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Eudesmane and Eremophilane Sesquiterpenes from the Fruits of Alpinia oxyphylla with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells.


ABSTRACT: Alpinia oxyphylla 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 (1) and 7β-hydroperoxy eudesma-3,11-diene-2-one (2), and a new eremophilane sesquiterpene, 3α-hydroxynootkatone (3), were isolated from the MeOH extract of dried fruits of A. oxyphylla along with eleven known sesquiterpenes (4-14). The structures were elucidated by the analysis of 1D/2D NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and optical rotation data. Compounds (1-3, 5-14) were evaluated for their protective effects against tert-butyl hydroperoxide (tBHP)-induced oxidative stress in adipose-derived mesenchymal stem cells (ADMSCs). As a result, treatment with isolated compounds, especially compounds 11 and 12, effectively reverted the damage of tBHP on ADMSCs in a dose-dependent manner. In particular, 11 and 12 at 50 µM improved the viability of tBHP-toxified ADMSCs by 1.69 ± 0.05-fold and 1.61 ± 0.03-fold, respectively.

SUBMITTER: Thapa P 

PROVIDER: S-EPMC8004014 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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Eudesmane and Eremophilane Sesquiterpenes from the Fruits of <i>Alpinia oxyphylla</i> with Protective Effects against Oxidative Stress in Adipose-Derived Mesenchymal Stem Cells.

Thapa Punam P   Lee Yoo Jin YJ   Nguyen Tiep Tien TT   Piao Donglan D   Lee Hwaryeong H   Han Sujin S   Lee Yeon Jin YJ   Han Ah-Reum AR   Choi Hyukjae H   Jeong Jee-Heon JH   Nam Joo-Won JW   Seo Eun Kyoung EK  

Molecules (Basel, Switzerland) 20210321 6


<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>). Th  ...[more]

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