共查询到20条相似文献,搜索用时 31 毫秒
1.
《Bioorganic & medicinal chemistry letters》2020,30(4):126884
In this article, a series of 22 triarylpyrazole derivatives were evaluated for in vitro antiinflammatory activity as inhibitors of nitric oxide (NO) and prostaglandin E2 (PGE2) release induced by lipopolysaccharide (LPS) in murine RAW 264.7 macrophages. The synthesized compounds 1a-h, 2a-f and 3a-h were first examined for their cytotoxicity for determination of the non-toxic concentration for antiinflammatory screening, so that the inhibitory effects against NO and PGE2 production were not caused by non-specific cytotoxicity. Compounds 1h and 2f were the most active PGE2 inhibitors with IC50 values of 2.94 μM and 4.21 μM, respectively. Western blotting and cell-free COX-2 screening revealed that their effects were due to inhibition of COX-2 protein expression. Moreover, compound 1h exerted strong inhibitory effect on the expression of COX-2 mRNA in LPS-induced murine RAW 264.7 macrophages. 相似文献
2.
Huan Liu Yi Li Xiang-Ying Wang Bo Wang Hai-Yun He Ji-Yan Liu Ming-Li Xiang Jun He Xiao-Hua Wu Li Yang 《Bioorganic & medicinal chemistry letters》2013,23(8):2349-2352
In our previous study, a series of 6-aryl-3-amino-thieno[2,3-b]pyridine derivatives exhibited potent antiproliferative activities and an unique hepatocellular carcinoma (HCC)-specific anticancer activity was also observed. In further anti-inflammatory research, thienopyridine derivative 1a showed potent inhibition of nitric oxide (NO) production. So a series of thienopyridine analogues of 1a were synthesized and evaluated for anti-inflammatory activities. The structure–activity relationships (SARs) revealed that the most potent analogues 1f and 1o were identified as potent inhibitors of NO production with IC50 values of 3.30 and 3.24 μM, respectively. These results suggest that these 6-aryl-3-amino-thieno[2,3-b]pyridine derivatives might potentially constitute a novel class of anti-inflammatory agents, which require further studies. 相似文献
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Jae Yeon Kim Hyo Jin Lim Da Yeon Lee Ji Sun Kim Do Hee Kim Hwa Jin Lee Hee Doo Kim Raok Jeon Jae-Ha Ryu 《Bioorganic & medicinal chemistry letters》2009,19(3):937-940
The overproduction of nitric oxide (NO) and prostaglandin E2 (PGE2) causes neurodegenerative diseases, such as Alzheimer’s disease and Parkinson’s disease. Four lignans, (+)-eudesmin (1), (+)-magnolin (2), (+)-yangambin (3) and a new structure named as epimagnolin B (4) were isolated from Magnolia fargesii (Magnoliaceae) as the inhibitors of NO production in LPS-activated microglia. The most potent compound 4 inhibited the production of NO and PGE2 and the expression of respective enzyme iNOS and COX-2 through the suppression of I-κB-α degradation and nuclear translocation of p65 subunit of NF-κB. 相似文献
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Siwattra Choodej Damrong Sommit Khanitha Pudhom 《Bioorganic & medicinal chemistry letters》2013,23(13):3896-3900
Two new rearranged limonoids, harperforatin (1) and harperfolide (2), and a new chromone, harperamone (3), were isolated from fruits and roots of Harrisonia perforata, together with eight known compounds. Their structures were elucidated on the basis of spectroscopic data. Harperfolide (2) exhibited potent anti-inflammatory activity by suppressing nitric oxide (NO) production from activated macrophages with IC50 value of 6.51 μM. Furthermore, its effect is mediated by reduction of iNOS protein expression, attributable to the inhibitory action of LPS-induced NO production. 相似文献
6.
