Site selective synthesis and anti-inflammatory evaluation of Spiro-isoxazoline stitched adducts of arteannuin B

Rasool, Javeed Ur; Sawhney, Gifty; Shaikh, Majeed; Nalli, Yedukondalu; Madishetti, Sreedhar; Ahmed, Zabeer; Ali, Asif

doi:10.1016/j.bioorg.2021.105408

Cited by 8 publications

(3 citation statements)

References 47 publications

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“…Quercetin [ 31 ], pinocembrin [ 32 , 33 ], pogostone [ 34 ], adenosine [ 35 ], ferulic acid [ 36 ], echimidine-N-oxide [ 37 ], purines including adenine, guanine, xanthine and hypoxanthine [ 38 , 39 , 40 ] have strong antibacterial or antifungal effects on diarrheal pathogens, such as Escherichia coli , Salmonella , Staphylococcus aureus , Dysentery bacilli , Pseudomonas aeruginosa , Streptococcus and Clostridioides difficile , in addition, hypoxanthine can speed the excretion of fecal harmful microbiota and toxic substances via shorting gastrointestinal transit time [ 41 ]. Pro-inflammatory substances can also cause diarrhea by impairing the intestinal mucosal barrier with pro-inflammatory cytokines [ 42 ], but quercetin [ 31 ], arteannuin and kynurenine [ 43 , 44 ], ferulic acid [ 45 ], purines [ 46 ], inosine [ 47 , 48 ], guanosine [ 49 ] and benzene-1,2,4-triol [ 50 ] can reduce diarrhea by increasing IFN-γ level or inhibiting the production of pro-inflammatory cytokines [ 48 , 51 , 52 , 53 ]. Supplementation with Perilla frutescens leaf to Holstein cows changed the composition of differential metabolites in the milk and many differential metabolites with antibacterial and anti-inflammatory effects had been identified [ 17 ], results of our experiment also indicated that maternal supplementation with fermented compound Chinese medicine feed additive accumulated lots of high-level differential metabolites in milk which have antibacterial, anti-inflammatory and immune enhancing properties.…”

Section: Discussionmentioning

confidence: 99%

Untargeted Metabolomics Profiling Reveals Beneficial Changes in Milk of Sows Supplemented with Fermented Compound Chinese Medicine Feed Additive

Zou

Deng

et al. 2022

Animals

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Different untargeted metabolomics approaches were used to identify the differential metabolites between milk samples collected from two groups. Sows were supplemented with fermented compound Chinese medicine feed additive at levels of 0 g/d/sow (control group, n = 10) and 50 g/d/sow (experimental group, n = 10), respectively, from d 104 of gestation to d 25 of lactation, samples of colostrum and mature milk were collected. Data indicated that supplementing fermented compound Chinese medicine feed additive to sows significantly increased the concentrations of quercetin, pinocembrin, chlorogenic acid, methyl succinic acid, L-tryptophan, adenosine, guanine, arteannuin, ferulic acid, echimidine N-oxide, pogostone and kynurenine in the colostrum and inosine, guanosine, benzene-1,2,4-triol, hypoxanthine, adenine, trehalose 6-phosphate in mature milk, respectively. Seven pathways (flavone and flavanol biosynthesis, galactose metabolism, phenylpropanoid biosynthesis, stilbenoid and gingerol biosynthesis, flavonoid biosynthesis, ABC transporters and purine metabolism) in colostrum and two pathways (sucrose metabolism and retrograde endocannabinoid signaling) in mature milk were significantly enriched in the experimental group compared to control group, respectively. The supplementation of fermented compound Chinese medicine feed additive to sows increased the level of antibacterial and anti-inflammatory ingredients in milk and the findings of this study hint that supplementation with fermented compound Chinese medicine feed additive in sows is beneficial for the improvement of milk quality.

