scholarly journals Natural Flavones and Flavonols: Relationships among Antioxidant Activity, Glycation, and Metalloproteinase Inhibition

Cosmetics ◽  
2020 ◽  
Vol 7 (3) ◽  
pp. 71 ◽  
Author(s):  
Simone Ronsisvalle ◽  
Federica Panarello ◽  
Giusy Longhitano ◽  
Edy Angela Siciliano ◽  
Lucia Montenegro ◽  
...  

Reactive oxygen and nitrogen species as well as advanced glycation endproducts (AGEs) and metalloproteinases (MMPs) play a key role in the development and progression of degenerative processes of body tissues, including skin. Natural antioxidant flavonoids could be beneficial in inhibiting AGEs’ formation and MMPs’ expression. In this study, the antioxidant activity of flavones (luteolin, apigenin, and chrysin) and flavonols (mirycetin, quercetin, and kaempferol) was compared with their inhibitory effects on both metalloproteinases’ (MMP-1, MMP-2, MMP-9, MMP-13) and AGEs’ formation. Comparisons were performed taking into account the hydroxyl group arrangement and the physico-chemical parameters the binding dissociation enthalpy (BDE), ionization potential (IP), partition coefficient (log P), and topological polar surface area (TPSA). Increasing the number of hydroxyl groups led to a proportional enhancement of antioxidant activity while an inverse relationship was observed plotting the antioxidant activity vs. BDE and IP values. All flavonoids acted as AGEs, MMP-1, and MMP-13 inhibitors, but they were less effective against MMP-2 and MMP-9. The inhibition of MMP-1 seemed to be related to the TPSA values while high TPSA and low log P values seemed important conditions for inhibiting MMP-13. Overall, our data suggest that an estimation of flavonoid activity could be anticipated based on their physico-chemical parameters.

2015 ◽  
Vol 107 ◽  
pp. 55-65 ◽  
Author(s):  
Ileana Ramazzina ◽  
Annachiara Berardinelli ◽  
Federica Rizzi ◽  
Silvia Tappi ◽  
Luigi Ragni ◽  
...  

2016 ◽  
Vol 97 (7) ◽  
pp. 2215-2222 ◽  
Author(s):  
Marisol Juan-Borrás ◽  
Juan Soto ◽  
Luis Gil-Sánchez ◽  
Ana Pascual-Maté ◽  
Isabel Escriche

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2199 ◽  
Author(s):  
Katarzyna Sidoryk ◽  
Anna Jaromin ◽  
Nina Filipczak ◽  
Piotr Cmoch ◽  
Marcin Cybulski

A series of caffeic acid derivatives were synthesized via a modified Wittig reaction which is a very important tool in organic chemistry for the construction of unsaturated carbon–carbon bonds. All reactions were performed in water medium at 90 °C. The aqueous Wittig reaction worked best when one unprotected hydroxyl group was present in the phenyl ring. The olefinations in the aqueous conditions were also conducted with good yields in the presence of two unprotected hydroxyl groups. When the number of the hydroxyl groups was increased to three, the reaction yields were worse, and the derivatives 12, 13, and 18 were obtained with 74%, 37%, and 70% yields, respectively. Nevertheless, the Wittig reaction using water as the essential medium is an elegant one-pot synthesis and a greener method, which can be a safe alternative for implementation in organic chemistry. The obtained compounds were tested for their antioxidant activity, and 12, 13, and 18 showed the highest activities. Moreover, all synthesized compounds displayed no cytotoxicity, and can therefore be used in the pharmaceutical or cosmetic industry.


Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6585
Author(s):  
Janez Mravljak ◽  
Lara Slavec ◽  
Martina Hrast ◽  
Matej Sova

Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3H)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TEACCUPRAC, to obtain key information about the structure–antioxidant activity relationships of a diverse set of substituents at position 2 of the main quinazolinone scaffold. Regarding the antioxidant activity, ABTS and TEACCUPRAC assays were more sensitive and gave more reliable results than the DPPH assay. To obtain antioxidant activity of 2-phenylquinazolin-4(3H)-one, the presence of at least one hydroxyl group in addition to the methoxy substituent or the second hydroxyl on the phenyl ring in the ortho or para positions is required. An additional ethylene linker between quinazolinone ring and phenolic substituent, present in the second series (compounds 25a and 25b), leads to increased antioxidant activity. Furthermore, in addition to antioxidant activity, the derivatives with two hydroxyl groups in the ortho position on the phenyl ring exhibited metal-chelating properties. Our study represents a successful use of three different antioxidant activity evaluation methods to define 2-(2,3-dihydroxyphenyl)quinazolin-4(3H)-one 21e as a potent antioxidant with promising metal-chelating properties.


