scholarly journals Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 420
Author(s):  
Grażyna Kubiak-Tomaszewska ◽  
Piotr Roszkowski ◽  
Emilia Grosicka-Maciąg ◽  
Paulina Strzyga-Łach ◽  
Marta Struga

Flavonoids and polyunsaturated fatty acids due to low cytotoxicity in vitro studies are suggested as potential substances in the prevention of diseases associated with oxidative stress. We examined novel 6-hydroxy-flavanone and 7-hydroxy-flavone conjugates with selected fatty acids (FA) of different length and saturation and examined their cytotoxic and antioxidant potential. Our findings indicate that the conjugation with FA affects the biological activity of both the original flavonoids. The conjugation of 6-hydroxy-flavanone increased its cytotoxicity towards prostate cancer PC3 cells. The most noticeable effect was found for oleate conjugate. A similar trend was observed for 7-hydroxy-flavone conjugates with the most evident effect for oleate and stearate. The cytotoxic potential of all tested conjugates was not specific towards PC3 because the viability of human keratinocytes HaCaT cells decreased after exposure to all conjugates. Additionally, we showed that esterification of the two flavonoids decreased their antioxidant activity compared to that of the original compounds. Of all the tested compounds, only 6-sorbic flavanone showed a slight increase in antioxidant potential compared to that of the original compound. Our data show that conjugated flavonoids are better absorbed and enhance cytotoxic effects, but the presence of FA lowered the antioxidant potential.

2020 ◽  
Vol 16 ◽  
Author(s):  
Benedetta Bocchini ◽  
Bruna Goldani ◽  
Fernanda S.S. Sousa ◽  
Paloma T. Birmann ◽  
Cesar A. Brüning ◽  
...  

Background: Quinoline derivatives have been attracted much attention in drug discovery and synthetic derivatives of these scaffolds present a range of pharmacological activities. Therefore, organoselenium compounds are valuable scaffolds in organic synthesis because their pharmacological activities and their use as versatile building blocks for regio-, chemio-and stereoselective reactions. Thus, the synthesis of selenium-containing quinolines has great significance, and their applicability range from simple antioxidant agents, to selective DNA-binding and photocleaving agents. Objective: In the present study we describe the synthesis and antioxidant activity in vitro of new 7-chloroN(arylselanyl)quinolin-4-amines 5 by the reaction of 4,7-dichloroquinoline 4 with (arylselanyl)-amines 3. Methods: For the synthesis of 7-chloro-N(arylselanyl)quinolin-4-amines 5, we performed the reaction of (arylselanyl)- amines 3 with 4,7-dichloroquinoline 4 in the presence of Et3N at 120 °C in a sealed tube. The antioxidant activities of the compounds 5 were evaluated by the following in vitro assays: 2,2- diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, 2,2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), ferric ion reducing antioxidant power (FRAP), nitric oxide (NO) scavenging and superoxide dismutase-like activity (SOD-Like). Results: 7-Chloro-N(arylselanyl)quinolin-4-amines 5a-d has been synthesized in yields ranging from 68% to 82% by the reaction of 4,7-dichloroquinoline 4 with arylselanyl-amines 3a-d using Et3N as base, at 120 °C, in a sealed tube for 24 hours and tolerates different substituents, such as -OMe and -Cl, in the arylselanyl moiety. The obtained compounds 5a-d presented significant results with respect to the antioxidant potential, which had effect in the tests of inhibition of radical’s DPPH, ABTS+ and NO, as well as in the test that evaluates the capacity (FRAP) and in the superoxide dismutase-like activity assay (SOD-Like). It is worth mentioning that 7-chloro-N(arylselanyl)quinolin-4-amine 5b presented excellent results, demonstrating a better antioxidant capacity when compared to the others. Conclusion: According to the obtained results 7-chloro-N(arylselanyl)quinolin-4-amines 5 were synthesized in good yields by the reaction of 4,7-dichloroquinoline with arylselanyl-amines and tolerates different substituents in the arylselanyl moiety. The tested compounds presented significant antioxidant potential in the tests of inhibition of DPPH, ABTS+ and NO radicals, as well as in the FRAP and superoxide dismutase-like activity assays (SOD-Like).


Author(s):  
Letiele Bruck de Souza ◽  
Amanda Leitão Gindri ◽  
Thainara de Andrade Fortes ◽  
Jefferson Enderle ◽  
Rafael Roehrs ◽  
...  

2008 ◽  
Vol 56 (24) ◽  
pp. 11694-11699 ◽  
Author(s):  
Anika E. Wagner ◽  
Patricia Huebbe ◽  
Tetsuya Konishi ◽  
M. Mamunur Rahman ◽  
Meiko Nakahara ◽  
...  

2020 ◽  
Vol 0 (0) ◽  
Author(s):  
Anna Muzykiewicz-Szymańska ◽  
Joanna Zielonka-Brzezicka ◽  
Joanna Siemak ◽  
Adam Klimowicz

SummaryIntroduction: Due to the content of nutrients and taste attributes, the plant sprouts could become a valuable component of a healthy diet.Objective: The aim of the study was to evaluate the antioxidant potential of various sprouts extracts depending on the processing method of the plant material.Methods: The extracts in 96%(v/v) ethanol were prepared from fresh, frozen, dry and homogenized sprouts of alfalfa, broccoli, radish, lentil, mung bean, beetroot, sunflower, and kale, using ultrasound-assisted extraction. The antioxidant potential and total polyphenols content were evaluated by the in vitro methods.Results: The highest antioxidant activity was observed for beetroot and kale as well as broccoli sprouts extracts. The lower potential, in general, was observed in the case of alfalfa, lentil, and mung bean sprouts samples. The lowest activity was observed most frequently for the extracts from dry material, whereas the highest for homogenized as well as frozen and fresh.Conclusion: The plant sprouts, particularly beetroot, kale, and broccoli, could be a valuable source of natural antioxidants.


