New flavonoid glycoside from Vicia faba L.
الموضوعات :
1 - Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut 71524, Egypt
الکلمات المفتاحية: HPLC, New flavonoid glycoside, <i>Vicia faba</i> L, 1D and 2D NMR analyses,
ملخص المقالة :
Kaempferol 4´-O-α-rhamnopyranosyl-3-O-α-rhamnopyranosyl-(1→6)-β- glucopyranoside (1), a new flavonoid glycoside, along with eight known ones (2-9) were isolated from the flowers of Vicia faba L. (Leguminosae) which were identified as kaempferol 3-O-α-arabinopyranosyl-5-O-α-rhamnopyranoside (2), kaempferol 7-O-α-rhamnopyranoside (3), kaempferol 3-O-α-arabinopyranosyl- 7-O-α-rhamnopyranoside (4), kaempferol 3-O-rutinoside (5), kaempferol 3-O-α-rhamnopyranosyl-(1→3)-β-galactopyranosyl-7-O-α-rhamnopyranoside (6), kaempferol-3-O-β-galactopyranosyl-7-O-α-rhamnopyranoside (7), kaempferol-3-O-α-rhamnopyranosyl(1→6)-β-galactopyranosyl-7-O-α- rhamnopyranoside (8) in addition to a quercetin derivative; quercitin-3´-O-α- rhamnopyranosyl-4´-(3´´-acetyl)-β-galactopyranoside (9). Structure elucidation of the new compound was established based on 1D and 2D NMR analyses including 1H-, 13C-NMR, and HMBC experiments, in addition to HR-TOF-MS spectrometry using matrix assisted laser desorption ionization (MALDI).
Allam, A.E., Nafady, A.M., Nakagawa, T., Takemoto, N., Shimizu, K., 2017. Effect of polyphenols from Vicia faba L on lipase activity and melanogenesis. Nat. Prod. Res. 2, 1-6.
Amarowicz, R., Pegg, R.B., 2008. Legumes as a source of antioxidants. Eur. J. Lipid Sci. Tech. 110, 865-878.
Bouchenak, M., Lamri-Senhadji, M., 2013. Nutritional quality of legumes, and their role in cardiometabolic risk prevention: a review. J. Med. Food. 16, 1-14.
Crépon, K., Marget, P., Peyronnet, C., Carrouée, B., Arese, P., Duc, G., 2010. Nutritional value of faba bean (Vicia faba L.) seeds for feed and food. Field Crops Res. 115(3), 329-339.
Duc, G., 1997. Faba bean (Vicia faba L.). Field Crops Res. 53(1), 99-109.
Mejri, F., Selmi, S., Martins, A., Baati, T., Chaabane, H., Njim, L., Serralheiro, M.L., Rauter, A.P., Hosni, K., 2018. Broad bean (Vicia faba L.) pods: a rich source of bioactive ingredients with antimicrobial, antioxidant, enzyme inhibitory, anti-diabetic and health-promoting properties. Food Funct. 9, 2051-2069.
Hasegawa, T., Takano, F., Takata, T., Niiyama, M., Ohta, T., 2008. Bioactive monoterpene glycosides conjugated with gallic acid from the leaves of Eucalyptus globulus. Phytochemistry 69, 747-753.
Zhou, J., Xie, G., Yan, X., 2011. Encyclopedia of Traditional Chinese Medicines-Molecular Structures. SSBM. 4, 423.
Kapinová, A., Kubatka, P., Kružliak, P., Mokáň, M., Péč, M., Kassayová, M., Bojková, B., Dobrota, D., 2015. Chlorella pyrenoidosa, young barley and fruit peel polyphenols in rat breast cancer model-the effects on plasma lipid metabolism. Biologia (Bratisl) 70(2), 268-272.
Ablajan, K., Abliz, Z., Shang, X.Y., He, J.M., Zhang, R.P. and Shi, J.G., 2006. Structural characterization of flavonol 3,7-di-O-glycosides and determination of the glycosylation position by using negative ion electrospray ionization tandem mass spectrometry. J. Mass Spectrom. 41,352-360.
Köpke, U., Nemecek, T., 2010. Ecological services of faba bean. Field Crops Res. 115(3), 217-233.
Lambert, J.B., Shurvell, H.F., Lightner, D.A., Cooks, R.G., 1998. Organic Structural Spectroscopy. Prentice Hall, New Jersey. 320-352.
Manguro, L.O.A., Ugi, I., Lemmen, P., Hermann, R., 2003. Flavonol glycosides of Warburgia ugandensisleaves. Phytochemistry. 64, 891-896.
Markham, K.R., Ternai, B., Stanley, R., Geiger, H., Mabry, T.J., 1978. Carbon-13 NMR studies of flavonoids—III. Tetrahedron 34, 1389-1397.
Mulvihill, E.E., Huff, M.W., 2010. Antiatherogenic propertises of flavonoids: Implications for cardiovascular health. Can J. Cardiol. 26, 17-21.
Petpiroon, N., Suktap, C., Pongsamart, S., Chanvorachote, P., Sukrong, S., 2015. Kaempferol-3-O-rutinoside from Afgekia mahidoliae promotes keratinocyte migration through FAK and Rac1 activation. J. Nat. Med. 69(3), 340-348.
Piotr G., Cristina M., Małgorzata K., Juana F. 2014. Non-nutritive compounds in Fabaceae family seeds and the improvement of their nutritional quality by traditional processing-a review. Pol. J. Food Nutr. Sci. 64(2), 75-89.
Rabey, J.M., Vered, Y., Shabtai, H., Graff, E., Harsat, A., Korczyn, A.D., 1993. Broad bean (Vicia faba) consumption and Parkinson’s disease. Adv. Neurol. 60, 681-684.
Susanne, N., Sascha R., Monika, S., 2015. Identification of complex, naturally occurring flavonoid glycosides in Vicia faba and Pisum sativum leaves by HPLC-DAD-ESI-MSn and the genotypic effect on their flavonoid profile. Food Res. Int. 76, 114-121.
Veit, M., Pauli, G.,1999. Major flavonoids from Arabidopsis thaliana leaves. J. Nat. Prod. 62, 1301-1303.
Wynne, G., Graeme, W., Tom, S., Gavin, R., 1999. Epicuticular waxes and volatiles from faba bean (Vicia faba) flowers. Phytochemistry 52(4), 607-612.
Xu, L.R., Zhou, P., Zhi, Y.E., Wu, J., Zhang, S., 2009. Three new flavonol triglycosides from Derris trifoliata. J. Asian Nat. Prod Res. 11(1),79-84.