Flavonoids from Cephalaria gigantea flowers

Movsumov, I. S.; Garaev, E. A.; Исаев, М. И.

doi:10.1007/s10600-006-0250-z

Cited by 15 publications

(10 citation statements)

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“…They contain a great variety of compounds with pharmaceutical activity such as alkaloids, iridoids, flavonoids and triterpenoid saponins (Caliskan et al, 1994). Several triterpene saponins and flavonoids have been isolated from this plant which includes giganteosides D and E (Mshvildadze et al, 2001;Movsumov et al, 2006). Some of these compounds showed interesting antileishmanial, antifungal and antiprotozoal activities Despite the wide usage of this plant in traditional medicine, there is dearth of information on the scientific evaluation of its biological activities.…”

Section: Introductionmentioning

confidence: 99%

In vitro studies on the antimicrobial, antioxidant and antidiabetic potential of Cephalaria gigantea

Mbhele

Balogun

Kazeem

et al. 2015

Bangladesh J Pharmacol

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Section: Introductionmentioning

confidence: 99%

In vitro studies on the antimicrobial, antioxidant and antidiabetic potential of Cephalaria gigantea

Mbhele

Balogun

Kazeem

et al. 2015

Bangladesh J Pharmacol

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“…Chromatograms were visualized using a diazo reagent and alcoholic KOH (10%) to identify at least six coumarintype compounds that were separated over a column of silica gel (fraction:sorbent, 1:250, h = 80, d = 3 cm, elution by C 6 H 6 :CHCl 3 with increasing concentration of the latter after 1 L). The separation was monitored using UV light and PC.Fraction 1 afforded 1 (0.058 g) and 2 (0.043); fraction 2, 3 (0.033); fraction 3, 4 (0.034); EtOAc fraction, 5 (0.048) and 6 (0.065).Physicochemical and chemical methods (PC, TLC, UV and IR spectroscopy, specific rotation, melting point, acid and enzymatic hydrolysis) were used to identify the isolated compounds [4]. Products from acid hydrolysis of 5 and 6 contained D-glucose according to polarography and chromatography using n-BuOH:CH 3 CO 2 H:H 2 O (4:1:2) and (CH 3 )2CO:n-BuOH:H 2 O (7:2:1).…”

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“…Physicochemical and chemical methods (PC, TLC, UV and IR spectroscopy, specific rotation, melting point, acid and enzymatic hydrolysis) were used to identify the isolated compounds [4]. Products from acid hydrolysis of 5 and 6 contained D-glucose according to polarography and chromatography using n-BuOH:CH 3 CO 2 H:H 2 O (4:1:2) and (CH 3 )2CO:n-BuOH:H 2 O (7:2:1).…”

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Coumarins from Eucalyptus viminalis leaves

et al. 2009

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The genus Eucalyptus L'Her numbers over 500 species [1]. According to the USSR State Pharmacopoeia, XIth Ed., leaves of E. viminalis Labill. are an official plant raw material [2].We have previously reported research on hydroxycinnamic acids, flavonoids, and tanning agents from leaves of E. viminalis [3]. In continuation of that work we have isolated and identified six coumarins from this raw material.Air-dried leaves of E. viminalis (5.0 kg) were extracted with purified water (15.0 L) at 95°C for 2 h and left to stand for 12 h. The extraction was carried out three times with new portions of purified water. The aqueous extracts were combined (40.6 L), evaporated at 85°C in a vacuum-circulator apparatus at 690 mm Hg to a volume of 1.0 L, and left to stand for 4 d. The supernatant liquid was separated. Polysaccharides were precipitated first from the aqueous solution by adding a three-fold amount of EtOH (96%). The precipitate was filtered off. The filtrate was evaporated to an aqueous residue that was fractionated using CHCl 3 , EtOAc, and BuOH. The completeness of the fraction separations was monitored using PC and TLC.Next the CHCl 3 and EtOAc fractions were studied. Paper chromatography showed that the CHCl 3 fraction contained coumarins, chlorophylls, phospholipids, and triterpene compounds; the EtOAc extract, coumarins, flavonoids, and hydroxycinnamic acids. The CHCl 3 fraction was treated successively with NH 4 OH and NaHCO 3 and NaOH solutions (1%), by which the coumarins were transferred to the aqueous phase as salts. The resulting aqueous solutions were acidified with HCl to pH 4-5 and re-extracted with CHCl 3 (fractions 1, 2, and 3, respectively). The CHCl 3 and EtOAc fractions were evaporated. The dry solid was dissolved in a small amount of EtOH (96%), spotted using a capillary on chromatographic paper impregnated beforehand with formamide-acetone (1:3), and chromatographed in descending mode using CHCl 3 and hexane. Chromatograms were visualized using a diazo reagent and alcoholic KOH (10%) to identify at least six coumarintype compounds that were separated over a column of silica gel (fraction:sorbent, 1:250, h = 80, d = 3 cm, elution by C 6 H 6 :CHCl 3 with increasing concentration of the latter after 1 L). The separation was monitored using UV light and PC.Fraction 1 afforded 1 (0.058 g) and 2 (0.043); fraction 2, 3 (0.033); fraction 3, 4 (0.034); EtOAc fraction, 5 (0.048) and 6 (0.065).Physicochemical and chemical methods (PC, TLC, UV and IR spectroscopy, specific rotation, melting point, acid and enzymatic hydrolysis) were used to identify the isolated compounds [4]. Products from acid hydrolysis of 5 and 6 contained D-glucose according to polarography and chromatography using n-BuOH:CH 3 CO 2 H:H 2 O (4:1:2) and (CH 3 )2CO:n-BuOH:H 2 O (7:2:1).Thus, the compounds isolated from leaves of E. viminalis were identified as: 1, C 9 H 6 O 3 , mp 228-230°C, λ max 231, 258, 327 nm; 7-hydroxycoumarin or umbelliferone; 2, C 10 H 8 O 4 , mp 202-204°C, λ max 230, 255, 296, 346 nm; 6-methoxy-7-hydroxycoumarin...