2021 ◽  
Vol 25 (03) ◽  
pp. 677-682
Author(s):  
Amara Javaid

The present study was conducted to evaluate the in vitro antioxidant activity of Ficus carica, commonly known as fig. Methanol and ethanol extracts of F. carica leaves were subjected to 2, 2-diphenyl-1-picryhydrazyl (DPPH) free radical scavenging activity assay where ascorbic acid being positive control had an IC50 value of 3.98±0.26 while methanol and ethanol fractions showed an IC50 of 101.76±1.12 and 93.12±1.17 respectively exhibiting their high antioxidant potential. DPPH assay was also performed on high performance liquid chromatography (HPLC) elutions. Most active antioxidant components in ethanol extract were eluted between 17–18 min, and those in methanol were eluted over 14–15 min and upon ultra-high performance liquid chromatography-mass spectrometery (Orbitrap Liquid Chromatography-Mass Spectrometry) were identified to be 13-Docosenamide, (Z)- for ethanol and ficusin for methanol fraction. Thus, it is concluded that these two components are most probable determinants of antioxidant potential of F. carica leaf extracts. © 2021 Friends Science Publishers


2020 ◽  
Vol 11 (3) ◽  
pp. 2986-2992
Author(s):  
Jambula Dinesh Babu ◽  
Venugopalan Santhosh Kumar

Cadaba farinosa (family Capparidaceae) is generally known as “Indian cadaba” in the traditional ayurvedic system. The current study, aerial parts of different concentrates (Pet.ether, ethyl acetate and methanol) of Cadaba farinose was evaluated for its in-vitro antioxidant potential by Diphenylpicrylhydrazyl radical, and total antioxidant activity taking ascorbate as standard and superoxide radical activity taking Quercetin as the standard for the in-vitro methods. The methanolic concentrates of Cadaba farinose& ascorbic acid exhibited antioxidant potential possessing IC50 208µg/ml & 66µg/ml (Diphenylpicrylhydrazyl radical) , 188µg/ml & 57µg/ml (total antioxidant). The methanolic concentrates of Cadaba farinose & quercetin exhibited antioxidant potential possessing IC50 252µg/ml & 60µg/ml (superoxide radical). The IC50 value was originated that methanolic concentrates of Cadaba farinose more efficient in Diphenylpicrylhydrazyl radical, superoxide radical activity, total antioxidant activity compared EA & PE concentrates. The difference in scavenging potential of the extracts can be due to variation in the percentage of bioactive compound present in different solvents. Invitro antioxidant studies show methanolic concentrates of Cadaba farinose have better antioxidant activity. This result indicates that aerial parts of methanolic concentrate Cadaba farinose could serve as a natural antioxidant, which may be useful in preventing free radical-induced diseases.


2017 ◽  
Vol 13 (1) ◽  
pp. 56-59
Author(s):  
Aura M. Blandón ◽  
Oscar M. Mosquera ◽  
Antônio E. G. Sant’ana ◽  
Aldenir F. Dos Santos ◽  
Luana L. S. Pires

The present study describes the in vitro antioxidant activity of methanol extracts of 34 plant species collected in the Colombian coffee-growing eco-region belonging to Euphorbiaceae, Piperaceae and Solanaceae families. The antioxidant properties of extracts were evaluated by determining radical scavenging power measured with a DPPH assay. The methanolic extracts of  Hyeronimia antioquiensis, Mabea montana, and Alchornea grandis species (Euphorbiaceae), presents EC50 values equal to 0.686, 12.35, and 13.01 µg/mL, respectively, showing high antioxidant potential.


2020 ◽  
Vol 11 (2) ◽  
pp. 1545-1550
Author(s):  
Mythri M ◽  
Sanal Dev K T ◽  
Kottai Muthu A

Cassia absus (Linn)Cassia absus(Linn) (family Fabaceae ) is generally known as “chaksu ” inan ayurvedic traditional system.The current study,aerial parts of different concentrates(Pet.ether, ethyl acetate and methanol) of Cassia absus, was evaluated for its in-vitro antioxidant potential byDiphenylpicrylhydrazyl radical,nitric oxide activity andtotal antioxidant activitytaking ascorbate as the standardfor all the three methods. The IC50 value was originated that methanolic concentrates of Cassia absusmore efficient inDiphenylpicrylhydrazyl radical,nitric oxide activity, total antioxidant activitycompared EA&PEconcentrates.The methanolic concentrates of Cassia absus& ascorbic acid exhibited antioxidant potential possessing IC50230µg/ml &130µg/ml (Nitric oxide). 205µg/ml &57µg/ml (total antioxidant),195µg/ml & 66µg/ml (Diphenylpicrylhydrazyl radical)respectively. The difference in the scavenging potential of the extracts can be due to variation in the percentage of bioactive compounds present in different solvents. Invitroantioxidant studiesobviouslyshow the methanolic concentrates of Cassia absushave better antioxidant activity. This result indicates that aerial parts of methanolic concentratesCassia absuscould serve as a natural antioxidant, which may be useful in preventfree radical-induced diseases.


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