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Novel macromolecules derived from coumarin: synthesis and antioxidant activity.

Al-Amiery AA, Al-Majedy YK, Kadhum AA, Mohamad AB - Sci Rep (2015)

Bottom Line: The rational design of 4-hydroxycoumarins with tailor-made antioxidant activities is required nowadays due to the wide variety of pharmacologically significant, structurally interesting of coumarins and researcher orientation toward green chemistry and natural products.A simple and unique coumarins have been achieved by reaction of 4-hydroxycoumarin with aromatic aldehyde accompanied with the creation of a macromolecules have 2-aminothiazolidin-4-one.The scavenging abilities of new compounds against stable DPPH radical (DPPH•) and hydrogen peroxide were done and the results show that the compounds exhibited high antioxidant activates.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemical and Process Engineering, Universiti Kebangsaan Malaysia (UKM), Bangi, Selangor 43000, Malaysia.

ABSTRACT
The rational design of 4-hydroxycoumarins with tailor-made antioxidant activities is required nowadays due to the wide variety of pharmacologically significant, structurally interesting of coumarins and researcher orientation toward green chemistry and natural products. A simple and unique coumarins have been achieved by reaction of 4-hydroxycoumarin with aromatic aldehyde accompanied with the creation of a macromolecules have 2-aminothiazolidin-4-one. The molecular structures of the compounds were characterized by the Fourier transformation infrared and Nuclear magnetic resonance spectroscopies, in addition to CHN analysis. The scavenging abilities of new compounds against stable DPPH radical (DPPH•) and hydrogen peroxide were done and the results show that the compounds exhibited high antioxidant activates.

No MeSH data available.


Related in: MedlinePlus

Effect of compound (1–6) toward hydrogen peroxide.
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f3: Effect of compound (1–6) toward hydrogen peroxide.

Mentions: The role of antioxidant is to remove free radicals. One important mechanism through which this is achieved is by donating hydrogen to free radicals in its reduction to nonreactive species14. Addition of hydrogen would remove the odd electron feature which is responsible for radical reactivity. Free radicals have been a subject of significant interest among scientists in the past decade. Their broad range of effects in biological systems has drawn the attention of many workers15. It has been proven that free radicals play an important role in the pathogenesis of certain diseases and aging16. Many synthetic antioxidant components have shown toxic and/or mutagenic effects, and therefore attention has been paid to naturally occurring antioxidants. Compounds (1–6) were screened for in vitro antioxidant activity using DPPH (2,2-diphenyl-1-picrylhydrazyl) radical and H2O2 (hydrogen peroxide). They show good antioxidant activity (Figs 2 and 3). The hydrogen-donating activity, measured using 2,2-diphenyl-1-picrylhydrazyl and hydrogen peroxide radicals as hydrogen acceptor, showed that significant association could be found between the concentration of the new synthesized molecule and the percentage of inhibition. Through 2,2-diphenyl-1-picrylhydrazyl and hydrogen peroxide test, compounds (1–6) have been shown to reduce the stable radical. According to Fig. 2 the synthesized compounds (1), (3) and (5), possessing 88%, 92%, and 89.6% DPPH radical scavenging activity. These compounds contain 3,4-dihydroxyphenyl ring. Compounds with these substituents are expected to possess antioxidant activity17, since hydrogen donation leads to formation of a stable quinoid-structure. It has been reported that two hydroxyl groups are important for antioxidant activity1819. The scavenging effect increased with the increasing concentrations of test compounds. In DPPH method, the maximum scavenging activity was 92% at a concentration 1000 μg/mL for compound (3) and the minimum scavenging activity was 16% at a concentration of 250 μg/mL for compound (6). The antioxidant activities of (1–6) were done using DPPH (2,2-diphenyl-1-picrylhydrazyl) radical and H2O2 (hydrogen peroxide) scavenging methods. Ascorbic acid was used as the standard. Figures 2 and 3, indicates the antioxidant activities of (1–6).


