C-/O-GLYCOSYL FLAVONES OF SILENE ITALICA
Abstract
Chemical research of Silene genus focused on the study of terpene compounds including ecdysteroids and triterpenoids, to the detriment of other classes of compounds. One of these poorly estimated group of substances are flavonoids, namely C-/O-glycosyl flavones, widely represented within the family Caryophyllaceae. Early studies revealed the presence of some C-glycosyl flavones (Zemtsova, Dzhumyrko, 1976; Darmogray, 1977), but a detailed study of the flavonoids was not conducted. Application of high performance chromatography with diode-array detection and electrospray ionization mass-spectrometry detection (HPLC-DAD-ESI-MS) allowed to found 14 flavonoids, which are C-, O- and C,O-glycosyl flavones in the aerial part of S. italica of Georgia origin. Ten components were discovered in S. italica for first time. The identified C-glycosides included monoglycosides as isoorientin, isovitexin, isoscoparin (chrysoeryol-6-C-glucoside) and diglycosides as carlinoside (luteolin-6-C-glucoside-8-C-arabinoside), schaftoside (apigenin-6-C-glucoside-8-C-arabinoside), isoschaftoside (luteolin-6-C-arabinoside-8-C-glucoside) and genkwanin-6-C-glucoside-8-C-arabinoside. Two O-glycosides, cosmosiin and cynaroside, and mixed C,O-glycosides as saponarin, isovitexin-2′′-O-arabinoside, isovitexin-6′′-O-arabinoside and O-hexosides od schaftosude and genkwanin-6-C-glucoside- 8-C-arabinoside were not previously identified in Silene genus. The known literature data (Mamadalieva et al., 2014) and the present data demonstrate the useful role of C-/O-glycosyl flavones in the systematics of the genus Silene.
Downloads
References
Mamadalieva N.Z., Lafont R., Wink M. Diversity, 2014, vol. 6, pp. 415–499. DOI: 10.3390/d6030415.
Mamadalieva N.Z. Bol. Latinoamer. Caribe Plantas Med. Arom., 2012, vol. 11, pp. 474–497.
Flora SSSR [Flora of the USSR], ed. V.L. Komarov. Moscow, Leningrad, 1936, vol. VI, pp. 577–691. (in Russ.).
Meng Y., Whiting P., Zibareva L., Bertho G., Girault J.-P., Lafont R., Dinan L. J. Chromatogr. A., 2001, vol. 935, pp. 309–319. DOI: 10.1016/S0021-9673(01)00893-7.
Zibareva L. Arch. In-sect. Biochem. Physiol, 2000, vol. 43, no. 1, pp. 1–8. DOI: 10.1002/(SICI)1520-6327(200001)43:1%3C1::AID-ARCH1%3E3.0.CO;2-D
Darmograi V.N. Chem. Nat. Comp., 1977, vol. 13, pp. 102–103. DOI: 10.1007/BF00566187.
Olennikov D.N., Kashchenko N.I. Chem. Nat. Comp., 2017, vol. 53, pp. 1199–1201. DOI: 10.1007/s10600-017-2239-1.
Olennikov D.N. Chem. Nat. Comp., 2019, vol. 55, pp. 107–110. DOI: 10.1009/s11720-012-2242-4.
Zemtsova G.N., Dzhumyrko S.F. Farmatsiya, 1976, vol. XXV, no. 3, pp. 26–29. (in Russ.).
Siewek F., Herrmann K. Grotjahn L., Wray V. Z. Naturforsch. C, 1985, vol. 40, pp. 8–12. DOI: 10.1515/znc-1985-1-204.
Wirasutisna K.R., Gleye J., Moulis C., Stanislas E., Moretti C. Phytochemistry, 1986, vol. 25, pp. 558–559. DOI: 10.1016/S0031-9422(00)85531-4.
Hostettmann K., Jacot-Guillarmod A. Helv. Chim. Acta, 1976, vol. 59, pp. 1584–1591. DOI: 10.1002/hlca.19760590517.
Bouillant M.L., Ferreres de Arce F., Favre-Bonvin J., Chopin J., Zoll A., Mathieu G. Phytochemistry, 1984, vol. 23, pp. 2653–2657. DOI: 10.1016/S0031-9422(00)84119-9.
Olennikov D.N., Chirikova N.K., Kashchenko N.I., Nikolaev V.M., Kim S.-W., Vennos C. Front. Pharmacol., 2018, vol. 9, article 756. DOI: 10.3389/fphar.2018.00756.
Olennikov D.N., Kashchenko N.I., Chirikova N.K., Gornostai T.G., Selyutina I.Yu., Zilfikarov I.N. Int. J. Molec. Sci., 2017, vol. 18, E2579. DOI: 10.3390/ijms18122579.
Li Q., Wang L., Dai P., Zeng X., Qi X., Zhu L., Yan T., Wang Y., Lu L., Hu M., Wang X., Liu Z. J. Chromatogr. A, 2015, vol. 1395, pp. 116–128. DOI: 10.1016/j.chroma.2015.03.069.
Chopin M.J., Bouillant M.L., Wagner H., Galle K. Phytochemistry, 1974, vol. 13, pp. 2583–2586. DOI: 10.1016/S0031-9422(00)86940-X.
Oxelman B., Rautenberg A., Thollesson M., Larsson A., Frajman B., Eggens F., Petri A., Aydin Z., Töpel M., Brandtberg-Falkman A. Sileneae taxonomy and systematics, 2013, URL: http://www.sileneae.info.
Copyright (c) 2019 Khimiia rastitel'nogo syr'ia (Chemistry of plant raw material)
This work is licensed under a Creative Commons Attribution 4.0 International License.
This work is licensed under a Creative Commons Attribution 4.0 International License.
The authors, which are published in this journal, agree to the following conditions:
1. Authors retain the copyright to the work and transfer to the journal the right of the first publication along with the work, at the same time licensing it under the terms of the Creative Commons Attribution License, which allows others to distribute this work with the obligatory indication of the authorship of this work and a link to the original publication in this journal .
2. The authors retain the right to enter into separate, additional contractual agreements for the non-exclusive distribution of the version of the work published by this journal (for example, to place it in the university depository or to publish it in a book), with reference to the original publication in this journal.
3. Authors are allowed to post their work on the Internet (for example, in a university repository or on their personal website) before and during the review process of this journal, as this may lead to a productive discussion, as well as more links to this published work.
