Lipids and Terpenoids from the Deep-Sea Fungus Trichoderma lixii R22 and Their Antagonism against Two Wheat Pathogens
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Elucidation
2.2. Antifungal Activity of Isolated Compounds
3. Materials and Methods
3.1. General Experimental Producres
3.2. Fungal Material and Fermentation
3.3. Extraction and Isolation
3.4. Spectral and Physical Data of Compounds 1–5
3.5. ECD Determination for Mo2-Complex of 5
3.6. Assay for Antifungal Activity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Position | 1 (in DMSO-d6) | 1 (in CDCl3) | 2 (in DMSO-d6) | 2 (in CD3OD) |
---|---|---|---|---|
1 | 1.02, d (6.2) | 1.23, d (6.2) | 1.03, d (6.2) | 1.18, d (6.2) |
2 | 3.77, m | 4.05, m | 3.77, m | 3.97, m |
3a | 2.36, m | 2.53, m | 2.30, dd (13.4, 7.1) | 2.43, br dd (13.8, 7.6) |
3b | 2.26, br dd (13.3, 5.8) | 2.46, m | 2.21, dd (13.4, 5.8) | 2.37, br dd (13.8, 5.2) |
6a | 6.54, br d (16.1) | 6.47, br d (16.1) | 3.21, dd (16.4, 6.8) | 3.28, br d (6.7) |
6b | 3.18, dd (16.4, 7.2) | |||
7 | 6.14, dt (16.1, 6.7) | 6.05, dt (16.1, 6.9) | 5.60, br ddd (15.3, 7.2, 6.8) | 5.71, dtt (15.3, 6.7, 1.1) |
8 | 2.38, m | 2.49, m | 5.69, br dd (15.3, 5.0) | 5.79, br dt (15.3, 5.2) |
9 | 2.62, t (7.3) | 2.62, t (7.0) | 3.89, br s | 4.04, br dd (5.2, 1.1) |
11 | 2.10, s | 2.17, s | ||
12a | 4.95, d (16.5) | 4.89, s | 4.75, d (17.9) | 4.78, s |
12b | 4.91, d (16.5) | 4.69, d (17.9) | ||
OH-2 | 4.63, br d (4.1) | 4.62, br d (4.3) | ||
OH-9 | 4.68, m |
Position | 1 (in DMSO-d6) | 1 (in CDCl3) | 2 (in DMSO-d6) | 2 (in CD3OD) |
---|---|---|---|---|
1 | 23.2, CH3 | 23.5, CH3 | 23.3, CH3 | 23.3, CH3 |
2 | 64.8, CH | 66.7, CH | 64.6, CH | 67.0, CH |
3 | 33.2, CH2 | 33.5, CH2 | 33.1, CH2 | 34.1, CH2 |
4 | 122.0, C | 123.4, C | 123.1, C | 125.0, C |
5 | 156.0, C | 155.7, C | 162.0, C | 164.1, C |
6 | 121.1, CH | 121.5, CH | 29.6, CH2 | 31.0, CH2 |
7 | 138.6, CH | 138.3, CH | 124.0, CH | 126.5, CH |
8 | 26.8, CH2 | 27.3, CH2 | 133.8, CH | 134.4, CH |
9 | 41.2, CH2 | 42.2, CH2 | 61.0, CH2 | 63.0, CH2 |
10 | 207.4, C | 207.1, C | ||
11 | 29.8, CH3 | 30.1, CH3 | ||
12 | 69.3, CH2 | 69.9, CH2 | 71.2, CH2 | 73.1, CH2 |
13 | 174.8, C | 176.0, C | 174.7, C | 177.7, C |
Position | 3 (in CD3OD) | 4 (in DMSO-d6) | 5 (in CD3OD) |
---|---|---|---|
1 | 1.13, d (6.4) | 1.64, br d (6.5) | 2.28, s |
2 | 3.71, qd (6.4, 5.0) | 5.61, dqd (15.4, 6.5, 1.2) | |
3 | 3.79, m | 5.40, m | 6.16, d (15.7) |
4a | 1.95, m | 3.82, m | 7.30, dd (15.7, 10.7) |
4b | 1.82, m | ||
5a | 1.95, m | 3.75, ddd (9.0, 4.4, 3.4) | 6.48, br dd (15.3, 10.7) |
