scholarly journals Polygokingiasides A and B: Two New Spirostane Glycosides From the Roots of Polygonatum kingianum With Nitric Oxide Inhibitory Activity

2021 ◽  
Vol 16 (1) ◽  
pp. 1934578X2098563
Author(s):  
Tran Thi Thu Ha ◽  
Trinh Quang Huy ◽  
Pham The Chinh ◽  
Phan Van Kiem
Keyword(s):  
Nitric Oxide ◽  
Mass Spectrometry ◽  
Spectral Data ◽  
Inhibitory Effect ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Ionization Mass ◽  
Raw 264.7 ◽  
Extensive Analysis ◽  
Resolution Electron

Two new spirostane glycosides, named polygokingiaside A (1) and polygokingiaside B (2), and 6 known spirostane glycosides, (25 R)-26- O-( β-d-glucopyranosyl)-furost-5-en-3 β,22 α,26-triol 3- O-β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (3), (25 S)-26- O-( β-d-glucopyranosyl)-furost-5-en-3 β,22 α,26-triol 3- O-β-d-glucopyranosyl-(1→2)- β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (4), (25 R)-26- O-( β-d-glucopyranosyl)-furost-5-en-3 β,22 α,26-triol 3- O-β-d-glucopyranosyl-(1→2)- β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (5), (23 S,25 R)-spirostan-5-en-3 β,23-dihydroxy-12-one-3- O-β-d-glucopyranosyl-(1→2)- β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (6), (24 S,25 R)-spirostan-5-en-3 β,24-dihydroxy-12-one-3- O-β-d-glucopyranosyl-(1→2)- β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (7), and (25 R)-spirostan-5-en-3 β-hydroxy-12-one-3- O-β-d-glucopyranosyl-(1→4)- β-d-galactopyranoside (8), were isolated from the roots of Polygonatum kingianum Collett & Hemsl. (Asparagaceae). Their structures were determined by extensive analysis of high-resolution electron spray ionization mass spectrometry and nuclear magnetic resonance spectral data, as well as by comparison of the spectral data with those reported in the literature. Anti-inflammatory activity of compounds 1-8 was evaluated by their inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. At a concentration of 20 µM, compounds 1-8 exhibited a modest inhibitory effect on NO production in LPS-stimulated RAW246.7 cells with inhibitory values ranging from 9.5 ± 0.8% to 33.8 ± 2.1%.

scholarly journals A New Phenylethanoid Glycoside From the Leaves of Rosmarinus officinalis With Nitric Oxide Inhibitory Activity

2020 ◽  
Vol 15 (10) ◽  
pp. 1934578X2096908
Author(s):  
Le Thi Huyen ◽  
Le Thi Oanh ◽  
Nguyen Thi Son ◽  
Nguyen Thi Minh Thu ◽  
Nguyen Huy Hoang ◽  
...  
Keyword(s):  
Spectral Data ◽  
Cytotoxic Effect ◽  
Rosmarinus Officinalis ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Ionization Mass ◽  
Phenylethanoid Glycoside ◽  
Extensive Analysis ◽  
Resolution Electron ◽  
Ionization Mass Spectrum

A new phenylethanoid glycoside, named rosmacinalis (1), and 6x known compounds {2-phenylethyl O-α-L-rhamnopyranosyl-(1‴→6″)- O-β-D-glucopyranoside (2), clinopodiolide C (3), rosmanol (4), 7 α-methoxyrosmanol (5) 7 β-methoxyrosmanol (6) and carnosol (7)} were isolated from the leaves of Rosmarinus officinalis. Their structures were determined by extensive analysis of high-resolution electron spray ionization mass spectrum and nuclear magnetic resonance spectral data, as well as by comparison of the spectral data with those reported in the literature. Anti-inflammatory activity of compounds 1‐7 was evaluated by their inhibition of NO production in lipopolysaccharide-stimulated RAW 264.7 cells. At a concentration of 100 µM, compounds 1 and 2 exhibited inhibitory rates of 47.1% ± 2.2% and 44.5% ± 1.3%, respectively, while compounds 3‐7 showed a cytotoxic effect. After dilution to a concentration of 20 µM, except compound 7, compounds 1‐6 did not show a cytotoxic effect. Their NO inhibitory rates ranged from 14.2% ± 1.3% to 31.1% ± 1.9%.

