TY - JOUR
T1 - Eudesmane and eremophilane sesquiterpenes from the fruits of alpinia oxyphylla with protective effects against oxidative stress in adipose-derived mesenchymal stem cells
AU - Thapa, Punam
AU - Lee, Yoo Jin
AU - Nguyen, Tiep Tien
AU - Piao, Donglan
AU - Lee, Hwaryeong
AU - Han, Sujin
AU - Lee, Yeon Jin
AU - Han, Ah Reum
AU - Choi, Hyukjae
AU - Jeong, Jee Heon
AU - Nam, Joo Won
AU - Seo, Eun Kyoung
N1 - Funding Information:
Acknowledgments: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2019R1C1C1009929).
Publisher Copyright:
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.
PY - 2021/3/2
Y1 - 2021/3/2
N2 - 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.
AB - 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.
KW - Adipose-derived mesenchymal stem cell
KW - Alpinia oxyphylla
KW - Antioxidant
KW - Eremophilane sesquiterpene
KW - Eudesmane sesquiterpene
KW - Oxidative stress
UR - http://www.scopus.com/inward/record.url?scp=85103920385&partnerID=8YFLogxK
U2 - 10.3390/molecules26061762
DO - 10.3390/molecules26061762
M3 - Article
C2 - 33801065
AN - SCOPUS:85103920385
VL - 26
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 6
M1 - 1762
ER -