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Isolation and Characterization of Flavonoids Isolated from Leaves of Benalu Jeruk (Scurrula fusca G. Don) as Antioxidant
Corresponding Author(s) : Helmina Br. Sembiring
Asian Journal of Chemistry,
Vol. 29 No. 8 (2017): Vol 29 Issue 8
Abstract
Two flavonoids were isolated from leaves of Benalu Jeruk (Scurrula fusca G. Don) by extracting the leaves powder with methanol. The methanol extract was partitioned with ethyl acetate. The ethyl acetate extract was then partitioned further with mixture of methanol and n-hexane. The methanolic layer was separated and hydrolyzed with 2 N HCl to give flavonoid aglycon. This flavonoid aglycon was purified by column chromatography (SiO2, chloroform-methanol = 100:0 ~ 80:20) to produce two flavonoids, flavonoid A (3,7-dihydroxy-5-methyl-3’,4’-dihydrofurano-flavonol) and flavonoid B (3,5,7,4’-tetrahydroxyflavonol or kaempferol). The antioxidant activity test for flavonoids A and B gave IC50 9.383 and 8.713 mg/mL respectively with ascorbic acid as comparison (IC50 12.08 mg/mL). Chemical structure was determined based on spectroscopy data interpretation [FT-IR, UV, 1-D NMR (1H NMR, 13C NMR and DEPT), 2-D NMR (1H-1H COSY, 1H-13C HMQC, 1H-13C HMBC) and LC-MS].
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- S. Chatterjee, Z. Niaz, S. Gautam, S. Adhikari, P.S. Variyar and A. Sharma, Food Chem., 101, 515 (2007); https://doi.org/10.1016/j.foodchem.2006.02.008.
- P. Molyneux, Songklanakarin J. Sci. Technol., 26, 211 (2004).
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- H. Shibuya, K. Ohashi and I. Kitagawa, Pure Appl. Chem., 71, 1109 (1999); https://doi.org/10.1351/pac199971061109.
- J.P. Fisher, G.K. Phoenix, S.W. Smith, M.C. Press and D.D. Cameron, Redistriguting the Wealth: Interactions Between Plant Parasitism and Parasite Litter in Semi-Natural Grassland Crassland Communities, 11th World Congress on Parasitic Plants, Martina Franca, Italy, 7-12 June (2011).
- M.C. Press and G.K. Phoenix, New Phytol., 166, 737 (2005); https://doi.org/10.1111/j.1469-8137.2005.01358.x.
- V. Barao, G. Von Arx and G.C.T. Ceccantini, Modification on Wood Hydraulic Conductivity and Embolism Increase in Tipuana Tipu Parasitized by Struthanthus vulgaris, 11th World Congress on Parasitic Plants, Martina Franca, Italy, 7-12 June (2011).
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- P.J. Deshmukh, Int. J. Adv. Biotechnol. Res., 2, 431 (2011).
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- H.B. Sembiring, T. Barus, L. Marpaung and P. Simanjuntak, Int. J. PharmTech. Res., 8, 24 (2015).
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- K. Biemann, Spectral Data for Structure Determination of Organic Compounds, Springer-Verlag Berlind Heildelberg (1983).
- P.F. Pinheiro and G.C. Justino, in ed. V. Rao, Structural Analysis of Flavonoids and Related Compounds – A Review of Spectroscopic Applications, In: Phytochemicals – A Global Perspective Their Role in Nutrition and Health, InTech, Chap. 2, pp. 33-56 ( 2012).
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References
S. Chatterjee, Z. Niaz, S. Gautam, S. Adhikari, P.S. Variyar and A. Sharma, Food Chem., 101, 515 (2007); https://doi.org/10.1016/j.foodchem.2006.02.008.
P. Molyneux, Songklanakarin J. Sci. Technol., 26, 211 (2004).
T. Ishizu, H. Winarno, E. Tsujino, T. Morita and H. Shibuya, Chem. Pharm. Bull. (Tokyo), 50, 489 (2002); https://doi.org/10.1248/cpb.50.489.
H. Shibuya, K. Ohashi and I. Kitagawa, Pure Appl. Chem., 71, 1109 (1999); https://doi.org/10.1351/pac199971061109.
J.P. Fisher, G.K. Phoenix, S.W. Smith, M.C. Press and D.D. Cameron, Redistriguting the Wealth: Interactions Between Plant Parasitism and Parasite Litter in Semi-Natural Grassland Crassland Communities, 11th World Congress on Parasitic Plants, Martina Franca, Italy, 7-12 June (2011).
M.C. Press and G.K. Phoenix, New Phytol., 166, 737 (2005); https://doi.org/10.1111/j.1469-8137.2005.01358.x.
V. Barao, G. Von Arx and G.C.T. Ceccantini, Modification on Wood Hydraulic Conductivity and Embolism Increase in Tipuana Tipu Parasitized by Struthanthus vulgaris, 11th World Congress on Parasitic Plants, Martina Franca, Italy, 7-12 June (2011).
J.B. Runyon, J.F. Tooker, M.C. Mescher and C.M.D. Modreas, Parasitic Plants in Agriculture: Chemical Ecology of Germination and Host- Plant Location as Targets for Sustainable Control: A Review Springer Science+Business Media B.V., pp. 123-136 (2009).
P.J. Deshmukh, Int. J. Adv. Biotechnol. Res., 2, 431 (2011).
F.H. Bamane, J.H. Badr and O.A.R.M. Amin, Afr. J. Biotechnol., 11, 14380 (2012); https://doi.org/10.5897/AJB12.2093.
H.B. Sembiring, T. Barus, L. Marpaung and P. Simanjuntak, Int. J. PharmTech. Res., 8, 24 (2015).
B. Ginting, L. Marpaung, T. Barus and P. Simanjuntak, Asian J. Chem., 28, 199 (2016); https://doi.org/10.14233/ajchem.2016.19342.
J. Dai and R.J. Mumper, Molecules, 15, 7313 (2010); https://doi.org/10.3390/molecules15107313.
K.R. Markham and M.B. Thomas, The Systematic Identification of Flavonoids, Springer-Verlag, New York-Heidelberg-Berlin (1970).
K. Biemann, Spectral Data for Structure Determination of Organic Compounds, Springer-Verlag Berlind Heildelberg (1983).
P.F. Pinheiro and G.C. Justino, in ed. V. Rao, Structural Analysis of Flavonoids and Related Compounds – A Review of Spectroscopic Applications, In: Phytochemicals – A Global Perspective Their Role in Nutrition and Health, InTech, Chap. 2, pp. 33-56 ( 2012).
J.H. Simpson, Organic Structure Determination Using 2-D NMR Spectroscopy A Problem-Based Approach, Elsevier Inc., Canada (2008).
S.P. Piaru, R. Mahmud, A.M.S. Abdul Majid and Z.D. Mahmoud Nassar, Asian Pac. J. Trop. Med., 5, 294 (2012); https://doi.org/10.1016/S1995-7645(12)60042-X.