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“…Their structures were elucidated by chromatography; alkaline degradation; acetylation; methylation; UV, IR, and PMR spectroscopy; and melting point [3][4][5][6][7].…”

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Flavonoids from leaves of Pyrus communis, Malus sylvestris, and Malus domestica

Кисличенко

Novosel

2007

Chem Nat Compd

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Flavonoids form one of the most common groups of phenolic compounds and are widely distributed in the plant world. Hydroxyls in their molecules are responsible for their antioxidant activity, which is considered one of the required properties of drugs for treating such diseases as cancer, atherosclerosis, hypertension, infarct, etc. Flavonoids have a variety of effects on the human organism. They exhibit capillary strengthening, antioxidant, antiradiation, antitumor, anti-inflammatory, antiatherosclerotic, spasmolytic, hypotensive, estrogenic, and bactericidal activities. The main property of these compounds is their low toxicity and more often the lack of it [1, 2].We investigated leaves of common pear Pyrus communis L., wild apple Malus sylvestris L., and domestic apple M. domestica Borkh. varieties Antonovka, Glory, and Whitesap, which are widely used in folk medicine to treat various pathologies. The goal of our work was to isolate and identify flavonoids from these types of raw material [2].Ground and air-dried raw material was extracted with ethanol (50%) in a 1:10 (material:extractant) ratio. The aqueous alcohol extracts were combined and evaporated in vacuo to an aqueous residue. The resinous precipitate that formed on standing contained chlorophyll and was removed. The aqueous solution was treated successively with CHCl 3 , ethylacetate, and butanol. The ethylacetate and butanol fractions were evaporated to dryness and chromatographed over a polyamide column (d, 1.5; h, 50 cm) with elution by CHCl 3 and a CHCl 3 :EtOH mixture with a gradually increasing concentration of the latter to 20%. Thus, we isolated 18 compounds of flavonoid nature [3].The structures of the isolated compounds were elucidated using physicochemical, chemical, and biochemical analytical methods (PC and TLC; UV, IR, and PMR spectroscopy; optical activity; melting points; acid and enzymatic hydrolysis) [3].The products from acid hydrolysis of compound 2 contained according to chromatographic and physicochemical methods (acetylation, methylation, alkaline degradation, melting point, direct and differential UV spectroscopy using ionizing and complexing reagents) the aglycon phloretin; 6, apigenin; 8, luteolin; 10, kaempferol; and 12-16, quercetin. Compound 16 contained glucose and rhamnose; 2, 6, 8, 10, and 14, glucose; 12, galactose; 13, rhamnose; and 15, arabinose. The structures of the carbohydate substituents were elucidated using enzymatic hydrolysis by rhamnodiastase and grapevine snail enzyme.Acid hydrolysis of 1, 3, 4, 5, 7, 9, 11, 17, and 18 enabled them to be assigned as flavonoid aglycons. Their structures were elucidated by chromatography; alkaline degradation; acetylation; methylation; UV, IR, and PMR spectroscopy; and melting point [3][4][5][6][7].Thus, the investigations of the compounds isolated from leaves of pear and apple varieties identified them as the following. 1, C 15 H 14 O 5 , mp 257°C, λ max 225, 286 nm; 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone or phloretin; 2, C 21 H 24 O 10 , mp 170-171°C, λ...

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Flavonoids from Cephalaria gigantea flowers

Cited by 15 publications

References 3 publications

<i>In vitro</i> studies on the antimicrobial, antioxidant and antidiabetic potential of <i>Cephalaria gigantea</i>

<i>In vitro</i> studies on the antimicrobial, antioxidant and antidiabetic potential of <i>Cephalaria gigantea</i>

Coumarins from Eucalyptus viminalis leaves

Flavonoids from leaves of Pyrus communis, Malus sylvestris, and Malus domestica

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