《Bioorganic & medicinal chemistry letters》2014,24(2):571-575
The regulations of NO and PGE2 productions are research topics of interest in the field of antiinflammatory drug development. In the present study, a series of tricyclic fused coumarin sulfonate derivatives was synthesized and evaluated for their abilities to inhibit NO and PGE2 productions in LPS-induced RAW 264.7 macrophages. Among all the target compounds, compound 1g possessing p-(trifluoromethyl)phenyl and fused cycloheptane moieties showed the highest inhibitory effects on NO and PGE2 productions. Compound 1g not only inhibited COX-2 activity but also reduced expressions of COX-2 and iNOS. Furthermore, ADME profiling showed that compounds 1g, 1j, 1m, and 1n are estimated to be orally bioavailable. 相似文献
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Shin SY Shin MC Shin JS Lee KT Lee YS 《Bioorganic & medicinal chemistry letters》2011,21(15):4520-4523
Sulfuretin is one of major constituents of Rhus verniciflua that exerts anti-inflammatory activities. Some of aurones were synthesized as sulfuretin derivatives and evaluated for their abilities to inhibit NO and PGE2 production in LPS-induced RAW 264.7 cells in order to reveal the relationship. Of the aurones synthesized in the present study, 2h and 2i, which possess C-6 hydroxyl group in A-ring and methoxy substituents in B-ring, more potently inhibited NO and PGE2 production and were less cytotoxic than sulfuretin. 相似文献
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Zunhua Yang Tuyen N. Truong Tuan-Anh N. Pham Jae-Won Lee Sung-Soo Kim Haeil Park 《Bioorganic & medicinal chemistry》2012,20(21):6256-6259
A number of 1,5-diarylimidazole analogs were synthesized and evaluated their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin E2 production. Reactions of 1,5-diarylimidazoles with halogenating reagents (NCS, NBS, NIS) afforded halogenated analogs. Among the analogs tested, compounds Ib, IIa, IIb and IIe exhibited significantly improved inhibitory activities against COX-2-mediated PGE2 production from LPS-induced RAW 264.7 cells compared to those of the parent 1,5-diarylimidazoles. Especially, the analogs Ib (IC50 = 0.55 μM) and IIa (IC50 = 0.58 μM) showed best results. Halogenation on the 1,5-diarylimidazole ring enhanced inhibitory activities against COX-2 catalyzed PGE2 production, however, inhibitory activities were significantly varied by position(s) and species of the substituted halogen(s). 相似文献
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Le Ba Vinh Hyun-Jae Jang Nguyen Viet Phong Kyoungwon Cho Sung Sun Park Jong Seong Kang Young Ho Kim Seo Young Yang 《Bioorganic & medicinal chemistry letters》2019,29(8):965-969
Using various chromatographic techniques, 23 triterpene saponins (1–23) were isolated from an ethanol extract of Stauntonia hexaphylla, including two new compounds (12 and 15). Their chemical structures were established by comprehensive spectroscopic methods such as 1D- and 2D-NMR, and HR-ESI-MS, and chemical reactions. The anti-inflammatory activities of the isolated saponins were determined using the nitric oxide (NO) assay. Compound 13 exhibited the greatest inhibitory effect (IC50?=?0.59?μM). In addition to NO, compound 13 suppressed the secretion of PGE2, IL-1β, and IL-6, but not TNF-α, and inhibited the protein expression of iNOS and COX-2 in LPS-activated RAW264.7 cells. The chemical derivatives of the isolated compounds were studied using structure–activity relationships. The results suggested that compound 13 isolated from S. hexaphylla might be useful for treating inflammation. This is the first comprehensive study of saponins from the leaves of S. hexaphylla based on anti-inflammatory extract screening guidelines. 相似文献
10.
Qing Lu Hai-bo Li Qian-qian Pang Wei-yang Zhang Zhen-zhen Su Da-bo Pan Xin-Sheng Yao Yang Yu 《Bioorganic & medicinal chemistry letters》2019,29(14):1774-1778
Five new phenylpropanoid allopyranosides (1–5), along with five known compounds (6–10) were isolated from the rhizomes of Cimicifuga dahurica. Their structures were established by means of spectroscopic analyses and chemical methods, as well as comparison with literatures. The anti-inflammatory activities of all isolates were evaluated. Compounds 6, 9 and 10 exhibited inhibitory effects on PGE2 production in LPS stimulated RAW 264.7 macrophages with IC50 values of 19.72, 6.33 and 39.90 µM, respectively. 相似文献
11.
