Isolation and Structure Elucidation of Soulatro Coumarin From Stem Bark of Calophyllum soulattri Burm F and In Vivo Antiplasmodial Activity by Using Mice Infected by Plasmodium berghei
Abstract
The soulatro coumarin compound was isolated and elucidated from the stem bark of Calophyllum soulattri Burm F, the samples were collected from Jayapura Papua Irian Island in Indonesia. Isolation process was done by maceration at room temperature in methanol, than partitioned in a mixture of n hexane-water (1:1), followed by dichloromethane-water (1:1) and ethyl acetate-water (1:1). A portion of ethyl acetate extract was subjected to column chromatography over silica gel packed and eluted with n-hexane a gradient of ethyl acetate to 100% followed by CHCl3 in MeOH (20:1, 10 :1, 5:1, 1:1). Fraction B (CHCl3 in MeOH 20:1) was subjected to column chromatography over silica gel 300 mesh and eluted with EtOAc-MeOH mixtures of increasing polarity. Faction with the same Rf valeus were combined and eluted with EtOAc-MeOH (19:1) showed one spot on TLC. They were combined and evaporated to yield a solid than was recrystallized in mixture of CH2Cl2-methanol to give soulatro coumarin compound. The structure was determinated by spectroscopic analysis, in particular by 1D and 2D NMR techniques, from these spectra data conclution that compound is soulatro coumarin. Antimalarial assay was tested against Plasmodium berghei parasite as in vivo using 18 mices rodent wich was infected by Plasmodium berghei parasite. The soulatro coumarin showed activity against P. berghei with dosage 0.0005867 mM/1 kg body weight ; 0.005867 mM/1 kg bw; 0.05867 mM/1 kg bw; 0.5867 mM/1 kg bw 5.867 mM/1 kg bw and 58.67 mM/1 kg bw could inhibite growth rate of parasite = 57.32%; 63.37%; 43.02%; 53.49%; 47.67% respectively.
Keywords : Antiplasmodial activity, coumarin, Calophyllum soulattri Burm. F, in vivo, Chloroquine, Plasmodium berghei.
Full Text:
PDFReferences
Abbas, J., 2008, Isolation and structure elucidation biological active compound from C. soulattrii Burm. F., C. incrasaptum M. R. Henderson and Wyatt Smith and C. tomentosum Wright., Doctoral Disertation, University of Indonesia, Jakarta.
Abbas. J., Hanafi, M., Kardono, L.B.S., Que-Wei Qin. and Kosela, S., 2009, Cytotoxic coumarin from Calophyllum Incrasaptum M.R Henderson & Wyatt-Smith (Guttiferae), Int. J. Appl. Chem., 4(3), 205-208.
Abbas. J., M. Hanafi. and Kardono L.B.S., 2009, Antioksidant Activity of Coumarin Compound From Stem Bark Of Calophyllum Incrasaptum, Proceeding of Natural Products Simposium XIV. Natural Products Resources as Well Known for Treatment of Cancer.
Abbas. J., Nina, A.S., Hanafi, M., 2009, Antimalarial Activity of Some Plants Traditionally Used in Treatment of Malaria in Indonesia, Proceding Chemistry Seminar XVIII. Santika Hohel, Yogyakarta.
Akhouri, R.R., Sharma, A., Malhota, P. and Sharma, A., 2008, Role of Plasmodium falciparum thrombospondin-related Anonymous Protein in Host-cell interactions, Malar. J., 7(63), 1-11. CrossRef
Ampofo, S.A. and Waterman, P.G., 1986, Xanthones and neoflavonoids from Two Asian Species of Calophyllum, Phytochemistry, 25(11), 2617-2620. CrossRef
Bennett, G.J., and Lee, H.H., 1989, Xanthones from Guttiferae, Phytochemistry, 28(4), 967-998. CrossRef
Cao, S.G., Sim. K.W., Pereira. J. and Goh, S.H, 1998a, Coumarins from Calophyllum teysmannii, Phytochemistry., 47(5), 773-777. CrossRef
Cao, S.G., Wu, X.H., Sim, K.Y., Tan, Benny, H.K., Vittal, J.J., Pereira, J.T. and Goh, S.H., 1998b, Minor coumarins from Calophyllum teysmannii var inophylloide and Synthesis of Cytotoxic Calanone Derivates, Helv. Chim. Acta., 81(5), 1404-1416. CrossRef
Crane, S., Aurore, G., Joseph, H., Mouloungui, Z. and Bourgeois, P., 2005, Composition of Fatty Acids Triacylglycerols and Unsaponifiable Matter in Calophyllum calaba L. Oil from Guadeloupe, Phytochemistry., 66(15), 1825-1831. CrossRef
Dharmaratne, H,R,W. and Nishanthi, W.M. Wijesinghe, 1997, Trioxygenated Diprenylated Chromenxanthone from Calophyllum Moonii, Phytochemistry., 46(7), 1293-1295. CrossRef
Dharmaratne, H,R,W., Sotheeswaran, S., Balasubramaniam, S., 1984, Triterpenes and Neoflavonoids of Calophyllum lankaesis and Calophyllum thwaitesii, 23(11), 2601-2603.
