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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.
Highlights
Химические исследования указывают на присутствие в представителях рода различных классов соединений, в том числе экдистероидов, моно, сескви- и тритерпеноидов, простых фенолов, флавоноидов, N-содержащих соединений и других [1]
Chemical research of Silene genus focused on the study of terpene compounds including ecdysteroids and triterpenoids, to the detriment of other classes of compounds
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
Summary
Для этого измельченное растительное сырье (610 г) экстрагировали 70% этанолом (1 : 15) в УЗ-ванне (100 Вт, частота 35 кГц) при 40 °С в течение 3 ч дважды. Анализ осуществляли на жидкостном хроматографе LCMS-8050 (Shimadzu, Columbia, MD, USA), соединенном с диодно-матричным детектором (ДМД) и 3Q детектором с ионизацией электрораспылением (ИЭР/МС; electrospray ionization, ESI), используя колонку GLC Mastro C18 (150×2.1 мм, Ø 3 мкм; Shimadzu, Kyoto, Japan). Фракцию SPE-2 разделяли с использованием препаративной ВЭЖХ [колонка LiChrospher® 100 RP-18 (250×10 мм, Ø 10 мкм; Dionex, Sunnyvale, CA, USA); элюент A – вода, элюент В – ацетонитрил; программа градиента – 0–20 мин 10–20% B, 20–60 мин 20–100% B, 60–64 мин 100% B; скорость потока – 2 мл/мин, температура колонки – 30 °C] порциями по 0.5 г, собирая фракции с временами выхода 12.0–12.5 мин (фракция f-24) и 14.5–15.0 (фракции f-29), которые рехроматографировали в тех же условиях дважды. Спектр ЯМР 13С (125 Гц, МеОН-d4, d, м.д.): 163.5 (С-2), 102.1 (С-3), 181.3 (С-4), 160.1 (С-5), 107.3 (С-6), 164.8 (С-7), 103.1 (С-8), 159.3 (С-9), 102.9 (С-10), 121.0 (С-1′), 128.4 (С-2′, С-6′), 115.9 (С-3′, С-5′), 161.2 (С-4′), 56.7 (7-О-СН3); 6-С-β-D-глюкопираноза: 73.3 (С-1′′), 71.0 (С-2′′), 78.7 (С-3′′), 70.1 (С-4′′), 81.3 (С5′′), 60.5 (С-6′′); 8-С-α-L-арабинопираноза: 72.5 (С-1′′′), 68.4 (С-2′′′), 75.2 (С-3′′′), 69.0 (С-4′′′), 70.6 (С-5′′′)
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