Novel macromolecules derived from coumarin: synthesis and antioxidant activity.

Al-Amiery AA, Al-Majedy YK, Kadhum AA, Mohamad AB - Sci Rep (2015)

Effect of compound (1–6) toward hydrogen peroxide.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4488837&req=5

f3: Effect of compound (1–6) toward hydrogen peroxide.
Mentions: The role of antioxidant is to remove free radicals. One important mechanism through which this is achieved is by donating hydrogen to free radicals in its reduction to nonreactive species14. Addition of hydrogen would remove the odd electron feature which is responsible for radical reactivity. Free radicals have been a subject of significant interest among scientists in the past decade. Their broad range of effects in biological systems has drawn the attention of many workers15. It has been proven that free radicals play an important role in the pathogenesis of certain diseases and aging16. Many synthetic antioxidant components have shown toxic and/or mutagenic effects, and therefore attention has been paid to naturally occurring antioxidants. Compounds (1–6) were screened for in vitro antioxidant activity using DPPH (2,2-diphenyl-1-picrylhydrazyl) radical and H2O2 (hydrogen peroxide). They show good antioxidant activity (Figs 2 and 3). The hydrogen-donating activity, measured using 2,2-diphenyl-1-picrylhydrazyl and hydrogen peroxide radicals as hydrogen acceptor, showed that significant association could be found between the concentration of the new synthesized molecule and the percentage of inhibition. Through 2,2-diphenyl-1-picrylhydrazyl and hydrogen peroxide test, compounds (1–6) have been shown to reduce the stable radical. According to Fig. 2 the synthesized compounds (1), (3) and (5), possessing 88%, 92%, and 89.6% DPPH radical scavenging activity. These compounds contain 3,4-dihydroxyphenyl ring. Compounds with these substituents are expected to possess antioxidant activity17, since hydrogen donation leads to formation of a stable quinoid-structure. It has been reported that two hydroxyl groups are important for antioxidant activity1819. The scavenging effect increased with the increasing concentrations of test compounds. In DPPH method, the maximum scavenging activity was 92% at a concentration 1000 μg/mL for compound (3) and the minimum scavenging activity was 16% at a concentration of 250 μg/mL for compound (6). The antioxidant activities of (1–6) were done using DPPH (2,2-diphenyl-1-picrylhydrazyl) radical and H2O2 (hydrogen peroxide) scavenging methods. Ascorbic acid was used as the standard. Figures 2 and 3, indicates the antioxidant activities of (1–6).

Bottom Line: The rational design of 4-hydroxycoumarins with tailor-made antioxidant activities is required nowadays due to the wide variety of pharmacologically significant, structurally interesting of coumarins and researcher orientation toward green chemistry and natural products.A simple and unique coumarins have been achieved by reaction of 4-hydroxycoumarin with aromatic aldehyde accompanied with the creation of a macromolecules have 2-aminothiazolidin-4-one.The scavenging abilities of new compounds against stable DPPH radical (DPPH•) and hydrogen peroxide were done and the results show that the compounds exhibited high antioxidant activates.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemical and Process Engineering, Universiti Kebangsaan Malaysia (UKM), Bangi, Selangor 43000, Malaysia.

ABSTRACT
The rational design of 4-hydroxycoumarins with tailor-made antioxidant activities is required nowadays due to the wide variety of pharmacologically significant, structurally interesting of coumarins and researcher orientation toward green chemistry and natural products. A simple and unique coumarins have been achieved by reaction of 4-hydroxycoumarin with aromatic aldehyde accompanied with the creation of a macromolecules have 2-aminothiazolidin-4-one. The molecular structures of the compounds were characterized by the Fourier transformation infrared and Nuclear magnetic resonance spectroscopies, in addition to CHN analysis. The scavenging abilities of new compounds against stable DPPH radical (DPPH•) and hydrogen peroxide were done and the results show that the compounds exhibited high antioxidant activates.

No MeSH data available.


Related in: MedlinePlus