Antibacterial activity, phenolics

A number of tests have been deseribed which imitate, at least in part, the principle of the phenol eoeffieient test for liquid disinfectants. A culture of the test organism is mixed intimately with the semi-sohd preparation, and the mixture subcultuied by means of a loop into a suitable broth designed to disperse the base and neutrahze the antibacterial activity of the medicament. 

Oya, A., Yoshida, S., Abe, Y., Iizuka, T. and Makiyama, N., Antibacterial activated carbon fiber derived from phenolic resin containing silver nitrate, Carbon, 1993, 31(1), 71 73. 

Friedman, M., Ftenika, P. R., Mandrell, R. E. (2003b). Antibacterial activities of phenolic benzaldehydes and benzoic acids against Campylobacter jejuni, Escherichia coli. Listeria monocytogenes, and Salmonella enterica. J. Food Prot., 66, 1811-1821. 

Interestingly, the undifferentiated antibacterial activity against both methicillin-susceptible and -resistant strains of Staphylococcus aureus was suggestive of an alternative mechanism of action compared to that of typical (3-lactams. The molecular modeling approach allowed the identification of interactions through oxygenated functions such as phenolic OH, which are valuable for the antibacterial activity [294]. 

Vivas et al. 1997). Recently, the evaluation of the dual antioxidant and antibacterial activity of 21 phenolic compounds mainly present in Vitis Vinifera L. belonging to different groups was examined (Garcfa-Ruiz et al. 2008b). Structure-activity relationships were probed for both antimicrobial and antioxidant properties of wine phenolics, confirming the potential of these compounds as an alternative to sulphites in winemaking. 

In general, phenols possess good antibacterial activity. Chlorocresol is active against Ps. aeruginosa at concentrations of 1000 p.g/ml [54,56] and chlorbutol at 5000 pg/ml. Phenols probably exert their primary effect by interfering with the integrity of the cytoplasmic membrane [57]. 

Thoma K, Ullmann E, Fickel O. The antibacterial activity of phenols in the presence of polyoxyethylene stearates and polyethylene glycols [in German]. Arch Pharm 1970 303 289— 296. 

Oya, A., Kimura, M., Sugo, T., et al. (1994). Antibacterial activated carbon fiber derived from methyl methacrylate-grafted phenolic resin fiber. Carbon, 32, 107-10. 

In vitro antibacterial activity limited to Gram-negative bacteria has been demonstrated using aqueous leaf extracts and phenolic components of coltsfoot (Anonymous, 1996). 

The MIC of the acetates esculetin 2Ac (2a) and fraxetin 2Ac (4a ) were found to be equal to those of the parent compounds 2 and 4. Most probably, acetylation of the phenolic OH does not alter the antibacterial activity of the hydroxycoumarins. Compounds 4 and 4a are the most potent inhibitors of S. aureus among the tested Fraxinus ornus components. 

T. Esaki, "Quantitative Drug Design Studies. VI Quantitative Structure-Activity Relationships of lonizable Substances Antibacterial Activities of Phenols", Chem. Pharm. Bull, 1987, 35, 3105 - 3111. 

A toxicological study of the methanolic extract of M. grandiflora heartwood led to the identification of menisperine (N-methyl isocorydine) (38), a phenolic quaternary alkaloid [62]. Toxicity of this methanol extract was ultimately due to the neuromuscular blocking action of the alkaloid. Davis isolated this alkaloid and two antibacterial compounds, parthenolide (1) and anonaine (39), from M grandiflora [63]. Parthenolide, from the yellowed leaves of M. grandiflora exihibited antibiotic activity against Bacillus subiilis at an MIC (minimum inhibitory concentration) of 3 Xg ml 1. Anonaine demonstrated antibacterial activity at 100 mg ml against... 

Phenolic constituents of M grandiflora L., namely magnolol (6), honokiol (7), and 3, 5 -diallyl-2 -hydroxy-4-methoxy-biphenyl (46) were found to have good antibacterial activity against Bacillus subtilis. Staphylococcus aureus, and Mycobacterium smegatis when compared to streptomycin sulfate [67]. Additionally, magnolol and honokiol were found to be... 

The simplest form of a Free Wilson analysis is presented in eq. 192 [22], which describes the antibacterial activities of phenol and isomeric chlorophenols (51, R = H, Cl one to five chlorine atoms) vs. Staphylococcus aureus at least the linearity of the structure-activity relationship can be derived from eq. 192 on the other hand, although most probably lipophilicity is responsible for the variance in the biological activities, no Hansch equation can be derived, because each other physicochemical property of the chlorine atom will give identical results. 

An example of the application of the DARC-PELCO approach is given in eq. 199 (PC = phenol coefficient) [421], which describes the antibacterial activities of linear and branched alcohols (54) however, the result is trivial, because the compounds... 

Amodiaquine is a congener of chloroquine and is employed for the treatment of overt malarial attacks and for suppression. Although it is more active than chloroquine both in vitro and m vivo against certain strains of Plasmodium falciparum with decreased sensitivity to chloroquine, amodiaquine is not recommended for routine use in the treatment of such infections (1). It appears that phenolic hydroi l is essential to the activity of amodiaquine since the removal of this group depresses, and its methylation completely destroys antibacterial activity (2). Amodiaquine has been synthesized and patented under the name of Camoquin by Parke, Davis and Company in 1949 (3). It is used medicinally in the form of its dihydrochloride. 

Pinosylvin (3,5-stilbenediol) ( )-form needles, insoluble in water, soluble in acetone. )- and (Z)-isomers occur together with the corresponding mono- and dimethyl ethers in pines, firs, and conifers. Pinosylvin has antifungal and antibacterial activities and protects the wood against rot, as a disinfectant it is 30-times stronger than phenol and is highly toxic for fish. As a result of condensation with lignin, pinosylvin prevents sulfite dissolution of wood. Pinosylvin monomethyl ether acts as an antifeedant for certain rabbit species. ... 

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