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

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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Chemical Constituents from Scindapsus officinalis (Roxb.) Schott. and Their Anti–Inflammatory Activities

Molecules ◽

10.3390/molecules23102577 ◽

2018 ◽

Vol 23 (10) ◽

pp. 2577 ◽

Cited By ~ 2

Author(s):

Hongjing Dong ◽

Yanling Geng ◽

Xueyong Wang ◽

Xiangyun Song ◽

Xiao Wang ◽

...

Keyword(s):

Chemical Constituents ◽

2D Nmr ◽

No Production ◽

Inhibitory Effects ◽

Nmr Data ◽

Extensive Analysis ◽

Ic50 Values ◽

Monoterpene Glycoside ◽

Anti Inflammatory

One new monoterpene glycoside (1), one new phenyl glycoside (2), one new caffeoyl derivative (3), were isolated from Scindapsus officinalis (Roxb.) Schott., along with four known compounds (4–7). Structures of the isolated compounds were elucidated by extensive analysis of spectroscopic data, especially 2D NMR data and comparison with literatures. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production in vitro. Compounds 3 and 7 exhibited moderate inhibitory effects on NO production with IC50 values of 12.2 ± 0.8 and 18.9 ± 0.3 μM, respectively.

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

Natural Product Communications ◽

10.1177/1934578x1601101025 ◽

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.

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Lanostane Triterpenoids from the Fruiting Bodies of Fomes officinalis and Their Anti-Inflammatory Activities

Molecules ◽

10.3390/molecules25204807 ◽

2020 ◽

Vol 25 (20) ◽

pp. 4807

Author(s):

Jianxin Han ◽

Wei Liu ◽

Miaomiao Li ◽

Yanpei Gu ◽

Ying Zhang ◽

...

Keyword(s):

Spectroscopic Data ◽

2D Nmr ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

Fruiting Bodies ◽

C 23 ◽

Inhibitory Activities ◽

Cox 2 ◽

Anti Inflammatory

In the current study, further chemical investigation of the fruiting bodies of Fomes officinalis led to isolate seven new 24-methyl-lanostane triterpenoids, named officimalonic acids I−O (1–7). Their structures were elucidated based on the analysis of spectroscopic data (HR-MS, 1D and 2D NMR, UV, IR). Compounds 1−3 possessed an unusual C-23 spirostructure moiety, while compounds 4−7 had 23,26-lactone unit. Anti-inflammatory assay revealed that compounds 3 and 5 exhibited significant inhibitory activities against NO production in LPS-induced RAW 264.7 cells and cyclooxygenase (COX-2).

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α-Glucosidase Inhibitory and Anti-Inflammatory Coumestans from the Roots of Dolichos trilobus

Planta Medica ◽

10.1055/a-0746-8622 ◽

2018 ◽

Vol 85 (02) ◽

pp. 112-117 ◽

Cited By ~ 5

Author(s):

Meng-Yuan Jiang ◽

Ming Luo ◽

Kai Tian ◽

Yan-Hong Li ◽

Jing-Xian Sun ◽

...

Keyword(s):

Spectroscopic Data ◽

Data Interpretation ◽

Raw 264.7 Cells ◽

Raw 264.7 ◽

Nitric Oxide Production ◽

Murine Macrophage ◽

Cytotoxic Effects ◽

Ic50 Values ◽

Anti Inflammatory ◽

Related Compounds

AbstractFour new coumestans dolichosins A – D (1–4) were isolated from the roots of Dolichos trilobus, together with four known compounds: isosojagol (5), phaseol (6), psoralidin (7), and 4″,5″-dehydroisopsoralidin (8). Their structures were elucidated on the basis of spectroscopic data interpretation, mass spectrometric analyses, and the comparison with literature data of related compounds. The anti-inflammatory activity of these compounds (1–8) was evaluated through the inhibition of nitric oxide production in lipopolysaccharide-activated murine macrophage RAW 264.7 cells, in which compounds 1 and 6 displayed moderate inhibitory activity and no cytotoxic effects. In a α-glucosidase inhibitory assay, compounds 1 and 5–8 exhibited appreciable inhibition on α-glucosidase. Especially compounds 1, 7, and 8 showed IC50 values lower than 20.0 µM.

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Cordyceps militaris Fungus Extracts-Mediated Nanoemulsion for Improvement Antioxidant, Antimicrobial, and Anti-Inflammatory Activities

Molecules ◽

10.3390/molecules25235733 ◽

2020 ◽

Vol 25 (23) ◽

pp. 5733

Author(s):

Esrat Jahan Rupa ◽

Jin Feng Li ◽

Muhammad Huzaifa Arif ◽

Han Yaxi ◽

Aditi Mitra Puja ◽

...

