Brominated furanone and epigallocatechin gallate (EGCG) are naturally occurring polyphenolic compounds that can be derived from sources such as Delisea pulchra algae and green tea, respectively. These compounds may have potential health benefits and antimicrobial properties. Biofilm formation and bacterial motility are virulence factors that seem to be involved in the autoinducer 2 (AI-2)-mediated quorum sensing (QS) response of Campylobacter. In this study, the anti-QS activities of 2(5H)-furanone, EGCG, and a citric-based disinfectant were tested against Campylobacter jejuni. The minimal bactericidal concentration (MBC) was determined by a microdilution method, and the AI-2 activity was measured by bioluminescence. For motility tests, subinhibitory concentrations of each compound were mixed with semisolid Muller Hinton agar. Biofilm formation was quantified in broth-containing microplates after staining with safranin. The MBC of tested compounds ranged from 0.3 to 310 μg/mL. Subinhibitory concentrations of all of the antimicrobial compounds significantly decreased (19 to 62 %) the bacterial motility and reduced biofilm formation. After treatment with EGCG, furanone, and the disinfectant, AI-2 activity was decreased by 60 to 99 % compared to control. In conclusion, 2(5H)-furanone, EGCG, and the disinfectant exert bactericidal effects against C. jejuni and disturb QS activity and reduce motility and biofilm formation. These compounds may be naturally occurring alternatives to control C. jejuni.

• MeSH
• biofilmy účinky léků   MeSH
• Campylobacter jejuni účinky léků   genetika   fyziologie   MeSH
• dezinficiencia farmakologie   MeSH
• gama-butyrolakton analogy a deriváty   farmakologie   MeSH
• katechin analogy a deriváty   farmakologie   MeSH
• kyselina citronová farmakologie   MeSH
• mikrobiální testy citlivosti MeSH
• quorum sensing účinky léků   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• butenolide MeSH Prohlížeč
• dezinficiencia MeSH
• epigallocatechin gallate MeSH Prohlížeč
• gama-butyrolakton MeSH
• katechin MeSH
• kyselina citronová MeSH

Tornabeatins A, B, C and D, have been isolated as new natural products from the lichenized ascomycete Tornabea scutellifera, and their structures elucidated using UV, IR, MS, 1D and 2D NMR spectral data and chemical degradation.

• MeSH
• antibakteriální látky chemie   izolace a purifikace   farmakologie   MeSH
• antifungální látky chemie   izolace a purifikace   farmakologie   MeSH
• antitumorózní látky chemie   izolace a purifikace   farmakologie   MeSH
• Artemia účinky léků   MeSH
• Ascomycota chemie   MeSH
• chromatografie plynová MeSH
• gama-butyrolakton chemie   izolace a purifikace   farmakologie   MeSH
• hmotnostní spektrometrie MeSH
• ježovky účinky léků   MeSH
• magnetická rezonanční spektroskopie MeSH
• molekulární struktura MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• antibakteriální látky MeSH
• antifungální látky MeSH
• antitumorózní látky MeSH
• gama-butyrolakton MeSH

Six symmetrical 3,6-diaryl (aryl=phenyl, 2-, 3- and 4-tolyl, 2,4- and 3,5-xylyl) substituted furo[3,4-c]furanones (DFF) were synthesized. The computational analysis, based on density functional theory, found eight possible centrosymmetrical slipped π-stack arrangements, formed according to electron repulsion minimization principle, as for previously reported for π-isoelectronic diketopyrrolopyrroles (DPP). One of these slipped stack arrangements was found to form infinite columns in the crystals of a new polymorph of parent phenyl derivative (with centre-to-centre distance CC=6.975 Å), other three types of stacks were found for 3-tolyl (CC=6.153 Å), 4-tolyl (CC=3.849 Å) and 2,4-xylyl (CC=4.856 Å) derivatives by single crystal X-ray diffractometry. All six derivatives show intense solution fluorescence in blue/green region, with a maximum driven entirely by a number and position of methyl substituents on phenyl rings. On the other hand, the solid-state fluorescence from yellow over orange to red is observed only for four derivatives and its presence/absence, spectral position and vibronic structure is driven exclusively by the slips in π-stacks (with interplanar distance always less than 3.5 Å) of almost planar DFF molecules, resulting in J-type emission, H-type excimer-like emission and H-type quenching.

