Acylphloroglucinol Derivatives from Garcinia multiflora with Anti-Inflammatory Effect in LPS-Induced RAW264.7 Macrophages

Two new acylphloroglucinol derivatives, 13,14-didehydroxygarcicowin C (1) and 13,14-didehydroxyisoxanthochymol (2), have been isolated from the stems of Garcinia multiflora, together with seven known compounds (3–9). The structures of new compounds 1 and 2 were elucidated by MS and extensive 1D/2D NMR spectroscopic analyses. Among the isolates, 13,14-didehydroxy-isoxanthochymol (2) and sampsonione B (3) exhibited inhibition against lipopolysaccharide (LPS)-induced NF-κB activation in macrophages at 30 μM with relative luciferase activity values (inhibitory %) of 0.75 ± 0.03 (24 ± 4%) and 0.12 ± 0.03 (88 ± 4%), respectively. Additionally, sampsonione B (3) reduced LPS-induced nitric oxide (NO) production in murine RAW264.7 macrophages and did not induce cytotoxicity against RAW 264.7 cells after 24 h treatment. Compound 3 is worth further investigation and may be expectantly developed as an anti-inflammatory drug candidate.

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Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives

Molecules ◽

10.3390/molecules24183336 ◽

2019 ◽

Vol 24 (18) ◽

pp. 3336 ◽

Cited By ~ 2

Author(s):

Ping-Chen Tu ◽

Han-Chun Tseng ◽

Yu-Chia Liang ◽

Guan-Jhong Huang ◽

Te-Ling Lu ◽

...

Keyword(s):

2D Nmr ◽

Raw 264.7 Cells ◽

No Production ◽

Isolation And Characterization ◽

Whole Plant ◽

Phytochemical Investigation ◽

Ic50 Value ◽

Anti Inflammatory ◽

New Compounds ◽

First Time

Phytochemical investigation of the whole plant of Tradescantia albiflora Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (1), that was isolated from natural sources for the first time, a new butenolide, 5-O-acetyl bracteanolide A (2), and a new apocarotenoid, 2β-hydroxyisololiolide (11), together with 25 known compounds (compounds 3–10 and 12–28). The structures of the new compounds were elucidated by analysis of their spectroscopic data, including MS, 1D, and 2D NMR experiments, and comparison with literature data of known compounds. Furthermore, four butenolides 4a–4d were synthesized as novel derivatives of bracteanolide A. The isolates and the synthesized derivatives were evaluated for their preliminary anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Among them, the synthesized butenolide derivative n-butyl bracteanolide A (4d) showed enhanced NO inhibitory activity compared to the original compound, with an IC50 value of 4.32 ± 0.09 μg/mL.

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Purification, characterization, crystal structure and NO production inhibitory activity of three new sesquiterpenoids from homalomena occulta

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229618013815 ◽

2018 ◽

Vol 74 (11) ◽

pp. 1440-1446

Author(s):

Qi Zhang ◽

Li Ma ◽

Zhaoxia Qu ◽

Guige Hou ◽

Yanan Wang ◽

...

Keyword(s):

Crystal Structure ◽

Single Crystal ◽

2D Nmr ◽

Inhibitory Effect ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

X Ray Diffraction ◽

X Ray ◽

Spectroscopic Analyses

Two new isodaucane-type sesquiterpenoids, namely (1R,4S,5S,6R,7S,10R)-isodauc-6,7,10-triol, C15H28O3, (1), and (1R,4S,5S,6S,7S,10R)-isodauc-6,7,10-triol, (2), and a new eudesmane-type sesquiterpenoid, 1β,4β,5α-trihydroxyeudesmane, (3), were obtained from the rhizomes of homalomena occulta with the aid of column chromatography. Their structures were elucidated based on extensive spectroscopic analyses, including 1D NMR, 2D NMR and HRESIMS. The structure of (1) was confirmed by single-crystal X-ray diffraction and the absolute configuration was assigned with respect to that of the precursor. The single-crystal structure reveals that adjacent molecules of (1) embrace through two groups of intermolecular O—H...O hydrogen bonds to generate a two-dimensional sheet with a 63-net topology. The three compounds were evaluated for their activity against lipopolysaccharide-induced production of nitrogen oxide (NO) in RAW 264.7 cells, and (1) showed an inhibitory effect on NO production, with IC50 values of 5.7±0.22 µM.