5b | 1.82, m | ||
6a | 3.82, m | 1.97, ddd (11.9, 8.5, 3.4) | 6.37, dd (15.3, 5.8) |
6b | 1.72, m | ||
7 | 3.53, ddd (8.9, 5.3, 3.2) | 3.85, q (8.5) | 4.05, ddd (5.8, 5.3, 0.9) |
8a | 1.64, m | 3.51, ddd (9.4, 5.3, 3.1) | |
8b | 1.42, m | ||
9a | 2.30, m | 1.71, m | 1.61, m |
9b | 2.15, m | 1.58, m | 1.43, m |
10a | 5.72, dt (15.2, 7.0) | 2.09, m | 2.19, m |
10b | 1.91, m | 2.03, m | |
11 | 6.09, dd (15.2, 10.3) | 5.40, m | 5.45, m |
12 | 6.31, dt (17.0, 10.3) | 5.40, m | 5.45, m |
13a | 5.06, dd (17.0, 2.0) | 1.60, br d (4.9) | 1.64, br d (4.7) |
13b | 4.93, dd (10.3, 2.0) | ||
CH3O-8 | 3.14, s | ||
OH-4 | 4.75, br d (4.7) | ||
OH-7 | 4.43, br d (8.5) |
Position | 3 (in CD3OD) | 4 (in DMSO-d6) | 5 (in CD3OD) |
---|---|---|---|
1 | 19.5, CH3 | 17.7, CH3 | 27.0, CH3 |
2 | 70.2, CH | 125.4, CH | 201.6, C |
3 | 85.0, CH | 131.8, CH | 131.1, CH |
4 | 27.9, CH2 | 72.6, CH | 145.5, CH |
5 | 27.8, CH2 | 78.3, CH | 130.5, CH |
6 | 84.1, CH | 32.6, CH2 | 145.3, CH |
7 | 73.5, CH | 73.6, CH | 76.2, CH |
8 | 34.2, CH2 | 104.5, C | 74.9, CH |
9 | 29.8, CH2 | 32.1, CH2 | 33.8, CH2 |
10 | 135.7, CH | 26.4, CH2 | 29.8, CH2 |
11 | 132.7, CH | 131.5, CH | 132.1, CH |
12 | 138.6, CH | 124.0, CH | 126.2, CH |
13 | 115.1, CH2 | 17.8, CH3 | 18.1, CH3 |
CH3O-8 | 47.4, CH3 |
Compound | MIC (μg/mL) | Lethal Rate (at 100 μg/mL) | |
---|---|---|---|
Fusarium graminearum ACCC39334 | Gaeumannomyces graminis ACCC38864 | Artemia salina | |
1 | 25.0 ± 0.0 | – | 15.6 ± 5.2% |
2 | 25.0 ± 0.0 | – | 15.2 ± 2.1% |
3 | – | – | 4.7 ± 1.3% |
4 | – | – | 19.9 ± 3.7% |
5 | – | – | 7.2 ± 5.3% |
6 | – | 12.5 ± 0.0 | 23.4 ± 5.4% |
7 | – | – | 0.0 ± 0.0% |
carbendazim | 6.1 ± 0.0 | 6.1 ± 0.0 | |
CuSO4 | 100.0 ± 0.0% |
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Li, C.-P.; Shi, Z.-Z.; Fang, S.-T.; Song, Y.-P.; Ji, N.-Y. Lipids and Terpenoids from the Deep-Sea Fungus Trichoderma lixii R22 and Their Antagonism against Two Wheat Pathogens. Molecules 2023, 28, 6220. https://doi.org/10.3390/molecules28176220
Li C-P, Shi Z-Z, Fang S-T, Song Y-P, Ji N-Y. Lipids and Terpenoids from the Deep-Sea Fungus Trichoderma lixii R22 and Their Antagonism against Two Wheat Pathogens. Molecules. 2023; 28(17):6220. https://doi.org/10.3390/molecules28176220
Chicago/Turabian StyleLi, Chang-Peng, Zhen-Zhen Shi, Sheng-Tao Fang, Yin-Ping Song, and Nai-Yun Ji. 2023. "Lipids and Terpenoids from the Deep-Sea Fungus Trichoderma lixii R22 and Their Antagonism against Two Wheat Pathogens" Molecules 28, no. 17: 6220. https://doi.org/10.3390/molecules28176220