• Klíčová slova
• density functional theory, diketopyrrolopyrroles, fluorescence, furofuranones, polymorphism, regioisomerism,
• Publikační typ
• časopisecké články MeSH

A series of racemic 3-phenyl-5-methyl-2H,5H-furan-2-ones related to a natural product, (-)incrustoporine, was synthesized, and their antifungal activity evaluated. The key structural feature, furanone ring, was closed via H2SO4-mediated cyclization of 2-phenylpent-4-enoic acids. The compounds displayed antifungal activity, especially against filamentous fungi. Expressed as the minimum inhibition concentration (MIC) in micromol/L, the activity of the most promising derivative against Absidia corymbifera matched that of ketoconazole (31.25 micromol/L). In terms of microg/mL, the substance was more active (7.6 microg/mL) than this standard antifungal drug (16.6 microg/mL).

• MeSH
• antifungální látky chemická syntéza   chemie   farmakologie   MeSH
• chlorbenzeny chemická syntéza   chemie   farmakologie   MeSH
• cyklizace MeSH
• gama-butyrolakton analogy a deriváty   chemická syntéza   chemie   farmakologie   MeSH
• houby účinky léků   MeSH
• ketokonazol farmakologie   MeSH
• lidé MeSH
• molekulární struktura MeSH
• racionální návrh léčiv MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• 3-(3,4-dichlorophenyl)-5-methyl-2H,5H-furan-2-one MeSH Prohlížeč
• antifungální látky MeSH
• chlorbenzeny MeSH
• gama-butyrolakton MeSH
• incrustoporin MeSH Prohlížeč
• ketokonazol MeSH

Quorum sensing is a widespread form of cell-to-cell communication, which is based on the production of signaling molecules known as autoinducers (AIs). The first group contains highly species-specific N-acyl homoserine lactones (N-AHLs), generally known as AI-1, which are produced by AHL synthase. The second group, possessing the characteristic structure of a furanone ring, are known as AI-2. The enzyme responsible for their production is S-ribosylhomocysteine lyase (LuxS). In Campylobacter jejuni, AI-2 and LuxS play a role in many important processes, including biofilm formation, stress response, motility, expression of virulence factors, and colonization. However, neither the receptor protein nor the exact structure of the AI-2 molecule have been identified to date. Similarly, little is known about the possible existence of AHL-synthase producing AI-1 and its impact on gene expression. Recently, an analogue of homoserine lactone, called cjA, was isolated from a cell-free supernatant of C. jejuni strain 81-176 and from the food isolate c11. The molecule cjA particularly impacted the expression of virulence factors and biofilm formation. This review summarizes the role of AI-2 and cjA in the context of biofilm formation, motility, stress responses, and expression of virulence factors.

• Klíčová slova
• Autoinducer 2, Campylobacter jejuni, Gene expression, Quorum sensing, cjA,
• MeSH
• bakteriální proteiny genetika   metabolismus   MeSH
• biofilmy růst a vývoj   MeSH
• Campylobacter jejuni genetika   metabolismus   patogenita   MeSH
• druhová specificita MeSH
• faktory virulence metabolismus   MeSH
• fyziologický stres fyziologie   MeSH
• gama-butyrolakton analogy a deriváty   genetika   metabolismus   MeSH
• homoserin analogy a deriváty   genetika   metabolismus   MeSH
• laktony metabolismus   MeSH
• quorum sensing MeSH
• regulace genové exprese u bakterií * MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• přehledy MeSH
• Názvy látek
• bakteriální proteiny MeSH
• faktory virulence MeSH
• gama-butyrolakton MeSH
• homoserin MeSH
• homoserine lactone MeSH Prohlížeč
• laktony MeSH
• N-octanoylhomoserine lactone MeSH Prohlížeč

Low molecular weight signaling compounds (LMWC) are important players in regulating various aspects of Streptomyces biology. Their exact roles in certain strain will ultimately depend on overall configuration of regulatory network and thus cannot be predicted on basis of in silico studies. Here, we explored S. ghanaensis gene SSFG_07725 (afsAgh) presumably involved in initial steps of formation of γ-butyrolactone LMWC. Disruption of afsAgh impaired aerial mycelium formation and increased the transcription of pleiotropic regulatory gene adpAgh, whereas level of moenomycin production remained virtually unaffected. We provide evidence that morphogenetic deficiency of afsAgh-minus mutant was caused by inability to produce diffusible LMWC. Possible links between γ-butyrolactone signaling and various aspects of S. ghanaensis biology are discussed.