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The anti-inflammatory effect ofAgaricus brasiliensisis partly due to its linoleic acid content

Food & Function ◽

10.1039/c7fo01172e ◽

2017 ◽

Vol 8 (11) ◽

pp. 4150-4158 ◽

Cited By ~ 9

Author(s):

Papawee Saiki ◽

Yasuhiro Kawano ◽

Leo J. L. D. Van Griensven ◽

Koyomi Miyazaki

Keyword(s):

Linoleic Acid ◽

Acid Content ◽

Linoleic Acid Content ◽

Inflammatory Activity ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

Anti Inflammatory ◽

Inflammatory Effect

Linoleic acid fromA. brasiliensiscould reduce NO production and inflammatory activity in RAW 264.7 cells by inhibition of p50 andviaactivation of PPARα.

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Effects of Shiranuhi flower extracts and fractions on lipopolysaccharide-induced inflammatory responses in murine RAW 264.7 cells

Turkish Journal of Biochemistry ◽

10.1515/tjb-2016-0209 ◽

2018 ◽

Vol 43 (4) ◽

pp. 375-384 ◽

Cited By ~ 1

Author(s):

Chang-Gu Hyun ◽

Min-Jin Kim ◽

Sang Suk Kim ◽

Ji Hye Ko ◽

Young Il Moon ◽

...

Keyword(s):

Cell Viability ◽

Inflammatory Responses ◽

Antioxidant Activities ◽

Mapk Signaling ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

Dependent Manner ◽

Anti Inflammatory ◽

Inflammatory Effect

Abstract Objective In this study, we evaluated the anti-inflammatory effect of Shiranuhi flower in RAW 264.7 cells. Methods The effects of the extracts and solvent fractions on cell viability and LPS-induced inflammatory responses were investigated in RAW 264.7 cells. Results The results showed that the ethyl acetate fraction (HEF) significantly decreased NO production in RAW 264.7 cells; however, cell viability was not affected. In addition, ELISA assay revealed that HEF significantly inhibited the productions of PGE2, TNF-α, and IL-6. As well, using Western blot analysis, it was observed that HEF significantly reduced the expression levels of iNOS and COX-2 in a dose dependent manner. Furthermore, we detected a reduced phosphorylation of mitogen-activated protein kinases such as p38, JNK, and ERK1/2. This indicates that HEF regulates LPS-induced inflammatory responses, at least in part, via suppressing the MAPK signaling pathway. Correlation analysis also showed that anti-inflammatory activities were highly correlated to antioxidant activities in this study. Characterization of the Shiranuhi flowers for flavonoid contents using HPLC showed varied quantity of narirutin and hesperidin. Conclusion Overall, the results demonstrate that HEF may be a potential anti-inflammatory agent. In addition, our findings contribute to understanding the molecular mechanism underlying the anti-inflammatory effect of Shiranuhi flower.

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Streptoglycerides E–H, Unsaturated Polyketides from the Marine-Derived Bacterium Streptomyces specialis and Their Anti-Inflammatory Activity

Marine Drugs ◽

10.3390/md20010044 ◽

2022 ◽

Vol 20 (1) ◽

pp. 44

Author(s):

Hee Jae Shin ◽

Chang-Su Heo ◽

Cao Van Anh ◽

Yeo Dae Yoon ◽

Jong Soon Kang

Keyword(s):

Spectroscopic Data ◽

2D Nmr ◽

Ring System ◽

Membered Ring ◽

Inflammatory Activity ◽

Raw 264.7 Cells ◽

No Production ◽

Nmr Data ◽

Ic50 Values ◽

Anti Inflammatory

Four new streptoglycerides E–H (1–4), with a rare 6/5/5/-membered ring system, were isolated from a marine-derived actinomycete Streptomyces specialis. The structures of 1–4 were elucidated by detailed analysis of HRESIMS, 1D and 2D NMR data and ECD spectra as well as comparison of their spectroscopic data with those reported in literature. Compounds 1–4 showed significant anti-inflammatory activity by inhibiting lipopolysaccharide (LPS)-induced nitric oxide (NO) production in Raw 264.7 cells with IC50 values ranging from 3.5 to 10.9 µM. Especially, 2 suppressed mRNA expression levels of iNOS and IL-6 without cytotoxicity.

