Chromone Derivatives with α-Glucosidase Inhibitory Activity from the Marine Fungus Penicillium thomii Maire
Abstract
:1. Introduction
2. Results
3. Materials and Methods
3.1. General Experimental Procedure
3.2. Fungal Strain and Identification
3.3. Fermentation, Extraction, and Isolation
3.4. α-Glucosidase Assay
3.5. Antioxidant Activity
3.6. Computational Details
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Position | 1 a | 2 b | 3 b | |||
---|---|---|---|---|---|---|
δH | δC | δH | δC | δH | δC | |
2 | 170.6 | 170.0 | 170.4 | |||
3 | 6.25, s | 107.8 | 6.10, s | 110.1 | 6.15, s | 110.4 |
4 | 182.0 | 183.9 | 184.0 | |||
4a | 104.6 | 105.3 | 106.2 | |||
5 | 161.3 | 163.2 | 163.0 | |||
6 | 6.36, d (1.9) | 98.0 | 6.18, d (1.9) | 100.0 | 6.33, d (2.0) | 99.2 |
7 | 165.2 | 165.9 | 167.4 | |||
8 | 6.61, d (1.9) | 92.5 | 6.33, d (1.9) | 95.0 | 6.54, d (2.0) | 93.5 |
8a | 157.8 | 159.9 | 159.8 | |||
9 | 2.69, t (6.5) | 32.9 | 2.81, dd (14.5, 3.9) 2.63, dd (14.5, 8.8) | 43.2 | 2.82, dd (14.3, 3.9) 2.66, dd (14.3, 8.7) | 43.2 |
10 | 1.77, m | 22.3 | 4.0, m | 70.0 | 4.0, m | 69.9 |
11 | 1.69, m | 34.0 | 1.57, m | 38.1 | 1.56, m | 38.0 |
12 | 4.52, m | 79.9 | 1.45, m 1.56, m | 26.3 | 1.43, m 1.54, m | 26.2 |
13 | 2.27, m 1.80, m | 27.3 | 1.65, m | 26.0 | 1.65, m | 25.9 |
14 | 2.49, m | 28.3 | 2.32, t (7.2) | 35.0 | 2.35, t (7.3) | 34.7 |
15 | 177.1 | 177.7 | 176.0 | |||
5-OCH3 | ||||||
7-OCH3 | 3.84, s | 56.1 | 3.87, s | 56.5 | ||
15-OCH3 | 3.65, s | 52.0 |
Position | 4 | 5 | 6 | |||
---|---|---|---|---|---|---|
δH | δC | δH | δC | δH | δC | |
2 | 169.7 | 169.6 | 172.4 | |||
3 | 6.04, s | 111.3 | 6.05, s | 111.3 | 6.05, s | 108.4 |
4 | 180.1 | 180.1 | 184.0 | |||
4a | 109.1 | 109.2 | 105.2 | |||
5 | 162.1 | 162.1 | 163.2 | |||
6 | 6.49, d (2.1) | 97.3 | 6.50, d (2.1) | 97.2 | 6.17, d (2.0) | 100.0 |
7 | 166.3 | 166.3 | 165.9 | |||
8 | 6.62, d (2.1) | 94.0 | 6.64, d (2.1) | 94.0 | 6.31, d (2.0) | 94.9 |
8a | 161.8 | 161.8 | 159.9 | |||
9 | 2.63, t (7.5) | 34.4 | 2.63, t (7.7) | 34.3 | 2.64, t (7.6) | 34.9 |
10 | 1.76, m | 27.8 | 1.76, m | 27.7 | 1.75, m | 27.8 |
11 | 1.52, m | 26.1 | 1.52, m | 26.0 | 1.52, m | 26.0 |
12 | 1.52, m | 37.6 | 1.54, m | 37.6 | 1.53, m | 37.6 |
13 | 3.99, m | 69.3 | 4.0, m | 69.1 | 3.99, m | 69.1 |
14 | 2.41, m | 43.6 | 2.41, dd (15.1, 8.1) 2.50, dd (15.1, 4.9) | 43.2 | 2.39, dd (15.3, 7.9) 2.46, dd (15.3, 5.1) | 43.3 |
