Eudesmane and Eremophilane Sesquiterpenes from the Fruits of <i>Alpinia oxyphylla</i> with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells
<i>Alpinia oxyphylla</i> Miquel (Zingiberaceae) has been reported to show antioxidant, anti-inflammatory, and neuroprotective effects. In this study, two new eudesmane sesquiterpenes, 7α-hydroperoxy eudesma-3,11-diene-2-one (<b>1</b>) and 7β-hydroperoxy eudesma-3,11-diene-2-o...
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2021-03-01
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| author | Punam Thapa Yoo Jin Lee Tiep Tien Nguyen Donglan Piao Hwaryeong Lee Sujin Han Yeon Jin Lee Ah-Reum Han Hyukjae Choi Jee-Heon Jeong Joo-Won Nam Eun Kyoung Seo |
| author_facet | Punam Thapa Yoo Jin Lee Tiep Tien Nguyen Donglan Piao Hwaryeong Lee Sujin Han Yeon Jin Lee Ah-Reum Han Hyukjae Choi Jee-Heon Jeong Joo-Won Nam Eun Kyoung Seo |
| author_sort | Punam Thapa |
| collection | DOAJ |
| description | <i>Alpinia oxyphylla</i> Miquel (Zingiberaceae) has been reported to show antioxidant, anti-inflammatory, and neuroprotective effects. In this study, two new eudesmane sesquiterpenes, 7α-hydroperoxy eudesma-3,11-diene-2-one (<b>1</b>) and 7β-hydroperoxy eudesma-3,11-diene-2-one (<b>2</b>), and a new eremophilane sesquiterpene, 3α-hydroxynootkatone (<b>3</b>), were isolated from the MeOH extract of dried fruits of <i>A. oxyphylla</i> along with eleven known sesquiterpenes (<b>4</b>–<b>14</b>). The structures were elucidated by the analysis of 1D/2D NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and optical rotation data. Compounds (<b>1</b>–<b>3</b>, <b>5</b>–<b>14</b>) were evaluated for their protective effects against <i>tert</i>-butyl hydroperoxide (tBHP)-induced oxidative stress in adipose-derived mesenchymal stem cells (ADMSCs). As a result, treatment with isolated compounds, especially compounds <b>11</b> and <b>12,</b> effectively reverted the damage of tBHP on ADMSCs in a dose-dependent manner. In particular, <b>11</b> and <b>12</b> at 50 µM improved the viability of tBHP-toxified ADMSCs by 1.69 ± 0.05-fold and 1.61 ± 0.03-fold, respectively. |
| first_indexed | 2024-03-10T13:02:52Z |
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| id | doaj.art-5cd2068d8a4742aa968b3fba9ec8ad25 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T13:02:52Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5cd2068d8a4742aa968b3fba9ec8ad252023-11-21T11:24:08ZengMDPI AGMolecules1420-30492021-03-01266176210.3390/molecules26061762Eudesmane and Eremophilane Sesquiterpenes from the Fruits of <i>Alpinia oxyphylla</i> with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem CellsPunam Thapa0Yoo Jin Lee1Tiep Tien Nguyen2Donglan Piao3Hwaryeong Lee4Sujin Han5Yeon Jin Lee6Ah-Reum Han7Hyukjae Choi8Jee-Heon Jeong9Joo-Won Nam10Eun Kyoung Seo11College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongsangbukdo 38541, KoreaCollege of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, KoreaCollege of Pharmacy, Yeungnam University, Gyeongsan, Gyeongsangbukdo 38541, KoreaCollege of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, KoreaCollege of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, KoreaCollege of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, KoreaCollege of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, KoreaAdvanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeollabuk-do, Jeongeup-si 56212, KoreaCollege of Pharmacy, Yeungnam University, Gyeongsan, Gyeongsangbukdo 38541, KoreaCollege of Pharmacy, Yeungnam University, Gyeongsan, Gyeongsangbukdo 38541, KoreaCollege of Pharmacy, Yeungnam University, Gyeongsan, Gyeongsangbukdo 38541, KoreaCollege of Pharmacy, Graduate School of Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, Korea<i>Alpinia oxyphylla</i> Miquel (Zingiberaceae) has been reported to show antioxidant, anti-inflammatory, and neuroprotective effects. In this study, two new eudesmane sesquiterpenes, 7α-hydroperoxy eudesma-3,11-diene-2-one (<b>1</b>) and 7β-hydroperoxy eudesma-3,11-diene-2-one (<b>2</b>), and a new eremophilane sesquiterpene, 3α-hydroxynootkatone (<b>3</b>), were isolated from the MeOH extract of dried fruits of <i>A. oxyphylla</i> along with eleven known sesquiterpenes (<b>4</b>–<b>14</b>). The structures were elucidated by the analysis of 1D/2D NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and optical rotation data. Compounds (<b>1</b>–<b>3</b>, <b>5</b>–<b>14</b>) were evaluated for their protective effects against <i>tert</i>-butyl hydroperoxide (tBHP)-induced oxidative stress in adipose-derived mesenchymal stem cells (ADMSCs). As a result, treatment with isolated compounds, especially compounds <b>11</b> and <b>12,</b> effectively reverted the damage of tBHP on ADMSCs in a dose-dependent manner. In particular, <b>11</b> and <b>12</b> at 50 µM improved the viability of tBHP-toxified ADMSCs by 1.69 ± 0.05-fold and 1.61 ± 0.03-fold, respectively.https://www.mdpi.com/1420-3049/26/6/1762<i>Alpinia oxyphylla</i>eudesmane sesquiterpeneeremophilane sesquiterpeneadipose-derived mesenchymal stem cellantioxidantoxidative stress |
| spellingShingle | Punam Thapa Yoo Jin Lee Tiep Tien Nguyen Donglan Piao Hwaryeong Lee Sujin Han Yeon Jin Lee Ah-Reum Han Hyukjae Choi Jee-Heon Jeong Joo-Won Nam Eun Kyoung Seo Eudesmane and Eremophilane Sesquiterpenes from the Fruits of <i>Alpinia oxyphylla</i> with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells Molecules <i>Alpinia oxyphylla</i> eudesmane sesquiterpene eremophilane sesquiterpene adipose-derived mesenchymal stem cell antioxidant oxidative stress |
| title | Eudesmane and Eremophilane Sesquiterpenes from the Fruits of <i>Alpinia oxyphylla</i> with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells |
| title_full | Eudesmane and Eremophilane Sesquiterpenes from the Fruits of <i>Alpinia oxyphylla</i> with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells |
| title_fullStr | Eudesmane and Eremophilane Sesquiterpenes from the Fruits of <i>Alpinia oxyphylla</i> with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells |
| title_full_unstemmed | Eudesmane and Eremophilane Sesquiterpenes from the Fruits of <i>Alpinia oxyphylla</i> with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells |
| title_short | Eudesmane and Eremophilane Sesquiterpenes from the Fruits of <i>Alpinia oxyphylla</i> with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells |
| title_sort | eudesmane and eremophilane sesquiterpenes from the fruits of i alpinia oxyphylla i with protective effects against oxidative stress in adipose derived mesenchymal stem cells |
| topic | <i>Alpinia oxyphylla</i> eudesmane sesquiterpene eremophilane sesquiterpene adipose-derived mesenchymal stem cell antioxidant oxidative stress |
| url | https://www.mdpi.com/1420-3049/26/6/1762 |
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