A Hydroxylated Lupeol‐Based Triterpenoid Ester Isolated from the Scurrula parasitica Parasitic on Nerium indicum. Issue 5 (May 2015)

• Record Type: Journal Article
• Authors: Liu, Quan‐Yu; Wang, Fei; Zhang, Lei; Xie, Jie‐Ming; Li, Peng; Zhang, Yong‐Hong
• Is Part Of: Helvetica chimica acta. Volume 98:Issue 5(2015:May)
• Page Start: 627
• Page End: 632
• Publication Date: 2015-05
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201400254
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>(3<italic>β</italic>, 7<italic>β</italic>)‐7‐Hydroxylup‐20(29)‐en‐3‐yl hexadecanoate (<bold>1</bold>), a new lupeol‐based triterpenoid ester, along with sixteen known compounds, 7<italic>β</italic>, 15<italic>α</italic>‐dihydroxylup‐20(29)‐ene‐3<italic>β</italic>‐<italic>O</italic>‐palmitate (<bold>2</bold>), lupeol palmitate (<bold>3</bold>), lupeol (<bold>4</bold>), 3‐oxolup‐20(29)‐ene (<bold>5</bold>), ursolic acid (<bold>6</bold>), cycloeucalenol (<bold>7</bold>), stigmasterol (<bold>8</bold>), <italic>β</italic>‐sitosterol (<bold>9</bold>), <italic>β</italic>‐daucosterol (<bold>10</bold>), quercetin (<bold>11</bold>), quercetin 3‐<italic>O</italic>‐<italic>α</italic>‐<sc>L</sc>‐arabinoside (<bold>12</bold>), quercetin 3‐<italic>O</italic>‐<italic>α</italic>‐<sc>L</sc>‐rhamnoside (<bold>13</bold>), catechin (<bold>14</bold>), gitoxigenin 3‐<italic>O</italic>‐<italic>α</italic>‐<sc>L</sc>‐rhamnoside (<bold>15</bold>), gitoxigenin 3‐<italic>O</italic>‐<italic>α</italic>‐<sc>D</sc>‐glucoside (<bold>16</bold>), and digitoxigenin 3‐<italic>O</italic>‐<italic>α</italic>‐<sc>L</sc>‐rhamnoside (<bold>17</bold>), was isolated from the leaves of the Southern China mistletoe, <italic>Scurrula parasitica</italic><sc>Linn</sc> parasitic on <italic>Nerium indicum</italic><sc>Mill</sc>. Their structures were elucidated by spectroscopic analyses, including 2D‐NMR techniques. Cytotoxic activities of compounds <bold>1</bold>–<bold>7</bold> and <bold>11</bold>–<bold>17</bold> were evaluated against three cancer cell lines, PANC‐1, HL‐60, and SGC‐7901, revealing that compounds <bold>4, 6, 11</bold>, and <bold>15</bold>–<bold>17</bold> exhibited effective cytotoxicities, while others were inactive. A structureactivity relationship study of compounds <bold>1</bold>–<bold>5</bold> indicated that the 3‐OH group in lupeol‐based triterpenoids is essential for antitumor activity.</p> </abstract>