of a Xanthone-Rich Mangosteen (Garcina mangostana) product in humans. J. Agric. Food Chem. 57, 8788-8792.
Kumar, S. S., Samydurai, P., Ramakrishnan, R., Nagarajan, N. 2014. Gas chromatography and mass spectrometry analysis of bioactive constituents of adiantum capillus –veneris L. Int. J. Pharm. Pharm. Sci. 6, 60-63.
Kumar, A., Kumar, T. A., Raheman, H. 1976. Biodiesel production from jatropha oil (Jatropha curcas) with high free fatty acids: An optimized process. Biomass. Bioenerg. 31, 569-575.
Lim, T. K. 2012. Calophyllum inophyllum. Fruits in Edible Medicinal and non-medicinal Plants. Netherland: Springer, 7-20.
Montgomery, D. C. 2005. Design and analysis of experiments. New York: John Wiley and Sons, Inc.
Noldin, V. F., Isaias, D. B., Filho, V. C. 2006. Calophyllum genus: Chemical and pharmacological importance. Quim. Nova. 29, 549-554.
Palempalli, U. D., Gandhi, U., Kalantari, P., Vunta, H., Arner, R. J., Narayan, V., Ravindran, A., Prabhu, K. S. 2009 Gambogic acid covalently modifies IκB kinase-β subunit to mediate suppression of lipopolysaccharide-induced activation of NF-κB in macrophages. Biochem. J. 419, 401-409.
Patil, A. D., Freyer, A. J., Eggleston, D. S., Haltiwanger, R. C., Bean, M. F., Taylor, P. B., Caranfa, M. J., Breen, A. L., Bartus, H. R., Johnson, R. K., Hertzberg, R. P., Westly, J. W. 1993. The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum Linn. J. Med. Chem. 36, 4131-4138.
Sadek, Paul. 2002. The HLPC Solvent Guide. United States of America: Wiley of Interscience.
Sahoo, P. K., Das, L. M., Babu, M. K. G., Naik, S. N. 2007. Biodiesel development from high acid value polanga seed oil and performance evaluation in a CI engine. Fuel. 86, 448–454.
Sathyaselvabala, V., Ponnusamy, S., Periyaraman, P. M., Selvaraj, D. K., Thangaraj, V., Subramanian, S. 2011. Two step biodiesel production from Calophyllum inophyllum oil : Studies on thermodynamic and kinetic modelling of modified zeolite catalysed pre-treatment. Can. J. Chem. Eng. 9999, 1-8.
Shiu, P., Gunawan, S., Hsieh, W. H., Kasim, N. S., Ju, Y. H. 2010. Biodiesel production from rice bran by a two-step in-situ proces. Bioresour. Technol. 101, 984-989.
Singh, S. P., Singh, D. 2010. Biodiesel production through the use of different sources and characterization of oils and their esters as the substitute of diesel : A review. Renew. Sust. Energ. Rev. 14, 200–216.
Su, X. H., Zhang, M. L., Li, L. G., Huo, C. H., Gu, Y. C. 2008. Chemical constituent of the plants of the genus Calophyllum. Chem. Biodivers. 5, 2579-2608.
Susanto, D. F., Aparamarta, H. W., Widjaja, A., Gunawan, S. 2017. Identification of phytochemical compounds in Calophyllum inophyllum leaves. Asian Pac. J. Trop. Biomed. 7, 773-781.
Syukriah, A. R., Liza, M. S., Harisun, Y., Fadzillah, A. A. M. 2014. Effect of solvent extraction on antioxidant and antibacterial activities from Quercus infectoria (Manjakani). Int. Food. Res. J. 21, 1067-1073.
Venkanna, B. K., Reddy, C. V. 2009. Biodiesel production and optimization from Calophyllum inophyllum linn oil (honne oil) – A three stage method. Bioresour. Technol. 100, 5122–5125.
Whitney, E., Sharon, R. R. 2011. In Peggy, W. (ed). Understanding Nutrition (Twelfth ed.). California: Wadsworth, Cengage Learning.
Wong, R. H. X., Berry, N. M., Coates, A. M., Buckley, J.D., Bryan, J., Kunz, I., Howe, P. R. C. 2013. Chronic resveratrol consumption improves brachial flow-mediated dilatation in healthy obese adults. J. Hypertens. 31, 1819–1827.
Ye, F., Liang, Q., Li, H., Zhao, G. 2015. Solvent effects on phenolic content, composition, and antioxidant activity of extracts from florets of sunflower (Helianthus annuus L.). Ind. Crops Prod. 76, 574–581.
Yimdjo, M. C., Azebaze, A. G., Nkengfack, A. E., Meyer, A. M., Bodo, B. 2004. Antimicrobial and cytotoxic agents from Calophyllum inophyllum. Phytochem. 65, 2789-2795.
Yoswathana, N. 2013. Accelerated extraction of Xanthone from Mangosteen pericarp using ultrasonic technique. Afr. J. Pharm. Pharmacol. 7, 302-309.