15 | 174.5 | 174.0 | 175.7 | |||
5-OCH3 | 3.89, s | 56.5 | 3.89, s | 56.5 | ||
7-OCH3 | 3.90, s | 52.0 | 3.91, s | 56.5 | ||
15-OCH3 | 3.67, s | 52.0 |
Position | 7 | 8 | ||
---|---|---|---|---|
δH | δC | δH | δC | |
2 | 170.4 | 170.4 | ||
3 | 6.15, s | 110.4 | 6.15, s | 110.4 |
4 | 184.0 | 184.0 | ||
4a | 106.2 | 106.2 | ||
5 | 163.0 | 163.0 | ||
6 | 6.32, d (1.9) | 99.1 | 6.32, d (2.0) | 99.1 |
7 | 167.3 | 167.3 | ||
8 | 6.52, d (1.9) | 93.5 | 6.53, d (2.0) | 93.4 |
8a | 159.8 | 159.8 | ||
9 | 2.82, dd (14.3, 3.7) 2.65, dd (14.3, 8.4) | 43.3 | 2.83, dd (14.3, 3.5) 2.66, dd (14.3, 8.8) | 43.3 |
10 | 4.0, m | 70.1 | 4.0, m | 70.0 |
11 | 1.55, m | 38.4 | 1.57, m | 38.1 |
12 | 1.41, m | 26.5 | 1.48, m 1.57, m | 26.3 |
13 | 1.37, m | 30.3 | 1.54, m | 29.1 |
14 | 1.37, m | 30.2 | 2.25, m | 33.1 |
15 | 1.62, m | 26.1 | 6.95, dd (15.7, 7.0) | 150.6 |
16 | 2.28, t (7.4) | 35.1 | 5.81, d (15.7) | 123.0 |
17 | 177.9 | 170.5 | ||
5-OCH3 | ||||
7-OCH3 | 3.86, s | 56.5 | 3.87, s | 56.5 |
Compounds | α-Glucosidase Inhibitory | Antioxidant | ||
---|---|---|---|---|
% Inhibition (667 μM) | IC50 (μM) | % Inhibition (1000 μM) | IC50 (μM) | |
1 | −3.43 | 7.24 | ||
2 | 15.10 | 35.7 | 1970 ± 156 | |
3 | 23.78 | 20.4 | ||
4 | −9.718 | 12.2 | ||
5 | 1.41 | 11.2 | ||
6 | 27.3 | 842 ± 11 | 33.8 | |
7 | 25.2 | 917 ± 8 | 23.6 | |
8 | 41.7 | 1017 ± 22 | 19.3 | |
9 | 40.18 | 688 ± 24 | 18.1 | |
10 | 74.66 | 268 ± 25 | 21.8 | |
Acarbose a | 27.7 | 1330 | ||
Vitamin C a | 96.4 | 26.7 |
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Han, S.; Liu, Y.; Liu, W.; Yang, F.; Zhang, J.; Liu, R.; Zhao, F.; Xu, W.; Cheng, Z. Chromone Derivatives with α-Glucosidase Inhibitory Activity from the Marine Fungus Penicillium thomii Maire. Molecules 2021, 26, 5273. https://doi.org/10.3390/molecules26175273
Han S, Liu Y, Liu W, Yang F, Zhang J, Liu R, Zhao F, Xu W, Cheng Z. Chromone Derivatives with α-Glucosidase Inhibitory Activity from the Marine Fungus Penicillium thomii Maire. Molecules. 2021; 26(17):5273. https://doi.org/10.3390/molecules26175273
Chicago/Turabian StyleHan, Shouye, Yu Liu, Wan Liu, Fan Yang, Jia Zhang, Ruifeng Liu, Fenqin Zhao, Wei Xu, and Zhongbin Cheng. 2021. "Chromone Derivatives with α-Glucosidase Inhibitory Activity from the Marine Fungus Penicillium thomii Maire" Molecules 26, no. 17: 5273. https://doi.org/10.3390/molecules26175273