Dharmaratne, H.R.W., Perera. D.S.M., Marasinghe. G.P.K .and Jamie, 1999, A Chromene Acid From Calophyllum Cordato-Oblongum, Phytochemistry, 15(1), 111-113. CrossRef
Fotie, J., Nkkengfack, A.E., Rukunga, G., Tolo, F., Peter, M.G., Heydenreich, M., et al., 2003, In Vivo Antimalarial Activity of Some Oxygenated Xanthones, Ann. Trop. Med. Parasitol, 97(7), 683-688. CrossRef
Guilet, D., Seraphin, D., Rondeau, D., Richommme, P. and Bruneton, J., 2001, Cytotoxic coumarin from Calophyllum dispar, Phytochemistry, 58(4), 571-575. Link
Gustafon K.R., Bokesch.H.R., Fuller.R.W., Cardellina. J.H., Kadushin. M.R., Soejarto.D.D., et al., 1994, Calanone, A Novel Coumarin From Calophyllum teysmannii, Tetrahedron Lett., 35(32), 5821-5824. CrossRef
Hay, A.E., Hélesbeux, J.J., Duval, O., Labaïed, M., Grellier, P. and Richomme P., 2004, Antimalarial xanthones from Calophyllum caledonicum and Garcinia vieillardii, Life Sci., 75(25), 3077-3085. CrossRef
Ignatuschenko, M.V., Winter, R.W., Bachinger, H.P., Hinrichs, D.J. and Riscoe, M.K., 1997., Xanthones As Antimalarial Agents: Studies of A Possible Mode of Action, FEBS Lett., 409(1), 67-73. Link
Ito C., Itoigawa, M., Mishina, Y., Filho, C,V., Enjo, F., Tokuda, H., et al., 2003, Chemical Consttuent of Calophyllum Brasiliense : Structure of The Three New Coumarin And Cancer Chemopreventive Activity of 4-Subtituted Coumarin, J. Nat. Prod., 66(3), 368-371. CrossRef
Khan M.R., Kihara, M. and Omoloso.A.D, 2002, Antimicrobial Activity of Calophyllum Soulattri, Fitoterapia, 73(7-8), 741-743. Link
Kijjoa,A., Gonzales,M.J., Afonso, C,M., Pinto, M.M., Anantachoke, C. and Herz, W., 2000, Xanthon from Calophyllum teysmannii var. inophylloide, Phytochemistry, 53(8), 1021-1024. Link
Krungkrai, S.R., 2001, Activity of Some Oxygenated Xanthones, Ann. Trop. Med. Parasitol, 97(7), 683-688.
Limuna, M., Tosa, H., Tanaka, T. and Yonemori, S., 1993, Two Xanthones From Root Bark Of Calophyllum Inophyllum, Phytochemistry, 35(2), 527-532. CrossRef
Reyes-Chilpa, R., Estrada-Muñiz, E., Apan, T.R., Amekraz, B., Aumelas, A., Jankowski, C.K., et al, 2004, Cytotoxic Effects Of Mammea Type Coumarins From Calophyllum Brasiliense, Life Sci., 75(13), 1635-1647. CrossRef
Samarawera., Ravelanjato B. and Kuneneshch N., 1983, Pyranocoumarin from the Stem Bark and Leaves of C. Soulattri, Phytochemistry, 26(11), 2973-2987.
Soerianegara, I. and Lemmens, R.H.M.J, 1994, Plant Resources of South-East Asia, Timber Trees Mayor Commercial Timber, Prosea, 5(1), 610-817. Link
Trager, W. and Jensen, J.B., 1976, Human Malarial Parasites In Continuous Culture, Science, 193(4254), 673-675. Link
DOI: http://dx.doi.org/10.14499/indonesianjcanchemoprev2iss2pp242-254
Copyright (c) 2017 Indonesian Journal of Cancer Chemoprevention
Indexed by:
Indonesian Society for Cancer Chemoprevention