Pimarane-Type Diterpenes with Anti-Inflammatory Activity from Arctic-Derived Fungus Eutypella sp. D-1
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Analysis of Compounds
2.2. Evaluation of the Inhibitory Effect on the NO Release
2.3. Evaluation of Anti-Inflammatory Activity Based on Zebrafish Model
3. Materials and Methods
3.1. General Experimrntal Procedures
3.2. Fungal Strain
3.3. Fermentation
3.4. Extraction and Isolation
3.5. ECD Calculations
3.6. Assay of Anti-Inflammatory Activity Based on LPS-Induced RAW264.7 Model
3.7. Assay of Anti-Inflammatory Activity Based on Zebrafish Model
3.8. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Data Availability Statement
Conflicts of Interest
References
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Position | 1 * | 2 * | 3 * | |||
---|---|---|---|---|---|---|
δc, type | δH, mult. (J in Hz) | δc, type | δH, mult. (J in Hz) | δc, type | δH, mult. (J in Hz) | |
1a | 38.46, CH | 3.30, m | 32.5, CH | 3.26, m | 30.58, CH2 | 1.95, m |
1b | 1.52, m | |||||
2a | 25.62, CH2 | 2.28, m | 27.0, CH2 | 2.34, m | 17.34, CH2 | 1.69, m |
2b | 2.22, dd, (12.62, 4.95) | 1.51, m | 1.65, m | |||
3a | 74.90, CH | 5.21, m | 73.0, CH | 5.12, d, (1.1) | 36.36, CH2 | 1.91, m |
3b | 1.36, m | |||||
4 | 41.51, C | 40.6, C | 41.32, C | |||
5 | 125.88, C | 126.5, C | 138.79, C | |||
6 | 153.37, C | 179.8, C | 143. 82, C | |||
7 | 115.25, CH | 6.86, s | 145.4, C | 181.80, C | ||
8 | 137.12, C | 122.3, C | 133.71, C | |||
9 | 75.42, CH | 4.29, m | 78.0, C | 147. 97, CH | 7.04, d, (1.86) | |
10 | 40.13, C | 167.2, C | 38.73, C | |||
11a | 31.62, CH2 | 1.96, m | 35.1, CH2 | 2.04, m | 29.36, CH2 | 1.84, m |
11b | 1.77, m | 1.50, m | 1.57, m | |||
12a | 22.64, CH2 | 2.74, m | 28.2, CH2 | 1.52, m | 25.66, CH2 | 1.92, m |
12b | 2.18, m | 1.80, m | ||||
13 | 125.84, C | 44.3, C | 74.86, C | |||
14 | 138.70, C | 80.1, CH | 4.40, s | 44.45, C | ||
14-OCH3 | 57.5, OCH3 | 3.34, s | ||||
15a | 63.96, CH2 | 3.73, m | 143.2, CH | 5.69, dd, (17.8, 11.1) | 70.49, CH2 | 4.48, d, (8.10) |
15b | 3.16, d, (11.36) | |||||
16a | 21.45, CH3 | 2.17, s | 113.6, CH2 | 5.01, dd, (11.2, 1.0) | 22.38, CH3 | 1.17, s |
16b | 5.08, d, (1.0) | |||||
17 | 171.50, C | 25.5, CH3 | 1.20, s | 29.73, CH3 | 1.20, s | |
18a | 18.78, CH3 | 0.90, d, (7.51) | 65.2, CH2 | 4.35, d, (10.5) | 23.17, CH3 | 1.12, s |
18b | 4.79, d, (10.5) | |||||
19 | 18.64, CH3 | 0.98, d, (7.51) | 21.0, CH3 | 1.36, s | 145.36, CH | 5.88, q, (6.41) |
20a | 34.06, CH | 2.37, m | 72.3, CH2 | 4.42, t, (7.95) | 112.63, CH2 | 5.08, m |
20b | 3.75, dd, (8.7, 7.4) | |||||
21 | 176.80, C | 170.1, C | ||||
22a | 65.42, CH2 | 5.0, d, (11.19) | 21.1, CH3 | 2.0, s | ||
22b | 4.30, m | |||||
23 | 21.81, CH3 | 1.54, s | 176.6, C | |||
24 | 23.06, CH3 | 1.18, s | 34.3, CH | 2.53, m | ||
25 | 140.86, CH | 5.83, q, (7.24) | 19.1, CH3 | 1.13, d, (7.0) | ||
26 | 116.44, CH2 | 5.21, m | 19.1, CH3 | 1.14, d, (7.0) |
Compound | Inhibition (%) |
---|---|
1 | <20 |
2 | <20 |
3 | 60.93 |
4 | 89.4 |
5 | 84.2 |
6 | 23.17 |
7 | <20 |
Dexamethasone | 72.85 |
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Ning, Y.; Zhang, S.; Zheng, T.; Xu, Y.; Li, S.; Zhang, J.; Jiao, B.; Zhang, Y.; Ma, Z.; Lu, X. Pimarane-Type Diterpenes with Anti-Inflammatory Activity from Arctic-Derived Fungus Eutypella sp. D-1. Mar. Drugs 2023, 21, 541. https://doi.org/10.3390/md21100541
Ning Y, Zhang S, Zheng T, Xu Y, Li S, Zhang J, Jiao B, Zhang Y, Ma Z, Lu X. Pimarane-Type Diterpenes with Anti-Inflammatory Activity from Arctic-Derived Fungus Eutypella sp. D-1. Marine Drugs. 2023; 21(10):541. https://doi.org/10.3390/md21100541
Chicago/Turabian StyleNing, Yaodong, Shi Zhang, Te Zheng, Yao Xu, Song Li, Jianpeng Zhang, Binghua Jiao, Yun Zhang, Zengling Ma, and Xiaoling Lu. 2023. "Pimarane-Type Diterpenes with Anti-Inflammatory Activity from Arctic-Derived Fungus Eutypella sp. D-1" Marine Drugs 21, no. 10: 541. https://doi.org/10.3390/md21100541