Rutin from Hedera colchica

Alaniya, M. D.; Komissarenko, N. F.; Кемертелидзе, Э. П.

doi:10.1007/bf00564766

Chem Nat Compd

1971

DOI: 10.1007/bf00564766

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Rutin from Hedera colchica

M. D. Alaniya¹,

N. F. Komissarenko²,

Э. П. Кемертелидзе³

Abstract: By paper chromatography in various systems, we have established the presence in the leaves of Hedera colchica C. Koch (Colchis ivy) of four substances of flavonoid nature. For their isolation, the raw material was extracted with methanol, the extract was evaporated, the residue was dissolved in water, and the solution was purified with chloroform. The aqueous liquid so purified was concentrated and treated with acetone. The acetone solution yielded a yellow substance with the composition C27H30016 (yield 0.6%)… Show more

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Cited by 4 publications

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“…Thus, the stems and leaves acquire a green color during active vegetation whereas they become reddish during winter. We collected samples of the plant in Tbilisi (Georgia) in January and July 2007 in order to explain the essence of this phenomenon.The flavonol glycoside rutin has been previously isolated from H. colchica [2]. Rutin was not observed in the aqueous alcohol extract of a sample collected in January.…”

mentioning

confidence: 85%

“…The flavonol glycoside rutin has been previously isolated from H. colchica [2]. Rutin was not observed in the aqueous alcohol extract of a sample collected in January.…”

mentioning

confidence: 85%

“…The site of attachment of the sugar was determined by oxidative destruction of the glycoside [4,6]. This formed a biose identical to rutinose [2] that was bonded to C 3 of the aglycon. The chemical shifts of the aromatic protons did not correlate with those for the flavylium cation because the isolated anthocyan glycoside was the hemiacetal form [5].…”

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confidence: 99%

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Anthocyan glycoside from Hedera colchica

Alaniya¹,

Kavtaradze²,

Skhirtladze³

2008

Chem Nat Compd

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Hedera colchica is an evergreen vine [1]. Observations carried out by us on separate specimens of H. colchica showed that the color changes depending on the vegetative phase. Thus, the stems and leaves acquire a green color during active vegetation whereas they become reddish during winter. We collected samples of the plant in Tbilisi (Georgia) in January and July 2007 in order to explain the essence of this phenomenon.The flavonol glycoside rutin has been previously isolated from H. colchica [2]. Rutin was not observed in the aqueous alcohol extract of a sample collected in January. It was found that the rutin content varies depending on the season. Rutin accumulated most (0.57%) in summer. In January, its content decreases to only traces whereas the anthocyan content changes in the opposite direction. Anthocyan pigment was completely absent in the summer sample whereas its content in the January sample reached 0.52%.Aerial parts of the plant collected in January were extracted by the method proposed for isolating anthocyan pigments [3]. The extraction was performed using methanol containing conc. HCl (0.1%) at room temperature in the dark. The resulting extract was purified by adsorption chromatography over cellulose sorbent and using reversed-phase HPLC (Agilent HP 1100, Palo Alto, USA) with a UV detector and fixed wavelength of 520 nm. We used an XTerra column (300 × 7.8 mm) packed with Silica gel RP-18 adsorbent (5 μm). The mobile phase flow rate was 2 mL/min. Samples (5 mg) (the fraction containing anthocyan pigment produced by chromatography over cellulose) were dissolved in methanol (100 μL) and injected into the chromatograph. The mobile phase was binary solutions of CH 3 CN and H 2 O containing trifluoroacetic acid (0.1%, from 10:90 to 60:40). The duration was 60 min; retention time of anthocyan, 15.63 min.A pure compound that in daylight on PC gave a pink spot; in UV light, a bright pinkish-red fluorescence; and in ammonia vapor and upon spraying with aqueous NaOH solution (1%), a bright blue color, was produced. IR spectrum (KBr, ν, cm −1 ): 3300-3400 (OH), 1655 (C=O), 1615-1430 (Ar). UV spectrum (MeOH containing HCl, 0.01%, λ max , nm): 520.Addition of methanolic AlCl 3 (5%) caused a bathochromic shift of 30 nm, which is typical of anthocyans containing free hydroxyls in the 3′-and 4′-positions [4].Acid hydrolysis gave D-glucose, L-rhamnose, and the aglycon with mp >300°C (dec.). UV spectrum (MeOH, 0.01% HCl, λ max , nm): 535; +AlCl 3 , 565. This indicated the presence of an o-dihydroxy group in the side chain. Alkaline cleavage of the algycon formed phloroglucinol and protocatechoic acid. Chromatography by PC using n-BuOH:HCl (2 N) (1:1, upper phase) and CH 3 CO 2 H:HCl:H 2 O (5:1:5), R f 0.68 and 0.35, corresponded to cyanidin [4].Stepwise acid hydrolysis of the glycoside by Hcl (4%) in methanol for 25-30 min gave an intermediate and L-rhamnose. The site of attachment of the sugar was determined by oxidative destruction of the glycoside [4,6]. This formed a biose identical to rutinose [2] that was ...

