Inhibition of prostaglandin E2 production by synthetic Wogonin analogs

Gurung, Santosh K.; Kim, Hyun Pyo; Park, Haeil

doi:10.1007/s12272-009-2101-5

Cited by 17 publications

(12 citation statements)

References 10 publications

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“…The structures of the obtained compounds were confirmed by NMR spectra analysis. Spectroscopic data of the products 6 – 12 are in agreement with literature data. ,,− …”

Section: Methodssupporting

confidence: 87%

Regioselective ortho-Hydroxylations of Flavonoids by Yeast

Sordon

Anna

Popłoński

et al. 2016

J. Agric. Food Chem.

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Natural flavonoids, such as naringenin, hesperetin, chrysin, apigenin, luteolin, quercetin, epicatechin, and biochanin A, were subjected to microbiological transformations by Rhodotorula glutinis. Yeast was able to regioselectively C-8 hydroxylate hesperetin, luteolin, and chrysin. Naringenin was transformed to 8- and 6-hydroxyderivatives. Quercetin, epicatechin, and biochanin A did not undergo biotransformation. A metabolic pathway for the degradation of chrysin has been elucidated. The metabolism of chrysin proceeds via an initial C-8 hydroxylation to norwogonin, followed by A-ring cleavage to 4-hydroxy-6-phenyl-2H-pyran-2-one.

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“…The structures of the obtained compounds were confirmed by NMR spectra analysis. Spectroscopic data of the products 6 – 12 are in agreement with literature data. ,,− …”

Section: Methodssupporting

confidence: 87%

Regioselective ortho-Hydroxylations of Flavonoids by Yeast

Sordon

Anna

Popłoński

et al. 2016

J. Agric. Food Chem.

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“…Other than the OH groups in meta-position to each other (at C(5) and C(7)) and the absence of a functional group at C (6), no other structural features could be identified as being essential for the activities of these four compounds. Interestingly, our observations are similar to those reported by other groups; i.e., wogonin analogs without MeO group at C(8) are unable to inhibit prostaglandin E 2 production [25], and alkylation at C(5) and C(7) of wogonin (2) results in analogs with reduced inhibitory activity [26]. Compound 28 only differs from 26 by lacking a MeO group at C(3').…”

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confidence: 90%

Activities of Wogonin Analogs and Other Flavones against Flavobacterium columnare

Tan

Schrader

Khan

et al. 2015

Chemistry & Biodiversity

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In our on-going pursuit to discover natural products and natural product-based compounds to control the bacterial species Flavobacterium columnare, which causes columnaris disease in channel catfish (Ictalurus punctatus), we synthesized flavone and chalcone analogs, and evaluated these compounds, along with flavonoids from natural sources, for their antibacterial activities against two isolates of F. columnare (ALM-00-173 and BioMed) using a rapid bioassay. The flavonoids chrysin (1a), 5,7-dihydroxy-4'-methoxyflavone (11), isorhamnetin (26), luteolin (27), and biochanin A (29), and chalcone derivative 8b showed strong antibacterial activities against F. columnare ALM-00-173 based on minimum inhibition concentration (MIC) results. Flavonoids 1a, 8, 11, 13 (5,4'-dihydroxy-7-methoxyflavone), 26, and 29 exhibited strong antibacterial activities against F. columnare BioMed based upon MIC results. The 24-h 50% inhibition concentration (IC50 ) results revealed that 27 and 29 were the most active compounds against F. columnare ALM-00-173 (IC50 of 7.5 and 8.5 mg/l, resp.), while 26 and 29 were the most toxic compound against F. columnare BioMed (IC50 of 9.2 and 3.5 mg/l, resp.). These IC50 results were lower than those obtained for wogonin against F. columnare ALM-00-173 and F. columnare BioMed (28.4 and 5.4 mg/l, resp.). However, based on MIC results, none of the compounds evaluated in this study were as active as wogonin (MIC 0.3 mg/l for each F. columnare isolate). Further modification of the wogonin structure to enhance antibacterial is of interest.

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“…The concentration of PGE2 in lung is higher than in other organs and plasma under normal physiological condition and is further released in lung in response to proinflammatory insults when stimulated by LPS, TGF‐β, or PAR‐2 (Vancheri et al, ). In macrophages and microglial cells, LPS‐induced PGE2 expression is inhibited by wogonin via COX‐2 (Gurung et al, ; Yeh et al, ). Based on our results and evidences gathered, we are confident in suggesting that the prevention of LPS‐induced ALI by wogonin was due to inhibition of iNOS and COX‐2 expression via NF‐κB pathway.…”

Section: Discussionmentioning

confidence: 99%

Protective effect of wogonin on endotoxin‐induced acute lung injury via reduction of p38 MAPK and JNK phosphorylation

Wei

Sun

Yang

et al. 2016

Environmental Toxicology

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Acute lung injury (ALI) is a serious inflammatory disorder which remains the primary cause of incidence and mortality in patients with acute pulmonary inflammation. However, there is still no effective medical strategy available clinically for the improvement of ALI. Wogonin, isolated from roots of Scutellaria baicalensis Georgi, is a common medicinal herb which presents biological and pharmacological effects, including antioxidation, anti-inflammation, and anticancer. Preadministration of wogonin inhibited not only lung edema but also protein leakage into the alveolar space in murine model of lipopolysaccharide (LPS)-induced ALI. Moreover, wogonin not only reduced the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 but also inhibited the phosphorylation of mitogen-activated protein kinase (MAPK) induced by LPS. We further found wogonin inhibited the phosphorylation of p38 MAPK and JNK at a concentration lower than ERK. In addition, inhibition of lung edema, protein leakage, expression of iNOS and COX-2, and phosphorylation of p38 MAPK and JNK were all observed in a parallel concentration-dependent manner. These results suggest that wogonin possesses potential protective effect against LPS-induced ALI via downregulation of iNOS and COX-2 expression by blocking phosphorylation of p38 MAPK and JNK. © 2016 Wiley Periodicals, Inc. Environ Toxicol 32: 397-403, 2017.

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Inhibition of prostaglandin E2 production by synthetic Wogonin analogs

Cited by 17 publications

References 10 publications

Regioselective ortho-Hydroxylations of Flavonoids by Yeast

Regioselective ortho-Hydroxylations of Flavonoids by Yeast

Activities of Wogonin Analogs and Other Flavones against Flavobacterium columnare

Protective effect of wogonin on endotoxin‐induced acute lung injury via reduction of p38 MAPK and JNK phosphorylation

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