A new isoflavone glycoside, genistein 7-O-xylosyl 8-C-glucoside (1), was isolated from the leaves of Retama sphaerocarpa. Its structure was elucidated by spectroscopic methods.The genus Retama is located in the Atlas regions and the Sahara [1] (Arabic common name Rctem) and represented by three species in the flora of Algeria: Retama monosperma, Retama retam, and Retama sphaerocarpa. The last one is used to cure rabies in folk medicinal traditions in the east of Algeria. Investigations of Retama sphaerocarpa have led to the isolation of alkaloids [2-4], isoflavonoids [5][6][7], and flavonoids [8][9][10][11]. Previous studies showed that isoflavonoid glucosides are common in this genus. We now report the results of chemical examination of the methanolic extract of the flowering stems of R. sphaerocarpa Boissier (Fabaceae).The powdered aerial parts (950 g) of R. sphaerocarpa were extracted with 70% MeOH. The MeOH extract was evaporated to dryness. The residue was dissolved in boiling water and extracted with ethyl acetate and n-BuOH successively. Solvents were evaporated and the residue of the ethyl acetate and n-BuOH extracts was dissolved in small volumes of MeOH. Two-dimensional paper chromatography using 15% AcOH and BAW (n-BuOH-AcOH-H 2 O, 4:1:5 upper phase) as solvents had shown that the ethyl acetate and n-BuOH extracts contain almost the same compounds representing flavonoids. The n-BuOH extract was applied to a column of polyamide MN SC6 and eluted with a gradient of toluene-MeOH with increasing polarity. Compound 1 was isolated by preparative PC on Whatman 3MM paper using 15% AcOH, then by preparative TLC on polyamid DC6 eluting with H 2 O-MeOH-methyl ethyl acetone-acetylacetone 13:3:3:1).
UDC 547.972 Retama sphaerocarpa (Fabaceae), known in Algeria as "Retam", was collected during flowering in the Souk Naamane Region east of Algeria in June 2002, and the species was identified by Dr. H. Laouer from the Department of Biology (University of Setif, Algeria) on the basis of Quezel and Santa (1963) [1]. A voucher specimen (P00383267) has been deposited in the Herbarium of Museum National d'Histoire Naturelle, Paris, FranceThis research is a contribution to the chemical study of some plants growing in Algeria, with the objective of discovering natural products with potential biological activity. As part of our continuing study of Retama sphaerocarpa [2] we have undertaken a reexamination of the chemical constituents of the aerial parts and roots of R. sphaerocarpa. We report here the isolation and identification of two flavonoids; these compounds are new for this genus. The leaves of Retama sphaerocarpa were investigated for antimicrobial properties. All fractions showed activity against Staphylococcus aureus.Air-dried powder from the aerial parts (950 g) of R. sphaerocarpa was extracted three time with boiling 70% MeOH. The MeOH extract was evaporated to dryness.The residue was dissolved in boiling water and extracted with ethyl acetate and n-BuOH successively. The solvents was evaporated. and the residue of the ethyl acetate and n-BuOH extracts was dissolved in small volumes of MeOH. Analysis by two-dimensional paper chromatography using 15% AcOH and BAW (n-BuOH-AcOH-H 2 O 4:1:5 upper phase) as solvents revealed identical separation of the flavonoids in the acetate and n-BuOH extracts. The n-BuOH extract was applied to a column of polyamide MN SC6 and eluted with a gradient of toluene-MeOH with increasing polarity. Two flavonoids (1, 2), contained in several fractions, were isolated by preparative PC on whatman 3MM paper using AcOH 15%, then by preparative TLC on polyamide DC6 eluted with (H 2 O-MeOH-methylethylacetone:acetylacetone) 13:3:3:1.Purification of each compound for spectral analysis was carried out using MeOH over Sephadex LH-20. The chemical structures of the compounds were determined using UV, 1D, and 2D NMR spectrometry.
Six flavonoids, namely 6-methoxykaempferol (1), 6-methoxykaempferol 7-O-glucoside (2), kaempferol 7-O-glucoside (3), 6methoxyluteolin (4), patuletin 7-O-glucoside (5), and hispidulin 7-O-glucoside (6), were isolated from a n-butanolic fraction of Centaurea microcarpa Coss et Dur. flowers. This work describes for the first time the phytochemical composition of this endemic Algerian plant.
Retama sphaerocarpa Boissier is a species of the Fabaceae family [1]. This plant is used to cure rabies in the medicinal folk traditions of the east of Algeria. In the present paper we report the result obtained on the qualitative and quantitative analysis of secondary metabolites extracted from the medicinal plant R. sphaerocarpa, which has been the subject of several chemical and pharmacological investigations [2][3][4][5][6]. The aerial parts of this plant were collected during flowering in the Souk Naamane Region east of Algeria in May, June 2002.The air-dried powdered aerial parts (950 g) of R. sphaerocarpa were extracted with 70% MeOH. The MeOH extract was evaporated to dryness. The residue was dissolved in boiling water and extracted with ethyl acetate and n-BuOH successively. The solvents was evaporated and the residue of the ethyl acetate and n-BuOH extracts was dissolved in small volumes of MeOH. Two-dimensional paper chromatography using 15% AcOH and BAW (n-BuOH-AcOH-H 2 O, 4:1:5 upper phase) as solvents shows that the acetate and n-BuOH extract contains almost the same compounds representing flavonoids. The n-BuOH extract was applied to a column of polyamide MN SC6 and eluted with a gradient of toluene-MeOH with increasing polarity. Three flavonoids (1-3) contained in several fractions were isolated by preparative PC on Whatman 3MM paper using 15% AcOH, then by preparative TLC on polyamid DC6 eluted with H 2 O-MeOH-methylethylketone-acetylacetone, 13:3:3:1.The isoflavonoid glycoside (genistein 7-O-β-glucoside) was isolated from the intermediate fraction by crystallization. This compound has already been isolated from this plant [2]. Purification of each compound for spectral analysis was carried out using MeOH over Sephadex LH-20. These compounds were identified using UV and 1 H NMR spectra, chemical transformations, and comparison with authentic samples [7][8][9]. Flavonoids 1-2 are isolated for the first time from this genus. Compound 3 has been reported previously from another species of Retama [10] and from R. sphaerocarpa for the first time.
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