Kaempferol coumaroyl glucorhamnoside from Ginkgo biloba

Nasr, Chamel; Haag–Berrurier, M.; Lobstein-Guth, A.; Anton, Robert

doi:10.1016/0031-9422(86)88051-7

Cited by 44 publications

(14 citation statements)

References 5 publications

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“…The HPLC fingerprint of the total extract showed that these seven compounds accounted for 54% of the total peak area of the 34 peaks observed in the HPLC chromatogram (Figure 1). All seven compounds were obtained as yellow amorphous powders and their structures were determined based on a comparison of their MS and NMR spectral data with those in the literature [5][6][7][8]. Compounds 1-7 were identified as quercetin (6), and kaempferol 3-O-α-(6′′′-pcoumaroyl glucopyranosyl-β-1,2-rhamnopyranoside) (7), respectively ( Figure 2).…”

Section: Isolation and Structural Elucidation Of The Fgsmentioning

confidence: 99%

Quantitative Analysis of the Flavonoid Glycosides and Terpene Trilactones in the Extract of Ginkgo biloba and Evaluation of Their Inhibitory Activity towards Fibril Formation of β-Amyloid Peptide

et al. 2014

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Abstract:The standard extract of Ginkgo biloba leaves (EGb761) is used clinically in Europe for the symptomatic treatment of impaired cerebral function in primary degenerative dementia syndromes, and the results of numerous in vivo and in vitro studies have supported such clinical use. The abnormal production and aggregation of amyloid β peptide (Aβ) and the deposition of fibrils in the brain are regarded as key steps in the onset of Alzheimer's Disease (AD), and the inhibition of Aβ aggregation and destabilization of the preformed fibrils represent viable approaches for the prevention and treatment of AD. Flavonoid glycosides and terpene trilactones (TTLs) are the two main components of EGb761 which represent 24 and 6% of the overall content, respectively. In our research, seven abundant flavonoid glycosides 1-7 were isolated from the extract of Ginkgo biloba leaves and characterized by spectroscopic analysis. Furthermore, an ultra-high performance liquid chromatography method was established for the simultaneous quantification of these seven flavonoids. The inhibitory activities of these flavonoids, as well as four TTLs, i.e., ginkgolides A, B, and C and bilobalide (compounds 8-11), were evaluated towards Aβ42 fibril formation using a thioflavin T fluorescence assay. It was found that three flavonoids 1, 3 and 4 exhibited moderate inhibitory activities, whereas the other four flavonoids 2, 5, 6 OPEN ACCESSMolecules 2014, 19 4467 and 7, as well as the four terpene trilactones, showed poor activity. This is the first report of the inhibition of Aβ fibril formation of two characteristic acylated flavonoid glycosides 6, 7 in Ginkgo leaves, on the basis of which the structure-activity relationship of these flavonoids 1-7 was discussed.

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Section: Isolation and Structural Elucidation Of The Fgsmentioning

confidence: 99%

Quantitative Analysis of the Flavonoid Glycosides and Terpene Trilactones in the Extract of Ginkgo biloba and Evaluation of Their Inhibitory Activity towards Fibril Formation of β-Amyloid Peptide

et al. 2014

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“…Excellent linear correlation was obtained in plots for all the antioxidants studied. By using Equation 5, n values could be determined. The value used for ε for galvinoxyl at 428 nm in Equation 5 was 1.50 × 10 5 M −1 cm −1 , and the cell length, l, was 1 cm.…”

Section: Molar Extinction Coefficient Of Galvinoxylmentioning

confidence: 99%

“…The well-defined but complex product consists of two major groups of substances, flavonoid glycosides and terpenoids (2,3). The flavonoid fraction is composed of three flavonols, quercetin, kaempferol and isorhamnetin, which are linked to a sugar (2,4,5). The terpenoid fraction is composed of ginkgolides and bilobalides (6).…”

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confidence: 99%

Stoichiometric and kinetic studies on Ginkgo biloba extract and related antioxidants

