Antimicrobial Activity of Hydroxylactone obtained by Biotransformation of Bromo- and Iodolactone with Gem-Dimethylcyclohexane Ring

Grabarczyk, Małgorzata; Mączka, Wanda; Wińska, Katarzyna; Żarowska, Barbara; Anioł, Mirosław

doi:10.5935/0103-5053.20130238

Cited by 11 publications

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“…Usually strains of genus Fusarium were very good biocatalysts for halolactones and transform halolactones independently of halogen. Contrary to the results described in our earlier papers [26,28,29,32] from five strains of genus Fusarium, only one was able to convert the chosen substrates into product with a good yield. Independent of the structure of the compound, the best substrate for biotransformation was bromolactone 3, which was converted by eight strains.…”

Section: Scheme 1 Synthesis Of Halolactones 2-4contrasting

confidence: 54%

“…The mechanism of such reaction was similar to SN2 substitution and OH group was usually introduced in an equatorial position. This kind of transformation most often is catalysed by haloalcane dehalogenases during Our earlier experience [23,[27][28][29][30][31] indicated that the most common reaction for halolactones during biotransfomation was the conversion into hydroxylactones. The mechanism of such reaction was similar to S N 2 substitution and OH group was usually introduced in an equatorial position.…”

Section: Scheme 1 Synthesis Of Halolactones 2-4mentioning

confidence: 99%

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Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

et al. 2016

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Abstract:The aim of the study was to obtain biological active compounds during biotransformation. Three bicyclic halolactones with methylcyclohexane ring (2-chloro-4-methyl-9-oxabicyclononan-8-one, 2-bromo-4-methyl-9-oxabicyclo[4.3.0]nona--8-one and 2-iodo-4-methyl-9-oxabicyclo[4.3.0]nonan-8-one) obtained from the corresponding γ,δ-unsaturated acid were subjected to a screening biotransformation using 22 fungal strains. Two of these strains (Cunninghamella japonica AM472 and Fusarium culmorum AM10) were able to transform halolactones into 2-hydroxy-4-methyl-9-oxabicyclo[4.3.0]nonan-8-one by hydrolytic dehalogenation with good yield. The biotransformation product was structurally different from its synthetically prepared analog.All halolactones and hydroxylactones were tested for their biological activity. The chlorolactone inhibited growth of Staphylococcus aureus (max ∆OD = 0), Escherichia coli (max ∆OD = 0.3) and Candida albicans (max ∆OD = 0) strains. Bromolactone caused inhibition of growth of Staphylococcus aureus (max ∆OD = 0) and Fusarium linii (max ∆OD = 0) strains. Iodolactone limited growth of Staphylococcus aureus (max ∆OD = 0), Escherichia coli (max ∆OD = 0.25), Candida albicans (max ∆OD = 0.45) and Pseudomonas fluorescens (max ∆OD = 0.42) strains. Hydroxylactone caused inhibition of growth of Staphylococcus aureus (max ∆OD = 0.36) and Pseudomonas fluorescens (max ∆OD = 0.39) strains only. The test performed on aphids Myzus persicae (Sulz.) showed that chloro-and bromolactone exhibited deterrent activity after 24 h (ID = 0.5 and 0.4, respectively), while hydroxylactone was a weak attractant (ID = −0.3).

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Section: Scheme 1 Synthesis Of Halolactones 2-4contrasting

confidence: 54%

Section: Scheme 1 Synthesis Of Halolactones 2-4mentioning

confidence: 99%

Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

et al. 2016

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“…As part of our ongoing research on the biotransformation of halolactones with a methyl-substituted cyclohexane rings [ 30 , 31 , 32 , 33 , 34 , 35 ], in this paper we present further examples of a biohydroxylation of chloro-, bromo- and iodolactones containing a methylcyclohexane ring. We examined the effect of the methyl group position in the cyclohexane ring on the ability of microorganisms to replace the halogen atom with a hydroxy group.…”

Section: Introductionmentioning

confidence: 99%

Lactones with Methylcyclohexane Systems Obtained by Chemical and Microbiological Methods and Their Antimicrobial Activity

et al. 2015

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Abstract:Eight new lactones (δ-chloro-, δ-bromo-and δ-iodo-γ-lactones), each with a methylcyclohexane ring, were obtained by chemical means from (4-methylcyclohex-2-en-1-yl) acetic acid or (6-methylcyclohex-2-en-1-yl) acetic acid. Whole cells of ten fungal strains (Fusarium species, Syncephalastrum racemosum and Botrytis cinerea) were tested on their ability to convert these lactones into other products. Some of the tested fungal strains transformed chloro-, bromo-and iodolactone with a methyl group at C-5 into 2-hydroxy-5-methyl-9-oxabicyclo[4.3.0]nonan-8-one during hydrolytic dehalogenation. When the same lactones had the methyl group at C-3, no structural modifications of halolactones were observed. In most cases, the optical purity of the product was low or medium, with the highest rate for chlorolactone (45.4%) and iodolactone (45.2% and 47.6%). All of the obtained compounds were tested with reference to their smell. Seven halolactones and the hydroxylactone obtained via biotransformation of halolactones with 5-methylcyclohexane ring were examined for their antimicrobial activity. These compounds were capable of inhibiting growth of some bacteria, yeasts and fungi. OPEN ACCESSMolecules 2015, 20 3336

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“…Hydroxylactone completely inhibited the growth of Micrococcus flavus, Pseudomonas fluorescens and Alternaria species and retarded the growth of Bacillus cereus, Debaryomyces hansenii and Penicillium species. Hydroxylactone showed no effect on growth of Escherichia coli, Bacillus subtilis, Saccharomyces cerevisiae, Yarrowia lipolytica, Schizosaccharomyces pombe, Rhodotorula rubra and Aspergillus niger [37]. Pinicoloform is an unbranched acyclic compound which contains a trichloromethyl group.…”

Section: Compound Possessing Antimicrobial Activitymentioning

confidence: 99%

Functionally Substituted Chemical Organic Compounds: Potential Antimicrobial Substances

Ganbar¹

2019

OAJMB

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The development of resistance to antimicrobial agents is a global health problem for humans as well as animals. Over the past decade, the rate of microbial resistance to antibiotics has alarmingly increased. Factors contributing to this ever increasing antibiotic resistance pertain to microorganism as well as excessive and unwise use of the antibiotics. Biofilm formation and use of efflux pumps are the examples of microbial factors responsible for emergence of antimicrobial resistance. To ameliorate this condition, it is dire need of time to develop new antimicrobial agents. In this regard, chemical organic compounds are best available substances with potential antimicrobial properties. This review summarizes the antimicrobial activities of some important organic compounds as well as potential of functionally substituted chemical organic compounds as probable antimicrobial agents of future. These important organic compounds include functionally substituted derivatives of cyclohexane, quaternary ammonium compounds, hydrazones, pyrazolone, triazole, thiones, isatin, indole, chalcones, quinoxaline, anthraquinones, coumarins, thiophenes, piperidine, benzoxazolinone, phthalazinone, sulfones, thiazole and volatile organic compounds.

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Antimicrobial Activity of Hydroxylactone obtained by Biotransformation of Bromo- and Iodolactone with Gem-Dimethylcyclohexane Ring

Cited by 11 publications

References 0 publications

Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

Lactones with Methylcyclohexane Systems Obtained by Chemical and Microbiological Methods and Their Antimicrobial Activity

Functionally Substituted Chemical Organic Compounds: Potential Antimicrobial Substances

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