ChemInform Abstract: QSAR of Flavylium Salts as Inhibitors of Xanthine Oxidase

Amić, Dragan; Davidović-Amić, Dušanka; Bešlo, Drago; Lučić, Bono; Trinajstić, Nenad

doi:10.1002/chin.199901242

Cited by 20 publications

(35 citation statements)

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“…[33] Flavonoids are predominantly located in aerial parts of the plants because synthesis of quercetin and other flavonoid derivatives is induced by the sunlight. [3] The role of flavonoids as radical scavengers [34] in the extracts of M. sativa aerial parts is confirmed in this work by the observed negative correlation (P < 0.05) between TF and RSA IC50. However, coefficient of determination was relatively low (r 2 = 0.2944).…”

Section: Radical Scavenging Activity Of the Extractssupporting

confidence: 75%

Multi-response Optimization of Ultrasound-assisted Extraction of Bioactive Components from Medicago Sativa L.

2017

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Response surface methodology was used to optimize experimental conditions for ultrasound-assisted extraction of functional components from Medicago sativa L. (Fabaceae) aerial parts. The procedure was performed according to the Box-Behnken design. The independent variables were ethanol concentration (X1), temperature (X2), and pH (X3), while the responses were extraction yield, DPPH radical scavenging activity of the extracts (RSA IC50), content of total phenols (TP), total flavonoids (TF) and total phenolic acids (TPA). The response values of the extracts prepared at optimum conditions (X1, X2, X3) were: yield (162 mg/ml, 20 %, 60 °C, 5.5), TP (6.63 mg/ml, 100 %, 60 °C, 5.5), TF (0.292 mg/ml, 100 %, 23 °C, 5.5), TPA (0.275 mg/ml, 100 %, 23 °C, 8.5) and RSA IC50 (3.97 mg/ml, 40 %, 60 °C, 7.0). The predicted values matched well with the observed ones indicating the suitability of the selected models for extraction of bioactive compounds from M. sativa.

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Section: Radical Scavenging Activity Of the Extractssupporting

confidence: 75%

Multi-response Optimization of Ultrasound-assisted Extraction of Bioactive Components from Medicago Sativa L.

2017

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“…Additionally, this substitution profile also rules the conformational behaviour of the systems, namely their flexibility, the formation of hydrogen bonds -either intra-or intermolecularly -and the preference for planar or skewed relative orientations of the substituent groups. Therefore, the beneficial activity of the flavones and isoflavones under study relies on their structural and conformational behaviour [34][35][36]. Besides determining biological activity, these strict structure-activity relationships (SAR's) modulate the systemic distribution and bioavailability of the compounds within the cell.…”

Section: Introductionmentioning

confidence: 99%

A conformational study of hydroxyflavones by vibrational spectroscopy coupled to DFT calculations

Machado

Carvalho

Otero

et al. 2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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This article appeared in a journal published by Elsevier. The attached copy is furnished to the author for internal non-commercial research and education use, including for instruction at the authors institution and sharing with colleagues.Other uses, including reproduction and distribution, or selling or licensing copies, or posting to personal, institutional or third party websites are prohibited. The conformational preferences of a series of hydroxyflavones were studied by Raman and FTIR spectroscopies, coupled to Density Functional Theory calculations. Special attention was paid to the effect of hydroxyl substitution, due to its importance on the biological activity of these compounds. Their conformational preferences were found to be determined mainly by the orientation of the hydroxylic groups at C 7 and within the catechol moiety, leading to the occurrence of distinct conformers in the solid state. A complete assignment of the experimental spectra was carried out for these molecules, in the light of their most stable conformers and the corresponding predicted vibrational pattern.

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“…The 8-deuterated patuletin, (8-D)patuletin (1a), was isolated as a new compound during these investigations. Moreover, flavonols which are more active as antioxidant agents than flavones [3] [4] [19] showed more reactivity towards H/D exchange as compared to flavones. Rate constants of the H/D exchange of selected flavonols and flavones were H-NMR studies.…”

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confidence: 99%

Specific Deuteration in Patuletin and Related Flavonoids via Keto–Enol Tautomerism: Solvent‐ and Temperature‐Dependent ¹H‐NMR Studies

Faizi

Siddiqi

Naz

et al. 2010

Helvetica Chimica Acta

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An H/D exchange process in patuletin (1) and its derivatives in D-donor solvents (e.g., CF 3 COOD), which occurs regioselectively at C(8) was observed for the first time during NMR studies. The effect of substituents and temperature on the deuteration of various flavonoids (see Fig. 1) which include apigenin, chrysin, galangin, kaempferol, luteolin, morin, myricetin, patuletin, patulitrin, and quercetin, as well as derivatives of patuletin was examined extensively under NMR conditions. The rate constant of deuteration at C(8) of patuletin (1) and two flavones, luteolin (3) and apigenin (12), was also determined in CF 3 COOD. The D-atom was introduced into the flavonoids via a keto -enol tautomerism (Scheme 1). During these studies, monodeuterated patuletin was also obtained as a new compound. The examined flavonoids have been reported to possess significant pharmacological activities, and their deuterated derivatives would be of importance for the identification and quantification of these compounds in biological matrices.

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ChemInform Abstract: QSAR of Flavylium Salts as Inhibitors of Xanthine Oxidase

Cited by 20 publications

References 1 publication

Multi-response Optimization of Ultrasound-assisted Extraction of Bioactive Components from Medicago Sativa L.

Multi-response Optimization of Ultrasound-assisted Extraction of Bioactive Components from Medicago Sativa L.

A conformational study of hydroxyflavones by vibrational spectroscopy coupled to DFT calculations

Specific Deuteration in Patuletin and Related Flavonoids via Keto–Enol Tautomerism: Solvent‐ and Temperature‐Dependent ¹H‐NMR Studies

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ChemInform Abstract: QSAR of Flavylium Salts as Inhibitors of Xanthine Oxidase

Cited by 20 publications

References 1 publication

Multi-response Optimization of Ultrasound-assisted Extraction of Bioactive Components from Medicago Sativa L.

Multi-response Optimization of Ultrasound-assisted Extraction of Bioactive Components from Medicago Sativa L.

A conformational study of hydroxyflavones by vibrational spectroscopy coupled to DFT calculations

Specific Deuteration in Patuletin and Related Flavonoids via Keto–Enol Tautomerism: Solvent‐ and Temperature‐Dependent 1H‐NMR Studies

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Specific Deuteration in Patuletin and Related Flavonoids via Keto–Enol Tautomerism: Solvent‐ and Temperature‐Dependent ¹H‐NMR Studies