Relationship between the lipophilicity of gallic acid n-alquil esters’ derivatives and both myeloperoxidase activity and HOCl scavenging

Rosso, Rober; Vieira, Tiago O.; Leal, Paulo César; Nunes, Ricardo José; Yunes, Rosendo A.; Creczynski-Pasa, Tânia B.

doi:10.1016/j.bmc.2006.05.038

Cited by 41 publications

(34 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Considering that lipophilicity is an important property for the development of bioactive compounds (31), the theoretical lipophilicity values of the alkyl gallates were expressed as calculated partition coefficients (C log P), as previously reported (20) (Table 1). By comparisons of the determined MIC values with the C log P values, we noticed that the anti-X.…”

Section: Resultsmentioning

confidence: 99%

“…citri subsp. citri activity of gallic acid (3,4,5-trihydroxybenzoic acid), an intermediate of the hydrolysable tannin biosynthesis pathway in plants ( [13][14][15] which, together with its natural and semisynthetic derivatives, has been associated with a broad spectrum of biological actions (16)(17)(18)(19)(20)(21). Moreover, gallic acid and derivatives demonstrated antimicrobial properties.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Antibacterial Activity of Alkyl Gallates against Xanthomonas citri subsp. citri

et al. 2013

View full text Add to dashboard Cite

The plant-pathogenic bacterium Xanthomonas citri subsp. citri is the causal agent of Asiatic citrus canker, a serious disease that affects all the cultivars of citrus in subtropical citrus-producing areas worldwide. There is no curative treatment for citrus canker; thus, the eradication of infected plants constitutes the only effective control of the spread of X. citri subsp. citri. Since the eradication program in the state of São Paulo, Brazil, is under threat, there is a clear risk of X. citri subsp. citri becoming endemic in the main orange-producing area in the world. Here we evaluated the potential use of alkyl gallates to prevent X. citri subsp. citri growth. These esters displayed a potent anti-X. citri subsp. citri activity similar to that of kanamycin (positive control), as evaluated by the resazurin microtiter assay (REMA). The treatment of X. citri subsp. citri cells with these compounds induced altered cell morphology, and investigations of the possible intracellular targets using X. citri subsp. citri strains labeled for the septum and centromere pointed to a common target involved in chromosome segregation and cell division. Finally, the artificial inoculation of citrus with X. citri subsp. citri cells pretreated with alkyl gallates showed that the bacterium loses the ability to colonize its host, which indicates the potential of these esters to protect citrus plants against X. citri subsp. citri infection.

show abstract

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Antibacterial Activity of Alkyl Gallates against Xanthomonas citri subsp. citri

et al. 2013

View full text Add to dashboard Cite

show abstract

“…These different effects may be associated with the differing levels of hydrophobicity associated with each compound. Studies carried out by Dodo et al, 48) Rosso et al, 14) and Locatelli et al, 45) indicated that the hydrophobicity of the alkyl chain of gallate derivatives is important in terms of antiproliferative and antioxidant activity, and the alkyl chain might contribute to improving the cell permeability or the interaction with hydrophobic pockets in the target molecule.…”

Section: Discussionmentioning

confidence: 99%

“…13,46) Also, they presented antioxidant activity by inhibiting ROS production as well as scavenging them. 14,56) In this way we understand that the increase in p53 gene expression induced by gallic acid and dodecyl gallate is related to the antioxidant status and not to the apoptotic events, since these compounds present high antioxidant power.…”

Section: Discussionmentioning

confidence: 99%

“…For instance, synthetic GA derivatives with eight or more carbon atoms in the side-chain were more efficient than GA in antiviral, antifungal, antioxidant and anticancer activities, wherein dodecyl gallate (DGA) can be mentioned as the most active. 10,11,13,14) This is the first evaluation of GA and DGA as liver injury protector by using both, acute and chronic CCl 4 intoxication models. For this purpose, oxidative stress, liver function, lipid profile, histomorphological changes and expression of p53 gene were evaluated.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Gallic Acid and Dodecyl Gallate Prevents Carbon Tetrachloride-Induced Acute and Chronic Hepatotoxicity by Enhancing Hepatic Antioxidant Status and Increasing p53 Expression

Perazzoli

Perondi

Baratto

et al. 2017

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

Gallic acid (3,4,5-trihydroxybenzoic acid, GA), a natural phenolic acid has been reported as a strong antioxidant. Therefore the present study was designed to evaluate the effects of GA and dodecyl gallate (DGA) against acute and chronic carbon tetrachloride (CCl 4 )-induced hepatotoxicity. For acute model, rats were orally treated with GA and DGA for 7 d prior to CCl 4 by intraperitoneally (i.p.) injection. For the chronic model, rats were orally treated with GA or DGA and CCl 4 i.p. twice a week for four weeks. In both acute and chronic models, the CCl 4 -treated groups showed significantly increase in serum hepatic enzyme activities and histopathologic alterations, as well as a disruption in antioxidative status. In contrast, the treatment with GA and DGA restored serum hepatic enzymes activities, improved histopathologic alterations, increased glutathione (GSH) and decreased lipid peroxidation levels. The activities of liver antioxidant enzymes were increased by GA and DGA only in acute model. The expression of p53 gene increased about 3.5 times after GA and DGA treatments, which could result in cell death of damaged hepatocytes preventing of a lifelong liver failure. Thus, these results suggest that GA and DGA has the potential to prevent liver damages as the case of fibrosis condition.

show abstract