Sterols from a Vietnamese Wood-Rotting Phellinus sp.

Phytochemical examination of the methanolic extract from fruit bodies of an unidentified Vietnamese Phellinus species led to the isolation of four compounds, one of which is a new steroid, 25-hydroxy-ergosta-7,24(28)-dien-3β -ol, named phellinol, together with senexonol, trametenolic acid B and ergosta-4,6,8(14),22-tetraen-3-one. Their structures were determined by 2D NMR, MS, IR and UV spectroscopy. In addition, the absolute configuration of senexonol was established by X-ray crystallographic analysis of its p-bromobenzoate derivative as 22(R)-hydroxy-4(S),14(S)- dimethyl-cholesta-8,24-dien-3-one. All compounds moderately suppressed the lipopolysaccharide (LPS)-induced production of nitric oxide (NO) in RAW 264.7 cells.

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Marylosides A-G, Norcycloartane Glycosides from Leaves of Cymbidium Great Flower ‘Marylaurencin’

Molecules ◽

10.3390/molecules24132504 ◽

2019 ◽

Vol 24 (13) ◽

pp. 2504

Author(s):

Tatsuro Yoneyama ◽

Kanako Iseki ◽

Masaaki Noji ◽

Hiroshi Imagawa ◽

Toshihiro Hashimoto ◽

...

Keyword(s):

Nitric Oxide ◽

Interferon Γ ◽

Crystallographic Analysis ◽

Chemical Degradation ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

Moderate Activity ◽

X Ray ◽

Ifn Γ

Seven novel norcycloartane glycosides, maryloside A–G (1–7), were isolated from the leaves of Cymbidium Great Flower ‘Marylaurencin’, along with a known norcycloartane glycoside, cymbidoside (8). These structures were determined on the basis of mainly NMR experiments as well as chemical degradation and X-ray crystallographic analysis. The isolated compounds (1–6 and 8) were evaluated for the inhibitory activity on lipopolysaccharide (LPS) and interferon-γ (IFN-γ)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Consequently, 1 and 3 exhibited moderate activity.

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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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Acanthocyclamine A From the Indonesian Marine Sponge Acanthostrongylophora ingens

Australian Journal of Chemistry ◽

10.1071/ch14107 ◽

2014 ◽

Vol 67 (9) ◽

pp. 1205 ◽

Cited By ~ 5

Author(s):

Ariyanti S. Dewi ◽

Tri A. Hadi ◽

Nurrahmi D. Fajarningsih ◽

Joanne T. Blanchfield ◽

Paul V. Bernhardt ◽

...

Keyword(s):

Absolute Configuration ◽

Marine Sponge ◽

National Park ◽

Biosynthetic Pathway ◽

Methanolic Extract ◽

2D Nmr ◽

X Ray ◽

X Ray Crystallography ◽

Dispersion Effects ◽

Manzamine Alkaloids

A new 3-alkylpiperidine compound (–)-acanthocyclamine A (1) has been obtained from the methanolic extract of Acanthostrongylophora ingens (order Haplosclerida, family Petrosiidae) collected from Wakatobi Marine National Park in South East Sulawesi, Indonesia. The structure of 1 was investigated by extensive 1D- and 2D-NMR experiments. The absolute configuration of 1 was established by X-ray crystallography from anomalous dispersion effects using Cu radiation as C2 (R), C3 (R), C7 (R), and C9 (R). A plausible biosynthetic scheme leading to 1 is presented, and compared with the biosynthetic pathway proposed for the manzamine alkaloids.

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

Scientific Reports ◽

10.1038/s41598-020-80804-1 ◽

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.

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Phaseolin Attenuates Lipopolysaccharide-Induced Inflammation in RAW 264.7 Cells and Zebrafish

Biomedicines ◽

10.3390/biomedicines9040420 ◽

2021 ◽

Vol 9 (4) ◽

pp. 420

Author(s):

Su-Jung Hwang ◽

Ye-Seul Song ◽

Hyo-Jong Lee

Keyword(s):

Nitric Oxide ◽

Nuclear Translocation ◽

Raw 264.7 Cells ◽

Network Pharmacology ◽

Raw 264.7 ◽

Dependent Manner ◽

Bioactive Constituents

Kushen (Radix Sophorae flavescentis) is used to treat ulcerative colitis, tumors, and pruritus. Recently, phaseolin, formononetin, matrine, luteolin, and quercetin, through a network pharmacology approach, were tentatively identified as five bioactive constituents responsible for the anti-inflammatory effects of S. flavescentis. However, the role of phaseolin (one of the primary components of S. flavescentis) in the direct regulation of inflammation and inflammatory processes is not well known. In this study, the beneficial role of phaseolin against inflammation was explored in lipopolysaccharide (LPS)-induced inflammation models of RAW 264.7 macrophages and zebrafish larvae. Phaseolin inhibited LPS-mediated production of nitric oxide (NO) and the expression of inducible nitric oxide synthase (iNOS), without affecting cell viability. In addition, phaseolin suppressed pro-inflammatory mediators such as cyclooxygenase 2 (COX-2), interleukin-1β (IL-1β), tumor necrosis factor α (TNF-α), monocyte chemoattractant protein-1 (MCP-1), and interleukin-6 (IL-6) in a dose-dependent manner. Furthermore, phaseolin reduced matrix metalloproteinase (MMP) activity as well as macrophage adhesion in vitro and the recruitment of leukocytes in vivo by downregulating Ninjurin 1 (Ninj1), an adhesion molecule. Finally, phaseolin inhibited the nuclear translocation of nuclear factor-kappa B (NF-κB). In view of the above, our results suggest that phaseolin could be a potential therapeutic candidate for the management of inflammation.

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A New Flavonol From Saussurea involucrata With Anti-Inflammatory Activity

Natural Product Communications ◽

10.1177/1934578x211007638 ◽

2021 ◽

Vol 16 (5) ◽

pp. 1934578X2110076

Author(s):

Sheng Pan ◽

Zi-Guan Zhu

Keyword(s):

Nitric Oxide ◽

Aerial Part ◽

Raw 264.7 Cells ◽

Raw 264.7 ◽

Spectroscopic Methods ◽

Soluble Extract ◽

Saussurea Involucrata ◽

Tnf Α ◽

Anti Inflammatory

A new flavonol named 6-(2'',3''-epoxy-3''-methylbutyl)-resokaempferol (1), together with five known compounds (2-6) were isolated from the EtOAc-soluble extract of the aerial part of Saussurea involucrata. Their structures were elucidated on the basis of spectroscopic methods. All compounds were evaluated for their anti-inflammatory effects by measuring the production of nitric oxide (NO) and TNF-α in vitro. Among them, compound 1 showed potential inhibitory activity on the production of NO and TNF-α in LPS-induced RAW 264.7 cells with IC50 values of 48.0 ± 1.5 and 41.4 ± 1.7 µM, respectively.

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