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Section: Discussionmentioning

confidence: 99%

Untargeted Metabolomics Profiling Reveals Beneficial Changes in Milk of Sows Supplemented with Fermented Compound Chinese Medicine Feed Additive

Zou

Deng

et al. 2022

Animals

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“…After fractionation with EtOAc: Hexane (1:9), the crude extract was subjected to chromatography over silica gel. White crystals of (1) were obtained (4.5g) [26].…”

Section: Collection Of Plant Material Extraction Isolation and Charac...mentioning

confidence: 99%

Arteannuin-B and its Spiro-isoxazoline Derivative Inhibits LPS Induced Pro-Inflammatory Responses in RAW 264.7 Macrophages and BALB/c Mice via down-regulation of NF-κβ/P38 MAPK Mediated Stress Signalling

Sawhney

Rasool

Saroch

et al. 2022

Preprint

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Amongst the most significant scientific findings in the last two decades has been the role of inflammatory processes in protecting the host against the causative agents of injury. In this work, we examined the anti-inflammatory activities of Arteannuin-B (1) and its novel spirocyclic-2-isoxazoline derivative (2). Various anti-inflammatory assays were performed in lipopolysaccharide (LPS) induced RAW 264.7 macrophages using enzyme-linked immunosorbent assay, flow cytometric analysis, and western blotting. As a result, treatment with (2) decreased LPS-stimulated inducible nitric oxide synthase protein expression (iNOS), as well as production of nitric oxide (NO), tumor necrosis factor-alpha (TNF-α), and interleukin-6 (IL-6) in LPS induced RAW 264.7 cells. Additionally, the effects of (1) and (2) in an acute inflammatory condition were investigated in-vivo by using models like carrageenan-induced paw edema assay, acetic acid-induced writhing and tail immersion model in experimental mice, suggesting that (2) is a more potent anti-inflammatory candidate as compared to (1) with very low cell toxicity. In addition, biocomputational studies and histopathological analysis were also performed to validate the efficiency of (2) as compared to (1).

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“…Compounds bearing an isoxazoline moiety are considered a significant class of nitrogen and oxygen atom-containing heterocyclic products, attracting attention from organic and medicinal chemists due to their large spectrum of biological properties such as antibacterial [1,2], antimicrobial [3], anti-inflammatory [4], anticancer [5,6], antidiabetic [7] and anti-Alzheimer effects [8]. Moreover, isoxazoline derivatives are also known by their agrochemical properties as herbicidal [9], insecticidal [10][11][12] and acaricidal agents [13].…”

Section: Introductionmentioning

confidence: 99%

(3-(4-Chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl Benzenesulfonate

Mokhi,

Chkirate,

Zhang

et al. 2023

Molbank

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A novel single crystal of (3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl benzenesulfonate has been synthetized via a one-pot sequential strategy under sonication. The single crystal has been investigated using X-ray diffraction analysis. Hydrogen bonding between C–H···O and C–H···N produces a layer structure in the crystal. According to a Hirshfeld surface analysis, interactions H···H (28.9%), H···O/O···H (26.7%) and H···C/C···H (15.8%) make the largest contributions to crystal packing. The optimized structure and the solid-state structure that was obtained through experiments are compared using density functional theory at the B3LYP/6-311 G + (d,p) level. The computed energy difference between the lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) is 4.6548 eV.

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Site selective synthesis and anti-inflammatory evaluation of Spiro-isoxazoline stitched adducts of arteannuin B

Cited by 8 publications

References 47 publications

Untargeted Metabolomics Profiling Reveals Beneficial Changes in Milk of Sows Supplemented with Fermented Compound Chinese Medicine Feed Additive

Untargeted Metabolomics Profiling Reveals Beneficial Changes in Milk of Sows Supplemented with Fermented Compound Chinese Medicine Feed Additive

Arteannuin-B and its Spiro-isoxazoline Derivative Inhibits LPS Induced Pro-Inflammatory Responses in RAW 264.7 Macrophages and BALB/c Mice via down-regulation of NF-κβ/P38 MAPK Mediated Stress Signalling

(3-(4-Chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl Benzenesulfonate

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