scholarly journals New Nitric Oxide Inhibitory Spirostane Glycosides from Polygonatum kingianum Collett & Hemsl

2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110412
Author(s):  
Tran Thi Thu Ha ◽  
Phan Van Kiem
Keyword(s):  
Nitric Oxide ◽  
Spectral Data ◽  
Positive Control ◽  
Raw 264.7 Cells ◽  
Ionization Mass ◽  
Inhibitory Effects ◽  
A Value ◽  
Resolution Electron ◽  
Ionization Mass Spectrum ◽  
Control Compound

Two new spirostane glycosides, (25 R)-12 β-hydroxyspirost-5-en-3 β-yl O- β-D-glucopyranosyl-(1→4)- β-D-galactopyranoside (1) and (25 S)-spirost-5-en-7-one-3 β-yl O- β-D-glucopyranosyl-(1→2)- β-D-glucopyranosyl-(1→4)- β-D-galactopyranoside (2), and a known spirostane glycoside, funkioside C (3), were isolated from the roots of Polygonatum kingianum Collett & Hemsl. (Asparagaceae). Their structures were determined by extensive analysis of mass spectrometry high resolution electron spray ionization mass spectrum and nuclear magnetic resonance spectral data, as well as by comparison of the spectral data with those reported in the literature. Compound 2 showed inhibitory effects on nitric oxide production in the lipopolysaccharide stimulated RAW 264.7 cells with an IC50 value of 8.78 ± 0.05 µM compared to a value of 7.12 ± 0.08 µM for the positive control compound, NG-monomethyl-L-arginine.

scholarly journals Lobatamunsolides A–C, Norlignans from the Roots of Pueraria lobata and their Nitric Oxide Inhibitory Activities in Macrophages

Biomolecules ◽  
2019 ◽  
Vol 9 (12) ◽  
pp. 755 ◽  
Author(s):  
Mun Seok Jo ◽  
Jae Sik Yu ◽  
Joo Chan Lee ◽  
Seoyoung Lee ◽  
Young-Chang Cho ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Mass Spectrometry ◽  
Inhibitory Effect ◽  
No Production ◽  
Ionization Mass ◽  
Pueraria Lobata ◽  
Amino Acid Residues ◽  
Phytochemical Investigation ◽  
Inos Protein Expression ◽  
New Compounds

Phytochemical investigation of the methanol (MeOH) extract of Pueraria lobata roots, known as “kudzu”, combined with liquid chromatography/mass spectrometry (LC/MS)-based analysis, resulted in the identification of four norlignans (1–4), including three new norlignans, lobatamunsolides A–C (1–3), and five known isoflavonoids (5–9). The structures of the new compounds were elucidated by a combination of spectroscopic methods, including 1D and 2D nuclear magnetic resonance (NMR) and high resolution (HR)-electrospray ionization mass spectrometry (ESIMS), and their absolute configurations were determined by chemical reaction and quantum chemical electronic circular dichroism (ECD) calculations. The isolated compounds (1–9) were evaluated for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compound 9 displayed the strongest NO inhibitory effect and compound 2 showed a weak effect. The potential mechanism of the effect of compound 9 was investigated by analysis of its molecular docking on the active site of inducible nitric oxide synthase (iNOS), which showed the potential interactions of compound 9 with key amino acid residues and the heme cofactor of iNOS. The mechanism as the inhibition of transcriptional iNOS protein expression was confirmed by western blotting experiments.

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.

scholarly journals Comparing the protective effects of resveratrol, curcumin and sulforaphane against LPS/IFN-γ-mediated inflammation in doxorubicin-treated macrophages

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Haidy A. Saleh ◽  
Eman Ramdan ◽  
Mohey M. Elmazar ◽  
Hassan M. E. Azzazy ◽  
Anwar Abdelnaser
Keyword(s):  
Nitric Oxide ◽  
Inflammatory Response ◽  
Raw 264.7 Cells ◽  
Inos Mrna ◽  
No Production ◽  
Raw 264.7 ◽  
Mrna Levels ◽  
Protective Effects ◽  
Tnf Α ◽  
Ifn Γ

