scholarly journals Benzophenone and Benzoylphloroglucinol Derivatives from Hypericum sampsonii with Anti-Inflammatory Mechanism of Otogirinin A

Molecules ◽  
2020 ◽  
Vol 25 (19) ◽  
pp. 4463 ◽  
Author(s):  
Chun-Yi Huang ◽  
Tzu-Cheng Chang ◽  
Yu-Jing Wu ◽  
Yun Chen ◽  
Jih-Jung Chen
Keyword(s):  
Nitric Oxide ◽  
Inhibitory Effect ◽  
No Production ◽  
Necrosis Factor Alpha ◽  
Aerial Parts ◽  
Arginase 1 ◽  
Potent Inhibition ◽  
Ic50 Values ◽  
Cytokine Tumor Necrosis Factor ◽  
Anti Inflammatory

Three new compounds, 4-geranyloxy-2-hydroxy-6-isoprenyloxybenzophenone (1), hypericumone A (2) and hypericumone B (3), were obtained from the aerial parts of Hypericum sampsonii, along with six known compounds (4–9). The structures of these compounds were determined through spectroscopic and MS analyses. Hypericumone A (2), sampsonione J (8) and otogirinin A (9) exhibited potent inhibition (IC50 values ≤ 40.32 μM) against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation. Otogirinin A (9) possessed the highest inhibitory effect on NO production with IC50 value of 32.87 ± 1.60 μM. The well-known proinflammatory cytokine, tumor necrosis factor-alpha (TNF-α) was also inhibited by otogirinin A (9). Western blot results demonstrated that otogirinin A (9) downregulated the high expression of inducible nitric oxide synthase (iNOS). Further investigations on the mechanism showed that otogirinin A (9) blocked the phosphorylation of MAPK/JNK and IκBα, whereas it showed no effect on the phosphorylation of MAPKs/ERK and p38. In addition, otogirinin A (9) stimulated anti-inflammatory M2 phenotype by elevating the expression of arginase 1 and Krüppel-like factor 4 (KLF4). The above results suggested that otogirinin A (9) could be considered as potential compound for further development of NO production-targeted anti-inflammatory agent.

scholarly journals Anti-Inflammatory Effects of Fucoxanthinol in LPS-Induced RAW264.7 Cells through the NAAA-PEA Pathway

Marine Drugs ◽  
2020 ◽  
Vol 18 (4) ◽  
pp. 222 ◽  
Author(s):  
Wenhui Jin ◽  
Longhe Yang ◽  
Zhiwei Yi ◽  
Hua Fang ◽  
Weizhu Chen ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Inhibitory Effect ◽  
Inflammatory Factors ◽  
Lipid Mediator ◽  
Peroxisome Proliferator ◽  
Necrosis Factor Alpha ◽  
Peroxisome Proliferator Activated Receptor ◽  
Tnf Α ◽  
Anti Inflammatory

Palmitoylethanolamide (PEA) is an endogenous lipid mediator with powerful anti-inflammatory and analgesic functions. PEA can be hydrolyzed by a lysosomal enzyme N-acylethanolamine acid amidase (NAAA), which is highly expressed in macrophages and other immune cells. The pharmacological inhibition of NAAA activity is a potential therapeutic strategy for inflammation-related diseases. Fucoxanthinol (FXOH) is a marine carotenoid from brown seaweeds with various beneficial effects. However, the anti-inflammatory effects and mechanism of action of FXOH in lipopolysaccharide (LPS)-stimulated macrophages remain unclear. This study aimed to explore the role of FXOH in the NAAA–PEA pathway and the anti-inflammatory effects based on this mechanism. In vitro results showed that FXOH can directly bind to the active site of NAAA protein and specifically inhibit the activity of NAAA enzyme. In an LPS-induced inflammatory model in macrophages, FXOH pretreatment significantly reversed the LPS-induced downregulation of PEA levels. FXOH also substantially attenuated the mRNA expression of inflammatory factors, including inducible nitric oxide synthase (iNOS), interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-α), and markedly reduced the production of TNF-α, IL-6, IL-1β, and nitric oxide (NO). Moreover, the inhibitory effect of FXOH on NO induction was significantly abolished by the peroxisome proliferator-activated receptor α (PPAR-α) inhibitor GW6471. All these findings demonstrated that FXOH can prevent LPS-induced inflammation in macrophages, and its mechanisms may be associated with the regulation of the NAAA-PEA-PPAR-α pathway.

