Interplay of the intermolecular and intramolecular interactions in stabilizing the thione-based copper(I) complexes and their significance in protecting the biomolecules against metal-mediated oxidative damage

Chalana, Ashish; Kumar, Rakesh; Karri, Ramesh; Jha, Kunal Kumar; Kumar, Binayak; Roy, Gouriprasanna

doi:10.1016/j.poly.2021.115647

Cited by 14 publications

(7 citation statements)

References 84 publications

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“…In this catalytic process, Cu(II) and Fe(II) react with H 2 O 2 , and hydroxyl radicals ( • OH) are generated via the Fenton reaction. 59 Reactive oxygen species (ROS) are a result of cellular metabolism. Under physiological conditions, enzyme systems regulate ROS levels.…”

Section: ■ Discussionmentioning

confidence: 99%

“…In this catalytic process, Cu(II) and Fe(II) react with H 2 O 2 , and hydroxyl radicals ( • OH) are generated via the Fenton reaction. 59 …”

Section: Discussionmentioning

confidence: 99%

“…However, in the free form, they have a toxic effect because Cu(II) catalyzes the oxidation of ascorbic acid, and reactive oxygen systems (ROS) such as superoxide radicals (O 2 •– ) and H 2 O 2 are generated. In this catalytic process, Cu(II) and Fe(II) react with H 2 O 2 , and hydroxyl radicals ( • OH) are generated via the Fenton reaction …”

Section: Discussionmentioning

confidence: 99%

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Chemical Composition of Essential Oils from Nepeta transcaucasica Grossh. and Nepeta cataria L. Cultivated in Bulgaria and Their Antimicrobial and Antioxidant Activity

et al. 2023

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The genus Nepeta, belonging to the family Lamiaceae, includes about 300 species, most of which are used in folk medicine due to their pronounced biological properties. The aim of the present study was to evaluate the agrobiological characteristics of Nepeta transcaucasica (N. transcaucasica) Grossh. and Nepeta cataria (N. cataria) L., cultivated in Bulgaria, and obtain their essential oils and determine their antimicrobial and antioxidant activities. The agrobiological characteristics of the two species growing in Kazanlak were analyzed; therefore, high variability in the population of N. transcaucasica and comparative homogeneity in N. cataria was shown. The species N. transcaucasica contained 0.28% essential oil with main components β-citronellol (52.05%), eucalyptol (7.34%), β-citronellal (6.06%), germacrene D (5.45%), (Z)-β-ocimene (5.14%), and β-caryophyllene (3.06%). The species N. cataria consisted of 0.19% essential oil with main components β-citronellol (26.31%), geraniol (15.92%), neral (11.45%), nerol (9.56%), carvacrol (6.04%), and β-citronellal (5.35%). The antibacterial activity against Gram-positive bacteria Listeria monocytogenes and Staphylococcus aureus and Gram-negative bacteria Escherichia coli (E. coli) and Salmonella enterica subsp. enterica serovar Abony was determined. The essential oils showed antimicrobial activity only against E. coli. The diameters of the inhibition zones were found to be 26 mm for the species N. transcaucasica and 10 mm for the species N. cataria. The antioxidant activity of the two essential oils was also determined by four different methods, DPPH, ABTS, FRAP, and CUPRAC, with the highest values for the ABTS radical, for the species N. transcaucasica (48.72 μM TE/mL), and the species N. cataria (310 μM TE/mL).

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Section: ■ Discussionmentioning

confidence: 99%

“…In this catalytic process, Cu(II) and Fe(II) react with H 2 O 2 , and hydroxyl radicals ( • OH) are generated via the Fenton reaction. 59 …”

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Chemical Composition of Essential Oils from Nepeta transcaucasica Grossh. and Nepeta cataria L. Cultivated in Bulgaria and Their Antimicrobial and Antioxidant Activity

et al. 2023

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“…1a) whose expression is clearly tied in some way to quinone-derived oxidative stress, mediated in part by catechol-Fe III uptake 30 . The known ability of ET to form coordination complexes with Fe II and Cu I/II may suggest a role in suppressing redox cycling of one or both metals by host-derived H 2 O 2 and other potent ROS and RNS or in some other role in colonization or virulence 11,[70][71][72] .…”

Section: Discussionmentioning

confidence: 99%

Discovery and structure of a widespread bacterial ABC transporter specific for ergothioneine