AbstractDoxorubicin (DOX) chemotherapy is associated with the release of inflammatory cytokines from macrophages. This has been suggested to be, in part, due to DOX-mediated leakage of endotoxins from gut microflora, which activate Toll-like receptor 4 (TLR4) signaling in macrophages, causing severe inflammation. However, the direct function of DOX on macrophages is still unknown. In the present study, we tested the hypothesis that DOX alone is incapable of stimulating inflammatory response in macrophages. Then, we compared the anti-inflammatory effects of curcumin (CUR), resveratrol (RES) and sulforaphane (SFN) against lipopolysaccharide/interferon-gamma (LPS/IFN-γ)-mediated inflammation in the absence or presence of DOX. For this purpose, RAW 264.7 cells were stimulated with LPS/IFN-γ (10 ng/mL/10 U/mL) in the absence or presence of DOX (0.1 µM). Our results showed that DOX alone is incapable of stimulating an inflammatory response in RAW 264.7 macrophages. Furthermore, after 24 h of incubation with LPS/IFN-γ, a significant increase in tumor necrosis factor-alpha (TNF-α), interleukin-6 (IL-6), and inducible nitric oxide synthase (iNOS) mRNA levels was observed. Similarly, nitric oxide (NO) production and TNF-α and IL-6 protein levels were significantly upregulated. Moreover, in LPS/IFN-γ-treated macrophages, the microRNAs (miRNAs) miR-146a, miR-155, and miR-21 were significantly overexpressed. Interestingly, upon testing CUR, RES, and SFN against LPS/IFN-γ-mediated inflammation, only SFN was able to significantly reverse the LPS/IFN-γ-mediated induction of iNOS, TNF-α and IL-6 and attenuate miR-146a and miR-155 levels. In conclusion, SFN, at the transcriptional and posttranscriptional levels, exhibits potent immunomodulatory action against LPS/IFN-γ-stimulated macrophages, which may indicate SFN as a potential treatment for DOX-associated inflammation.

scholarly journals Inhibitory Effect of 1,5-Dimethyl Citrate from Sea Buckthorn (Hippophae rhamnoides) on Lipopolysaccharide-Induced Inflammatory Response in RAW 264.7 Mouse Macrophages

Foods ◽  
2020 ◽  
Vol 9 (3) ◽  
pp. 269 ◽  
Author(s):  
Su Cheol Baek ◽  
Dahae Lee ◽  
Mun Seok Jo ◽  
Kwang Ho Lee ◽  
Yong Hoon Lee ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Synthase ◽  
Sea Buckthorn ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Raw 264.7 ◽  
Tnf Α ◽  
Mouse Macrophages ◽  
Cox 2 ◽  
Oxide Synthase

Hippophae rhamnoides L. (Elaeagnaceae; commonly known as “sea buckthorn” and “vitamin tree”), is a spiny deciduous shrub whose fruit is used in foods and traditional medicines. The H. rhamnoides fruit (berry) is rich in vitamin C, with a level exceeding that found in lemons and oranges. H. rhamnoides berries are usually washed and pressed to create pomace and juice. Today, the powder of the aqueous extract of H. rhamnoides berries are sold as a functional food in many countries. As part of our ongoing effort to identify bioactive constituents from natural resources, we aimed to isolate and identify those from the fruits of H. rhamnoides. Phytochemical analysis of the extract of H. rhamnoides fruits led to the isolation and identification of six compounds, namely, a citric acid derivative (1), a phenolic (2), flavonoids (3 and 4), and megastigmane compounds (5 and 6). Treatment with compounds 1–6 did not have any impact on the cell viability of RAW 264.7 mouse macrophages. However, pretreatment with these compounds suppressed lipopolysaccharide (LPS)-induced NO production in RAW 264.7 mouse macrophages in a concentration-dependent manner. Among the isolated compounds, compound 1 was identified as the most active, with an IC50 of 39.76 ± 0.16 μM. This value was comparable to that of the NG-methyl-L-arginine acetate salt, a nitric oxide synthase inhibitor with an IC50 of 28.48 ± 0.05 μM. Western blot analysis demonstrated that compound 1 inhibited the LPS-induced expression of IKKα/β (IκB kinase alpha/beta), I-κBα (inhibitor of kappa B alpha), nuclear factor kappa-B (NF-κB) p65, iNOS (inducible nitric oxide synthase), and COX-2 (cyclooxygenase-2) in RAW 264.7 cells. Furthermore, LPS-stimulated cytokine production was detected using a sandwich enzyme-linked immunosorbent assay. Compound 1 decreased interleukin 6 (IL-6) and tumor necrosis factor alpha (TNF-α) production in LPS-stimulated RAW 264.7 cells. In summary, the mechanism of action of 1 included the suppression of LPS-induced NO production in RAW 264.7 cells by inhibiting IKKα/β, I-κBα, NF-κB p65, iNOS, and COX-2, and the activities of IL-6 and TNF-α.