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Anti-Inflammatory Investigations of Extracts of Zanthoxylum rhetsa

Evidence-based Complementary and Alternative Medicine ◽

10.1155/2021/5512961 ◽

2021 ◽

Vol 2021 ◽

pp. 1-15

Author(s):

Chureeporn Imphat ◽

Pakakrong Thongdeeying ◽

Arunporn Itharat ◽

Sumalee Panthong ◽

Sunita Makchuchit ◽

...

Keyword(s):

Chemical Composition ◽

Essential Oil ◽

Ethanolic Extract ◽

Inhibitory Effect ◽

No Production ◽

Water Distillation ◽

Raw264.7 Macrophages ◽

Tnf Α ◽

Anti Inflammatory ◽

Inflammatory Effect

Zanthoxylum rhetsa has been consumed in the diet in northern Thailand and also used as a medicament in ancient scripture for arthropathies. Thus, this study aimed to evaluate the activity of various extracts from differential parts of Z. rhetsa via inhibition of inflammatory mediators (NO, TNF-α, and PGE2) in RAW264.7 macrophages. The chemical composition in active extracts was also analyzed by GC/MS. The parts of this plant studied were whole fruits (F), pericarp (P), and seed (O). The methods of extraction included maceration in hexane, 95% ethanol and 50% ethanol, boiling in water, and water distillation. The results demonstrated that the hexane and 95% ethanolic extract from pericarp (PH and P95) and seed essential oil (SO) were the most active extracts. PH and P95 gave the highest inhibition of NO production with IC50 as 11.99 ± 1.66 μg/ml and 15.33 ± 1.05 μg/ml, respectively, and they also showed the highest anti-inflammatory effect on TNF-α with IC50 as 36.08 ± 0.55 μg/ml and 34.90 ± 2.58 μg/ml, respectively. PH and P95 also showed the highest inhibitory effect on PGE2 but less than SO with IC50 as 13.72 ± 0.81 μg/ml, 12.26 ± 0.71 μg/ml, and 8.61 ± 2.23 μg/ml, respectively. 2,3-Pinanediol was the major anti-inflammatory compound analyzed in PH (11.28%) and P95 (19.82%) while terpinen-4-ol constituted a major anti-inflammatory compound in SO at 35.13%. These findings are the first supportive data for ethnomedical use for analgesic and anti-inflammatory activity in acute (SO) and chronic (PH and P95) inflammation.

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Four new triterpenoids from Chisocheton paniculatus and their anti-inflammatory activities

Canadian Journal of Chemistry ◽

10.1139/v11-147 ◽

2012 ◽

Vol 90 (2) ◽

pp. 199-204 ◽

Cited By ~ 7

Author(s):

Ming-Hua Yang ◽

Jun-Song Wang ◽

Jian-Guang Luo ◽

Xiao-Bing Wang ◽

Ling-Yi Kong

Keyword(s):

Spectroscopic Data ◽

In Vitro Model ◽

2D Nmr ◽

No Production ◽

Moderate Activity ◽

Inhibitory Effects ◽

Raw264.7 Macrophages ◽

Anti Inflammatory ◽

Vitro Model

As part of our continuing effort to discover new potential anti-inflammatory agents, four new triterpenoids, chisopanins L-O (1–4), were isolated from the twigs of Chisocheton paniculatus. Their structures were established on the basis of detailed analysis of spectroscopic data, including IR, NMR (1D and 2D NMR), and HR-ESI-MS. Their inhibitory effects against nitric oxide (NO) production were evaluated in an in vitro model of lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Compounds 1, 3, and 4 were found to exhibit moderate activity with IC50 values less than 10 μmol/L.

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Bioactive PKS–NRPS Alkaloids from the Plant-Derived Endophytic Fungus Xylaria arbuscula

Molecules ◽

10.3390/molecules27010136 ◽

2021 ◽

Vol 27 (1) ◽

pp. 136

Author(s):

Ya Wang ◽

Sinan Zhao ◽

Tao Guo ◽

Li Li ◽

Tantan Li ◽

...