Zhang

González-Gutiérrez²,

Legg³

et al. 2022

Nat Commun

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L-Ergothioneine (ET), the 2-thioimidazole derivative of trimethylhistidine, is biosynthesized by select fungi and bacteria, notably Mycobacterium tuberculosis, and functions as a scavenger of reactive oxygen species. The extent to which ET broadly functions in bacterial cells unable to synthesize it is unknown. Here we show that spd_1642-1643 in Streptococcus pneumoniae, a Gram-positive respiratory pathogen, encodes an ET uptake ATP-binding cassette (ABC) transporter, designated EgtU. The solute binding domain (SBD) of EgtU, EgtUC, binds ET with high affinity and exquisite specificity in a cleft between the two subdomains, with cation-π interactions engaging the betaine moiety and a network of water molecules that surround the thioimidazole ring. EgtU is highly conserved among known quaternary amine compound-specific transporters and widely distributed in Firmicutes, including the human pathogens Listeria monocytogenes, as BilEB, Enterococcus faecalis and Staphylococcus aureus. ET increases the chemical diversity of the low molecular weight thiol pool in Gram-positive human pathogens and may contribute to antioxidant defenses in the infected host.

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“…•− ) and H 2 O 2 . Additionally, the Fenton reaction causes the Cu 2+ and Fe 2+ ions to interact with H 2 O 2 and produce hydroxyl radicals ( • OH) [37]. Proteins, DNA, and essential biological components like phospholipids are all damaged by ROS.…”

Section: Hydrogen Peroxide Scavenging Activitymentioning

confidence: 99%

Characterization of Polyphenols from Chenopodium botrys after Fractionation with Different Solvents and Study of Their In Vitro Biological Activity

Bojilov,

Manolov,

Nacheva

et al. 2023

Molecules

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In the present work, we have investigated the polyphenolic composition of Chenopodium botrys from Bulgaria. The polyphenols were fractionated with solvents of varying polarity (n-hexane, chloroform, ethyl acetate, and n-butanol). The fractions were analyzed by HPLC-PDA and UHPLC-MS. The ethyl acetate fraction contained mono- and di-glycosides of quercetin, di-glycosides of kaempferol, and isorhamnetin and monoglycosides of hispidulin and jaceosidine. We found quercetin triglycosides in the butanol fraction. The ethyl acetate and butanol fractions contained 168.82 mg/g Extr and 67.21 mg/g Extr of quercetin glycosides, respectively. The main components of the polyphenolic complex in C. botrys were 6-methoxyflavones (355.47 mg/g Extr), which were found in the chloroform fraction. The flavonoids pectolinarigenin, demethylnobiletin, and isosinensetin, and the glycosides of quercetin (triglycosides, acylglycosides), kaempferol, isorhamnetin, hispidiulin, and jaceosidine, were discovered and reported in Chenopodium botrys for the first time. We used in vitro methods to assess the biological activity against oxidative stress (hydrogen peroxide scavenging activity (HPSA) and hydroxyl radical scavenging activity (HRSA)), nitrosative stress (nitric oxide scavenging activity (NOSA)), anti-inflammatory activity (IAD inhibition), and anti-tryptic activity (ATA). Quercetin mono- and di-glycosides exhibited greater HPSA and HRSA (IC50 = 39.18, 105.03 µg/mL), while 6-methoxyflavones had a greater NOSA (IC50 = 146.59 µg/mL). The same components showed the highest ATA (IC50 ranging from 116.23 to 202.44 µg/mL).

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Interplay of the intermolecular and intramolecular interactions in stabilizing the thione-based copper(I) complexes and their significance in protecting the biomolecules against metal-mediated oxidative damage

Cited by 14 publications

References 84 publications

Chemical Composition of Essential Oils from Nepeta transcaucasica Grossh. and Nepeta cataria L. Cultivated in Bulgaria and Their Antimicrobial and Antioxidant Activity

Chemical Composition of Essential Oils from Nepeta transcaucasica Grossh. and Nepeta cataria L. Cultivated in Bulgaria and Their Antimicrobial and Antioxidant Activity

Discovery and structure of a widespread bacterial ABC transporter specific for ergothioneine

Characterization of Polyphenols from Chenopodium botrys after Fractionation with Different Solvents and Study of Their In Vitro Biological Activity

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