New Azaphilones from the Marine-Derived Fungus Penicillium sclerotiorum E23Y-1A with Their Anti-Inflammatory and Antitumor Activities
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation of New Compounds
No. | 1 a | 2 a | 3 b | 4 a | 5 a | 6 a | 7 a | 8 a | 9 a |
---|---|---|---|---|---|---|---|---|---|
1 | 4.35, dd (10.8, 5.2) | 4.35, dd (10.8, 5.2) | 4.35, dd (10.7, 5.2) | 4.36, dd (10.7, 5.3) | 4.35, dd (10.8, 5.2) | 4.86, dd, (10.9, 5.5) | 4.39, dd, (10.8, 5.3) | 4.28, dd, (10.7, 5.3) | 7.41, s |
3.80, dd (13.7,10.8) | 3.80, dd (13.6, 10.8) | 3.81, dd (13.6,10.7) | 3.79, dd (13.6, 10.7) | 3.80, dd (13.6, 10.7) | 3.81, dd, (13.4, 10.9) | 3.82, dd, (13.6, 10.9) | 3.73, dd, (13.8, 10.8) | ||
4 | 5.67, s | 5.67, s | 5.67, s | 5.67, s | 5.68, s | 5.94, s | 5.96, s | 5.52, s | 6.37, s |
5 | 5.80, brs | 5.79, s | 5.79, d (2.1) | 5.80, d (2.1) | 5.79, d (2.1) | 5.88, brs | 5.91, brs | 5.70, s | 5.53, s |
8 | 4.98, d (10.0) | 4.97, d (10.1) | 4.98, d (10.0) | 4.98, d (10.1) | 4.98, d (10.0) | 3.47, d (9.3) | 4.99, d (10.0) | 4.95, d (9.9) | 3.85, d (12.2) |
8a | 3.35, m | 3.35, m | 3.35, m | 3.34, m | 3.34, m | 3.04, m | 3.37, m | 3.27, m | |
9 | 6.00, d (15.9) | 5.98, d (16.1) | 6.19, d (15.6) | 6.12, d (15.5) | 6.18, d (15.4) | 6.85, d (15.6) | 6.84, d (15.7) | 2.51, t (7.3) | 6.93, d (15.8) |
10 | 6.31, d (15.9) | 6.42, d (16.1) | 6.43, d (15.5) | 6.37, d (15.5) | 6.39, d (15.4) | 6.70, d (15.7) | 6.65, d (15.7) | 2.68, m | 6.76, d (15.7) |
12 | 3.39, d (2.7) | 3.45, s | 3.49, d (2.1) | 3.38, d (8.8) | 3.30, d (9.6) | 2.33, s | 1.36, s | 2.17, s | 2.36, s |
13 | 1.53, m | 1.47, m | 1.53, m | 1.47, m | 1.64, m | 1.49, s | 1.49, s | 1.34, s | 1.58, s |
14 | 1.38, m | 1.40, m | 1.41, m | 1.62, m | 1.39, m | ||||
1.24, m | 1.28, m | 1.30, m | 1.07, m | 1.01, m | |||||
15 | 0.85, t (7.4) | 0.87, t (7.4) | 0.90, t (7.4) | 0.88, t (7.4) | 0.90, t (7.3) | 2.23, s | 2.20, s | 3.75, d (12.3) | |
16 | 1.35, s | 1.34, s | 1.35, s | 1.36, s | 1.36, s | ||||
17 | 1.29, s | 1.31, s | 1.35, s | 1.41, s | 1.24, s | 2.48, s | |||
18 | 0.90, d (6.8) | 0.83, d (6.5) | 0.86, d (6.8) | 0.97, d (6.6) | 1.04, d (6.5) | ||||
20 | 2.21, s | 2.20, s | 2.21, s | 2.21, s | 2.21, s | ||||
OCH3 | 3.16, s | 3.16, s | |||||||
21 | 4.71, d (5.0) | 4.74, d (4.0) | |||||||
22 | 1.62, m | 1.60, m | |||||||
23 | 1.60, m | 1.60, m | |||||||
1.20, m | 1.20, m | ||||||||
24 | 0.93, t (7.3) | 0.93, t (7.3) | |||||||
25 | 0.98, d (6.6) | 0.94, d (6.6) |
No. | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 |
---|---|---|---|---|---|---|---|---|---|
1 | 68.0 | 68.0 | 68.1 | 68.1 | 68.0 | 69.1 | 68.2 | 68.3 | 147.1 |
3 | 159.6 | 159.6 | 160.0 | 160.0 | 160.0 | 158.1 | 157.7 | 166.4 | 153.5 |
4 | 105.0 | 104.8 | 104.7 | 104.8 | 105.0 | 110.9 | 110.7 | 101.3 | 114.3 |
4a | 151.1 | 151.1 | 151.1 | 151.2 | 151.0 | 149.8 | 149.2 | 150.9 | 142.8 |
