Non-antibiotic antibacterial activity of dodecyl gallate

Kubo, Isao; Fujita, Ken‐ichi; Nihei, Ken Ichi; Masuoka, Noriyoshi

doi:10.1016/s0968-0896(02)00436-4

Cited by 80 publications

(49 citation statements)

References 21 publications

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“…13) A similar parabolic function of lipophilicity and antimicrobial activity is observed in Gram-positive bacteria and fungi. 11,14,15) The antibacterial pattern of alkyl gallates against R. solanacearum is entirely different from those of previously reported results.…”

Section: Effect Of Carbon Number Of Alkyl Gallatescontrasting

confidence: 92%

“…Various mechanisms of action have been suggested for the antibacterial activity of gallate esters, such as membrane disruption 12) or inhibition of respiration; 11,14) however, the conclusions are still unclear. The structure-activity relationship of gallates and parabens in R. solanacearum is different from their relationship in other bacteria, suggesting that the mechanism of action may differ and be specific to R. solanacearum.…”

Section: Antibacterial Activity Of Some Constituents In Geraniummentioning

confidence: 99%

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Antibacterial activity of alkyl gallates and related compounds against Ralstonia solanacearum

et al. 2011

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Antibacterial activity of alkyl gallates and their analogs against Ralstonia solanacearum was examined. Methyl gallate showed the strongest activity among the alkyl gallates; activity decreased as the carbon number of esters increased. This tendency of alkyl gallates to act against R. solanacearum was dissimilar to its previously reported action against Gram-negative and Gram-positive bacteria and fungi. Among related compounds with a differing position and number of phenolic hydroxyl groups, methyl 2,3-dihydroxybenzoate showed comparable or slightly stronger activity than methyl gallate. Geraniin, one of the characteristic secondary metabolites produced by Geranium spp., showed moderate activity.

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Section: Effect Of Carbon Number Of Alkyl Gallatescontrasting

confidence: 92%

Section: Antibacterial Activity Of Some Constituents In Geraniummentioning

confidence: 99%

Antibacterial activity of alkyl gallates and related compounds against Ralstonia solanacearum

et al. 2011

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“…Effects of ZP-CT-A on -lactamase activity Since the mechanisms concerning the inhibition oflactam 21,22) and the disruption of the cell membrane [23][24][25][26][27] were thought to be included in the effect of natural substances on the antibiotic-resistant bacteria, we examined those effects of ZP-CT-A. First, we examined the effect on -lactamase activity using strain PC1, which produces -lactamase constitutively, but not PBP 2a.…”

Section: Cooperative Effects Of Zp-ct-a and Oxacillin On The Growth Pmentioning

confidence: 99%

Polyphenolic Constituent Structures ofZanthoxylum piperitumFruit and the Antibacterial Effects of Its Polymeric Procyanidin on Methicillin-ResistantStaphylococcus aureus

Kusuda

Inada

Ogawa

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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“…5,6) Besides the antioxidant activity, other biological activities have been described for this group of molecules, mainly anticancer, [7][8][9][10] antibacterial and antifungal properties. [11][12][13][14][15][16] There are few reports about the antiviral activity of these compounds. In 1988, the potent inhibition of HSV-1 and HSV-2 by methyl gallate was described.…”

mentioning

confidence: 99%

Evaluation of Anti-HSV-2 Activity of Gallic Acid and Pentyl Gallate

Kratz

Andrighetti-Fröhner

Leal

et al. 2008

Biological & Pharmaceutical Bulletin

126

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Herpes simplex virus (HSV) is a DNA-containing enveloped virus that causes common viral infections in humans worldwide leading to a variety of diseases. HSV-1 and HSV-2 can be distinguished on the basis of clinical manifestations (the former is more frequently associated with oral cold sores, while the later causes genital ulcers) and biochemical and serological examinations. In most cases, HSV infection is usually benign or asymptomatic in immunocompetent individuals; however, in patients with an immature or compromised immune system, the infection can be serious and sometimes life-threatening. 1,2) Several nucleoside analogues have been approved for clinical use. Among those, acyclovir is widely used for the systemic treatment of HSV infections. It is a highly selective antiviral agent because it is specifically phosphorylated by viral thymidine kinase in infected cells. However, acyclovir-resistant HSV infection in immunocompromised patients such as transplanted patients and patients with AIDS has recently been observed. Therefore, it is desirable to develop new anti-HSV agents in order to substitute or complement the antiviral drugs available. 3,4)The synthetic n-alkyl esters of gallic acid (GA), also known as gallates, especially propyl, octyl and dodecyl gallates, are widely employed as antioxidants by food and pharmaceutical industries. 5,6) Besides the antioxidant activity, other biological activities have been described for this group of molecules, mainly anticancer, 7-10) antibacterial and antifungal properties. [11][12][13][14][15][16] There are few reports about the antiviral activity of these compounds. In 1988, the potent inhibition of HSV-1 and HSV-2 by methyl gallate was described. 17) In 2000, as part of the screening of phenolic compounds against HIV-1 integrase, gallic acid was found to be active. 18)More recently, the anti-HSV activity of several gallates was described by our research group, which proposed various structure-activity relationships regarding the antiviral, antioxidant and genotoxic effects.19) Furthermore, the pronounced anti-HSV-1 activity of octyl gallate, and its inhibitory effect against RNA viruses were also recently described. 20,21) In the present study, the anti-HSV-2 activity of gallic acid and pentyl gallate was evaluated followed by the determination of the site of antiviral activity of these compounds. MATERIALS AND METHODSCompounds GA and pentyl gallate (PG) (Fig. 1) were synthesized as previously described.19) The compounds (50 mM) were dissolved in dimethyl sulfoxide, stored at Ϫ20°C protected from light, and further diluted in culture medium prior to use.Cells and Virus African green monkey kidney cells (GMK AH1) were grown in Eagle's minimum essential medium (EMEM, Gibco BRL, Grand Island, NY, U.S.A.) supplemented with 2% fetal calf serum (FSC), 0.05% primaton substance (Kraft Inc., Norwich, CT, U.S.A.), 100 U/ml Göteborg, Sweden. Received November 23, 2007; accepted February 5, 2008; published online February 20, 2008 The synthetic n-alkyl esters of galli...

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Non-antibiotic antibacterial activity of dodecyl gallate

Cited by 80 publications

References 21 publications

Antibacterial activity of alkyl gallates and related compounds against Ralstonia solanacearum

Antibacterial activity of alkyl gallates and related compounds against Ralstonia solanacearum

Polyphenolic Constituent Structures ofZanthoxylum piperitumFruit and the Antibacterial Effects of Its Polymeric Procyanidin on Methicillin-ResistantStaphylococcus aureus

Evaluation of Anti-HSV-2 Activity of Gallic Acid and Pentyl Gallate

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