Shi

Niki

1998

Lipids

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Owing to increasing evidence showing the importance of lipid peroxidation in oxidative stress in vivo, the role and evaluation of antioxidants have received much attention. Ginkgo biloba extract (GBE), well-known as an efficient drug against diseases induced by free radicals, has been suggested to exert its effect by antioxidant action. A method was established to determine the activity of GBE as a hydrogen donor by stoichiometric and kinetic studies, and GBE was compared with several other antioxidants such as alpha-tocopherol, propyl gallate, and two kinds of flavonoids which are found in GBE, quercetin, and kaempferol. It was found that there were 6.62 x 10(19) active hydrogens in 1 g of GBE. Stoichiometric studies showed that one molecule of alpha-tocopherol reacted with one molecule of galvinoxyl radical. For quercetin, kaempferol and propyl gallate, the experimental stoichiometric numbers were 4.0, 1.9, and 3.1, respectively. The rates of reaction of antioxidants with galvinoxyl in ethanol were determined spectrophotometrically, using a stopped-flow technique. The second-order rate constant, k2, obtained at 25 degrees C was 0.13 (g/L)(-1)s(-1) for GBE and 5.9 x 10(3), 2.1 x 10(3), 1.2 x 10(4), and 2.4 x 10(3) M(-1)s(-1) for quercetin, kaempferol, propyl gallate, and alpha-tocopherol, respectively. The second-order rate constant, k2', on the molar basis of active hydroxyl groups in the tested substances obtained at 25 degrees C decreased in the order of propyl gallate > alpha-tocopherol > quercetin > GBE approximately kaempferol. This is the first study on GBE as an antioxidant which reports both stoichiometric and kinetic results.

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“…The detailed procedures and the chromatogram (SI Figure S3) are available in the Supporting Information. By comparing the MS (SI Table S1) and NMR data (SI Table S2) with those published previously, compounds of peaks 25 and 26 were finally identified as quercetin 3‐ O ‐2′′‐(6′′′‐ p ‐coumaroyl)glucosylrhamnoside (QCGR) and kaempferol 3‐ O ‐2′′‐(6′′′‐ p ‐coumaroyl)glucosylrhamnoside (KCGR), respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Among the 26 components, peaks 12, 18, 19, 23, 37, 38, and 39 were unambiguously identified as quercetin 3-O-rutinoside, kaempferol 3-O-rutinoside, isorhamnetin 3-O-rutinoside, kaempferol 3-O-2''-glucosylrhamnoside,a pigenin, kaempferol, and isorhamnetin by comparison with the reference compounds,r espectively.D ue to the fact that there weren oc ommerciallya vailable references for the two highest peaks (25 and 26) in the ultrafiltration chromatogram ( Figure 2B), the identification of the two compounds was performed by NMRs pectroscopy after collecting the target peaks by HPLC.A fter one-month accumulation using two semi-preparative HPLC instruments,~10 mg of each target compound was obtained.T he detailed procedures and the chromatogram (SI Figure S3) are available in the Supporting Information. By comparing the MS (SI Table S1) andN MR data (SI Ta ble S2)w ith those published previously, [34][35][36] compounds of peaks 25 and 26 were finally identified as quercetin 3-O-2''-(6'''-p-coumaroyl)glucosylrhamnoside (QCGR)a nd kaempferol 3-O-2''-(6'''-p-coumaroyl)glucosylrhamnoside (KCGR), respectively.…”

Section: Screening and Identification Of Xod Binders By Ultrafiltratimentioning

confidence: 93%

Integration of Multiple Analytical and Computational Tools for the Discovery of High‐Potency Enzyme Inhibitors from Herbal Medicines

et al. 2016

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Herbal medicines (HMs) are an important source of drugs. In this study, an efficient strategy integrating ultrafiltration LC-MS, microplate bioassays, and molecular docking was proposed to screen high-potency enzyme inhibitors from HMs. Using this strategy, the structure-activity relationships (SARs) including binding-affinity-based SAR, enzymatic-activity-based SAR, and structural-complementarity-based SAR of compounds in an HM can be analyzed to provide abundant information for drug discovery. A prominent advantage of the approach is that it offers a multidimensional perspective to understand enzyme-ligand interactions, which could help to avoid false-positive screening results brought by a single method. By using xanthine oxidase (XOD) as an illustrative case, two types of potent XOD inhibitors, including flavones and coumarins, were successfully screened out from an HM of Ginkgo biloba. The study is expected to set a solid foundation for multidisciplinary cooperation in drug discovery.

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Kaempferol coumaroyl glucorhamnoside from Ginkgo biloba

Cited by 44 publications

References 5 publications

Quantitative Analysis of the Flavonoid Glycosides and Terpene Trilactones in the Extract of Ginkgo biloba and Evaluation of Their Inhibitory Activity towards Fibril Formation of β-Amyloid Peptide

Quantitative Analysis of the Flavonoid Glycosides and Terpene Trilactones in the Extract of Ginkgo biloba and Evaluation of Their Inhibitory Activity towards Fibril Formation of β-Amyloid Peptide

Stoichiometric and kinetic studies on Ginkgo biloba extract and related antioxidants

Integration of Multiple Analytical and Computational Tools for the Discovery of High‐Potency Enzyme Inhibitors from Herbal Medicines

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