scholarly journals Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5911
Author(s):  
Hao-Chiun Chang ◽  
Shih-Wei Wang ◽  
Chin-Yen Chen ◽  
Tsong-Long Hwang ◽  
Ming-Jen Cheng ◽  
...  
Keyword(s):  
Gouty Arthritis ◽  
Dimethyl Ester ◽  
Stem Bark ◽  
Human Neutrophils ◽  
No Production ◽  
Necrosis Factor Alpha ◽  
Arginase 1 ◽  
Tnf Α ◽  
Anti Inflammatory ◽  
Fraxinus Chinensis

Qin Pi (Fraxinus chinensis Roxb.) is commercially used in healthcare products for the improvement of intestinal function and gouty arthritis in many countries. Three new secoiridoid glucosides, (8E)-4′′-O-methylligstroside (1), (8E)-4′′-O-methyldemethylligstroside (2), and 3′′,4′′-di-O-methyl-demethyloleuropein (3), have been isolated from the stem bark of Fraxinus chinensis, together with 23 known compounds (4–26). The structures of the new compounds were established by spectroscopic analyses (1D, 2D NMR, IR, UV, and HRESIMS). Among the isolated compounds, (8E)-4′′-O-methylligstroside (1), (8E)-4′′-O-methyldemethylligstroside (2), 3′′,4′′-di-O-methyldemethyloleuropein (3), oleuropein (6), aesculetin (9), isoscopoletin (11), aesculetin dimethyl ester (12), fraxetin (14), tyrosol (21), 4-hydroxyphenethyl acetate (22), and (+)-pinoresinol (24) exhibited inhibition (IC50 ≤ 7.65 μg/mL) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leuckyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, 9, 11, 14, 21, and 22 inhibited fMLP/CB-induced elastase release with IC50 ≤ 3.23 μg/mL. In addition, compounds 2, 9, 11, 14, and 21 showed potent inhibition with IC50 values ≤ 27.11 μM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation. The well-known proinflammatory cytokines, tumor necrosis factor-alpha (TNF-α) and interleukin 6 (IL-6), were also inhibited by compounds 1, 9, and 14. Compounds 1, 9, and 14 displayed an anti-inflammatory effect against NO, TNF-α, and IL-6 through the inhibition of activation of MAPKs and IκBα in LPS-activated macrophages. In addition, compounds 1, 9, and 14 stimulated anti-inflammatory M2 phenotype by elevating the expression of arginase 1 and Krüppel-like factor 4 (KLF4). The above results suggested that compounds 1, 9, and 14 could be considered as potential compounds for further development of NO production-targeted anti-inflammatory agents.

scholarly journals Anti-Inflammatory Flavonolignans from Triticum aestivum Linn. Hull

2020 ◽  
Vol 10 (23) ◽  
pp. 8656
Author(s):  
Ah-Reum Han ◽  
Yun-Seo Kil ◽  
Min Jeong Hong ◽  
Jisu Park ◽  
Hyeon Hwa Park ◽  
...  
Keyword(s):  
Triticum Aestivum ◽  
Crop Production ◽  
Ethyl Acetate Fraction ◽  
Inhibitory Effect ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Phytochemical Investigation ◽  
Ic50 Values ◽  
Anti Inflammatory ◽  
Food Grain

