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Isolation and Structure Elucidation of Soulatro Coumarin from Stem Bark

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Isolation and Structure Elucidation of Soulatro Coumarin from Stem Bark Indonesian Journal of Cancer Chemoprevention, June 2011 ISSN: 2088–0197 e-ISSN: 2355-8989 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 Jamilah Abbas1*, Achmad Darmawan1 and Syafruddin2 1Research Centre for Chemistry, Indonesian Institute of Sciences PUSPIPTEK. Serpong. 15314. Indonesia 2 Eijkman Institute for Molecular Biology, Diponegoro street no 69, Jakarta 104310. Indonesia 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. INTRODUCTION Andaman, Solomon Island, Northern Australia and Malaysia (Suryanegara et al., 1994). In Calophyllum soulattri Burm F [(local these research the stem bark of C. soulattri name: Sulatri (Sunda), slatri (Java), malang- Burm F (Guttiferae Family) was used and malang (Bangka)]. Vernacular Name : bintagor collected from Jaya Pura (Irian Island) in labu (Malaysia). Bintagor lanchar, mintak Indonesia. (Peninsular). C. soulattri is a wide spread but The bark, roots and latex of C. soulattri in many places rather uncommon tree of fairly are used in local as folk medicine. The fruits small dimentions, growing in lowland or lower are edible but sour. The latex may be used to montane rain forest or sometimes in swamp poison dogs. forest, up to 1700 m altitute. (Soerianegara et al., 1994). C. soulattri distributed in West Java, Central Java, Irian and Kalimantan Island and also distributed in Vietnam, Cambodia, Thailand, *Corresponding author email: [email protected] 242 Abbas, et al., 2011 Indones. J. Cancer Chemoprevent., 2(2), 242-254 A number of medicinal and therapeutic coumarin showed the most potent as anticancer properties have been described to various parts (Abbas, 2008). of C. soulattri, e.i root and leaves, including the We now report the isolation, structural treatment of rheumatism, varicose veins, elucidation and evaluation of the hemorrhoids and chronic ulcers (Crane et al., antiplasmodial activity of natural soulatro 2005). coumarin isolated from C. soulattri, in vivo Root and leaves of C. soulattri also used evaluation of the antiplasmodial activity has as rheumatic pain. Seed or other species are been done by using mice which it’s infected by used for scabies, ringworm, as an analgesic in Plasmodium berghei. leprosy, dermatoses, as diuretic, gonorrhea, The Genus Calophyllum is well known tumors, migraine and vertigo (Crane et al., as a source of biologically active compound 2005). In the Bulolo area in Papua New Guinea such us xanthones (Reye-Chipa et al., 1997; (PNG) the plant used for several diseases, such Kijjoa et al., 2000; Limuna, M et al., 1993), as dry skin, high blood pressure and malaria terpenoids (Cao et al., 1998), neoflavonoid (Khan et al., 2002). The balsem from the bark (Dharmaratne et al., 1984). Coumarin (Guilet et of Calophyllum sp used as a cicatrisan, infusion al., 2001 and Ito et al., 2003). Xanthones, or decoction of the leaves has been traditionally terpenoides, neoflavonoid were found in related used as an eye remedy in Asian (Iinuma et al., species. 1993). Prenylated xanthones have been Kalazeyloxanthone has been isolated reported to show antibacterial and antifungal from the root bark of C. soulattri by activities (Dharmaratne et al., 1997). The Dharmaratne (Dharmaratne et al. at 1984) anticancer activity of new coumarin was also (Fig.1) investigated against HeLa cell line and the new O OH HO O OH O O O O OH Figure 1. Structure of kalazeyloxanthone Figure 2.Structure of dombakinaxanthone Dombakinaxanthone (diprenylated coumarin (aziz coumarin) has also been chromenxanthone) has been isolated from the isolated from stem bark of other species of cold hexane extract of the root bark of C. Calophyllum, that coumarin has antimalarial soulattri (Dharmaratne et al., 1993) (Fig. 2). and cytotoxic acrivity (Abbas et al., 2009) (Fig. Jayapuracoumarin has also been isolated from 4). One kalocoumarin (brasimarin C) have also stem bark of C. soulattri that Jayapuracoumarin success isolated from C incrasaptum, that has antioxidant and antiplasmodial acrivity kalocoumarin has antimalarial activity too (Abbas et al., 2009) (Fig. 3). One new (Abbas et al., 2009) (Fig. 5). 