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Bioassay-Guided Isolation of Triterpenoids as α-Glucosidase Inhibitors from Cirsium setosum

1
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing 100048, China
2
Beijing Key Laboratory of Bioactive Substances and Functional Foods, Beijing Union University, Beijing 100023, China
3
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2019, 24(10), 1844; https://doi.org/10.3390/molecules24101844
Received: 24 April 2019 / Revised: 6 May 2019 / Accepted: 7 May 2019 / Published: 14 May 2019
(This article belongs to the Special Issue Natural Product Isolation, Identification and Biological Activity)
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Abstract

Cirsium setosum (C. setosum) has a potential antihyperglycemic effect, but it is unclear what bioactive components play a key role. According to the α-glucosidase inhibition activity, three new taraxastane-type triterpenoids of 3β-hydroxy-30-hydroperoxy-20-taraxastene (1), 3β-hydroxy-22α-methoxy-20-taraxastene (2), and 30-nor-3β,22α-dihydroxy-20-taraxastene (3), as well as five known taraxastane triterpenoids of 3β,22-dihydroxy-20-taraxastene (4), 20-taraxastene-3,22-dione (5), 3β-acetoxy-20-taraxasten-22-one (6), 3β-hydroxy-20-taraxasten-22-one (7), and 30-nor-3β-hydroxy-20-taraxastene (8) were obtained from the petroleum ether-soluble portion of the ethanol extract from C. setosum. All chemical structures of the compounds were elucidated by spectroscopic data analysis and compared with literature data. Compounds 48 were identified for the first time from this plant, and compounds 1, 2, 4, and 7 exhibited more potent α-glucosidase inhibitory activity—with IC50 values of 18.34 ± 1.27, 26.98 ± 0.89, 17.49 ± 1.42, and 22.67 ± 0.25 μM, respectively—than acarbose did (positive control, IC50 42.52 ± 0.32 μM). View Full-Text
Keywords: Cirsium setosum; α-glucosidase inhibitor; isolation and purification; triterpenoid Cirsium setosum; α-glucosidase inhibitor; isolation and purification; triterpenoid
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Li, X.; Zhong, X.; Wang, X.; Li, J.; Liu, J.; Wang, K.; Yue, J.; Yang, X.; Shang, X.; Lin, S. Bioassay-Guided Isolation of Triterpenoids as α-Glucosidase Inhibitors from Cirsium setosum. Molecules 2019, 24, 1844.

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