Synthesis of Ochnaflavone Analogs and Their Inhibitory Activity on PGE2 and NO Production Against LPS-treated RAW 264.7 Cells

2017 ◽  
Vol 38 (6) ◽  
pp. 681-683 ◽  
Author(s):  
Tuan-Anh Pham ◽  
Changwoo Han ◽  
Haeil Park
Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1305 ◽  
Author(s):  
Guodong Zhang ◽  
Huawei Geng ◽  
Chunxia Zhao ◽  
Fangyi Li ◽  
Zhen-Fa Li ◽  
...  

Russula vinosa Lindbl is a wild edible mushroom that is usually used for original material of food and soup and has rich nutritional value. What are the nutritional ingredients? In order to answer this question, we investigated the chemical constituents of this wild functional food. Six new compounds (1–6), together with nine known ones (7–15), were isolated from R. vinosa. The six new compounds were named as vinosane (1), rulepidadione C (2), (24E)-3,4-seco-cucurbita-4,24-diene-26,29-dioic acid-3-methyl ester (3), (24E)-3,4-seco-cucurbita-4,24-diene-26-oic acid-3-ethyl ester (4), (24E)-3β-hydroxycucurbita-5,24-diene-26,29-dioic acid (5), and (2S,3S,4R,2′R)-2-(2′-hydroxydocosanoylamino)eicosane-1,3,4-triol (6). Their structures were determined based on spectroscopic methods including HR-ESI-MS, 1D, and 2D NMR. Moreover, a cell counting kit-8 (CCK-8 kit) was used to screen for the cytotoxicity of compounds 1–5 and 7–13 on mouse macrophage RAW 264.7 cells. The results showed that compounds 1–5 and 7–13 had no obvious cytotoxicity. In addition, the inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse macrophage RAW 264.7 cells were evaluated. Compounds 1, 3, 4, 7, 12, and 13 showed moderate inhibitory activity on NO production.


2019 ◽  
Vol 7 (22) ◽  
pp. 3737-3740
Author(s):  
Novycha Auliafendri ◽  
Rosidah Rosidah ◽  
Yuandani Yuandani ◽  
Sri Suryani ◽  
Denny Satria

AIM: The objective of this study was to evaluate the inhibitory activity of Picria fel-terrae Lour on Nitric Oxide production toward RAW 264.7 cells. METHODS: The extraction was obtained by maceration method using n-hexane, ethyl acetate and ethanol solvents and then nitric oxide (NO) production was obtained using Griess reagent. RESULTS: Extract of Picria fel-terrae Lour herbs can reduce the NO production toward RAW 264.7 cells with induced by lipopolysaccharide has obtained nitric concentrations 12.5 and 25 μg/mL from n-hexane extract (72.50 ± 4.51 and 10.42 ± 1.82), ethyl acetate extract: (88.33 ± 6.51 and 30.83 ± 6.86), ethanol extract: (75.00 ± 1.91 and 22.08 ± 2.53). CONCLUSION: n-hexane extract of Picria fel-terrae Lour Herbs has a high potential to reduce the NO production in LPS-stimulated RAW 264.7 cells compared to ethyl acetate and ethanol extracts of Picria fel-terrae Lour Herbs.


2019 ◽  
Vol 57 (2) ◽  
pp. 200-212
Author(s):  
Aurachorn Inkanuwat ◽  
Romteera Sukaboon ◽  
Aphichart Karnchanatat ◽  
Papassara Sangtanoo ◽  
Tanatorn Saisavoey ◽  
...  

Nitric oxide (NO) plays a key role in the pathogenesis of inflammation and has been implicated in endotoxin-induced tissue injury. Chicken feather meal is a rich source of amino acids that may serve as a peptide hydrolysate to inhibit NO activity. Anti-inflammatory hydrolysates of chicken feather meal were prepared and fractionated into five samples based on molecular mass. The smallest fraction (<0.65 kDa) exhibited the highest NO inhibitory activity without cytotoxicity towards macrophage RAW 264.7 cells. Further subfractions were sufficient to obtain amino acid sequences by Q-TOF LC-MS/MS ESI analysis. Of these, the SNPSVAGVR (885.97 Da) peptide and its corresponding pure synthetic peptide have inhibitory activity against NO production by RAW 264.7 cells (IC50=(55.2±0.2) mM) without cytotoxicity. Reverse transcriptase polymerase chain reaction (RT-PCR) and quantitative real-time RT-PCR results revealed that the peptide of the obtained fraction reduced transcript expression levels of the pro-inflammatory cytokines iNOS, TNF-α, COX-2 and IL-6 in lipopolysaccharide-stimulated RAW 264.7 cells. These results suggest that the peptides derived from the chicken feather meal protein could potentially be used as a promising ingredient in functional foods or nutraceuticals against inflammatory diseases.


