Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E2 Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Journal of Natural Products
2019.0

Abstract

A new flavone glucoside, acacetin-7-<i>O</i>-(3″-<i>O</i>-acetyl-6″-<i>O</i>-malonyl)-β-d-glucopyranoside (<b>1</b>), two new phenolic glucosides, (3<i>R</i>,7<i>R</i>)-tuberonic acid-12-<i>O</i>-[6'-<i>O</i>-(<i>E</i>)-feruloyl]-β-d-glucopyranoside (<b>14</b>) and salicylic acid-2-<i>O</i>-[6'-<i>O</i>-(<i>E</i>)-feruloyl]-β-d-glucopyranoside (<b>15</b>), and two new phenylpropanoid glucosides, chavicol-1-<i>O</i>-(6'-<i>O</i>-methylmalonyl)-β-d-glucopyranoside (<b>17</b>) and chavicol-1-<i>O</i>-(6'-<i>O</i>-acetyl)-β-d-glucopyranoside(<b>18</b>), as well as 26 known compounds, <b>2</b>-<b>13</b>, <b>16</b>, and <b>19</b>-<b>31</b>, were isolated from the aerial parts of <i>Agastache rugose</i>. The structures of the new compounds were established by spectroscopic/spectrometric methods such as HRESIMS, NMR, and ECD. The anti-inflammatory effect of the isolated compounds was evaluated by measuring their inhibitory activities on prostaglandin E<sub>2</sub> (PGE<sub>2</sub>) in lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. New compounds <b>1</b>, <b>15</b>, <b>17</b>, and <b>18</b> inhibited LPS-induced PGE<sub>2</sub> production with IC<sub>50</sub> values of 16.8 ± 0.8, 33.9 ± 4.8, 14.3 ± 2.1, and 48.8 ± 4.4 μM, respectively. Compounds <b>5</b>, <b>7</b>, <b>9</b>-<b>11</b>, <b>13</b>, <b>19</b>, <b>20</b>, <b>22</b>, and <b>27</b>-<b>30</b> showed potent inhibitory activities with IC<sub>50</sub> values of 1.7-8.4 μM.

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