Antimicrobial Activity of Chalcones with a Chlorine Atom and Their Glycosides.

Chalcones, secondary plant metabolites, exhibit various biological properties. The introduction of a chlorine and a glucosyl substituent to the chalcone could enhance its bioactivity and bioavailability. Such compounds can be obtained through a combination of chemical and biotechnological methods.

The Influence of Flavonoids with -Br, -Cl Atoms and -NO, -CH Groups on the Growth Kinetics and the Number of Pathogenic and Probiotic Microorganisms.

The pursuit of novel or modified substances based on a natural origin, like flavonoids, is essential in addressing the increasing number of diseases and bacterial resistance to antibiotics, as well as in maintaining intestinal balance and enhancing overall gut health. The primary goal of this research was to evaluate the impact of specific flavonoid compounds-chalcones, flavanones, and flavones-substituted with -Br, -Cl, -CH, and -NO on both pathogenic and probiotic microorganisms. Additionally, this study aimed to understand these compounds' influence on standardized normal and pathologically altered intestinal microbiomes.

Flavone and 3-hydroxyflavone supplementation in cryopreservation medium protects canine sperm against apoptosis and lipid peroxidation.

Cryopreservation is a pivotal technique in safeguarding genetic material across diverse species, despite its inherent challenges linked to induced spermatozoa damage, notably apoptosis and lipid peroxidation (LPO). Given the insufficient antioxidant defense of spermatozoa against LPO, there is a rising interest in integrating additional additives into extenders to ameliorate mammalian semen quality. Among these additives, flavonoids have garnered considerable attention due to their potent antioxidative properties.

Synthesis, fungal biotransformation, and evaluation of the antimicrobial potential of chalcones with a chlorine atom.

Chalcones are intermediate products in the biosynthesis of flavonoids, which possess a wide range of biological properties, including antimicrobial and anticancer activities. The introduction of a chlorine atom and the glucosyl moiety into their structure may increase their bioavailability, bioactivity, and pharmacological use. The combined chemical and biotechnological methods can be applied to obtain such compounds.

The influence of the chlorine atom on the biological activity of 2'-hydroxychalcone in relation to the lipid phase of biological membranes - Anticancer and antimicrobial activity.

The study investigates the effect of the presence of a chlorine atom in the 2'-hydroxychalcone molecule on its interaction with model lipid membranes, in order to discern its potential pharmacological activity. Five chlorine derivatives of 2'-hydroxychalcone were synthesized and evaluated against liposomes composed of POPC and enriched with cationic (DOTAP) or anionic (POPG) lipids. The physicochemical properties of the compounds were initially simulated using SwissAdame software, revealing high lipophilicity (ilogP values: 2.

The Effect of Methyl-Derivatives of Flavanone on MCP-1, MIP-1β, RANTES, and Eotaxin Release by Activated RAW264.7 Macrophages.

Chemokines, also known as chemotactic cytokines, stimulate the migration of immune cells. These molecules play a key role in the pathogenesis of inflammation leading to atherosclerosis, neurodegenerative disorders, rheumatoid arthritis, insulin-resistant diabetes, and cancer. Moreover, they take part in inflammatory bowel disease (IBD).

Antimicrobial Properties of Flavonoid Derivatives with Bromine, Chlorine, and Nitro Group Obtained by Chemical Synthesis and Biotransformation Studies.

The search for new substances of natural origin, such as flavonoids, is necessary in the fight against the growing number of diseases and bacterial resistance to antibiotics. In our research, we wanted to check the influence of flavonoids with chlorine or bromine atoms and a nitro group on pathogenic and probiotic bacteria. We synthesized flavonoids using Claisen-Schmidt condensation and its modifications, and through biotransformation via entomopathogenic filamentous fungi, we obtained their glycoside derivatives.

Structural investigation of interactions between halogenated flavonoids and the lipid membrane along with their role as cytotoxic agents.

This study focuses on understanding the structural and molecular changes in lipid membranes under the influence of six halogenated flavonoid derivatives differing in the number and position of substitution of chlorine and bromine atoms (D1-D6). Utilizing various analytical techniques, including fluorometric methods, dynamic light scattering (DLS), attenuated Fourier transform infrared spectroscopy (ATR- FTIR), and FT-Raman spectroscopy, the research aims to elucidate the mechanisms underlying the interaction of flavonoids with cell membranes. Additionally, the study includes in silico analyses to explore the physicochemical properties of these compounds and their potential pharmaceutical applications, along with toxicity studies to assess their effects on cancer, normal, and red blood cells.

Methoxychalcones as potential anticancer agents for colon cancer: Is membrane perturbing potency relevant?

Chalcones are naturally produced by many plants, and constitute precursors for the synthesis of flavons and flavanons. They were shown to possess antibacterial, antifungal, anti-cancer, and anti- inflammatory properties. The goal of the study was to assess the suitability of three synthetic methoxychalcones as potential anticancer agents.

In Vitro Anti-Inflammatory Activity of Methyl Derivatives of Flavanone.

Inflammation plays an important role in the immune defense against injury and infection agents. However, the inflammatory chronic process may lead to neurodegenerative diseases, atherosclerosis, inflammatory bowel diseases, or cancer. Flavanones present in citrus fruits exhibit biological activities, including anti-oxidative and anti-inflammatory properties.

Biotransformation of Flavonoids with -NO, -CH Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi.

Combining chemical and microbiological methods using entomopathogenic filamentous fungi makes obtaining flavonoid glycosides possible. In the presented study, biotransformations were carried out in cultures of KCH J1.5, KCH J2, and KCH J2.

