Constituents from leaves of <i>Macaranga hemsleyana</i>.

Abstract

<h4>Objective</h4>To study constituents of the leaves of <i>Macaranga hemsleyana</i>, and evaluate their inhibitory effects against NOD-like receptor thermal protein domain associated protein 3 (NLRP3) inflammasome activation, and antiproliferative activity.<h4>Methods</h4>The constituents were isolated and purified by column chromatography on MCI gel CHP20P/P120, silica gel, Sephadex LH-20, and HPLC. The structures of compounds were determined by 1D, 2D NMR, and HR-ESI-MS data. The inhibitory effect of compounds on inflammasome activation was determined by lactate dehydrogenase (LDH) procedure. The antiproliferative activity was evaluated using MTT assay.<h4>Results</h4>The study led to the isolation of 23 compounds, including one new compound, identified as (2<i>Z</i>)-3-[4-(<i>β</i>-<i>D</i>-glucopyranosyloxy)-2'-hydroxy-5'-methoxyphenyl]-2-propenoic acid (<b>1</b>), together with 22 known compounds recognized as 1,4-dihydro-4-oxo-3-pyridinecarbonitrile (<b>2</b>), methyl 4-methoxynicotinate (<b>3</b>), 4-methoxynicotinonitrile (<b>4</b>), 1-(3-<i>O</i>-<i>β</i>-<i>D</i>-glucopyranosyl-4,5-dihydroxyphenyl)-ethanone (<b>5</b>), neoisoastilbin (<b>6</b>), isoastilbin (<b>7</b>), aromadendrin <b>(8</b>), neoastilbin (<b>9</b>), astilbin (<b>10</b>), quercitrin (<b>11</b>), neoschaftoside (<b>12</b>), apigenin 6,8-bis-<i>C</i>-<i>α</i>-<i>L</i>-arabinoside (<b>13</b>), vitexin (<b>14</b>), bergenin (<b>15</b>), scopoletin (<b>16</b>), glucopyranoside salicyl (<b>17</b>), koaburside (<b>18</b>), benzyl <i>β</i>-<i>D</i>-glucoside (<b>19</b>), icariside B5 (<b>20</b>), roseoside (<b>21</b>), loliolide (<b>22</b>), and adenosine (<b>23</b>). The tested compounds did not show LDH inhibition nor antiproliferative activity.<h4>Conclusion</h4>Compound <b>1</b> was a new glycoside. Compounds <b>2</b> and <b>3</b> were obtained for the first time from natural source. The 22 known compounds constituted of alkaloids (<b>2</b>-<b>4</b>, <b>23</b>), phenolics (<b>5</b>, <b>15</b>, <b>17</b>, <b>18</b>), flavonoids (<b>6</b>-<b>14</b>), coumarin (<b>16</b>), benzyl glycoside (<b>19</b>), and norsesquiterpenes (<b>20</b>-<b>22</b>). All the compounds, <b>1</b>-<b>23</b>, were revealed from <i>M. hemsleyana</i> for the first time. This is the initial uncovering of molecules <b>1</b>-<b>10</b>, <b>12</b>, <b>13</b>, <b>17</b>-<b>19</b>, and <b>23</b> from the genus <i>Macaranga</i>. The isolated compounds, <b>11</b>, <b>14</b>-<b>16</b>, and <b>20</b>-<b>22</b> established taxonomic classification of <i>M. hemsleyana</i> in Euphorbiaceae family. Flavonoids were outstanding as chemosystematic markers of <i>Macaranga</i> genus.