Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (sileneside D, 1) from S. jeniseensis Willd., apigenin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-8-C-α-L-arabinopyranoside (sileneside E, 2) and genkwanin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-8-C-α-L-arabinopyranoside (sileneside F, 3) from S. italica (L.) Pers., and apigenin-6-C-(2″-O-β-D-xylopyranosyl)-β-D-glucopyranoside-7-O-(6″″-O-feruloyl)-β-D-glucopyranoside (sileneside G, 4) from S. dioica (L.) Clairv. The structures of 1–4 were studied using UV, IR, and NMR spectroscopy and mass spectrometry.
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References
M. Richardson, Biochem. Syst. Ecol., 6, 283 (1978).
V. N. Darmograi, Chem. Nat. Compd., 13, 102 (1977).
D. N. Olennikov, N. I. Kashchenko, and N. K. Chirikova, Khim. Rastit. Syr′ya, No. 3, 119 (2019).
O. Mastenbroek, H. C. Prentice, R. Kamps-Heinsbroek, J. van Brederode, G. J. Niemann, and G. van Nigtevecht, Plant Syst. Evol., 141, 257 (1983).
D. N. Olennikov, N. K. Chirikova, N. I. Kashchenko, V. M. Nikolaev, S.-W. Kim, and C. Vennos, Front. Pharmacol., 9, 756 (2018).
W. Bylka and I. Matlawska, Acta Pol. Pharm., 54, 331 (1997).
C. A. Williams, A. L. Toscano De Brito, J. B. Harborne, J. Eagles, and P. G. Waterman, Phytochemistry, 37, 1045 (1994).
A. Marston, K. Hostettmann, and A. Jacot-Guillarmod, Helv. Chim. Acta, 59, 2596 (1976).
M. Jay, B. Voirin, A. Hasan, J.-F. Gonnet, and M.-R. Viricel, Biochem. Syst. Ecol., 8, 127 (1980).
J. Van Brederode and R. Kamps-Heinsbroek, Z. Naturforsch., C: J. Biosci., 36, 486 (1981).
K. Hoffmann-Bohm, H. Lotter, O. Seligmann, and H. Wagner, Planta Med., 58, 544 (1992).
A. Obmann, I. Werner, A. Presser, M. Zehl, Z. Swoboda, S. Purevsuren, S. Narantuya, C. Kletter, and S. Glasl, Carbohydr. Res., 346, 1868 (2011).
K. R. Markham and K. A. Mitchell, Z. Naturforsch., C: J. Biosci., 58, 53 (2003).
R. T. Sherwood, M. Shamma, J. L. Moniot, and J. R. Kroschewsky, Phytochemistry, 12, 2275 (1973).
V. Plouvier, M.-T. Martin, and J.-P. Brouard, Phytochemistry, 25, 546 (1986).
J. Liu, Y. Liu, Z. Dai, L. He, and S. Ma, J. Anal. Methods Chem., 2017, 4934309 (2017).
C. Xie, N. C. Veitch, P. J. Houghton, and M. S. J. Simmonds, Chem. Pharm. Bull., 51, 1204 (2003).
M. L. Bouillant, F. F. de Arce, J. Favre-Bonvin, J. Chopin, A. Zoll, and G. Mathieu, Phytochemistry, 23, 2653 (1984).
F. Senatore, M. D’Agostino, and I. Dini, J. Agric. Food Chem., 48, 2659 (2000).
J. Peng, G. Fan, Z. Hong, Y. Chai, and Y. Wu, J. Chromatogr. A, 1074, 111 (2005).
E. Besson, G. Dellamonica, J. Chopin, K. R. Markham, M. Kim, H.-S. Koh, and H. Fukami, Phytochemistry, 24, 1061 (1985).
T. Iwashina, A. Uehara, J. Kitajima, and T. Yukawa, Bull. Natl. Mus. Nat. Sci., Ser. B, 41, 33 (2015).
G. Zhou, H. Wu, T. Wang, R. Guo, J. Xu, Q. Zhang, L. Tang, and Z. Wang, Phytochem. Lett., 19, 241 (2017).
D. N. Olennikov and N. K. Chirikova, Chem. Nat. Compd., 55, 1032 (2019).
M. Ohkawa, J. Kinjo, Y. Hagiwara, H. Hagiwara, H. Ueyama, K. Nakamura, R. Ishikawa, M. Ono, and T. Nohara, Chem. Pharm. Bull., 46, 1887 (1998).
M.-A. Dubois, A. Zoll, M.-L. Bouillant, and J. Chopin, Phytochemistry, 21, 1141 (1982).
V. A. Kurkin, Chem. Nat. Compd., 39, 123 (2003).
M. Bokern, S. Heuer, V. Wray, L. Witte, T. Macek, T. Vanek, and D. Strack, Phytochemistry, 30, 3261 (1991).
M. A. Zielinska-Pisklak, D. Kaliszewska, M. Stolarczyk, and A. K. Kiss, J. Pharm. Biomed. Anal., 102, 54 (2015).
D. N. Olennikov, N. I. Kashchenko, N. K. Chirikova, A. G. Vasil′eva, A. I. Gadimli, J. I. Isaev, and C. Vennos, Antioxidants, 8, 307 (2019).
D. N. Olennikov, N. K. Chirikova, N. I. Kashchenko, T. G. Gornostai, I. Y. Selyutina, and I. N. Zilfikarov, Int. J. Mol. Sci., 18, 2579 (2017).
M. Akabane, A. Yamamoto, S. Aizawa, A. Taga, and S. Kodama, Anal. Sci., 30, 739 (2014).
D. N. Olennikov, A. I. Gadimli, J. I. Isaev, N. I. Kashchenko, A. S. Prokopyev, T. N. Katayeva, N. K. Chirikova, and C. Vennos, Metabolites, 9, 271 (2019).
V. M. Malikov and M. P. Yuldashev, Chem. Nat. Compd., 38, 358 (2002).
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The studies were sponsored by FASO Russia (AAAA-AA17-117011810037-0).
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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2020, pp. 884–890.
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Olennikov, D.N., Kashchenko, N.I. New C,O-Glycosylflavones from the Genus Silene. Chem Nat Compd 56, 1026–1034 (2020). https://doi.org/10.1007/s10600-020-03220-x
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DOI: https://doi.org/10.1007/s10600-020-03220-x