• MeSH
• bakteriální proteiny genetika   metabolismus   MeSH
• gama-butyrolakton metabolismus   MeSH
• mutace MeSH
• oligosacharidy metabolismus   MeSH
• Streptomyces enzymologie   genetika   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• bakteriální proteiny MeSH
• gama-butyrolakton MeSH
• moenomycin MeSH Prohlížeč
• oligosacharidy MeSH

5-Acetoxymethyl-3-(4-bromophenyl)-2,5-dihydrofuran-2-one previously described as highly antifungally active was found to provide the corresponding 5-methylene derivative via an unusual DMSO-promoted elimination of the ester group at C5 under antifungal assay conditions. Since the latter possessed nearly the same antifungal effect as that originally reported for the former, the 5-acetoxymethyl furanone just served as a precursor of the actual antifungally active species. A few series of compounds with alkyloxy, aryloxy and alkylidene substituents at C5 of the parent furanone structure were therefore prepared and evaluated. In line with the ease of elimination of the substituent from C5, low activities of the 5-alkoxy compounds were observed. On the other hand, their 5-aryloxymethyl congeners were found to be capable of liberating the antifungally active 5-methylene furanone into the testing medium. The antifungal effect of the 5-alkylidene derivatives was highly sensitive to substitution of the alkylidene moiety; a substituent in the allylic position was necessary for a compound to retain high activity. Parallel evaluation of cytostatic activity showed moderate activities of the antifungally active derivatives against HeLa S3 and CCRF-CEM lines. Cell cycle analysis of CCRF-CEM cells following the treatment with 5-methylene-3-(4-bromophenyl)-2,5-dihydrofuran-2-one revealed that this compound is a necrotic agent.

• MeSH
• antifungální látky chemická syntéza   chemie   farmakologie   MeSH
• apoptóza MeSH
• buněčné linie MeSH
• cytostatické látky chemická syntéza   chemie   farmakologie   MeSH
• furany chemická syntéza   chemie   farmakologie   MeSH
• HeLa buňky MeSH
• lidé MeSH
• mikrobiální testy citlivosti MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• antifungální látky MeSH
• cytostatické látky MeSH
• furan MeSH Prohlížeč
• furany MeSH

Plant-derived smoke stimulates seed germination in numerous plant species. Smoke also has a positive stimulatory effect on pollen germination and pollen tube growth. The range of plant families affected my smoke still needs to be established since the initial study was restricted to only three species from the Amaryllidaceae. The effects of smoke-water (SW) and the smoke-derived compounds, karrikinolide (KAR1 ) and trimethylbutenolide (TMB) on pollen growth characteristics were evaluated in seven different plant families. Smoke-water (1:1000 and 1:2000 v:v) combined with either Brewbaker and Kwack's (BWK) medium or sucrose and boric acid (SB) medium significantly improved pollen germination and pollen tube growth in Aloe maculata All., Kniphofia uvaria Oken, Lachenalia aloides (L.f.) Engl. var. aloides and Tulbaghia simmleri P. Beauv. Karrikinolide (10(-6) and 10(-7) m) treatment significantly improved pollen tube growth in A. maculata, K. uvaria, L. aloides and Nematanthus crassifolius (Schott) Wiehle compared to the controls. BWK or SB medium containing TMB (10(-3) m) produced significantly longer pollen tubes in A. maculata, K. uvaria and N. crassifolius. These results indicate that plant-derived smoke and the smoke-isolated compounds may stimulate pollen growth in a wide range of plant species.

