Flavonoids from Anvillea radiata Coss. & Dur. (Asteraceae)

Biochemical Systematics and Ecology
2006.0

Abstract

In a continuation of our study of Algerian medicinal plants, we investigated Anvillea radiata Coss. et Dur. We report herein 13 known flavonoids, namely: hispidulin 1, nepetin 2, jaceosidin 3, spinacetin 4, spinacetin 7-glucoside 5, patuletin 7-diglucoside 6, spinacetin 3-diglucoside 7, kaempferol 6-methyl ether 3-glucoside 8, quercetin 3-glucoside 9, patuletin 3-diglucoside 10, isorhamnetin 3-diglucoside 11, quercetin 3-rhamnoglucoside 12, quercetin 3-diglucoside 7 glucoside 13. Air dried aerial parts of A. radiata (500 g) were extracted three times with 70% MeOH (3 l). The MeOH extract was concentrated to dryness (38 g), the residue was dissolved in boiling water (400 ml), and the solution was extracted three times with n-BuOH (3×120 ml) giving 26.63 g of n-BuOH extract, from which 10 g were applied to a column of polyamide MN SC6 (Macherey-Nagel) and eluted with a gradient of toluene-MeOH with increasing polarity (100% of toluene to toluene-MeOH 60:40). Thirteen flavonoids 1–13 contained in four main fractions were isolated. Fraction 1 (1800 ml) (90:10), 2 (90:10) (3600 ml) and 3 (70:30) (1800 ml) were purified by preparative PC on Whatman 3 mm using 30% aqueous AcOH to afford compound 1 (6.7 mg), 2 (3.2 mg) and 3 (7.3 mg), respectively. Fraction 4 (60:40) (3000 ml) was purified by repeated TLC on polyamide MN DC6 (Macherey-Nagel) eluted with H2O, MeOH, ethylmethylketone, acetylacetone (13:3:3:1), and toluene, MeOH, ethylmethylketone (4:3:3) and PC on Whatman 3 mm using 30% aqueous AcOH to yield compounds 4 (2.1 mg), 5 (1.5 mg), 6 (1.9 mg), 7 (1.7 mg), 8 (1.1 mg), 9 (1.1 mg), 10 (0.9 mg), 11 (0.9 mg), 12 (1.2 mg) and 13 (2.0 mg). Final purification of each compound for spectral analysis was carried out using MeOH over Sephadex LH-20 (Pharmacia Fine Chemicals), prior to UV, MS and 1H spectral analysis. Hydrolysis of the glycosides (HCl 0.1 N 2 h) yielded the sugar residues and the aglycones, all of which were chromatographed with authentic samples. 1H NMR spectra were recorded in CD3OD at 300 MHz, and all the structures were in good agreement with literature data. A. radiata is a wild plant endemic of North Africa (steppes of Morocco and Algeria). Thirteen flavonoids from which four aglycones and nine flavonol glycosides were isolated. Flavonols were mostly glycosylated, especially at C-3 position (compounds 7–13). It is also interesting to notice that nine compounds from 13 were 6-methoxylated (compounds 1–8 and 10). All these compounds are detected for the first time in A. radiata. Except for compounds 1 and 2, all these flavonoids have not been previously described for the genus.

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