Three Pairs of Novel Enantiomeric 8-<i>O</i>-4′ Type Neolignans from <i>Saussurea medusa</i> and Their Anti-inflammatory Effects In Vitro
Three pairs of novel enantiomeric 8-<i>O</i>-4′ type neolignans (<b>1a</b>/<b>1b</b>–<b>3a</b>/<b>3b</b>), together with seven known analogues (<b>4</b>–<b>10</b>), were isolated from the whole plants of <i>Sau...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-11-01
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| Series: | International Journal of Molecular Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-0067/23/22/14062 |
| Summary: | Three pairs of novel enantiomeric 8-<i>O</i>-4′ type neolignans (<b>1a</b>/<b>1b</b>–<b>3a</b>/<b>3b</b>), together with seven known analogues (<b>4</b>–<b>10</b>), were isolated from the whole plants of <i>Saussurea medusa.</i> Their structures were elucidated by extensive spectroscopic data analysis and electric circular dichroism (ECD) calculations after chiral separations. All compounds were obtained from <i>S. medusa</i> for the first time, and compounds <b>1</b>–<b>3</b> and <b>5</b>–<b>10</b> had never been obtained from the genus <i>Saussurea</i> previously. The anti-inflammatory activities of the compounds were evaluated by determining their inhibitory activities on the production of NO and inducible nitric oxide synthase (iNOS) expression in LPS-stimulated RAW 264.7 cells. Compounds (+)-<b>1a</b>, (−)-<b>1b</b> and <b>5</b>–<b>7</b> inhibited NO production and had IC<sub>50</sub> values ranging from 14.3 ± 1.6 to 41.4 ± 3.1 μM. Compound <b>7</b> induced a dose-dependent reduction in the expression of iNOS in LPS-treated RAW 264.7 cells. Molecular docking experiments showed that all active compounds exhibited excellent docking scores (<−7.0 kcal/mol) with iNOS. Therefore, compounds (+)-<b>1a</b>, (−)-<b>1b</b> and <b>5</b>–<b>7</b> isolated from the whole plants of <i>S. medusa</i> may have therapeutic potential in inflammatory diseases. |
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| ISSN: | 1661-6596 1422-0067 |