Keyword(s):

Zeta Potential ◽

Tween 80 ◽

In Vitro Cytotoxicity ◽

Cordyceps Militaris ◽

Inflammatory Activity ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

Anti Inflammatory

This study aimed to produce and optimize a Cordyceps militaris-based oil-in-water (O/W) nanoemulsion (NE) encapsulated in sea buckthorn oil (SBT) using an ultrasonication process. Herein, a nonionic surfactant (Tween 80) and chitosan cosurfactant were used as emulsifying agents. The Cordyceps nanoemulsion (COR-NE) was characterized using Fourier-transform infrared spectroscopy (FT-IR), dynamic light scattering (DLS), and field-emission transmission electron microscope (FE-TEM). The DLS analyses revealed that the NE droplets were 87.0 ± 2.1 nm in diameter, with a PDI value of 0.089 ± 0.023, and zeta potential of −26.20 ± 2. The small size, low PDI, and stable zeta potential highlighted the excellent stability of the NE. The NE was tested for stability under different temperature (4 °C, 25 °C, and 60 °C) and storage conditions for 3 months where 4 °C did not affect the stability. Finally, in vitro cytotoxicity and anti-inflammatory activity were assessed. The results suggested that the NE was not toxic to RAW 264.7 or HaCaT (human keratinocyte) cell lines at up to 100 µL/mL. Anti-inflammatory activity in liposaccharides (LPS)-induced RAW 264.7 cells was evident at 50 µg/mL and showed inhibition of NO production and downregulation of pro-inflammatory gene expression. Further, the NE exhibited good antioxidant (2.96 ± 0.10 mg/mL) activity and inhibited E. coli and S. aureus bacterial growth. Overall, the COR-NE had greater efficacy than the free extract and added significant value for future biomedical and cosmetics applications.

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ANTI-INFLAMMATORY ACTIVITY OF TINOCRISPOSIDE BY INHIBITING NITRIC OXIDE PRODUCTION IN LIPOPOLYSACCHARIDES-STIMULATED RAW 264.7 CELLS

Asian Journal of Pharmaceutical and Clinical Research ◽

10.22159/ajpcr.2018.v11i4.23739 ◽

2018 ◽

Vol 11 (4) ◽

pp. 149 ◽

Cited By ~ 1

Author(s):

Adek Zamrud Adnan ◽

Muhammad Taher ◽

Tika Afriani ◽

Annisa Fauzana ◽

Dewi Imelda Roesma ◽

...

Keyword(s):

Nitric Oxide ◽

Inflammatory Diseases ◽

Positive Control ◽

Inflammatory Activity ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

Dependent Manner ◽

Anti Inflammatory

Objective: The aim of this study was to investigate in vitro anti-inflammatory activity of tinocrisposide using lipopolysaccharides (LPS)-stimulated RAW 264.7 macrophage cells. Tinocrisposide is a furano diterpene glycoside that was isolated in our previous study from Tinospora crispa.Methods: Anti-inflammatory effect was quantified spectrometrically using Griess method by measuring nitric oxide (NO) production after the addition of Griess reagent.Results: The sample concentrations of 1, 5, 25, 50, and 100 μM and 100 μM of dexamethasone (positive control) have been tested against the LPS-stimulated RAW 264.7 cells, and the results showed NO level production of 39.23, 34.00, 28.9, 20.25, 16.3, and 13.68 μM, respectively, and the inhibition level of 22.67, 33.00, 43.03, 60.10, 68.00, and 73%, respectively.Conclusions: From the study, it could be concluded that tinocrisposide was able to inhibit the formation of NO in the LPS-stimulated RAW 264.7 cells in concentration activity-dependent manner, with half-maximal inhibition concentration 46.92 μM. It can be developed as anti-inflammatory candidate drug because NO is a reactive nitrogen species which is produced by NO synthase. The production of NO has been established as a mediator in inflammatory diseases.

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Solvent Extraction and Identification of Active Anticariogenic Metabolites in Piper cubeba L. through 1H-NMR-Based Metabolomics Approach

Molecules ◽

10.3390/molecules23071730 ◽

2018 ◽

Vol 23 (7) ◽

pp. 1730 ◽

Cited By ~ 5

Author(s):

Raja Raja Mazlan ◽

Yaya Rukayadi ◽

M. Maulidiani ◽

Intan Ismail

Keyword(s):