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

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.

scholarly journals Naphthoquinone Derivatives with Anti-Inflammatory Activity from Mangrove-Derived Endophytic Fungus Talaromyces sp. SK-S009

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 576 ◽  
Author(s):  
Hongju Liu ◽  
Chong Yan ◽  
Changqun Li ◽  
Tingting You ◽  
Zhigang She
Keyword(s):  
Nitric Oxide ◽  
Endophytic Fungus ◽  
Raw 264.7 Cells ◽  
Inflammatory Factors ◽  
No Production ◽  
Raw 264.7 ◽  
Mrna Levels ◽  
Tnf Α ◽  
Ic50 Values ◽  
Oxide Synthase

Twelve 1, 4-naphthoquinone derivatives, including two new (1 and 2) and 10 known (3–12), were obtained from endophytic fungus Talaromyces sp. SK-S009 isolated from the fruit of Kandelia obovata. All structures were identified through extensive analysis of the nuclear magnetic resonance (NMR), mass spectrometry (MS) and circular dichroism (CD), as well as by comparison with literature data. These compounds significantly inhibited the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in the murine macrophage cell line (RAW 264.7 cells). The half maximal inhibitory concentration (IC50) values, except for compound 2, were lower than that of indomethacin (26.3 μM). Compound 9 inhibited the LPS-induced inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) mRNA expressions in RAW 264.7 macrophages. Additionally, compound 9 reduced the mRNA levels of pro-inflammatory factors interleukin (IL)1β, IL-6, and tumor necrosis factor (TNF)-α. The results of this study demonstrated that these 1, 4-naphthoquinone derivatives can inhibit LPS-induced inflammation.

scholarly journals In vitro and in vivo anti-inflammatory activities of a sterol-enriched fraction from freshwater green alga, Spirogyra sp.

2020 ◽  
Vol 23 (1) ◽  
Author(s):  
Lei Wang ◽  
You-Jin Jeon ◽  
Jae-Il Kim
Keyword(s):  
Nitric Oxide ◽  
Green Alga ◽  
Raw 264.7 Cells ◽  
Ros Generation ◽  
Prostaglandin E ◽  
No Production ◽  
Raw 264.7 ◽  
Anti Inflammatory

Abstract Background Inflammation plays a crucial role in the pathogenesis of many diseases such as arthritis and atherosclerosis. In the present study, we evaluated anti-inflammatory activity of sterol-rich fraction prepared from Spirogyra sp., a freshwater green alga, in an effort to find bioactive extracts derived from natural sources. Methods The sterol content of ethanol extract of Spirogyra sp. (SPE) was enriched by fractionation with hexane (SPEH), resulting 6.7 times higher than SPE. Using this fraction, the in vitro and in vivo anti-inflammatory activities were evaluated in lipopolysaccharides (LPS)-stimulated RAW 264.7 cells and zebrafish. Results SPEH effectively and dose-dependently decreased the production of nitric oxide (NO) and prostaglandin E2 (PGE2). SPEH suppressed the production of pro-inflammatory cytokines including interleukin-6 (IL-6), tumor necrosis factor-α (TNF-α), and IL-1β through downregulating nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression in LPS-stimulated RAW 264.7 cells without cytotoxicity. The in vivo test results indicated that SPEH significantly and dose-dependently reduced reactive oxygen species (ROS) generation, cell death, and NO production in LPS-stimulated zebrafish. Conclusions These results demonstrate that SPEH possesses strong in vitro and in vivo anti-inflammatory activities and has the potential to be used as healthcare or pharmaceutical material for the treatment of inflammatory diseases.

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