Poria cocos Wolf (Polyporaceae) has been used as a medicinal fungus to treat various diseases since ancient times. This study aimed to investigate the anti-inflammatory chemical constituents of the sclerotia of P. cocos. Based on bioassay-guided fractionation using lipopolysaccharide (LPS)-stimulated Raw264.7 cells, chemical investigation of the EtOH extract of the sclerotia of P. cocos resulted in the isolation and identification of eight compounds including six triterpenoids, namely poricoic acid A (1), 3-O-acetyl-16α-hydroxydehydrotrametenolic acid (2), polyporenic acid C (3), 3β-hydroxylanosta-7,9(11),24-trien-21-oic acid (4), trametenolic acid (5), and dehydroeburicoic acid (6), as well as (−)-pinoresinol (7) and protocatechualdehyde (8). The structures of the isolated compounds were determined by spectroscopic analysis, including 1H and 13C NMR spectra, and LC/MS analysis. The anti-inflammatory activities of the isolates were evaluated by estimating their effect on the production of nitric oxide (NO) and prostaglandin E2 (PGE2) in LPS-stimulated Raw264.7 as well as on the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Compounds 1–5 inhibited NO production and iNOS expression in LPS-stimulated Raw264.7 cells. Among them, compound 1 exerted the highest anti-inhibitory activity and reduced PGE2 levels via downregulation of COX-2 protein expression. The findings of this study provide experimental evidence that the sclerotia of P. cocos are a potential source of natural anti-inflammatory agents for use in pharmaceuticals and functional foods. Furthermore, the most active compound 1, seco-lanostane triterpenoid, could be a promising lead compound for the development of novel anti-inflammatory agents. 相似文献
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Seungjun Lee Dong-Cheol Kim Jin-Soo Park Jae-Young Son Jae Hak Sohn Ling Liu Yongsheng Che Hyuncheol Oh 《Bioorganic & medicinal chemistry letters》2017,27(15):3516-3520
Chemical investigation of the EtOAc extract of a marine-derived fungal isolate Penicillium sp. SF-5292 yielded a new polyketide-type metabolite, penicillospirone (1). The structure of 1 was determined by analysis of spectroscopic data such as 1D and 2D NMR spectra and MS data, and the final structure including absolute configuration was unambiguously established by single-crystal X-ray diffraction analysis. In the evaluation of its anti-inflammatory effects, 1 inhibited the overproduction of nitric oxide (NO) and prostaglandin E2 (PGE2) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages and BV2 microglia, and these inhibitory effects were correlated with the suppressive effect of 1 against overexpressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Furthermore, 1 also inhibited the production of pro-inflammatory cytokines such as tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6, and IL-12. Overall, the anti-inflammatory effect of 1 was suggested to be mediated through the negative regulation of NF-κB pathway. 相似文献
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Orapun Yodsaoue Chatchanok Karalai Chanita Ponglimanont Supinya Tewtrakul Suchada Chantrapromma 《Phytochemistry》2010,71(14-15):1756-1764
Anti-inflammatory assay-guided separation of extracts from the roots of Caesalpinia mimosoides Lamk. led to isolation of seven compounds: four diterpenes (1–4), a dimer (9), and two dibenzo[b,d]furans (10, 11) together with eleven known compounds. Their structures were elucidated by 1D- and 2D-NMR techniques as well as UV, IR, mass spectral data and comparison with literature values. The anti-inflammatory activities of all compounds were evaluated for inhibitory activities against lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264.7 cell lines. Compounds 4, 6, 8, and 12–14 were also tested for the inhibitory effect on LPS-induced tumor necrosis factor-alpha (TNF-α) release in RAW264.7 cells. The results indicated that 4 possessed potent inhibitory activity for both tests with IC50 values of 3.0 and 6.5 μM, respectively. 相似文献
16.
Chih-Hua Tseng Chih-Mei Cheng Cherng-Chyi Tzeng Shin-I Peng Chiao-Li Yang Yeh-Long Chen 《Bioorganic & medicinal chemistry》2013,21(2):523-531
β-Lapachone (β-LAPA), a natural product from the lapacho tree in South America, is a potential chemotherapeutic agent that exhibit a wide variety of pharmacological effects such as anti-virus, anti-parasitic, anti-cancer, and anti-inflammatory activities. In order to discover novel anti-inflammatory agents, we have synthesized a series of β-LAPA derivatives for evaluation. Among them, 4-(4-methoxyphenoxy)naphthalene-1,2-dione (6b) was found to be able to inhibit NO and TNF-α released in LPS-induced Raw 264.7 cells. Inhibition of iNOS and COX-2 was also observed in compound 6b treated cells. Mechanism studies indicated that 6b exhibited anti-inflammatory properties by suppressing the release of pro-inflammatory factors through down-regulating NF-κB activation. In addition, it suppressed NF-κB translocation by inhibiting the phosphorylation of p38 kinase. Our results also indicate that the inhibitory effect of 6b on LPS-stimulated inflammatory mediator production in Raw 264.7 cell is associated with the suppression of the NF-κB and MAPK signaling pathways. A low cytotoxicity (IC50 = 31.70 μM) and the potent anti-inflammatory activity exhibited by compound 6b make this compound a potential lead for developing new anti-inflammatory agents. Further structural optimization of compound 6b is on-going. 相似文献
17.
