New ent-kaurane diterpenes from the roasted arabica coffee beans and molecular docking to α-glucosidase

Hu, Guilin; Peng, Xing‐Rong; Ding, Dong; Nian, Yin; Gao, Ya; Wang, Xiaoyuan; Hong, Defu; Qiu, Ming‐Hua

doi:10.1016/j.foodchem.2020.128823

Cited by 20 publications

(34 citation statements)

References 17 publications

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“…Alpha-glucosidase is an enzyme that hydrolyzes the carbohydrates to monosaccharides in the final step of carbohydrate digestion. Therefore, inhibiting the activity of α -glucosidase can effectively inhibit sugar uptake, thereby achieving lowered blood sugar [ 46 ]. Diaphragma juglandis Fructus was found to improve symptoms of diabetes [ 8 ] and the total flavonoids from it showed significant α-glucosidase inhibitory activities [ 47 ].…”

Section: Resultsmentioning

confidence: 99%

The Chemical Constituents of Diaphragma Juglandis Fructus and Their Inhibitory Effect on α-Glucosidase Activity

et al. 2022

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In our current investigation, 37 constituents (1–37), including 11 megastigmanes (1–11), 17 flavonoids (12–28) and 9 phenylpropanoids (29–37), were isolated from a 70%-EtOH extract of Diaphragma juglandis Fructus. Among them, compounds 1–3, 12 and 29 were new compounds and their structures were elucidated on the basis of physicochemical evidence and meticulous spectroscopic analysis (NMR, HRESIMS and CD). Compounds 13, 16, 21 and 28 showed moderate inhibitory effect on α-glycosidase inhibitory activities, with IC50 values being in the range of 29.47–54.82 µM and stronger than the positive control (acarbose, 60.01 ± 4.82 µM).

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Section: Resultsmentioning

confidence: 99%

The Chemical Constituents of Diaphragma Juglandis Fructus and Their Inhibitory Effect on α-Glucosidase Activity

et al. 2022

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“…Notably, the 1 H– 1 H COSY spectrum of compound 1 showed the correlations from H-11/H-12/H-13, H-13/H-14, and the HMBCs of H-11 (δ H 1.80) and H-13 (δ H 1.56) with one quaternary carbon (C-9) indicated the presence of a five-membered spiro ring. Additionally, the HMBCs from H 3 -20 (δ H 0.75) to C-1 (δ C 33.6) and two quaternary carbons (C-9, δ C 59.1; C-10, δ C 42.4) prompted that compound 1 undergo rearrangement similar to villanovane II . The HMBCs from H 2 -6 (δ H 1.90) and H 2 -7 (δ H 2.23) to C-8 (δ C 153.9), from H-17 (δ H 4.78) to C-9 (δ C 59.1), and from H 3 -18 (δ H 1.20) to C-19 (δ C 181.4) proved that the positions of the double bond and carboxyl group were located at C-8 (17) and C-19, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…arabica and C. robusta. , With the continuous research on coffee composition, more and more various forms of diterpenes have been found in coffee. − …”

Section: Introductionmentioning

confidence: 99%

“…Previously, our team focused on diterpenes of Catimor in C. arabica, which can be divided into oxidized-type diterpenes, rearranged-type diterpenes, tetrahydrofuran-type diterpenes, lactam-type diterpenes, lactone-type diterpenes, Δ 4,18 -type diterpenes, degraded-type diterpenes, Villanova-type diterpenes, and atisane-type diterpenes. − Among them, lactam-type diterpene and atisane-type diterpene are reported in coffee for the first time. In addition, Catimor has the ability to resist coffee leaf rust.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, it was found that natural and effective α-glucosidase inhibitors with low toxicity and side effects can contribute to the prevention and treatment of diabetes. Drinking coffee is associated with the decreased risk of type 2 diabetes. , At the same time, studies have shown that the diterpenes in coffee have inhibitory effects on α-glucosidase, , and kahweol and kaurinic acid have hypoglycemic potential. , Therefore, we carried out the determination of α-glucosidase inhibitory activity on the coffee diterpenes discovered, which provided more evidence for the hypoglycemic reduction of coffee diterpenes.…”

Section: Introductionmentioning

confidence: 99%

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Unusual ent-Kaurane Diterpenes from the Coffea Cultivar S288 Coffee Beans and Molecular Docking to α-Glucosidase

Hong

Peng

et al. 2022

J. Agric. Food Chem.

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A total of 11 new (1−11) and 2 known (12 and 13) ent-kaurane diterpene derivatives were identified from the roasted beans of Coffea cultivar S288. Their structures were established by extensive spectroscopic analysis, including one-and twodimensional nuclear magnetic resonance (heteronuclear single-quantum correlation, heteronuclear multiple-bond correlation, correlation spectroscopy, and rotating-frame Overhauser enhancement spectroscopy), high-resolution electrospray ionization mass spectrometry, and X-ray analyses. Cafespirone acid A (1) represents the first example of diterpene featuring a spirocyclic skeleton constructed from a 6/6/5 tricyclic system. Cafeane acid A (2) possesses a 6/6/6/5 tetracyclic system as a result of the C/D ring rearrangement. Furthermore, compounds 1−12 were evaluated for their α-glucosidase inhibitory activity. The results showed that compounds 2, 4, 5, 6, 7, 10, and 11 had a moderate inhibitory effect on α-glucosidase, and half-maximal inhibitory concentration values of compounds 4, 6, 7, and 10 were 18.76 ± 1.46, 4.88 ± 0.03, 12.35 ± 0.91, and 12.64 ± 0.59 μM, respectively, compared to the positive control acarbose (60.71 ± 16.45 μM). Additionally, the molecular docking experiments showed that the carbonyl group at C-19 of compounds 4, 6, and 7 formed strong hydrogen bonds with ARG315, which may make them have moderate inhibitory activity.

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Applanoids A—E as the First Examples of C‐15/C‐20 Michael Adducts in Ganoderma Triterpenoids and Their PXR Agonistic Activity

Liang

et al. 2022

Chin. J. Chem.

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Ganoderma triterpenoids (GTs), a class of major active constituents of Ganoderma fungi, possess diverse structures and remarkable activities. In the present study, nine new GTs, namely applanoids A-I (1-9), were isolated from the medicinal fungus of Ganoderma applanatum. Their structures including absolute configurations were established by comprehensive spectroscopic analyses and ECD calculation. Applanoids A-E (1-5) represent the first example of GTs with 6/6/5/6/5 pentacyclic system and the formation of the ether ring between C-15 and C-20 involves Michael addition reaction. Furthermore, compounds 1-8 were evaluated for their human pregnane X receptor (hPXR) agonistic activity using dual-luciferase reporter gene assay, and the results showed that compounds 1, 2 and 4 can dose-dependently activate hPXR. This investigation further illustrated the structural diversity of GTs and provided new insights for searching PXR agonists from GTs.

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New ent-kaurane diterpenes from the roasted arabica coffee beans and molecular docking to α-glucosidase

Cited by 20 publications

References 17 publications

The Chemical Constituents of Diaphragma Juglandis Fructus and Their Inhibitory Effect on α-Glucosidase Activity

The Chemical Constituents of Diaphragma Juglandis Fructus and Their Inhibitory Effect on α-Glucosidase Activity

Unusual ent-Kaurane Diterpenes from the Coffea Cultivar S288 Coffee Beans and Molecular Docking to α-Glucosidase

Applanoids A—E as the First Examples of C‐15/C‐20 Michael Adducts in Ganoderma Triterpenoids and Their PXR Agonistic Activity

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