Wheat (Triticum aestivum Linn.; Poaceae) is a very common and important food grain and ranks second in total cereal crop production. A large amount of wheat hull is produced after threshing that, as the non-food part of wheat, is agro-waste, accounting for 15~20% of the wheat. This study aimed at biologically and phytochemically investigating wheat hull for its valorization as a by-product. In our ongoing search for natural product-derived anti-inflammatory agents, T. aestivum hull was evaluated for its nitric oxide (NO) production inhibition in lipopolysaccharide (LPS)-activated RAW 264.7 cells, and the phytochemical investigation of the ethyl acetate fraction showing inhibitory effect led to the isolation of a flavone (1) and seven flavonolignans (2–8). Compounds 2–8 have not yet been isolated from Triticum species. All compounds were evaluated for their LPS-induced NO production inhibition, and 1, 2, 4, 6, and 8 exhibited inhibitory effects with IC50 values ranging from 24.14 to 58.95 μM. These results suggest the potential of using T. aestivum hull as a source for producing anti-inflammatory components, enhancing its valorization as a by-product.

scholarly journals Chemical Profiles and Anti-inflammatory Activity of the Essential Oils from Seseli gummiferum and Seseli corymbosum subsp. corymbosum

2016 ◽  
Vol 11 (10) ◽  
pp. 1934578X1601101
Author(s):  
Alev Tosun ◽  
Jaemoo Chun ◽  
Igor Jerković ◽  
Zvonimir Marijanović ◽  
Maurizio A. Fenu ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Essential Oils ◽  
Inflammatory Activity ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Raw 264.7 ◽  
Gene Assay ◽  
Germacrene D ◽  
Ic50 Values ◽  
Anti Inflammatory

The anti-inflammatory activity of the essential oils from Seseli corymbosum subsp. corymbosum Pall. ex Sm. (SC) and Seseli gummiferum Boiss. & Heldr. subsp. corymbosum (SG) was investigated for the first time on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. The main constituents (determined by GC-FID and GC-MS analyses) were germacrene D (54.1%) and sabinene (22.4%) in SG oil and β-phellandrene (29.2%), α-phellandrene (8.2%) and germacrene D (2.5%) in SC oil. SC and SG oils inhibited nitric oxide (NO) production with IC50 values of 56.1 and 108.2 μg/mL, respectively. The oils also inhibited prostaglandin E2 (PGE2) with IC50 values of 49.4 μg/mL (SC oil) and 95.5 μg/mL (SG oil). The inhibitory effect of SC and SG oils was accompanied by dose-dependent decreases of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein expressions in LPS-induced RAW 264.7 cells. The research of the reporter gene assay on nuclear factor κB (NF-κB) showed that SC and SG oils inhibited NF-κB transcriptional activity. The obtained results suggest that SC and SG oils exert the anti-inflammatory effects in LPS-stimulated RAW 264.7 cells by suppressing NF-κB activation.

scholarly journals Nitric oxide (NO) radical inhibitory of hedyotis philippinensis and its marker compound, asperuloside

2014 ◽  
Vol 10 (1) ◽  
Author(s):  
Emi Norzehan Mohamad Mahbob ◽  
Rohaya Ahmad ◽  
Syahida Ahmad
Keyword(s):  
Nitric Oxide ◽  
Folk Medicine ◽  
No Production ◽  
Marker Compound ◽  
Methanolic Extracts ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Anti Inflammatory ◽  
Dose Dependent ◽  
Raw264.7 Macrophage

Hedyotis spesies have been used in Chinese folk medicine as a treatment for colds, stomatitis and various inflammations. In this study, three methanolic extracts of Hedyotis species (Hedyotis corymbosa, Hedyotis havilandii and Hedyotis philippinensis) were screened for their anti-inflammatory activity. The plant extracts along with asperuloside, the marker compound of H. philippinensis were tested for their anti-inflammatory effect against lipopolysaccharide (LPS) and interferon- (IFN-)-induced nitric oxide (NO) production using RAW264.7 macrophage cells. Among the three species, H. philippinensis (leaves and stems) showed good NO radical inhibitory activity (with IC50 values of 139.76±12.50 and 176.21±2.48 g/ml, respectively). Asperuloside, isolated as a major compound from the plant moderately inhibited LPS/IFN--induced NO production by 63% at a concentration of 100 M (45% cell viability) compared to L-NAME (77 %). Its IC50 value was found to be 75.45±2.25 M. Its inhibition was also found to be dose-dependent.