5 | 116.9 | 116.9 | 116.7 | 116.7 | 116.7 | 119.1 | 119.5 | 115.5 | 109.1 |
6 | 194.6 | 194.6 | 194.4 | 194.4 | 194.4 | 196.7 | 194.5 | 194.5 | 191.8 |
7 | 74.4 | 74.4 | 74.4 | 74.5 | 74.5 | 74.5 | 74.6 | 74.4 | 82.8 |
8 | 74.5 | 74.5 | 74.6 | 74.5 | 74.5 | 74.4 | 74.3 | 74.5 | 42.9 |
8a | 34.7 | 34.7 | 36.4 | 34.8 | 34.8 | 36.7 | 34.7 | 34.4 | 114.4 |
9 | 125.0 | 125.0 | 122.3 | 123.2 | 122.5 | 135.0 | 134.8 | 28.5 | 131.9 |
10 | 139.5 | 138.4 | 140.0 | 138.9 | 140.8 | 130.3 | 130.4 | 40.1 | 131.0 |
11 | 80.4 | 80.6 | 76.1 | 80.8 | 80.7 | 197.8 | 197.7 | 206.6 | 196.8 |
12 | 79.5 | 80.2 | 79.4 | 90.4 | 88.8 | 28.7 | 28.5 | 30.1 | 29.0 |
13 | 35.4 | 35.7 | 34.8 | 35.2 | 34.5 | 20.5 | 19.9 | 20.1 | 23.3 |
14 | 29.0 | 29.2 | 28.9 | 25.6 | 25.4 | 170.5 | 170.6 | 168.3 | |
15 | 11.9 | 12.0 | 12.0 | 11.2 | 11.1 | 20.8 | 20.8 | 57.2 | |
16 | 20.0 | 20.0 | 20.1 | 20.1 | 20.1 | 200.0 | |||
17 | 16.4 | 18.5 | 26.7 | 25.2 | 21.3 | 30.3 | |||
18 | 14.0 | 13.8 | 13.4 | 16.0 | 16.4 | ||||
19 | 170.6 | 170.6 | 170.6 | 170.6 | 170.5 | ||||
20 | 20.8 | 20.8 | 20.8 | 20.8 | 20.8 | ||||
OCH3 | 50.4 | 50.6 | |||||||
21 | 105.3 | 105.8 | |||||||
22 | 38.8 | 38.7 | |||||||
23 | 24.8 | 24.5 | |||||||
24 | 11.6 | 11.8 | |||||||
25 | 14.1 | 13.6 |
2.2. Bioassay
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Fungal Identification, Fermentation, and Extract
3.3. Isolation and Purification
3.4. NMR Calculation
3.5. ECD Calculation
3.6. Anti-Inflammatory Activity Test
3.7. Cytotoxic Detection
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound | IC50 ± SD (μM) a | ||||
---|---|---|---|---|---|
K562 | BEL-7402 | SGC-7901 | A549 | Hela | |
1 | – | – | – | – | – |
2 | – | – | – | – | – |
3 | – | – | – | – | – |
4 | 23.94 ± 0.11 | 60.66 ± 0.13 | 46.17 ± 0.17 | 60.16 ± 0.26 | 59.30 ± 0.60 |
5 | – | – | – | – | – |
6 | – | – | – | – | – |
7 | – | – | – | – | – |
8 | – | – | – | – | – |
9 | – | – | – | – | – |
cisplatin b | 3.08 ± 0.05 | 4.02 ± 0.06 | 4.11 ± 0.02 | 1.93 ± 0.02 | 11.29 ± 0.15 |
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Zeng, Y.; Wang, Z.; Chang, W.; Zhao, W.; Wang, H.; Chen, H.; Dai, H.; Lv, F. New Azaphilones from the Marine-Derived Fungus Penicillium sclerotiorum E23Y-1A with Their Anti-Inflammatory and Antitumor Activities. Mar. Drugs 2023, 21, 75. https://doi.org/10.3390/md21020075
Zeng Y, Wang Z, Chang W, Zhao W, Wang H, Chen H, Dai H, Lv F. New Azaphilones from the Marine-Derived Fungus Penicillium sclerotiorum E23Y-1A with Their Anti-Inflammatory and Antitumor Activities. Marine Drugs. 2023; 21(2):75. https://doi.org/10.3390/md21020075
Chicago/Turabian StyleZeng, Yanbo, Zhi Wang, Wenjun Chang, Weibo Zhao, Hao Wang, Huiqin Chen, Haofu Dai, and Fang Lv. 2023. "New Azaphilones from the Marine-Derived Fungus Penicillium sclerotiorum E23Y-1A with Their Anti-Inflammatory and Antitumor Activities" Marine Drugs 21, no. 2: 75. https://doi.org/10.3390/md21020075