243 Abbas, et al., 2011 Indones. J. Cancer Chemoprevent., 2(2), 242-254 O H 1 2 O 3 H 4 4a 2' 9 1' 3' 8a 5 6' 4' 5' O O 5a O O O 8 Me 8-Me 6 7 O O 7-Me Figure 3. Structure of Jayapuracoumarin Figure 4. Structures of new coumarin Figure 5. Structure of kalocoumarin (Aziz coumarin) (Brasimarin C) Three coumarin (teysmanone A, previously reported from stem bark and leaves teysmanone B, calanone) and two coumarin of C. soulattri by Samarawera (1983), and one (iophyllum C and iophyllum D) have been coumarin (soulatrolide) has also been isolated isolated from C teysmannii and C inophyllum from stem bark of C soulattri (Fig.6). respectively (Cao 1998) ). Two soulatro coumarine (pyranocoumarin) has been 4' 4' 4' 2' 5' 3' 5' 3' 5 13 5' 3' 14 12 2' 6' 6' 3 6' 1' 2' 1' 2' 11 O O OH 22' 1' 2' 2' OMe 6 4 5 4 5a 5 4 6 4a 4a 6 5 4 10 7 4a 3 3 3 12 7 2 8 9a 2 6a 2 8 10 HO 8a O 13 O 10a O 7 10a 10b O O O O 1 9 1 O 11 1 9 8 10 12' 62' 52' O O 2' 22' 9 O 6 2' 42' 2 2' 2' 32' 5 3 42' Teysmanone A Teysmanone B Calanone 4' 4' 5' 3' 14 15 14 5' 3' 13 15 6' 13 1' 2' 6' 12 O 1' 2' 12 O 5 4 11 6 4a 5 4 3 11 6 4a 3 6a 2 6a 2 10a 10b 7O O 10a 10b 7O O 1 12 O O 8 10 1 9 8 9 10 O O Inophyllum C Inophyllum E Figure 6. Structures of some coumarins (Teysmanoe A,.B, Calanone,Inophyllum C and Inophyllum D Two soulatro coumarine Samarawera (1983) and one coumarin (pyranocoumarin) has been previously reported (soulatrolide) has been isolated from stem bark from stem bark and leaves of C. soulattri by of C. soulattri. (Fig.7). 244 Abbas, et al., 2011 Indones. J. Cancer Chemoprevent., 2(2), 242-254 4' 5' 3' 14 15 13 6' 1' 2' 12 O 5 4 11 6 4a 3 6a 2 10a 7 10b O O O 1 8 9 10 OH Figure 7. Structure of soulatrolide from C. Soulattri Other author were repoted soulatro were used for column chromatography. coumarin as anticancer (Cao 1998a), anti HIV Precoated silica gel at alluminium plates (silica (Gustafon, 1994) and three new coumarins also gel 60 F254) were used for analytical TLC. Spot has cancer chemopreventive activity (Ito et al., were visualized by UV (254 and 365 nm), 2003). In this communication, we report the FeCl3 and 10% H2SO4 were used as spraying isolation and structure elucidation of a soulatro reagent followed by heating at 110oC. coumarin from stem bark of C. soulattri as antiplasmodial. C. soulattri was choised as a Plant Material source of antiplasmodial drug candidate, The stem bark of C. soulattri was because C. soulattri content some coumarin colected from Irian Island, Indonesia and the compounds, and according to some refferences, voucher specimen was identified and deposited coumarin have antiplasmodial activity. at the Herbarium Bogorience – LIPI. Bogor, Resistance of plasmodium to antimalarial Indonesia. drugs and their toxicity are contributing factors to the spread of the disease. This highlights the Extraction and Isolation of Plant need to develop quickly more effective and Materials less toxic new antimalarial drugs from C. The dried and powdered of the stem soulattri. The isolation of soulatro coumarin bark of C. soulattri (1 kg) was maserated by will be explained in the experimental methanol (3 x 2 litre x 7 days), solvent was procedures. removed under reduced pressured by rotary evaporator to gave 109,47 g methanol extract, MATERIALS AND METHODS which was then suspended in water and partitioned with n-hexane, dichloromethane and General Experimental Procedures ethyl acetate.
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