2019 ◽  
Vol 160 (40) ◽  
pp. 1567-1573 ◽  
Author(s):  
Kinga Makk-Merczel ◽  
András Szarka

Abstract: The relationship between the potentially developing complications of the 451 million people affected by diabetes and hyperglycaemia can be based on the enhanced generation of advanced glycation endproducts and the more intensive oxidative and carbonyl stress. Advanced glycation endproducts generated partly due to carbonyl stress play an important role in the pathogenesis of diabetic complications such as elevated arterial thickness, vascular permeability, enhanced angiogenesis or the more rigid vessels induced nephropathy, neuropathy, retinopathy. Furthermore, the elevated thrombocyte aggregation, the reduced fibrinolysis induced elevated coagulation, and the atherosclerosis or the mitochondrial dysfunction are important as well. The most potent target of both the non-oxidative and oxidative generation of advanced glycation endproducts can be the scavenging of α,β-unsaturated aldehydes. Although, aminoguanidine, the prototype of scavenger molecules, showed protection in different animal models, it failed in the human clinical studies. Finally, the clinical studies were terminated almost 20 years ago. The endogen dipeptide L-carnosine was also expected to mitigate the complications due to carbonyl stress. However, its clinical significance was limited by the serum carnosinases and by the consequent low serum stability and bioavailability. The carnosinase resistance of the molecule can be achieved by the change of the carboxyl group of the molecule to hydroxyl group. At the same time, the biosafety and the carbonyl stress scavenging activity of the molecule could be preserved. Although clinical studies could not be performed in the last six months, on the basis of the in vitro and in vivo results, carnosinole seems to be a promising compound to mitigate and prevent the diabetic complications. Thus it is worth to the attention of the clinicians. Orv Hetil. 2019; 160(40): 1567–1573.


Author(s):  
Prithviraj Bhandare ◽  
G.R. Naik

Biodiesel is becoming prominent among the alternatives to conventional petro-diesel due to economic, environmental and social factors. The quality of biodiesel is influenced by the nature of feedstock and the production processes employed. High amounts of free fatty acids (FFA) in the feedstock are known to be detrimental to the quality of biodiesel. In addition, oils with compounds containing hydroxyl groups possess high viscosity due to hydrogen bonding. American Standards and Testing Materials, (ASTM D 6751) recommends FFA content of not more than 0.5% in biodiesel and a viscosity of less than 6 mm2/s. In this experiment the seed oils of 30 Neem (Azadirachta indica. A. juss) biotypes were screened and evaluated for their physico-chemical parameters for their potential in biodiesel. The properties of Neem biodiesel were compared with Bureau of Indian Standards (BIS) and the fuel properties of diesel. Results showed that high amounts of FFA in oils produced low quality biodiesel while neutralized oils with low amounts of FFA produced high quality biodiesel. The quality of biodiesel from jatropha and castor oils was improved greatly by neutralising the crude oils.


2017 ◽  
Vol 68 (9) ◽  
pp. 2060-2065
Author(s):  
Elena Lacramioara Lisa ◽  
Geta Carac ◽  
Vasilica Barbu ◽  
Silvia Robu

Toothpastes containing different components which could have beneficial effects on oral health and the identification of better composition are always a research challenge. Our study aims are to evaluate the synergistic effect of propolis, myrrh, and chlorhexidine, separated and combined in some formulated toothpaste. To assess the electrochemical capacity by monitoring of physico-chemical parameters (pH conductivity), the mixture of these components in toothpaste into artificial saliva solution was performed in ambient medium and at 37oC. The antioxidant activity and the antimicrobial potential in vitro of toothpastes formulated against microorganisms that frequently colonize the oral cavity was performed also. It has been found that mixtures of chlorhexidine, propolis, and myrrh exhibit synergistic antioxidant activity with better potential than some commercial toothpaste, also the antibacterial activity shown that this activity is maintained in time against some strains.


2015 ◽  
Vol 62 (s9) ◽  
pp. 41-45 ◽  
Author(s):  
F. Šeršeň ◽  
M. Lácová

AbstractNineteen derivatives of coumarin were tested on the scavenging of 2,2-diphenyl-1-picrylhydrazyl, hydroxyl and superoxide anion radicals. It was found that antioxidant activity exhibits only such coumarins that contain hydroxyl groups. The derivatives without hydroxyl group showed very low antioxidant effectiveness or they were ineffective. On the other hand, the greatest antioxidant effectiveness was exhibited by coumarin derivatives that contained hydroxyl groups in 6 or 8 position, whereas the effectiveness of derivatives with one hydroxyl group in 4, 5 or 7 position was very low. Based on scavenging of the above-mentioned radicals, it was found that the most effective scavengers were 7,8-dihydroxy-4-methylcoumarin (i.e. compound that contains two hydroxyl groups in 7 and 8 positions), (7,8-dihydroxy-2-oxo-2H-chromen-4-yl)acetic acid (this compound contains in addition to two hydroxyl groups in 7 and 8 positions also one hydroxyl group in the acidic residue), esculetin (6,7-dihydroxycoumarin) and 6,7-dihydroxy-4-methylcoumarin.


2010 ◽  
Vol 120 (1) ◽  
pp. 261-267 ◽  
Author(s):  
Zheng Sun ◽  
Xiaofang Peng ◽  
Jin Liu ◽  
King-Wai Fan ◽  
Mingfu Wang ◽  
...  

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