scholarly journals Three new compounds isolated from the bulbs of Fritillaria pallidiflora Schrenk and their anti-inflammatory activity

2022 ◽  
Vol 47 ◽  
pp. 97-101
Author(s):  
Man-Li Zhang ◽  
Yuan Si ◽  
Guo-Xu Ma ◽  
Hong-Yan Wei ◽  
Xiao-Qin Xu ◽  
...  
2018 ◽  
Vol 68 (3) ◽  
pp. 251-273 ◽  
Author(s):  
Ahmed M. Gouda ◽  
Ahmed H. Abdelazeem ◽  
Ashraf N. Abdalla ◽  
Muhammad Ahmed

Abstract Towards optimization of the pyrrolizine-5-carboxamide scaffold, a novel series of six derivatives (4a-c and 5a-c) was prepared and evaluated for their anti-inflammatory, analgesic and anticancer activities. The (EZ)-7-cyano-6-((4-hydroxybenzylidene)amino)-N-(p-tolyl)-2,3-dihydro-1H-pyrrolizine-5-carboxamide (4b) and (EZ)-6-((4-chlorobenzylidene)-amino)-7-cyano-N-(p-tolyl)-2,3-dihydro-1H-pyrrolizine-5-carboxamide (5b) bearing the electron donating methyl group showed the highest anti-inflammatory activity while (EZ)-6-((4-chlorobenzylidene)amino)-7-cyano-N-phenyl-2,3-dihydro-1H-pyrrolizine-5-carboxamide (5a) was the most active analgesic agent. Cytotoxicity of the new compounds was evaluated against the MCF-7, A2780 and HT29 cancer cell lines using the MTT assay. Compounds 4b and 5b displayed high anticancer activity with IC50 in the range of 0.30–0.92 μmol L−1 against the three cell lines, while compound (EZ)-N-(4-chlorophenyl)-7-cyano-6-((4-hydroxybenzylidene)-amino)-2,3-dihydro-1H-pyrrolizine-5-carboxamide (4c) was the most active against MCF-7 cells (IC50 = 0.08 μmol L−1). Both the anti-inflammatory and anticancer activities of the new compounds were dependent on the type of substituent on the phenyl rings. Substituents with opposite electronic effects on the two phenyl rings are preferable for high cytotoxicity against the MCF-7 and A2780 cells. COX inhibition was suggested as the molecular mechanism of the anti-inflammatory activity of the new compounds while no clear relationship could be observed between COX inhibition and anticancer activity. Compound 5b, the most active against the three cell lines, induced dose-dependent early apoptosis with 0.1–0.2 % necrosis in MCF-7 cells. New compounds showed promising drug-likeness scores while the docking study revealed high binding affinity to COX-2. Taken together, this study highlighted the significant impact of the substituents on the anti-inflammatory and anticancer activity of pyrrolizine-5-carboxamides, which could help in further optimization to discover good leads for the treatment of cancer and inflammation.


2009 ◽  
Vol 74 (2) ◽  
pp. 103-115 ◽  
Author(s):  
Asif Husain ◽  
Mumtaz Alam ◽  
Nadeem Siddiqui

3-Arylidene-5-(4-methylphenyl)-2(3H)-furanones 2a-m were prepared from 3-(4-methyl-benzoyl)propanoic acid 1 and several aromatic aldehydes. Some of the selected furanones were reacted with ammonia gas and benzylamine to give corresponding 3-arylidene-1,3-dihydro-5-(4-methylphenyl)-2H-pyrrol- 2-ones 3a-h and 3-arylidene-1-benzyl-1,3-dihydro-5-(4-methylphenyl)-2H- -pyrrol-2-ones 4a-f, respectively, which were characterized on the basis of IR, 1H-NMR, mass spectral data and elemental analysis results. These compounds were tested for their anti-inflammatory and antibacterial activities. The compounds, which showed significant anti-inflammatory activity, were further screened for their analgesic and ulcerogenic activities. Three new compounds (2e, 2h and 4d), out of twenty-seven showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. The antibacterial activity is expressed as the corresponding MIC values.


2011 ◽  
Vol 76 (8) ◽  
pp. 1057-1067 ◽  
Author(s):  
Sadaf Gilani ◽  
Suroor Khan ◽  
Ozair Alam ◽  
Vijender Singh ◽  
Alka Arora

A series of thiazolidin-4-one (2a-h, 3a-h), azetidin-2-one (4a- h) and 1,3,4-oxadiazole (5a-h) derivatives of isoninicotinic acid hydrazide (INH) were synthesized in order to obtain new compounds with potential anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities. The structures of the new compounds were supported by their IR, 1H-NMR and mass spectral data. All compounds were evaluated for their anti-inflammatory activity by the carrageenan-induced rat paw edema test method. Eleven of the new compounds, out of 32, showed very good anti-inflammatory activity in the carrageenan-induced rat paw edema test, with significant analgesic activity in the tail immersion method together with negligible ulcerogenic action. The compounds, which showed less ulcerogenic action, also showed reduced malondialdehyde content (MDA), which is one of the by-products of lipid peroxidation. The study showed that the compounds inhibited the induction of gastric mucosal lesions and it can be suggested from the results that their protective effects may be related to inhibition of lipid peroxidation in the gastric mucosa.