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mentioning

confidence: 85%

“…The flavonol glycoside rutin has been previously isolated from H. colchica [2]. Rutin was not observed in the aqueous alcohol extract of a sample collected in January.…”

mentioning

confidence: 85%

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Anthocyan glycoside from Hedera colchica

Alaniya¹,

Kavtaradze²,

Skhirtladze³

2008

Chem Nat Compd

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“…Enzymatic hydrolysis of 3 produced genin 2 and a biose, which was identical to rutinose [7]. The 13 C NMR spectra of 1 and 2 (Table 1) indicated that only one carbinol C atom of the genin of 1 experienced a glycosylation effect and resonated at 88.1 ppm (C-3).…”

mentioning

confidence: 97%

“…The production of a less polar compound from 1 by absolute acetone and anhydrous copper sulfate suggested that the OH groups on C-2′ and C-3′ were free in the rhamnosyl units [6].…”

mentioning

confidence: 99%

Cycloascauloside a from Astragalus caucasicus leaves

et al. 2006

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In continuation of research on isoprenoids from plants of the genus Astragalus [1], we isolated from leaves of A. caucasicus Pall. (Leguminosae L.) compounds called cycloascaulosides A, B, and C. Herein the structure of cycloascauloside A is reported.The PMR spectrum of cycloascauloside A (1) contained two 1H doublets coupled in an AB-type system at 0.39-0.54 ppm with SSCC 2 J = 4.5 Hz in addition to signals for seven methyls at 0.80-1.78 ppm. This enabled 1 to be considered as a cycloartane triterpenoid [1][2][3]. This conclusion was confirmed by absorption bands in the IR spectrum at 3045 and 1452 cm -1 and the preparation of cyclogalegigenin (2) upon acid hydrolysis of 1 and its Smith decomposition [2][3][4]. The carbohydrate part of the hydrolysate contained D-glucose and L-rhamnose in a 1:1 ratio according to paper (PC) and gas chromatography [5]. 1: R = α-L-Rhap-(1→6)-β-D-(2-O-Ac)-Glcp 2: R = H 3: R = α-L-Rhap-(1→6)-β-D-Glcp 4: R = β-D-GlcpThe IR spectrum of 1 exhibited absorption bands at 1755 and 1240 cm -1 (ester); the PMR spectrum, a 3H singlet at 1.98 ppm belonging to an acetyl. As expected, the 13 C NMR spectrum of 1 contained signals for C atoms of one acetyl at 19.70 and 170.02 ppm.Glycoside 1 treated with dilute base solutions gave progenin 3, which underwent partial hydrolysis. The resulting products included cyclogalegigenin and glycoside 4, acid hydrolysis of which gave D-glucose and genin 2. Therefore, D-glucose was directly bound to cyclogalegigenin.

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Flavonoid glycosides from Astragalus galegiformis leaves

Alaniya

Kavtaradze

Bassarello³

et al. 2006

Chem Nat Compd

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New flavonoid oligosides, the structures of which were established by chemical transformations and UV, IR, PMR, and 13 C NMR spectra, were isolated from Astragalus galegiformis leaves.We reported earlier on the isolation from Astragalus galegiformis L. (Fabaceae L.) flowers of flavonoid glycosides that were derivatives of isorhamnetin, astragalegoside and isoastragalegoside, which possess diuretic and hyponitrogenous activity [1,2].Herein we examine the structure of flavonoid glycosides isolated from leaves of A. galegiformis. They are difficult to separate by chromatography (R f 0.34 ± 0.05) and isolate in pure states. This may be due to either H-bonds between the compounds or gums in the Astragalus species.We were able to isolate six compounds by using classical separation methods for flavonoids and their modifications. Two compounds turned out to be known flavonoids that were previously isolated from other Astragalus species, astragalin (1) and kaempferol (2) [3].The other compounds were new. We called them flagalosides (2-5). They all gave a positive qualitative reaction characteristic of flavonoid glycosides [4]. Their IR spectra contained absorption bands for hydroxyls (3200-3400 cm -1 ), γ-pyrone carbonyl (1665-1660 cm -1 ), and aromatic rings (1620, 1575 cm -1 ) [5].UV spectra of 3 and 4 in ethanol with added ionizing and complexing reagents produced absorption bands that revealed the absence of substituents on C 7 , C 5 , C 4 , and C 3′ ; for 2 and 5, the presence of substituents on C 7 and C 3 , and C 3 and C 3′ , respectively.Acid hydrolysis of the glycosides produced the aglycons quercetin (from 2-4) and isorhamnetin (from 5). The yields of the aglycons indicated that 2 was a tetraoside; 3, a pentaoside; 4, a trioside; and 5, a bioside. The carbohydrate part of 2 contained D-glucose, D-galactose, L-arabinose, and L-rhamnose bonded to C 3 and C 7 of quercetin; of 3, D-glucose, D-galactose, L-arabinose, D-xylose, and L-rhamnose also bonded to C 3 of quercetin.In view of the fact that 2 and 3 were isolated in minor amounts, it was not possible to establish their complete chemical structures.The PMR spectrum of 4 recorded in CD 3 OD (Table 1) contained a strong singlet at 12.8 ppm, which is characteristic of a 5-OH group. The presence of this hydroxyl was confirmed by the UV spectrum recorded in ethanol with added AlCl 3 , in which the absorption band at 401 nm underwent a bathochromic shift of 46 nm [6]. The size of bathochromic shifts produced by adding AcONa + H 3 BO 3 and MeONa is indicative of a dihydroxy group in the 3′,4′-positions and a free 4′-OH group [6]. Signals of aromatic protons are observable at weak field in the PMR spectra at 7.65, 6.90, and 6.92 (ring B) and 6.45 and 5.25 ppm (ring A). The chemical shifts and SSCC of protons in ring B indicated that they were located on C 2′ , C 5′ , and C 6′ ( Table 1).The 13 C NMR spectra led to an analogous conclusion, where signals for secondary C atoms at C-5, C-7, C-4′, and C-3′ were clearly observed. The chemical shift of C-3 was indicative of it...

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Rutin from Hedera colchica

Cited by 4 publications

References 0 publications

Anthocyan glycoside from Hedera colchica

Anthocyan glycoside from Hedera colchica

Cycloascauloside a from Astragalus caucasicus leaves

Flavonoid glycosides from Astragalus galegiformis leaves

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