Limits...
In Silico Discovery of Novel Potent Antioxidants on the Basis of Pulvinic Acid and Coumarine Derivatives and Their Experimental Evaluation.

Martinčič R, Mravljak J, Švajger U, Perdih A, Anderluh M, Novič M - PLoS ONE (2015)

Bottom Line: A pigment from the edible mushroom Xerocomus badius norbadione A, which is a natural derivative of pulvinic acid, was found to possess antioxidant properties.Since the pulvinic acid represents a novel antioxidant scaffold, several other derivatives were recently synthetized and evaluated experimentally, along with some structurally related coumarine derivatives.The obtained data formed the basis for the construction of several quantitative structure-activity and pharmacophore models, which were employed in the virtual screening experiments of compound libraries and for the prediction of their antioxidant activity, with the goal of discovering novel compounds possessing antioxidant properties.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Chemometrics, National Institute of Chemistry Slovenia, Hajdrihova 19, 1000, Ljubljana, Slovenia.

ABSTRACT
A pigment from the edible mushroom Xerocomus badius norbadione A, which is a natural derivative of pulvinic acid, was found to possess antioxidant properties. Since the pulvinic acid represents a novel antioxidant scaffold, several other derivatives were recently synthetized and evaluated experimentally, along with some structurally related coumarine derivatives. The obtained data formed the basis for the construction of several quantitative structure-activity and pharmacophore models, which were employed in the virtual screening experiments of compound libraries and for the prediction of their antioxidant activity, with the goal of discovering novel compounds possessing antioxidant properties. A final prioritization list of 21 novel compounds alongside 8 established antioxidant compounds was created for their experimental evaluation, consisting of the DPPH assay, 2-deoxyribose assay, β-carotene bleaching assay and the cellular antioxidant activity assay. Ten novel compounds from the tetronic acid and barbituric acid chemical classes displayed promising antioxidant activity in at least one of the used assays, that is comparable to or even better than some standard antioxidants. Compounds 5, 7 and 9 displayed good activity in all the assays, and were furthermore effective preventers of oxidative stress in human peripheral blood mononuclear cells, which are promising features for the potential therapeutic use of such compounds.

No MeSH data available.


a) Histogram of the second-order rate constants determined after 60 minutes from the initiation of the reaction; b) histogram of the second-order rate constants determined after 24 hours from the initiation of the reaction.AA–ascorbic acid; GA–gallic acid; QU–quercetin; TR–Trolox; AE–aesculin; SC–scopoletin; RE–resveratrol; CU–curcumin.
© Copyright Policy
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4608598&req=5

pone.0140602.g006: a) Histogram of the second-order rate constants determined after 60 minutes from the initiation of the reaction; b) histogram of the second-order rate constants determined after 24 hours from the initiation of the reaction.AA–ascorbic acid; GA–gallic acid; QU–quercetin; TR–Trolox; AE–aesculin; SC–scopoletin; RE–resveratrol; CU–curcumin.

Mentions: The kinetic behavior of the compounds was evaluated by calculating the second-order rate constants for the reaction with DPPH during the first 60 minutes, and also during the total 24 hours of incubation, where appropriate. When comparing the rate constants of the novel compounds during the first 60 minutes to the standard fast antioxidants (such as ascorbic acid, gallic acid, quercetin and Trolox), we found the kinetic behavior of the novel compounds to be slower, but still within the same order of magnitude. In the case of the rate constants during the total 24 hours, we found the kinetic behavior of the novel compounds to be similar to that of resveratrol and curcumin, and much more rapid than the action of aesculin and scopoletin (Table 2 and Fig 6).


In Silico Discovery of Novel Potent Antioxidants on the Basis of Pulvinic Acid and Coumarine Derivatives and Their Experimental Evaluation.

Martinčič R, Mravljak J, Švajger U, Perdih A, Anderluh M, Novič M - PLoS ONE (2015)

a) Histogram of the second-order rate constants determined after 60 minutes from the initiation of the reaction; b) histogram of the second-order rate constants determined after 24 hours from the initiation of the reaction.AA–ascorbic acid; GA–gallic acid; QU–quercetin; TR–Trolox; AE–aesculin; SC–scopoletin; RE–resveratrol; CU–curcumin.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4608598&req=5

pone.0140602.g006: a) Histogram of the second-order rate constants determined after 60 minutes from the initiation of the reaction; b) histogram of the second-order rate constants determined after 24 hours from the initiation of the reaction.AA–ascorbic acid; GA–gallic acid; QU–quercetin; TR–Trolox; AE–aesculin; SC–scopoletin; RE–resveratrol; CU–curcumin.
Mentions: The kinetic behavior of the compounds was evaluated by calculating the second-order rate constants for the reaction with DPPH during the first 60 minutes, and also during the total 24 hours of incubation, where appropriate. When comparing the rate constants of the novel compounds during the first 60 minutes to the standard fast antioxidants (such as ascorbic acid, gallic acid, quercetin and Trolox), we found the kinetic behavior of the novel compounds to be slower, but still within the same order of magnitude. In the case of the rate constants during the total 24 hours, we found the kinetic behavior of the novel compounds to be similar to that of resveratrol and curcumin, and much more rapid than the action of aesculin and scopoletin (Table 2 and Fig 6).

Bottom Line: A pigment from the edible mushroom Xerocomus badius norbadione A, which is a natural derivative of pulvinic acid, was found to possess antioxidant properties.Since the pulvinic acid represents a novel antioxidant scaffold, several other derivatives were recently synthetized and evaluated experimentally, along with some structurally related coumarine derivatives.The obtained data formed the basis for the construction of several quantitative structure-activity and pharmacophore models, which were employed in the virtual screening experiments of compound libraries and for the prediction of their antioxidant activity, with the goal of discovering novel compounds possessing antioxidant properties.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Chemometrics, National Institute of Chemistry Slovenia, Hajdrihova 19, 1000, Ljubljana, Slovenia.

ABSTRACT
A pigment from the edible mushroom Xerocomus badius norbadione A, which is a natural derivative of pulvinic acid, was found to possess antioxidant properties. Since the pulvinic acid represents a novel antioxidant scaffold, several other derivatives were recently synthetized and evaluated experimentally, along with some structurally related coumarine derivatives. The obtained data formed the basis for the construction of several quantitative structure-activity and pharmacophore models, which were employed in the virtual screening experiments of compound libraries and for the prediction of their antioxidant activity, with the goal of discovering novel compounds possessing antioxidant properties. A final prioritization list of 21 novel compounds alongside 8 established antioxidant compounds was created for their experimental evaluation, consisting of the DPPH assay, 2-deoxyribose assay, β-carotene bleaching assay and the cellular antioxidant activity assay. Ten novel compounds from the tetronic acid and barbituric acid chemical classes displayed promising antioxidant activity in at least one of the used assays, that is comparable to or even better than some standard antioxidants. Compounds 5, 7 and 9 displayed good activity in all the assays, and were furthermore effective preventers of oxidative stress in human peripheral blood mononuclear cells, which are promising features for the potential therapeutic use of such compounds.

No MeSH data available.