New ent-kaurane diterpenes from the roasted arabica coffee beans and molecular docking to α-glucosidase
| Autor: | Ya Gao, Ding Dong, Guilin Hu, Xiaoyuan Wang, Yin Nian, Xing-Rong Peng, Ming-Hua Qiu, Defu Hong |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Magnetic Resonance Spectroscopy
Double bond Protein Conformation Stereochemistry Arabica coffee Coffea 01 natural sciences Analytical Chemistry chemistry.chemical_compound 0404 agricultural biotechnology Glycoside Hydrolase Inhibitors Cooking Ent kaurane chemistry.chemical_classification α glucosidase Coffea arabica 010401 analytical chemistry alpha-Glucosidases 04 agricultural and veterinary sciences General Medicine 040401 food science 0104 chemical sciences Molecular Docking Simulation chemistry Diterpene Diterpenes Kaurane Two-dimensional nuclear magnetic resonance spectroscopy Heteronuclear single quantum coherence spectroscopy Food Science |
| Zdroj: | Food Chemistry. 345:128823 |
| ISSN: | 0308-8146 |
| DOI: | 10.1016/j.foodchem.2020.128823 |
| Popis: | Ten new (1–10) and five known (11–15) ent-kaurane diterpene derivatives were identified from the roasted beans of coffea arabica. Their structures were established by extensive spectroscopic analysis including 1D, 2D NMR (HSQC, HMBC, COSY, and ROESY), HRESIMS, and X-ray diffraction analysis. Compounds 1–3 were three types of rearranged ent-kaurane diterpenes, and compounds 4 and 5 were diterpene esters with a rare 6-hydroxyhexanoyl at C-17. Compounds 6, 8, 14, and 15 showed moderate inhibitory effect on α-glucosidase with IC50 values of 149.92 ± 2.52, 23.23 ± 1.03, 54.58 ± 4.21, 54.16 ± 3.95 μM, respectively, compared to the positive control (60.71 ± 16.45 μM). The results of activity assay showed that diterpenes with the double bond between C-15 and C-16 exhibited stronger α-glucosidase inhibitory activity. Further molecular docking experiments were adopted to discuss the mechanism of activity. |
| Databáze: | OpenAIRE |
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