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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Two New Chalcone Glycoside Compounds from Viburnum lantana (Family Caprifoliaceae) and Antioxidant Activity of its Hydroalcoholic Extract

Author(s): Ali Shafaghat* and Mohammad Shafaghatlonbar

Volume 16, Issue 2, 2019

Page: [93 - 98] Pages: 6

DOI: 10.2174/1570178615666180925125213

Price: $65

Abstract

In the present study, two novel chalcone glycosides, trans-3-ethoxy-4-O-(glucopyranoside) -2', 3', 4', 5', 6' -pentahydroxy chalcone (compound 1) and trans-3-methoxy-4-O-(glucopyranoside) -2', 3', 4', 5', 6' -pentahydroxy chalcone (compound 2) have been isolated from the leaves of Viburnum lantana L. The structures were elucidated by using 1H-NMR, 13C-NMR, 2D-NMR such as HMQC, HMBC and NOE experiments and UV-Vis, MS and IR spectra. The antioxidant property of hydroalcoholic extract was evaluated by DPPH style. The results revealed that the leave extract possesses significant antioxidant activity (IC50 = 52 µg/mL). This study indicates that hydroalcoholic extract of the leaves from this species is an important source of chalcone and flavonoid derivatives, as well as of useful natural antioxidants. These chalcone glycoside compounds were isolated for the first time from V. lantana leaves.

Keywords: Chalcone, Viburnum lantana, Caprifoliaceae, hydroalcoholic extract, antioxidant activity, HMBC.

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[1]
Mozaffarian, V. A Dictionary of Iranian Plant Names; Farhang Moaser Publishers: Tehran, Iran, 2007.
[2]
Prabhu, K.; Karar, P.K.; Hemalatha, S.; Ponnudurai, K. Int. J. Pharm. Ind. Res., 2011, 1, 219-241.
[3]
Altun, M.L.; Citoglu, G.S.; Yilmaz, B.S.; Coban, T. Int. J. Food Sci. Nutr., 2008, 59(3), 175-180.
[4]
Dajas, F.; Arredondo, F.; Echeverry, C.; Ferreira, M.; Morquio, A.; Rivera, F. Curr. Neuropharmacol., 2005, 3, 193-205.
[5]
Yilmaz, N.; Yayli, N.; Misir, G.; Cosuncelebi, K. Asian J. Chem., 2008, 20(5), 3324-3330.
[6]
Jovanovic, S.V.; Steenken, S.; Tosic, M.; Marjanovitz, B.; Simic, M.G. J. Am. Chem. Soc., 1994, 116, 4846-4851.
[7]
Akhavan, M.; Jahangiri, S.; Shafaghat, A. Ind. Crops Prod., 2015, 63, 114-118.
[8]
Jyothi, M.V.; Prasad, Y.R.; Venkatesh, P.; Sureshreddy, M. Chem. Sci. Trans., 2012, 1(3), 716-722.
[9]
Akihisa, T.; Tokuda, H.; Ukiya, M.; Iizuka, M.; Schneidera, S.; Ogasawara, K.; Mukainaka, T.; Iwatsuki, K.; Suzuki, T.; Nishino, H. Cancer Lett., 2003, 20, 133-137.
[10]
Potter, J.D. Lancet, 2005, 366, 527-530.
[11]
Fathy, M.S.; Afaf, H.S.; Amal, E.K.; Shahera, M.E. Molecules, 2002, 7, 245-251.
[12]
Kang, T.H.; Jeong, S.J.; Ko, W.G.; Kim, N.Y.; Lee, B.H.; Inagaki, M.; Miyamoto, T.; Higuchi, R.; Chui, K.Y. J. Nat. Prod., 2000, 63, 680-681.
[13]
Singh, V.P.; Bineeta, Y.; Pandey, V.B. Phytochemistry, 1999, 51, 587-590.
[14]
Demole, E.; Enggist, P. Helv. Chim. Acta, 1974, 7, 2087-2091.
[15]
She, G.; Guo, Z.; Haining, L.V.; She, D. Molecules, 2009, 14, 4190-4196.
[16]
Mathela, D.K.; Pant, A.K.; Mathela, C.S. Phytochemistry, 1984, 23, 2090.
[17]
Gao, Y.M.; Wang, M.Z.; Wang, J.P.; Zhao, Q.; Qin, H.Y.; Mu, H.J.; Guan, G.J. Chin. Tradit. Herbal Drugs, 1995, 26, 568-569.
[18]
Shafaghat, A.; Pirfarshi, F.; Shafaghatlonbar, M. Ind. Crops Prod., 2014, 62, 533-536.
[19]
Almahy, H.A.; Rahmani, M.; Sukari, M.A.; Ali, A.M. Pertanika J. Sci. Technol., 2003, 11(1), 73-81.
[20]
Akhavan, M.; Shafaghat, A.; Salimi, F. Nat. Prod. Res., 2013, 27(22), 2111-2117.
[21]
Fuendjiep, V.; Wandji, J.; Tillequin, F.; Mulholland, D.A.; Budzikiewicz, H.; Fomum, Z.T.; Nyemba, A.M.; Koch, M. Phytochemistry, 2002, 60(8), 803-806.
[22]
Giuseppina, C.; Luis, M.E.; Alessandra, B.; Nunziatina, T. J. Nat. Prod., 2003, 66(8), 1061-1064.
[23]
Yoshimura, M.; Sano, A.; Kamei, J.I.; Obata, A. J. Agric. Food Chem., 2009, 57(14), 6432-6437.
[24]
Harborne, J.B. Phytochemical Methods; Chapman & Hall: London, 1973, pp. 47-121.
[25]
Markham, K.R.; Ternai, B.; Stanly, R.; Geiger, H.; Mabry, T.J. Tetrahedron, 1978, 34, 1389-1397.
[26]
Porter, L.J. Advances in Research.. In: Harborne JB. (Eds.) The Flavonoids, Chapman & Hall: London, . , 1994.
[27]
Harborne, J.B.; Williams, C.A. Advances in Flavonoid Research; Chapman & Hall: London, 2000.
[28]
Chu, Y.H.; Chang, C.L.; Hsu, H.F. J. Sci. Food Agric., 2000, 80, 561-566.
[29]
Paulraj, R.; Hakraborty, K. Food Chem., 2010, 122, 31-41.
[30]
Shaidi, F.; Anitha, P.K.; Wanasundara, P.D. Crit. Rev. Food Sci. Nutr., 1992, 2, 67-103.
[31]
Markham, K.R. Techniques of Flavonoid Identification; Academic Press: London, 1982.
[32]
Mabry, T.J.; Markham, K.R.; Thomas, M.B. The Systematic Identification of Flavonoids; Springer: Berlin, 1970.
[33]
Reddy, M.K.; Reddy, M.V.B.; Jayakrishna, G.; Gunasekar, D.; Aux, C.; Bodo, B. Chem. Pharm. Bull., 2003, 51(2), 191-193.
[34]
Kiplimo, J.J.; Shahidul-Islam, M.D.; Koorbanally, N.A. Nat. Prod. Commun., 2011, 6(12), 1847-1850.
[35]
Hyun, K.S.; Ju, S.K.; Sam, S.K. Helv. Chim. Acta, 2010, 93, 2045-2051.
[36]
Feng, W.S.; Zheng, X.K.; Liu, Y.B.; Kuang, H.X. J. Asian Nat. Prod. Res., 2007, 9(1), 85-89.
[37]
Cheung, L.M.; Cheung, P.C.K.; Ooi, V.E.C. Food Chem., 2003, 81, 249-255.

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