The isolation from the epigeal part of Adonis vernalis L. (spring adonis) of a xyloside of homoorientin called adonivernith has been reported in the literature [1]. It was later established [2] that this flavonoid glycoside is a xyloside of orientin and not of homoorientin. Xylosides of orientin [3, 4] and of homoorientin [5] have also been isolated by other workers. We called the xyloside of orientin adonivernith and the xyloside of homoorientin homoadonivernith [6]. Orientin, homoorientin [1], and luteolin [7] have been found in small amounts in the herb spring adonis. All the flavonoid glycosides mentioned from this species are derivatives of the aglycone luteolin.We have studied the flavonoid composition of individual parts of adonis by paper chromatography. By the treatment with ammonia vapor of moist chromatograms sprayed with zirconyl chloride a substance fluorescing green was found, while under such conditions luteolin glycosides fluoresce orange [8]. The greatest amount of this substance was found in the stamens, from which it was isolated by preparative chromatography. The compound has Rf 0.23 (15% acetic acid) and 0.29 [butan-l-ol-acetic acid-water (4 : 1 : 2)], Xma x (in ethanol 268 and 340 nm). By UV spectroscopy, free hydroxy groups were found in positions 4 ', 5, and 7 [9]. The results of a chemical study of this flavonoid show that it is of C-glycosidic nature [6]. The substance underwent acid hydrolysis only after the action upon it of 15% hydrochloric acid for 6 h. The hydrolysis products were found to contain two substances, one of which was the initial substance while the second, with Rf 0.51 (15% acetic acid) was identified as saponaretin [10]. Hydrolysis with Kiliani's mixture [11] gave the aglycone apigenin. In the carbohydrate fraction we found D-glucose with a small amount of D-arabinose.On the basis of the physicoehemical investigation performed and by a comparison with an authentic sample, the flavonoid isolated was identified as vitexin. Thus, a C-glueoside of apigenin -vitexin -has been isolated from the flowers of the spring adonis for the first time.
B. M. K i r i c h e n k o , K. E . K o r e s h e h u k , G. A. D r o z d , a n d A . A. K r e m z e r a r v e n s i s UDC 547.972We have studied the epigeal part of Nigella arvensis L., family Ranunculaceae Juss.The plant was extracted with 70% ethanol. The extract was deposited on a column of polyamide s o rbent and eluted first with water until flavonoids appeared in the eluate, and then with 70% ethanol. The combined flavonoids were heated in 10% hydrochloric acid on the water bath for 6 h. In the hydrolytic p r o c e s s the absence of C-glycosides was established [1]. The hydrolysate was diluted with water and passed through a column of polyamide sorbent. After the column had been washed with water to neutrality, the aglycones were desorbed with 96% ethanol, and the solution was evaporated and rechromatographed, being eluted with m i x t u r e s of chloroform and ethanol. Three substances were isolated.The first substance had mp 273-275°C, Rf 0.46 (60% acetic acid) and 0.56 [benzene-ethyl a c i d -f o rm a m i d e (70 : 30 : 2 : 1)], )tma x in ethanol 265, 296, and 370 nm. UV spectroscopy showed the p r e s e n c e of free 3-, 5-, 7-, and 4*-hydroxy groups [2]. Phloroglucinol and p-hydroxybenzoic acid were found in the products of alkaline degradation.The results obtained, and also a chromatographic comparison with an authentic sample,enabled this substance to be identified as 3, 4", 5,7-tetrahydroxyflavone or kaempferol.The second substance had mp 311-313°C, Rf 0.35 (60% acetic acid) and 0.14 [benzene-ethyl a c e t a t eacetic a c i d -f o r m a m i d e (70 : 30 : 2 : 1)], hmax in ethanol 270, 310, and 375 nm. UV spectroscopy showed the p r e s e n c e of free hydroxy groups in positions 3, 5, 7, 3", and 4". Phloroglucinol and protocatechuic acid were found in the products of alkaline degradation.By its physicochemical p r o p e r t i e s , UV spectroscopy, and a comparison with an authentic sample, the substance was identified as 3, 3", 4", 5, 7-pentahydroxyflavone or quercetin.The third substance, having Rf 0.55 (60% acetic acid) and 0.93 [ b e n z e n e -e t h y l a c e t a t e -a c e t i c a c i df o r m a m i d e (70 : 30 : 2 : 1)] could not be obtained in the crystalline state.
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