Principal Component ◽

Oral Bacteria ◽

Inflammatory Activity ◽

Raw 264.7 Cells ◽

No Production ◽

Active Metabolites ◽

Polar Solvents ◽

1H Nuclear Magnetic Resonance ◽

Anti Inflammatory ◽

Extraction Liquid

The aim of this study was to determine the effects of different solvents for extraction, liquid–liquid partition, and concentrations of extracts and fractions of Piper cubeba L. on anticariogenic; antibacterial and anti-inflammatory activity against oral bacteria. Furthermore, 1H-Nuclear Magnetic Resonance (NMR) coupled with multivariate data analysis (MVDA) was applied to discriminate between the extracts and fractions and examine the metabolites that correlate to the bioactivities. All tested bacteria were susceptible to Piper cubeba L. extracts and fractions. Different solvents extraction, liquid–liquid partition and concentrations of extracts and fractions have partially influenced the antibacterial activity. MTT assay showed that P. cubeba L. extracts and fractions were not toxic to RAW 264.7 cells at selected concentrations. Anti-inflammatory activity evaluated by nitric oxide (NO) production in lipopolysaccharide (LPS) stimulated cells showed a reduction in NO production in cells treated with P. cubeba L. extracts and fractions, compared to those without treatment. Twelve putative metabolites have been identified, which are (1) cubebin, (2) yatein, (3) hinokinin, (4) dihydrocubebin, (5) dihydroclusin, (6) cubebinin, (7) magnosalin, (8) p-cymene, (9) piperidine, (10) cubebol, (11) d-germacrene and (12) ledol. Different extraction and liquid–liquid partition solvents caused separation in principal component analysis (PCA) models. The partial least squares (PLS) models showed that higher anticariogenic activity was related more to the polar solvents, despite some of the active metabolites also present in the non-polar solvents. Hence, P. cubeba L. extracts and fractions exhibited antibacterial and anti-inflammatory activity and have potential to be developed as the anticariogenic agent.

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Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

Molecules ◽

10.3390/molecules26216626 ◽

2021 ◽

Vol 26 (21) ◽

pp. 6626

Author(s):

Edwin R. Sukandar ◽

Sutin Kaennakam ◽

Pia Raab ◽

Xuehong Nöst ◽

Kitiya Rassamee ◽

...

Keyword(s):

2D Nmr ◽

Stem Bark ◽

No Production ◽

Hep G2 ◽

Pharmacological Studies ◽

Ic50 Values ◽

Hela S3 ◽

Anti Inflammatory ◽

First Time ◽

Mcf 7

Garcinia picrorhiza, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previously undescribed dihydroisocoumarin, 2′-hydroxyannulatomarin, and two undescribed furanoxanthones, gerontoxanthone C hydrate and 3′-hydroxycalothorexanthone. The structures of the new metabolites were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR and HRESIMS. Gerontoxanthone C hydrate possessed cytotoxicity against four cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC50 values ranging from 5.6 to 7.5 µM. Investigation on the anti-inflammatory activities showed that 3′-hydroxycalothorexanthone inhibited NO production in RAW 264.7 and BV-2 cell lines with IC50 values of 16.4 and 13.8 µM, respectively, whereas only (−)-annulatomarin possessed inhibition activity on COX-2 enzyme over 10% at 20 µM. This work describes the presence of 3,4-dihydroisocoumarin structures with a phenyl ring substituent at C-3, which are reported the first time in genus Garcinia. These findings also suggest the potential of furanxanthone derivatives as cytotoxic and anti-inflammatory agents for further pharmacological studies.

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Anti-Inflammatory Activity of 4-((1R,2R)-3-Hydroxy-1-(4-hydroxyphenyl)-1-methoxypropan-2-yl)-2-methoxyphenol Isolated from Juglans mandshurica Maxim. in LPS-Stimulated RAW 264.7 Macrophages and Zebrafish Larvae Model

Pharmaceuticals ◽

10.3390/ph14080771 ◽

2021 ◽

Vol 14 (8) ◽

pp. 771

Author(s):

Su-Hyeon Cho ◽

SeonJu Park ◽

Hoibin Jeong ◽

Song-Rae Kim ◽

Myeong Seon Jeong ◽

...

Keyword(s):

Nitric Oxide ◽

Inflammatory Responses ◽

Inflammatory Activity ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

Dependent Manner ◽

Juglans Mandshurica ◽

Zebrafish Larvae ◽

Anti Inflammatory

Juglans mandshurica Maxim., a traditional folk medicinal plant, is widely distributed in Korea and China. In our previous study, we isolated a new phenylpropanoid compound, 4-((1R,2R)-3-hydroxy-1-(4-hydroxyphenyl)-1-methoxypropan-2-yl)-2-methoxyphenol (HHMP), from J. mandshurica. In the present study, we evaluated the anti-inflammatory activity of HHMP on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells and zebrafish larvae. HHMP significantly inhibited LPS-induced nitric oxide (NO) and prostaglandin E2 production in a dose-dependent manner. Moreover, HHMP treatment considerably suppressed LPS-induced expression of inducible nitric oxide synthase and cyclooxygenase-2. We also demonstrated the mechanisms of HHMP inhibition of inflammatory responses in LPS-stimulated RAW 264.7 cells via Western blot analysis and immunofluorescence staining. Furthermore, HHMP significantly inhibited NO production in LPS-stimulated zebrafish larvae. Consequently, we established that HHMP significantly inhibited the LPS-induced activation of NF-κB and MAPK and the nuclear translocation of p65 in RAW 264.7 cells. Taken together, our findings demonstrate the effect of HHMP on LPS-induced inflammatory responses in vitro and in vivo, suggesting its potential to be used as a natural anti-inflammatory agent.

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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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