2009 ◽  
Vol 2009 (7) ◽  
pp. 448-451 ◽  
Author(s):  
Hanan M. Refaat ◽  
Omneya M. Khalil ◽  
Suzan M. Abuel-Maaty

In this study, a novel series of 6-oxopyridazinyl benzazoles and 3, 6-dioxopyridazinyl benzazoles were prepared from the starting compounds, 2-hydrazinobenzimidazole, 2-hydrazinobenzothiazole and 2-hydrazinobenzoxazole by reaction with butyric acid derivatives and cyclic anhydrides respectively. The structures of the new compounds were confirmed by elemental analysis as well as 1H NMR, IR and MS data. Some of the newly prepared compounds were subjected to evaluation for their anti-inflammatory activity using carrageenan induced paw edema at dose 100 mg kg−1 using indomethacin as a reference standard and were found to be bioactive.


2016 ◽  
Vol 71 (1) ◽  
pp. 23-29 ◽  
Author(s):  
Jin-Yu Li ◽  
Hong-Mei Li ◽  
Dan Liu ◽  
Ling-Huan Gao ◽  
Rong-Tao Li

AbstractPhytochemical investigation of the n-BuOH extract of the leaves of processed Epimedium koreanum led to the isolation of three new prenylflavonol glycosides, epimedkoresides A–C (1–3), along with the 15 known ones (4–18). The structures of the three new compounds were established on the basis of chemical and spectroscopic methods as 8-γ-hydroxy-γ,γ-dimethylpropyl-5,7,4′-trihydroxy-flavonol-3- O-β-d-glucopyranosyl(1 → 2)-α-l-rhamnopyranoside (1), 8-γ-hydroxy-γ,γ-dimethylpropyl-5,7,4′-trihydroxy-flavonol-3-O-α-l-rhamnopyranosyl(1 → 2)-α-l-rhamnopyranoside (2), and anhydroicaritin 3-O-α-l-rhamnopyranosyl(1 → 2)- α-l-rhamnopyranosyl-7-O-α-l-rhamnopyranosyl(1 → 2)-β-d-glucopyranoside (3), respectively. Additionally, partial structures were evaluated for their anti-inflammatory activity.


Marine Drugs ◽  
2021 ◽  
Vol 19 (11) ◽  
pp. 585
Author(s):  
Hui Lei ◽  
Xiaoxu Bi ◽  
Xiuping Lin ◽  
Jianglian She ◽  
Xiaowei Luo ◽  
...  

One strain-many compounds (OSMAC) manipulation of the sponge-derived fungus Pestalotiopsis heterocornis XWS03F09 resulted in the production of new secondary metabolites. The chemical study of the fermentation, cultivated on 3% artificial sea salt in the rice media, led to the isolation of twelve compounds, including eight new polyketide derivatives, heterocornols Q–X (1–8), one new ceramide (9), and three known analogues (10–12). The structures and absolute configurations of the new compounds were elucidated by spectroscopic data and calculated ECD analysis. Heterocornols Q (1) and R (2) are novel 6/5/7/5 tetracyclic polyketide derivatives featuring dihydroisobenzofuran and benzo-fused dioxabicyclo [4.2.1] nonane system, which might be derived from the acetyl-CoA by epoxidation, polyene cyclization, and rearrangement to form the core skeleton. Compound 12 showed moderate or weak antimicrobial activities against with MIC values ranging from 25 to 100 μg/mL. Heterocornols T and X (7 and 8) could inhibit the production of LPS-induced NO significantly, comparable to dexamethasone. Further Western blotting analysis showed 7 and 8 markedly suppressed the iNOS protein expression in LPS-induced RAW 264.7 cells in a dose-dependent manner. The result showed that 7 and 8 might serve as potential leads for development of anti-inflammatory activity.


Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 482 ◽  
Author(s):  
Lee ◽  
Kang ◽  
Choi ◽  
Lee ◽  
Lee ◽  
...  

Three new phenazine derivatives (1–3), along with known compounds (4–7) of saphenic acid derivatives, were isolated from a deep-sea sediment-derived yeast-like fungus Cystobasidium larynigs collected from the Indian Ocean. The structures of the new compounds (1–3) were determined by analysis of spectroscopic data, semi-synthesis and comparison of optical rotation values. All the isolated compounds (1–7), except for 2, showed nitric oxide (NO) production inhibitory effect against lipopolysaccharide (LPS)-induced murine macrophage RAW 264.7 cells without cytotoxicity at concentrations up to 30 μg/mL. This is the first report on the yeast-like fungus Cystobasidium laryngis producing phenazines and anti-inflammatory activity of 1–7 including saphenic acid (4).


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