scholarly journals The anti-inflammatory effects of Indonesian and Japanese bitter melon (Momordica charantia L.) fruit extracts on interleukin-1β-treated hepatocytes

2019 ◽  
Vol 9 (1) ◽  
pp. 16 ◽  
Author(s):  
Dinia Rizqi Dwijayanti ◽  
Tetsuya Okuyama ◽  
Tadayoshi Okumura ◽  
Yukinobu Ikeya ◽  
Mikio Nishizawa
Keyword(s):  
Nitric Oxide ◽  
Ethyl Acetate ◽  
Inflammatory Cytokine ◽  
Momordica Charantia ◽  
Interleukin 1Β ◽  
No Production ◽  
Bitter Melon ◽  
Inos Protein ◽  
Ic50 Values ◽  
Anti Inflammatory

Background: Bitter melon, Momordica charantia L. (Cucurbitaceae), grows in tropical to temperate regions in Asia, including Indonesia and Japan. Bitter melon contains triterpenoids, steroidal glycosides, flavonoids, and alkaloids. The green immature fruit of bitter melon is a popular vegetable in Indonesia and Japan and has been used as a traditional Indonesian medicine (Jamu) to treat microbial infections and diabetes mellitus. However, there are currently few reports about the pharmacological effects of the constituents of bitter melon.Objective: To compare the effects of Indonesian and Japanese bitter melon, the production of pro-inflammatory mediators, such as nitric oxide (NO) and pro-inflammatory cytokines, was monitored.Methods: Immature fruits of bitter melons collected from Indonesia and Japan were lyophilized and extracted with methanol. The resultant extracts were fractionated by hydrophobicity into ethyl acetate-soluble (A), n-butanol-soluble (B), and water-soluble (C) fractions. Primary cultured hepatocytes prepared from rat liver were treated with interleukin-1β (IL-1β) and each extract or fraction. Nitrite in the medium was measured, and the half-maximal inhibitory concentration (IC50) value was determined. Lactate dehydrogenase activity in the medium was measured to monitor cytotoxicity. The expression of inducible nitric oxide synthase (iNOS) was detected by western blot analysis. The mRNA levels were measured by reverse transcription-polymerase chain reaction. Results: Indonesian and Japanese bitter melon extracts (BMEs) suppressed NO production by IL-1β-treated hepatocytes without showing cytotoxicity. The IC50 values of the BMEs were 86 μg/mL (Indonesian) and 171 μg/mL (Japanese). Both BMEs suppressed iNOS protein expression. Fractions A and B of both BMEs suppressed NO production. The IC50 values of the Indonesian BME fractions A and B were comparable to those of Japanese BME. Fraction A of both BMEs decreased the levels of iNOS protein and mRNA, as well as those of pro-inflammatory cytokine mRNAs. Fraction C of both BMEs did not affect NO production.Conclusion: The ethyl acetate-soluble fraction (A) of Indonesian and Japanese BMEs exhibited a comparable ability to suppress the induction of the iNOS and pro-inflammatory cytokine genes. These data suggest that hydrophobic constituents in fraction A, such as cucurbitane-type triterpenoids, may be responsible for the observed anti-inflammatory effects of bitter melon from Indonesia and Japan.Keywords: Momordica charantia, nitric oxide, inflammation, Jamu, Goya.

scholarly journals Metabolomic Screening of Anti-Inflammatory Compounds from the Leaves of Actinidia arguta (Hardy Kiwi)