2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Haidy A. Saleh ◽  
Eman Ramdan ◽  
Mohey M. Elmazar ◽  
Hassan M. E. Azzazy ◽  
Anwar Abdelnaser

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.


2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Nilubon Sornkaew ◽  
Yuan Lin ◽  
Fei Wang ◽  
Guolin Zhang ◽  
Ratchanaporn Chokchaisiri ◽  
...  

Eight new diarylheptanoids, a 1.2:1 mixture of (3S)- and (3 R)-1-(4-hydroxyphenyl)-7-phenyl-(4 E,6 E)-4,6-heptadien-3-ol (1a and 1b), a racemic mixture of (3S)- and (3 R)-1-(4-hydroxyphenyl)-3-methoxy-7-phenyl-(4 E,6 E)-4,6-heptadiene (2a and 2b), a ca. 1:1 mixture of (3S)- and (3 R)-1-(4-hydroxy-3-methoxyphenyl)-3-methoxy-7-phenyl)-(4 E,6 E)-4,6-heptadiene (3a and 3b), 3-acetoxy-1-(3,4-dihydroxyphenyl)-7-phenylheptan-5-ol (4), (3 R)-1-(4,5-dihydroxyphenyl)-7-phenyl-(6 E)-6-hepten-3,2′-epoxide (5), and thirteen known diarylheptanoids, 6-12, a 3:1 mixture of 13a and 13b, and 14-17, were isolated from the rhizomes of Curcuma comosa from Sakon Nakhon, northeastern part of Thailand. The isolated compounds were evaluated for their antiinflammatory activities on the inhibition of lipopolysaccharide-induced nitric oxide production in macrophage RAW 264.7 cells and the diarylheptanoids 1a and 1b mixture and 14 exhibited potent inhibitory activity.


Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3910 ◽  
Author(s):  
Min-Seon Kim ◽  
Jin-Soo Park ◽  
You Chul Chung ◽  
Sungchan Jang ◽  
Chang-Gu Hyun ◽  
...  

Biorenovation is a microbial enzyme-catalyzed structural modification of organic compounds with the potential benefits of reduced toxicity and improved biological properties relative to their precursor compounds. In this study, we synthesized a novel compound verified as formononetin 7-O-phosphate (FMP) from formononetin (FM) using microbial biotransformation. We further compared the anti-inflammatory properties of FMP to FM in lipopolysaccharide (LPS)-treated RAW264.7 macrophage cells. We observed that cell viabilities and inhibitory effects on LPS-induced nitric oxide (NO) production were greater in FMP-treated RAW 264.7 cells than in their FM-treated counterparts. In addition, FMP treatment suppressed the production of proinflammatory cytokines such as prostaglandin-E2 (PGE2), interleukin-6 (IL-6), and interleukin-1β (IL-1β) in a dose-dependent manner and concomitantly decreased the mRNA expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2). We also found that FMP exerted its anti-inflammatory effects through the downregulation of the extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK), and nuclear factor kappa B (NF-κB) signaling pathways. In conclusion, we generated a novel anti-inflammatory compound using biorenovation and demonstrated its efficacy in cell-based in vitro assays.


2007 ◽  
Vol 2 (6) ◽  
pp. 1934578X0700200 ◽  
Author(s):  
Liva Harinantenaina ◽  
Yoshinori Asakawa

The phytochemical investigation of eight Jungermaniales liverwort species: Bazzania decrescens, B. madagassa (Lepidoziaceae), Plagiochila barteri, P. terebrans (Plagiochilaceae), Isotachis aubertii (Isotachidaceae), Mastigophora diclados (Lepicoleaceae), Radula appressa (Radulaceae), and Thysananthus spathulistipus (Lejeuneaceae), collected from Madagascar, has been carried out to afford new and structurally interesting terpenoids and aromatic compounds. The biological activities of the isolated secondary metabolites were determined and the herbertene-type sesquiterpenoids were shown to have antibacterial activity. A new ent-clerodane diterpene from Thysananthus spathulistipus and bis-bibenzyls-type aromatic compounds exhibited strong inhibition of NO production in RAW 264.7 cells, while marchantin C produced moderate α-glucosidase inhibition. The chemosystematics of the studied species are discussed.


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