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Benzophenone and Benzoylphloroglucinol Derivatives from Hypericum sampsonii with Anti-Inflammatory Mechanism of Otogirinin A.


ABSTRACT: Three new compounds, 4-geranyloxy-2-hydroxy-6-isoprenyloxybenzophenone (1), hypericumone A (2) and hypericumone B (3), were obtained from the aerial parts of Hypericum sampsonii, along with six known compounds (4-9). The structures of these compounds were determined through spectroscopic and MS analyses. Hypericumone A (2), sampsonione J (8) and otogirinin A (9) exhibited potent inhibition (IC50 values ? 40.32 ?M) against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation. Otogirinin A (9) possessed the highest inhibitory effect on NO production with IC50 value of 32.87 ± 1.60 ?M. The well-known proinflammatory cytokine, tumor necrosis factor-alpha (TNF-?) was also inhibited by otogirinin A (9). Western blot results demonstrated that otogirinin A (9) downregulated the high expression of inducible nitric oxide synthase (iNOS). Further investigations on the mechanism showed that otogirinin A (9) blocked the phosphorylation of MAPK/JNK and I?B?, whereas it showed no effect on the phosphorylation of MAPKs/ERK and p38. In addition, otogirinin A (9) stimulated anti-inflammatory M2 phenotype by elevating the expression of arginase 1 and Krüppel-like factor 4 (KLF4). The above results suggested that otogirinin A (9) could be considered as potential compound for further development of NO production-targeted anti-inflammatory agent.

SUBMITTER: Huang CY 

PROVIDER: S-EPMC7582647 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Benzophenone and Benzoylphloroglucinol Derivatives from <i>Hypericum sampsonii</i> with Anti-Inflammatory Mechanism of Otogirinin A.

Huang Chun-Yi CY   Chang Tzu-Cheng TC   Wu Yu-Jing YJ   Chen Yun Y   Chen Jih-Jung JJ  

Molecules (Basel, Switzerland) 20200928 19


Three new compounds, 4-geranyloxy-2-hydroxy-6-isoprenyloxybenzophenone (<b>1</b>), hypericumone A (<b>2</b>) and hypericumone B (<b>3</b>), were obtained from the aerial parts of <i>Hypericum sampsonii</i>, along with six known compounds (<b>4</b>-<b>9</b>). The structures of these compounds were determined through spectroscopic and MS analyses. Hypericumone A (<b>2</b>), sampsonione J (<b>8</b>) and otogirinin A (<b>9</b>) exhibited potent inhibition (IC<sub>50</sub> values ≤ 40.32 μM) against  ...[more]

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