Foods ◽  
2019 ◽  
Vol 8 (2) ◽  
pp. 47 ◽  
Author(s):  
Gyoung-Deuck Kim ◽  
Jin Lee ◽  
Joong-Hyuck Auh
Keyword(s):  
Nitric Oxide ◽  
Ethanol Extract ◽  
Inhibitory Effect ◽  
Reversed Phase ◽  
No Production ◽  
Actinidia Arguta ◽  
Bioassay Guided Fractionation ◽  
Anti Inflammatory ◽  
Ethanol Extracts

The metabolomic screening of potential anti-inflammatory compounds in the leaves of Actinidia arguta was performed by using LC-MS/MS. Ethanol extracts were prepared, and the anti-inflammatory effects were investigated based on nitric oxide (NO) synthesis and inducible nitric oxide synthase expression in lipopolysaccharide-induced RAW 264.7 macrophages. The 75% ethanol extract showed the highest inhibitory effect on nitric oxide (NO) production, and it was further separated by in vitro bioassay-guided fractionation using preparative LC with reversed-phase column separation. Through multiple steps of fractionation, sub-fraction 1-3 was finally purified, and caffeic acid derivatives, such as caffeoylthreonic acid and danshensu (salvianic acid A), were successfully identified as key anti-inflammatory compounds by LC-MS/MS and metabolomics analyses. This is the first study identifying anti-inflammatory compounds in A. arguta (Actinidia arguta) leaves through bioassay-guided fractionation and metabolomics screening. Results of this study would be useful for the application of A. arguta leaves as a nutraceutical.

scholarly journals Constituents Isolated from the Leaves of Glycyrrhiza uralansis and Their Anti-Inflammatory Activities on LPS-Induced RAW264.7 Cells

Molecules ◽  
2019 ◽  
Vol 24 (10) ◽  
pp. 1923 ◽  
Author(s):  
Liyao Wang ◽  
Kaixue Zhang ◽  
Shu Han ◽  
Liu Zhang ◽  
Haiying Bai ◽  
...  
Keyword(s):  
Electrospray Mass Spectrometry ◽  
Inhibitory Concentration ◽  
No Production ◽  
Chinese Medicines ◽  
Aerial Parts ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Anti Inflammatory ◽  
New Compounds ◽  
Anti Hiv

Licorice, the root and rhizome of Glycyrrhiza uralansis Fisch, is one of the most frequently used Traditional Chinese Medicines in rigorous clinical trials to remove toxins and sputum, and to relieve coughing. However, the aerial parts are not used so widely at present. It has been reported that the aerial parts have many bioactivities such as anti-microbial and anti-HIV activities. In this study, we aimed to discover the bioactive compounds from the leaves of G. uralensis. Four new compounds, licostilbene A-B (1–2) and licofuranol A-B (3–4), together with eight known flavonoids (5–12), were isolated and identified from the leaves of G. uralensis. Their structures were elucidated mainly by the interpretation of high-resolution electrospray mass spectrometry (HR-ESI-MS) and nuclear magnetic resonance (NMR) spectroscopic data. Compared with quercetin, which showed a 50% inhibitory concentration (IC50) value of 4.08 μg/mL, compounds 1–9 showed significant anti-inflammatory activities by inhibiting lipopolysaccharide (LPS)-induced nitric oxide (NO) production with IC50 values of 2.60, 2.15, 3.21, 3.25, 2.00, 3.45, 2.53, 3.13 and 3.17 μg/mL, respectively. The discovery of these active compounds is important for the prevention and treatment of inflammation.

scholarly journals Anti-Inflammatory Effects of Flavonoids: Genistein, Kaempferol, Quercetin, and Daidzein Inhibit STAT-1 and NF-κB Activations, Whereas Flavone, Isorhamnetin, Naringenin, and Pelargonidin Inhibit only NF-κB Activation along with Their Inhibitory Effect on iNOS Expression and NO Production in Activated Macrophages