• Klíčová slova
• Karrikinolide, pollen germination, pollen tube growth, smoke-water, trimethylbutenolide,
• MeSH
• furany farmakologie   MeSH
• gama-butyrolakton analogy a deriváty   farmakologie   MeSH
• kouř MeSH
• kultivační média MeSH
• liliovité účinky léků   MeSH
• pyl účinky léků   růst a vývoj   MeSH
• pylová láčka účinky léků   růst a vývoj   MeSH
• pyrany farmakologie   MeSH
• voda MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• butenolide MeSH Prohlížeč
• furany MeSH
• gama-butyrolakton MeSH
• karrikinolide MeSH Prohlížeč
• kouř MeSH
• kultivační média MeSH
• pyrany MeSH
• voda MeSH

Quorum-sensing control mediated by N-acylhomoserine lactone (AHL) signal molecules has been established as a key feature in the regulation of various metabolic traits in many bacteria. Approximately 300 strains representing 6 genera and 18 species of soil-borne and plant-associated Gram-negative bacteria isolated in various regions of the former USSR using two reporter systems were screened for AHL production. The production was observed in 17.5% of the screened bacterial strains. Positive response was detected in all of the 14 tested strains of Erwinia herbicola, in 41 of the 239 strains of Pseudomonas species; in all 5 strains of Xanthomonas ampelina, X. campestris pv. malvacearum, pv. translucens, pv. vesicatoria and in one strain of Pantoea stewartii. AHL assay of 41 strains of X. maltophilia (syn. Stenotrophomonas maltophilia) isolated from soils with Chromobacterium violaceum reporter has revealed no strains synthesizing these signal molecules; 26 strains analyzed with Agrobacterium tumefaciens reporter showed the same result.

• MeSH
• gama-butyrolakton analogy a deriváty   biosyntéza   metabolismus   MeSH
• gramnegativní bakterie růst a vývoj   metabolismus   MeSH
• půdní mikrobiologie * MeSH
• rostliny mikrobiologie   MeSH
• signální transdukce fyziologie   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• gama-butyrolakton MeSH
• homoserine lactone MeSH Prohlížeč

The biologically active molecules karrikinolide (KAR1) and trimethylbutenolide (TMB) present in wildfire smoke play a key role in regulating seed germination of many plant species. To elucidate the physiological mechanism by which smoke-water (SW), KAR1, and TMB regulate seed germination in photosensitive 'Grand Rapids' lettuce (Lactuca sativa), we investigated levels of the dormancy-inducing hormone abscisic acid (ABA), three auxin catabolites, and cytokinins (26 isoprenoid and four aromatic) in response to these compounds. Activity of the hydrolytic enzymes α-amylase and lipase along with stored food reserves (lipids, carbohydrate, starch, and protein) were also assessed. The smoke compounds precisely regulated ABA and hydrolytic enzymes under all light conditions. ABA levels under red (R) light were not significantly different in seeds treated with TMB or water. However, TMB-treated seeds showed significantly inhibited germination (33%) compared with water controls (100%). KAR1 significantly enhanced total isoprenoid cytokinins under dark conditions in comparison with other treatments; however, there was no significant effect under R light. Enhanced levels of indole-3-aspartic acid (an indicator of high indole-3-acetic acid accumulation, which inhibits lettuce seed germination) and absence of trans-zeatin and trans-zeatin riboside (the most active cytokinins) in TMB-treated seeds might be responsible for reduced germination under R light. Our results demonstrate that SW and KAR1 significantly promote lettuce seed germination by reducing levels of ABA and enhancing the activity of hydrolytic enzymes, which aids in mobilizing stored reserves. However, TMB inhibits germination by enhancing ABA levels and reducing the activity of hydrolytic enzymes.

• MeSH
• furany farmakologie   MeSH
• fytochrom metabolismus   MeSH
• gama-butyrolakton analogy a deriváty   farmakologie   MeSH
• klíčení účinky léků   MeSH
• kouř * MeSH
• lékové interakce MeSH
• pyrany farmakologie   MeSH
• regulátory růstu rostlin metabolismus   MeSH
• salát (hlávkový) účinky léků   metabolismus   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• furany MeSH
• fytochrom MeSH
• gama-butyrolakton MeSH
• karrikinolide MeSH Prohlížeč
• kouř * MeSH
• pyrany MeSH
• regulátory růstu rostlin MeSH
• trimethylbutenolide MeSH Prohlížeč