Furanones are analogues of acylated homoserine lactones with proven antifouling activity in both Gram-positive and Gram-negative bacteria though the interference of various quorum sensing pathways. In an attempt to find new strategies to prevent and control biofilm formation on stainless steel (SS) surfaces, different concentrations of six synthetic furanones were applied on biofilms formed by strains isolated from food, environmental, and clinical sources grown onto AISI 316 SS coupons. Among the furanones tested, (Z-)-4-Bromo-5-(bromomethylene)-2(5)-furanone and 3,4-Dichloro-2(5)-furanone significantly ( < 0.05) reduced the adhesion capacity (>1 log CFU cm) in 24 h treated biofilms. Moreover, individually conducted experiments demonstrated that (Z-)-4-Bromo-5-(bromomethylene)-2(5)-furanone was able to not only significantly ( < 0.05) prevent adhesion but also to reduce the growth rate of planktonic cells up to 48 h in a dose-dependent manner. LIVE/DEAD staining followed by epifluorescence microscopy visualisation confirmed these results show an alteration of the structure of the biofilm in furanone-treated samples. Additionally, it was demonstrated that 20 µmol L of 3,4-Dichloro-2(5)-furanone dosed at 0, 24 and 96 h was able to maintain a lower level of adhered cells (>1 log CFU cm; < 0.05). Since furanones do not pose a selective pressure on bacteria, these results represent an appealing novel strategy for the prevention of biofilm grown onto SS.
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http://dx.doi.org/10.3390/foods8120647 | DOI Listing |
Org Lett
October 2024
Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China.
A novel substrate-regulated [4+1] annulation of α-imidoyl sulfoxonium ylides with diazoketones under catalyst-free conditions is described. The reaction proceeds through a coupling of sulfoxonium ylides and in situ-generated ketenes to form the key reactive zwitterionic intermediates, followed by selective formation of C-C or C-O bonds to achieve five-membered ring systems. The cascade reaction permits the direct synthesis of synthetically useful 2-indanones and 3(2)-furanones, which expands the reaction pattern of sulfoxonium ylides in annulation transformation.
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September 2024
State Key Laboratory of Organometallic Chemistry and Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032, People's Republic of China.
Here, we report the preparation of lactones via Ni-catalyzed alkene hydroxylarylation and sequential intramolecular lactonization with O as a green oxidant and oxygen source. The bulky 1,3-diketone ligand is crucial by enabling Ni-catalyzed hydroxylarylation of alkenes, providing numerous phthalide and furanone derivatives with high efficiency under mild conditions. The synthetic value of this methodology was further demonstrated by the efficient synthesis of typhaphthalide and a monoamine oxidase B inhibitor.
View Article and Find Full Text PDFBiosensors (Basel)
August 2024
Avram and Stella Goldstein-Goren Department of Biotechnology Engineering, Ben-Gurion University of the Negev, Be'er Sheva 84105, Israel.
is an opportunistic Gram-negative bacterium that remains a prevalent clinical and environmental challenge. Quorum-sensing (QS) molecules are effective biomarkers in pinpointing the presence of . This study aimed to develop a convenient-to-use, whole-cell biosensor using reporters individually encapsulated within alginate-poly-L-lysine (alginate-PLL) microbeads to specifically detect the presence of bacterial autoinducers.
View Article and Find Full Text PDFJ Agric Food Chem
March 2024
Department of Chemistry, University of Turin, Via P. Giuria, 7, Turin 10125, Italy.
A methodology for the total and modulable synthesis of (4)-lachnophyllum lactone (), on a gram scale, is reported for the first time. The present work started with the design of a retrosynthetic pathway for the target compound, with the key step identified in Pd-Cu bimetallic cascade cross-coupling cyclization. (4)-Lachnophyllum lactone () is an acetylenic furanone previously isolated, in a low amount, from the organic extract of the autotrophic weed.
View Article and Find Full Text PDFJ Food Sci
March 2024
Laboratory of Biopolymers and Nanotechnology in Food (BioNano), Department of Agroindustrial Science and Technology, Federal University of Pelotas, Pelotas, Brazil.
Onion is rich in bioactive and volatile compounds with antioxidant activity. However, the pungent odor of volatile compounds (VOCs) released restricts its use. The encapsulation of red onion extract by electrospinning is an alternative to mask this odor and protect its bioactive compounds.
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