Format

Send to

Choose Destination
J Chem Inf Model. 2015 Dec 28;55(12):2552-61. doi: 10.1021/acs.jcim.5b00513. Epub 2015 Dec 15.

Assessing the Protective Activity of a Recently Discovered Phenolic Compound against Oxidative Stress Using Computational Chemistry.

Author information

1
Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa , San Rafael Atlixco 186, Col. Vicentina, Iztapalapa, C. P., 09340 México D. F., México.
2
Departamento de Física y Química Teórica, Facultad de Química, Universidad Nacional Autónoma de México , México D. F. 04510, México.

Abstract

The protection exerted by 3,5-dihydroxy-4-methoxybenzyl alcohol (DHMBA), a phenolic compound recently isolated from the Pacific oyster, against oxidative stress (OS) is investigated using the density functional theory. Our results indicate that DHMBA is an outstanding peroxyl radical scavenger, being about 15 times and 4 orders of magnitude better than Trolox for that purpose in lipid and aqueous media, respectively. It was also found to react faster with HOO(•) than other known antioxidants such as resveratrol and ascorbic acid. DHMBA is also predicted to be able to sequester Cu(II) ions, consequently inhibiting the OS induced by Cu(II)-ascorbate mixtures and downgrading the (•)OH production via the Haber-Weiss reaction. However, it is proposed that DHMBA is more efficient as a primary antioxidant (free radical scavenger), than as a secondary antioxidant (metal ion chelator). In addition, it was found that DHMBA can be efficiently regenerated in aqueous solution, at physiological pH. Such regeneration is expected to contribute to increase the antioxidant protection exerted by DHMBA. These results suggest that probably synthetic routes for this compound should be pursued, because albeit its abundance in nature is rather low, its antioxidant activity is exceptional.

PMID:
26624520
DOI:
10.1021/acs.jcim.5b00513
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center