Keyword(s):

Endophytic Fungus ◽

2D Nmr ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

Hep G2 ◽

Antitumor Activities ◽

Chemical Structures ◽

Spectroscopic Analyses ◽

Ic50 Values

A novel hybrid PKS–NRPS alkaloid, xylarialoid A (1), containing a 13-membered macrocyclic moiety and [5,5,6] fused tricarbocyclic rings, together with ten known cytochalasins (2–11), was isolated from a plant-derived endophytic fungus, Xylaria arbuscula. The chemical structures of all compounds were elucidated using 1D and 2D NMR, HR ESIMS spectroscopic analyses, and electronic circular dichroism (ECD) calculation. Compounds 1–3 and 10 exhibited significant antitumor activities against A549 and Hep G2 cell lines, with IC50 values of 3.6–19.6 μM. In addition, compound 1 showed potent anti-inflammatory activity against LPS-induced nitric oxide (NO) production in macrophage RAW 264.7 cells (IC50, 6.6 μM).

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Anti-Inflammatory Activity of Quercetogetin Isolated from Citrus Unshiu Peel Involves Suppression of NF-κB and MAPK Signaling Pathways in LPS-induced RAW264.7 Macrophages

10.20944/preprints201811.0229.v1 ◽

2018 ◽

Author(s):

Eun Suk Son ◽

Jeong-Wooung Park ◽

Hye Ran Park ◽

Woorijarang Han ◽

Dae Eun Yun ◽

...

Keyword(s):

Molecular Mechanisms ◽

Inflammatory Diseases ◽

Mapk Pathway ◽

Mapk Signaling ◽

Raw264.7 Cells ◽

Raw 264.7 Cells ◽

Citrus Peel ◽

Raw264.7 Macrophages ◽

Anti Inflammatory ◽

Inflammatory Effect

Citrus peel has been used in Asian traditional medicine for the treatment of cough, asthma, and bronchial disorders. However, the anti-inflammatory effect of quercetogetin (QUE), a polymethoxylated flavone isolated from the peel of citrus unshui is poorly understood. We investigated the anti-inflammatory effect and the molecular mechanisms of QUE in lipopolysaccharide (LPS)-induced RAW264.7 cells. QUE inhibited the production of NO and prostaglandin E2 by suppressing the LPS-induced expression of inducible nitric oxide synthase and cyclooxygenase-2 at both the mRNA and protein levels. QUE suppressed the production of proinflammatory cytokines, such as interleukin (IL)-1β, IL-6, and tumor necrosis factor-α. QUE also inhibited the translocation of the nuclear factor kappa B subunit, p65, into the nucleus by interrupting the phosphorylation of IκB-α in LPS-induced RAW 264.7 cells. Based on the finding that QUE significantly decreased p-ERK protein expression in LPS-induced RAW264.7 cells, we confirmed that suppression of the inflammatory process by QUE was mediated through the MAPK pathway. This is the first report on the strong anti-inflammatory effects of QUE, which is a compound that can potentially be used as a therapeutic agent for inflammatory diseases.

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Anti-Inflammatory Effect of Local Anaesthetic Ropivacaine in Lipopolysaccharide-Stimulated RAW264.7 Macrophages

Pharmacology ◽

10.1159/000496425 ◽

2019 ◽

Vol 103 (5-6) ◽

pp. 228-235 ◽

Cited By ~ 2

Author(s):

Li Wu ◽

Lu Li ◽

Fang Wang ◽

Xianwei Wu ◽

Xin Zhao ◽

...

Keyword(s):

Significant Inhibition ◽

Raw 264.7 Cells ◽

Raw 264.7 ◽

Raw 264.7 Macrophages ◽

Raw264.7 Macrophages ◽

Tnf Α ◽

Mitogen Activated Protein ◽

Anti Inflammatory ◽

Necrosis Factor ◽

Inflammatory Effect

The present manuscript intended to investigate the anti-inflammatory effect of ropivacaine on lipopolysaccharide-induced inflammation in RAW 264.7 macrophages. Results suggested that ropivacaine causes significant inhibition of generation of nitric oxide (NO), prostaglandin E2, tumor necrosis factor (TNF)-α, interleukin (IL)-6, and IL-1β, as well as expression of their synthesizing enzymes, inducible NO synthase, and cyclooxygenase-2. Moreover, ropivacaine causes inhibition of mitogen-activated protein kinases as well as nuclear factor-kappa B signaling pathway and apoptosis in RAW 264.7 cells. Based on the results, it has been suggested that ropivacaine showed beneficial effect against inflammation.

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