Antiinflammatory and neurological activity of pyrithione and related sulfur-containing pyridine N-oxides from Persian shallot (Allium stipitatum)

Krejčová, Petra; Kučerová, Petra; Stafford, G.I.; Jäger, Anna K.; Kubec, Roman

doi:10.1016/j.jep.2014.03.066

Cited by 29 publications

(17 citation statements)

References 21 publications

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“…Although the exact mechanism of the anti-inflammatory activity of pyridinethione remains unclear, the potential anti-inflammatory activity of pyridine derivatives has already been reported. 26 Krejčová et. al studied the anti-inflammatory and neurological activities of pyridine thione and four related sulfur-containing pyridine N-oxides, which are prominent constituents of plant Allium stipitatum, and found that 2-[(Methylthio)methyldithio]pyridine N-oxide had very high anti-inflammatory effects.…”

Section: Resultsmentioning

confidence: 99%

Redox Potential-Sensitive N-Acetyl Cysteine-Prodrug Nanoparticles Inhibit the Activation of Microglia and Improve Neuronal Survival

Markoutsa

2017

Mol. Pharmaceutics

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One hallmark of neuroinflammation is the activation of microglia, which triggers the production and release of reactive oxygen species (ROS), nitrate, nitrite, and cytokines. N-acetyl cysteine (NAC) is a free radical scavenger that is involved in the intracellular and extracellular detoxification of ROS in the brain. However, the clinical application of NAC is limited by its low bioavailability and short half-life. Herein, NAC was conjugated to a polymer through disulfide bond to form a NAC-prodrug nanoparticle (NAC-NP). Dynamic light scattering found that the NAC-NP has a size around 50 nm. In vitro study revealed that the release of NAC from NAC-NP is responsive to its environmental redox potential. In order to mimic neuroinflammation in vitro, microglial cells were stimulated by LPS (Lipopolysaccharide) and the effect of NAC-NP on activated microglia was investigated. The study found that the morphology as well as the expression of microgliosis marker lba-1 of the cells treated with NAC-NPs and LPS were close to those of control cells, indicating that NAC-NPs can inhibit the activation of microglia stimulated by LPS. Compared with free NAC, the production of ROS, NO3-, NO2-, tumor necrosis factor-α (TNF-α), and interleukin (IL)-1β from the LPS-stimulated microglia was considerably decreased when the cells were pretreated with NAC-NP. Furthermore, LPS-induced microglial phagocytocis of neurons was inhibited in the presence on NAC-NPs. These results indicated that NAC-NPs are more effective than free NAC in reversing the effect of LPS on microglia and subsequently protecting neurons.

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Section: Resultsmentioning

confidence: 99%

Redox Potential-Sensitive N-Acetyl Cysteine-Prodrug Nanoparticles Inhibit the Activation of Microglia and Improve Neuronal Survival

Markoutsa

2017

Mol. Pharmaceutics

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“…Thus, the structure of the pure fraction D 3/6e was determined as 2-(methyldithio)pyridine-3-carbonitrile (Figure 1). Previously, pyridine- N -oxide compounds were reported from A. stipitatum [25,26,28]; however, this is the first report on a naturally existing pyridine compound with a nitrile as a functional group from A. stipitatum .…”

Section: Discussionmentioning

confidence: 99%

Bioactive 2-(Methyldithio)Pyridine-3-Carbonitrile from Persian Shallot (Allium stipitatum Regel.) Exerts Broad-Spectrum Antimicrobial Activity

et al. 2019

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Antibiotic resistance is a problem that continues to challenge the healthcare sector, especially in clinically significant pathogens like methicillin-resistant Staphylococcus aureus (MRSA). Herein is described the isolation and structure elucidation of a bioactive compound from Allium stipitatum with antimicrobial activity. Crude Allium stipitatum dichloromethane extract (ASDE) was subjected to systematic purification by chromatographic procedures to afford various bioactive fractions. A fraction that exhibited anti-MRSA activity (4 µg·mL−1) was further characterized to determine the structure. The structure of the compound was elucidated as 2-(methyldithio)pyridine-3-carbonitrile (2-Medpy-3-CN). The 2-Medpy-3-CN compound, which was screened for antimicrobial activity, exhibited minimum inhibitory concentrations (MICs) in the range of 0.5 to >64 µg·mL−1 for tested bacterial species and 0.25 to 2 µg·mL−1 for Candida spp. Further studies are important to confirm the drug target and mechanism of action.

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“…(common shallot), makes it an important medicinal plant with unexplored medicinal properties. The bulbs of A. stipitatum have been reported to have wound healing [16], antispasmodic [18], and anti-inflammatory properties [19]. Recently, hydromethanolic extract of Persian shallot was shown to be effective against a panel of clinically important pathogens such as MRSA, methicillin-sensitive S. aureus (MSSA), S. epidermidis , Streptococcus pneumoniae , Escherichia coli , Salmonella typhimurium , Proteus mirabilis , and Klebsiella pneumoniae [20].…”

Section: Introductionmentioning

confidence: 99%

Allium stipitatum Extract Exhibits In Vivo Antibacterial Activity against Methicillin‐Resistant Staphylococcus aureus and Accelerates Burn Wound Healing in a Full‐Thickness Murine Burn Model

Karunanidhi

Ghaznavi‐Rad

Nathan

et al. 2017

Evidence-Based Complementary and Alternative Medicine

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The in vivo antibacterial and burn wound healing potency of Persian shallot bulbs (Allium stipitatum) were explored in a mice burn model infected with methicillin-resistant Staphylococcus aureus (MRSA). Hexane (ASHE) and dichloromethane (ASDE) extracts were tested. Female BALB/c mice were inflicted with third-degree thermal injury followed by infection with MRSA. ASHE and ASDE formulated with simple ointment base (SOB) at concentrations of 1%, 2%, and 5% (w/w) were topically applied to burn wounds twice a day for 20 days. Silver sulfadiazine (1%) served as drug positive control. Microbiological analysis was carried out on 1, 2, 3, 4, and 5 days postwounding (dpw) and histopathological analysis at the end of the experiment (20 dpw). Both ointments demonstrated strong antibacterial activity with complete elimination of MRSA at 48–72 h after infection. The rate of wound contraction was higher (95–100%) in mice groups treated with ASHE and ASDE ointments after 15 dpw. Histological analysis revealed significant increase (p < 0.05) in epithelialization and collagenation in treated groups. The ASHE and ASDE were found to be relatively noncytotoxic and safe to Vero cell line (383.4 μg mL−1; 390.6 μg mL−1), suggesting the extracts as safe topical antibacterial as well as promising alternatives in managing thermal injuries.

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Antiinflammatory and neurological activity of pyrithione and related sulfur-containing pyridine N-oxides from Persian shallot (Allium stipitatum)

Cited by 29 publications

References 21 publications

Redox Potential-Sensitive N-Acetyl Cysteine-Prodrug Nanoparticles Inhibit the Activation of Microglia and Improve Neuronal Survival

Redox Potential-Sensitive N-Acetyl Cysteine-Prodrug Nanoparticles Inhibit the Activation of Microglia and Improve Neuronal Survival

Bioactive 2-(Methyldithio)Pyridine-3-Carbonitrile from Persian Shallot (Allium stipitatum Regel.) Exerts Broad-Spectrum Antimicrobial Activity

Allium stipitatum Extract Exhibits In Vivo Antibacterial Activity against Methicillin‐Resistant Staphylococcus aureus and Accelerates Burn Wound Healing in a Full‐Thickness Murine Burn Model

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