Novel -Methylglucoside Derivatives of Flavanone in Interaction with Model Membrane and Transferrin.

Flavonoids were biotransformed using various microorganisms, in order to obtain new compounds with potentially high biological activity. The aim of this work was to determine and compare the biological activity of four novel 6-methylflavanone -methylglucosides. The tested compounds have the same flavonoid core structure and an attached -methylglucose and hydroxyl group at different positions of ring A or B.

Regiospecific Hydrogenation of Bromochalcone by Unconventional Yeast Strains.

This research aimed to select yeast strains capable of the biotransformation of selected 2'-hydroxybromochalcones. Small-scale biotransformations were carried out using four substrates obtained by chemical synthesis (2'-hydroxy-2″-bromochalcone, 2'-hydroxy-3″-bromochalcone, 2'-hydroxy-4″-bromochalcone and 2'-hydroxy-5'-bromochalcone) and eight strains of non-conventional yeasts. Screening allowed for the determination of the substrate specificity of selected microorganisms and the selection of biocatalysts that carried out the hydrogenation of tested compounds in the most effective way.

Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds.

Flavonoid compounds are secondary plant metabolites with numerous biological activities; they naturally occur mainly in the form of glycosides. The glucosyl moiety attached to the flavonoid core makes them more stable and water-soluble. The methyl derivatives of flavonoids also show increased stability and intestinal absorption.

4'-Methylflavanone Glycosides Obtained Using Biotransformation in the Entomopathogenic Filamentous Fungi Cultures as Potential Anticarcinogenic, Antimicrobial, and Hepatoprotective Agents.

Flavonoid compounds exhibit numerous biological activities and significantly impact human health. The presence of methyl or glucosyl moieties attached to the flavonoid core remarkably modifies their physicochemical properties and improves intestinal absorption. Combined chemical and biotechnological methods can be applied to obtain such derivatives.

The modulating effect of methoxy-derivatives of 2'-hydroxychalcones on the release of IL-8, MIF, VCAM-1 and ICAM-1 by colon cancer cells.

Colon cancer is one of the leading causes of death in the world. The search for effective and minimally invasive methods of treating colon cancer is the aim of modern medicine. Chalcones and their derivatives have shown an anticancer activity.

Fungal Biotransformation of 2'-Methylflavanone and 2'-Methylflavone as a Method to Obtain Glycosylated Derivatives.

Methylated flavonoids are promising pharmaceutical agents due to their improved metabolic stability and increased activity compared to unmethylated forms. The biotransformation in cultures of entomopathogenic filamentous fungi is a valuable method to obtain glycosylated flavones and flavanones with increased aqueous solubility and bioavailability. In the present study, we combined chemical synthesis and biotransformation to obtain methylated and glycosylated flavonoid derivatives.

Interaction of 4'-methylflavonoids with biological membranes, liposomes, and human albumin.

The aim of the study was to compare the impact of three synthesized chemical compounds from a group of methylated flavonoids, i.e. 2'-hydroxy-4-methylchalcone (3), 4'-methylflavanone (4), and 4'-methylflavone (5), on a red blood cell membranes (RBCMs), phosphatidylcholine model membranes (PC), and human serum albumin (HSA) in order to investigate their structure-activity relationships.

Biotransformation of 5,7-Methoxyflavones by Selected Entomopathogenic Filamentous Fungi.

5,7-Dimethoxyflavone, a chrysin derivative, occurs in many plants and shows very low toxicity, even at high doses. On the basis of this phenomenon, we biotransformed a series of methoxy-derivatives of chrysin, apigenin, and tricetin obtained by chemical synthesis. We used entomopathogenic fungal strains with the confirmed ability of simultaneous hydroxylation/demethylation and glycosylation of flavonoid compounds.

The Callus of and Biotransform Flavanones into the Corresponding Flavones.

In vitro plant cultures are gaining in industrial importance, especially as biocatalysts and as sources of secondary metabolites used in pharmacy. The idea that guided us in our research was to evaluate the biocatalytic potential of newly obtained callus tissue towards flavonoid compounds. In this publication, we describe new ways of using callus cultures in the biotransformations.

Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi.

The synthesis and biotransformation of five flavones containing methoxy substituents in the B ring: 2'-, 3'-, 4'-methoxyflavones, 2',5'-dimethoxyflavone and 3',4',5'-trimethoxyflavone are described. Strains of entomopathogenic filamentous fungi were used as biocatalysts. Five strains of the species (KCh J1.

New 6,19-oxidoandrostan derivatives obtained by biotransformation in environmental filamentous fungi cultures.

Background: Steroid compounds with a 6,19-oxirane bridge possess interesting biological activities including anticonvulsant and analgesic properties, bacteriostatic activity against Gram-positive bacteria and selective anti-glucocorticoid action, while lacking mineralocorticoid and progestagen activity.

Results: The study aimed to obtain new derivatives of 3β-acetyloxy-5α-chloro-6,19-oxidoandrostan-17-one by microbial transformation. Twelve filamentous fungal strains were used as catalysts, including entomopathogenic strains with specific activity in the transformation of steroid compounds.

Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones.

Six γ-oxa-ε-lactones, 4-phenyl-3,4-dihydro-2-1,5-benzodioxepin-2-one () and its five derivatives with methoxy groups in different positions of A and B rings (-), were synthesized from corresponding flavanones. Three of the obtained lactones (,,) have not been previously described in the literature. Structures of all synthesized compounds were confirmed by complete spectroscopic analysis with the assignments of signals on H and C-NMR spectra to the corresponding atoms.