2007 ◽  
Vol 2007 ◽  
pp. 1-10 ◽  
Author(s):  
Mari Hämäläinen ◽  
Riina Nieminen ◽  
Pia Vuorela ◽  
Marina Heinonen ◽  
Eeva Moilanen
Keyword(s):  
Nitric Oxide ◽  
Transcription Factor ◽  
Inhibitory Effect ◽  
Inos Expression ◽  
No Production ◽  
Dependent Manner ◽  
Activated Macrophages ◽  
Naturally Occurring ◽  
Anti Inflammatory ◽  
Oxide Synthase

In inflammation, bacterial products and proinflammatory cytokines induce the formation of large amounts of nitric oxide (NO) by inducible nitric oxide synthase (iNOS), and compounds that inhibit NO production have anti-inflammatory effects. In the present study, we systematically investigated the effects of 36 naturally occurring flavonoids and related compounds on NO production in macrophages exposed to an inflammatory stimulus (lipopolysaccharide, LPS), and evaluated the mechanisms of action of the effective compounds. Flavone, the isoflavones daidzein and genistein, the flavonols isorhamnetin, kaempferol and quercetin, the flavanone naringenin, and the anthocyanin pelargonidin inhibited iNOS protein and mRNA expression and also NO production in a dose-dependent manner. All eight active compounds inhibited the activation of nuclear factor-κB (NF-κB), which is a significant transcription factor for iNOS. Genistein, kaempferol, quercetin, and daidzein also inhibited the activation of the signal transducer and activator of transcription 1 (STAT-1), another important transcription factor for iNOS. The present study characterises the effects and mechanisms of naturally occurring phenolic compounds on iNOS expression and NO production in activated macrophages. The results partially explain the pharmacological efficacy of flavonoids as anti-inflammatory compounds.

scholarly journals Diterpenoids Isolated from Podocarpus macrophyllus Inhibited the Inflammatory Mediators in LPS-Induced HT-29 and RAW 264.7 Cells

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4326
Author(s):  
ChoEen Kim ◽  
DucDat Le ◽  
Mina Lee
Keyword(s):  
Nitric Oxide ◽  
Inhibitory Effect ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Raw 264.7 ◽  
Sexually Transmitted ◽  
Anti Inflammatory ◽  
Extracellular Regulated Kinase ◽  
Oxide Synthase ◽  
Ht 29

Species of Podocarpus are used traditionally in their native areas for the treatment of fevers, asthma, coughs, cholera, chest pain, arthritis, rheumatism, and sexually transmitted diseases. To identify natural products having efficacy against inflammatory bowel disease (IBD), we identified a new, 16-hydroxy-4β-carboxy-O-β-D-glucopyranosyl-19-nor-totarol (4) together with three known diterpenoids from P. macrophyllus. Furthermore, all the extracts, fractions, and isolates 1-4 were investigated for their anti-inflammatory effects by assessing the expression on nitric oxide (NO) production and proinflammatory cytokines in lipopolysaccharide (LPS)-stimulated RAW 264.7 and HT-29 cells. Among them, nagilactone B (2) exhibited a potent anti-inflammatory effect against NO production on RAW 264.7 cells; therefore, nagilactone B was further assessed for anti-inflammatory activity. Western blot analysis revealed that nagilactone B significantly decreased the expression of LPS-stimulated protein, inducible nitric oxide synthase (iNOS), cyclooxygenase (COX)-2, and phosphorylated extracellular regulated kinase (pERK)1/2. In addition, nagilactone B downregulated tumor necrosis factor (TNF)-α, interleukin (IL)-6, and IL-8 levels in LPS-induced macrophages and colonic epithelial cells. To our best knowledge, this is the first report on the inhibitory effect of nagilactone B (pure state) and rakanmakilactone G against NO production in LPS-stimulated RAW 264.7 cells. Thus, diterpenoids isolated from P. macrophyllus could be employed as potential therapeutic phytochemicals for IBD.

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