Fatma Sri Wahyuni1, Khozirah Shaari2, Johnson Stanslas3, Nordin HJ Lajis2, Dachriyanus Hamidi1,4
1Faculty of Pharmacy, Andalas University, Kampus Limau Manis, 4Faculty of Nursing, Andalas University, Padang, West Sumatra 25163, Indonesia, 2Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 3Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400 UPM, Serdang, Selangor, Malaysia
ABSTRACT
Objective: To isolate compounds from the roots of Garcinia cowa and to evaluated their cytotoxic activity against breast (MCF-7), prostate (DU-145), and lung (H-460) cell lines. Materials and Methods: The ground air-dried root was sequentially macerated with hexane, dichloromethane (DCM), ethyl acetate (EtOAc), and methanol. The DCM soluble extract was fractionated by vacuum liquid chromatography, column chromatography, and radial chromatography over silica gel with hexane, EtOAc and methanol as eluent in progressively increasing polarity manner; to yield three compounds. Their structures were elucidated based on their spectroscopic data and their comparison with those of the literature. The cytotoxicity of isolated compounds was carried out against human cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide colorimetric assay. The extract was added at various concentrations (0.1, 1, 10 and 100 µg/ ml). The level of cytotoxicity was determined by calculating the level of IC50 that was based on the percentage of the cell death following the 24 h incubation with the extract. Results: Phytochemical study on the roots of G. cowa
yielded rubraxanthone (3), cowanine (4) and 1,5-dihydroxyxanthone (5). Compound 4 with an IC50 value of 4.1 ± 1.0 µM, 5.4 ± 2.3 µM and 11.3 ± 10.0
µM against MCF-7, H-460, and DU-145, respectively while compound 3 was found to be in active. Conclusion: The results indicate that G. cowa roots could be important sources of natural cytotoxic compounds.
Key words: Cytotoxic activity, DU-145, Garcinia cowa Roxb., H-460, MCF-7, nuclear magnetic resonance, spectroscopy, structure elucidation, xanthone
SUMMARY
tIsolation of cytotoxic compounds from Garcinia cowa
tCowanine is the active constituent from the roots of Garcinia cowa tComplete nuclear magnetic resonance assignment of isolated compounds
tMS fragmentation of rubraxanthone.
Correspondence:
Prof. Dachriyanus Hamidi,
Faculty of Pharmacy, Andalas University, Padang, West Sumatra 25163, Indonesia. JO *OEJB<> BOE UIF CBSL BT BO BOUJQZSFUJD BHFOU JOhBJMBOE<> 4PNF
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Cite this article as: Wahyuni FS, Shaari K, Stanslas J, Lajis NH, Dachriyanus H.
Cytotoxic properties and complete nuclear magnetic resonance assignment of isolated xanthones from the root of Garcinia cowa Roxb.. Phcog Mag 2016;12:S52-S6.
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Cytotoxic Properties and Complete Nuclear Magnetic Resonance
Assignment of Isolated Xanthones from the Root of
Garcinia
MATERIALS AND METHODS
General
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The isolation of cowanin 4, rubraxanthone 3 and
1,5-dihyroxyxanthone 5 from the roots of
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CONCLUSION
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Figure 2: EI-MS fragmentation of rubraxanthone 3
Table 2: The 1H-NMR, 13C-NMR, COSY and HMBC data of cowanin 4
Position δC δH HMBC
-
-
-
)T C-2, C-4a, C-9a
B -
)T C-6, C-7, C-8a
B -
-
-
-
-B -
-
-B -
)E+ C-2, C-1, C-2’, C-3’
)U+ C-4’, C-5’
-
)T C-2’, C-3’, C-5’
-
)T C-2’, C-3’, C-4’
)E+ C-7, C-8, C-8a, C-3’, C-2’
)U+ C-9’, C-5’
-
)CU+ C-3’C-9’C-2’C-5’C-6’C-7’
)CU+ C-4’, C-5’, C-3’, C-2’, C-9’
U)CU+
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T) C-10’, C-7’, C-6’
T) C-5’$, C-2’
T) C-8’, C-7’, C-6’
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Acknowledgments
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Financial support and sponsorship
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Con
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REFERENCES
1.Rao RR. Ethnobotany of Meghalaya: Medicinal plants used by Khasi and Garo tribes. Econ Bot 1981;35:4-9.
2.na Pattalung P, Thongtheeraparp W, Wiriyachitra P, Taylor WC. Xanthones of Garcinia cowa. Planta Med 1994;60:365-8.
3.Murakami A, Jiwajinda S, Koshimizu K, Ohigashi H. Screening for in vitro anti-tumor promoting activities of edible plants from Thailand. Cancer Lett 1995;95:139-46.
4.Jantan I, Jumuddin FA, Saputri FC, Rahman K. Inhibitory effects of the extracts of Garcinia
species on human low-density lipoprotein peroxidation and platelet aggregation in relation to
their total phenolic contents. J Med Plants Res 2011;5:2699-709.
5.Shen J, Yang JS. Two new xanthones from the stems of Garcinia cowa. Chem Pharm Bull (Tokyo) 2006;54:126-8.
6.Jena BS, Jayaprakasha GK, Sakariah KK. Organic acids from leaves, fruits, and rinds of
Garcinia cowa. J Agric Food Chem 2002;50:3431-4.
7.Mahabusarakam W, Chairerk P, Taylor WC. Xanthones from Garcinia cowa Roxb. latex. Phytochemistry 2005;66:1148-53.
8.Panthong K, Pongcharoen W, Phongpaichit S, Taylor WC. Tetraoxygenated xanthones from the fruits of Garcinia cowa. Phytochemistry 2006;67:999-1004.
9.Wahyuni FS, Lindsay TB, Dachriyanus, Dianita R, Jubahar J, Lajis NH, et al. A new ring-reduced tetraprenyltoluquinone and a prenylated xanthone from Garciniacowa. Aust J Chem 2004;57:223-6.
10.Mosmann T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55-63.
11.Ampofo SA, Waterman PG. Xanthones from three Garcinia species. Phytochemistry 1986;25:2351-5.
12.Silverstein RM, Webster FX. Spectrometric Identiication of Organic Compounds. 6th ed.
Singapore: Wiley; 1997.
13.Lee HH, Chan HK. 1,3,6-Trihydroxy-7-methoxy-8-(3,7-dimethyl-2,6-octadienyl) xanthone from
Garciniacowa. Phytochemistry 1977;16:2038-40. Table 3:1H-NMR, 13C-NMR and HMBC data of 1,5-dihydroxyxanthone 5
Position δC δH HMBC
-
)CE+)[ C-9a, C-4
)U+)[ C-4a, C-1
)CE+)[ C-2, C9a, C-4a
B -
-
-B -
)EE+BOE)[ C-5a, C-8
)U+)[ C-6, C-5
)EE+BOE)[ C-9, C-5a, C-6
B -
-
-B -
-1-O) - )CT C-2, C-9a
5-O) - )CT
-).#$)FUFSPOVDMFBSNVMUJQMFCPOEDPSSFMBUJPO/.3/VDMFBSNBHOFUJD SFTPOBODF
Table 4: Cytotoxic activity of isolated compounds toward three cancer cell lines
Compound IC50 (μM)
MCF-7 H-460 DU-145
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ABOUT AUTHOR
Prof. Dachriyanus Hamidi, is chair of Research Laboratory at Faculty of Pharmacy, Andalas University. He involve in Drug Discovery Research at Faculty of Pharmacy, Andalas University.