Jongmin Ahn Hee-Sung Chae Young-Won Chin Jinwoong Kim 《Bioorganic & medicinal chemistry letters》2017,27(12):2807-2811
New alkaloids, houttuynamide B and C (1, 2) and houttuycorine (14), were isolated from the aerial parts of Houttuynia cordata Thunb. in addition to eighteen known alkaloids. Their structures were elucidated through extensive spectroscopic analysis. All the isolates were tested for their inhibitory activity against NO production in RAW 264.7 cells stimulated by LPS. Of the tested compounds, compound 15 showed the most potent anti-inflammatory activity with an IC50 value of 8.7 μM. 相似文献
18.
Haiyan Che Byung Kyu Park Hyun Lim Hyun Pyo Kim Hyeun Wook Chang Jin-Hyun Jeong Haeil Park 《Bioorganic & medicinal chemistry letters》2009,19(1):74-76
In order to establish anti-inflammatory potential of biflavonoids, 17 biflavone derivatives having a 6-O-7″ linkage were synthesized and their effects on cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) were evaluated. The basic molecule (6-O-7″ biflavone) potently inhibited COX-2-mediated PGE2 production (IC50: < 2 μM), being less active on iNOS-mediated NO production (IC50: > 50 μM) from lipopolysaccharide-treated RAW 264.7 cells, a mouse macrophage cell line. Generally, the hydroxyl/methoxyl substitution(s) on the basic biflavone (6-O-7″) reduced the inhibitory activity of PGE2 production, while the effects on NO production were varied. It is suggested that the basic biflavone (6-O-7″) may have a potential for new anti-inflammatory agent. 相似文献
19.
Chen Zhong Xin-Hua Liu Jun Chang Jian-Ming Yu Xun Sun 《Bioorganic & medicinal chemistry letters》2013,23(15):4413-4418
Four types of resveratrol dimerized analogues were synthesized and evaluated in vitro on LPS-induced NO production in RAW 264.7 cells. The results showed that several compounds, especially those containing 1,2-diphenyl-2,3-dihydro-1H-indene core (type I), exhibited good inhibitory activities. Among 25 analogues, 12b showed a significant inhibitory activity (49% NO production at 10 μM, IC50 = 3.38 μM). Further study revealed that compound 12b could suppress LPS-induced iNOS expression, NO production, and IL-1β release in a concentration-dependently manner. The mechanism of action (MOA) involved for its anti-inflammatory responses was through signaling pathways of p38 MAPK and JNK1/2, but not ERK1/2. 相似文献
20.
Six new compounds, including a new compound with an unusual 2, 4, 6-cycloheptatrien ketone skeleton (1), two new diphenylpropanoid ethers (2, 3), a new protostane-type triterpenoid (4), two new norsesquiterpene (5a, 5b), and two new natural products (6, 7), together with eleven known compounds (8–18) were isolated from the aqueous extract of Alismatis Rhizoma (AR). Their structures were elucidated by a combination of 1D and 2D NMR (1H and 13C NMR, COSY, HSQC, HMBC, and NOESY), HRESIMS spectroscopic data, experimental and calculated electronic circular dichroism (ECD) spectra. Some of the compounds were evaluated for their inhibitory effects on nitric oxide (NO) production in LPS-induced RAW 264.7 cells. Two protostane-type triterpenoids, compounds 4 and 17, exhibited potent inhibitory activities with the IC50 values of 39.3 and 63.9 μM compared with indomethacin. In the meanwhile, their anti-inflammatory effects were also confirmed by acute inflammation model induced by CuSO4 in zebrafish. 相似文献