Chantriolides F–P, Highly Oxidized Withanolides with Hepatoprotective Activity from <i>Tacca chantrieri</i>
Eleven highly oxidized withanolides, chantriolides F–P (<b>1</b>–<b>11</b>), together with six known analogues (<b>12</b>–<b>17</b>), were isolated from the rhizomes of <i>Tacca chantrieri</i>. Their structures were established on the basis...
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MDPI AG
2022-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/23/8197 |
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| author | Yue Yang Fei Zhou Min Wang Mukhammadrizo Turanazarov Xiao-Rong Wang Changqiang Ke Sheng Yao Ligen Lin Chunping Tang Yang Ye |
| author_facet | Yue Yang Fei Zhou Min Wang Mukhammadrizo Turanazarov Xiao-Rong Wang Changqiang Ke Sheng Yao Ligen Lin Chunping Tang Yang Ye |
| author_sort | Yue Yang |
| collection | DOAJ |
| description | Eleven highly oxidized withanolides, chantriolides F–P (<b>1</b>–<b>11</b>), together with six known analogues (<b>12</b>–<b>17</b>), were isolated from the rhizomes of <i>Tacca chantrieri</i>. Their structures were established on the basis of comprehensive spectroscopic data analysis and comparison with published NMR data, and their absolute configurations were further confirmed by experimental ECD data and single crystal X-ray diffraction analysis. The structures of compounds <b>5</b>–<b>8</b> contained a chlorine atom substituted at C-3. Compounds <b>1</b> and <b>12</b> are a pair of epimers isomerized at C-24 and C-25, while compounds <b>9</b> and <b>16</b> are isomerized at C-1, C-7, C-24, and C-25. Next, the hepatoprotective effect of all the isolates was evaluated on <i>tert</i>-butyl hydroperoxide (<i>t</i>-BHP)-injured AML12 hepatocytes. Compounds <b>5</b>–<b>11</b> and <b>16</b> significantly enhanced cell viability. Compound <b>8</b> decreased reactive oxygen species accumulation and increased glutathione level in <i>t</i>-BHP injured AML12 hepatocytes through promoting nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2). |
| first_indexed | 2024-03-09T17:39:34Z |
| format | Article |
| id | doaj.art-55f742b34b2c4680b972e23ac3b2e761 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T17:39:34Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-55f742b34b2c4680b972e23ac3b2e7612023-11-24T11:38:17ZengMDPI AGMolecules1420-30492022-11-012723819710.3390/molecules27238197Chantriolides F–P, Highly Oxidized Withanolides with Hepatoprotective Activity from <i>Tacca chantrieri</i>Yue Yang0Fei Zhou1Min Wang2Mukhammadrizo Turanazarov3Xiao-Rong Wang4Changqiang Ke5Sheng Yao6Ligen Lin7Chunping Tang8Yang Ye9State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, ChinaState Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Avenida da Universidade, Taipa, Macau 999078, ChinaNatural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, ChinaNatural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, ChinaXishuangbanna Research Institute of Nationality Medicine, Xishuangbanna Hospital of Traditional Dai Medicine, No. 8 Zhuangdong Western Road of Xishuangbanna Tourism and Resort Zone, Xishuangbanna 666100, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, ChinaState Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Avenida da Universidade, Taipa, Macau 999078, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, ChinaState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, ChinaEleven highly oxidized withanolides, chantriolides F–P (<b>1</b>–<b>11</b>), together with six known analogues (<b>12</b>–<b>17</b>), were isolated from the rhizomes of <i>Tacca chantrieri</i>. Their structures were established on the basis of comprehensive spectroscopic data analysis and comparison with published NMR data, and their absolute configurations were further confirmed by experimental ECD data and single crystal X-ray diffraction analysis. The structures of compounds <b>5</b>–<b>8</b> contained a chlorine atom substituted at C-3. Compounds <b>1</b> and <b>12</b> are a pair of epimers isomerized at C-24 and C-25, while compounds <b>9</b> and <b>16</b> are isomerized at C-1, C-7, C-24, and C-25. Next, the hepatoprotective effect of all the isolates was evaluated on <i>tert</i>-butyl hydroperoxide (<i>t</i>-BHP)-injured AML12 hepatocytes. Compounds <b>5</b>–<b>11</b> and <b>16</b> significantly enhanced cell viability. Compound <b>8</b> decreased reactive oxygen species accumulation and increased glutathione level in <i>t</i>-BHP injured AML12 hepatocytes through promoting nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2).https://www.mdpi.com/1420-3049/27/23/8197<i>Tacca chantrieri</i>structural elucidationwithanolideschantriolides F–Phepatoprotective effect |
| spellingShingle | Yue Yang Fei Zhou Min Wang Mukhammadrizo Turanazarov Xiao-Rong Wang Changqiang Ke Sheng Yao Ligen Lin Chunping Tang Yang Ye Chantriolides F–P, Highly Oxidized Withanolides with Hepatoprotective Activity from <i>Tacca chantrieri</i> Molecules <i>Tacca chantrieri</i> structural elucidation withanolides chantriolides F–P hepatoprotective effect |
| title | Chantriolides F–P, Highly Oxidized Withanolides with Hepatoprotective Activity from <i>Tacca chantrieri</i> |
| title_full | Chantriolides F–P, Highly Oxidized Withanolides with Hepatoprotective Activity from <i>Tacca chantrieri</i> |
| title_fullStr | Chantriolides F–P, Highly Oxidized Withanolides with Hepatoprotective Activity from <i>Tacca chantrieri</i> |
| title_full_unstemmed | Chantriolides F–P, Highly Oxidized Withanolides with Hepatoprotective Activity from <i>Tacca chantrieri</i> |
| title_short | Chantriolides F–P, Highly Oxidized Withanolides with Hepatoprotective Activity from <i>Tacca chantrieri</i> |
| title_sort | chantriolides f p highly oxidized withanolides with hepatoprotective activity from i tacca chantrieri i |
| topic | <i>Tacca chantrieri</i> structural elucidation withanolides chantriolides F–P hepatoprotective effect |
| url | https://www.mdpi.com/1420-3049/27/23/8197 |
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