Three New Asperentin Derivatives from the Algicolous Fungus Aspergillus sp. F00785
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation
No. | 1 | 2 | 3 | 4 | ||||
---|---|---|---|---|---|---|---|---|
δH a (J in Hz) | δC b | δH a (J in Hz) | δC b | δH a (J in Hz) | δC b | δH a (J in Hz) | δC b | |
1 | 169.6, C | 161.6, C | 170.0, C | 169.9, C | ||||
3 | 4.72, m | 76.5, CH | 4.60, m | 74.6, CH | 4.63, m | 76.3, CH | 4.72, m | 76.4, CH |
4 | 2.87, m | 33.6, CH2 | 2.92, dd, (16.2, 11.5) | 35.4, CH2 | 3.10, dd, (16.8, 3.4) | 27.3, CH2 | 2.86, m | 33.7, CH2 |
2.83, dd, (16.2, 2.9) | 2.62, dd, (16.8, 11.5) | |||||||
4a | 141.5, C | 144.0, C | 122.6, C | 141.8, C | ||||
5 | 6.42, s | 107.6, CH | 6.56, d, (2.0) | 106.8, CH | 134.3, C | 6.32, s | 106.7, CH | |
OH-5 | 5.20, s | |||||||
6 | 162.5, C | 162.6, C | 153.1, C | 162.9, C | ||||
OCH3-6 | 3.86, s | 56.2, CH3 | ||||||
7 | 6.56, s | 102.9, CH | 6.61, d, (2.0) | 100.1, CH | 6.34, s | 97.8, CH | 6.19, s | 102.0, CH |
8 | 163.8, C | 162.9, C | 157.8, C | 164.3, C | ||||
OCH3-8 | 3.94, s | 56.3, CH3 | ||||||
8a | 103.2, C | 106.8, C | 100.7, C | 101.7, C | ||||
1′ | 1.98, m; 1.82, m | 39.2, CH2 | 1.92, m; 1.83, m | 39.5, CH2 | 1.95, m; 1.78, m | 39.5, CH2 | 1.99, m; 1.87, m | 39.4, CH2 |
2′ | 4.10, m | 66.4, CH | 4.10, m | 66.2, CH | 4.05, m | 66.3, CH | 4.13, m | 66.5, CH |
3′ | 1.69, m; 1.35, m | 30.8, CH2 | 1.36, m | 30.9, CH2 | 1.64, m; 1.29, m | 30.8, CH2 | 1.73, m; 1.38, m | 30.9, CH2 |
4′ | 1.70, m; 1.62, m | 18.2, CH2 | 1.73, m; 1.64, m | 18.3, CH2 | 1.65, m; 1.56, m | 18.3, CH2 | 1.74, m; 1.65, m | 18.2, CH2 |
5′ | 1.68, m; 1.32, m | 31.3, CH2 | 1.72, m | 31.0, CH2 | 1.63, m; 1.26, m | 31.1, CH2 | 1.72, m; 1.36, m | 31.0, CH2 |
6′ | 3.94, m | 67.6, CH | 3.96, m | 67.7, CH | 3.89, m | 67.4, CH | 4.02, m | 67.9, CH |
CH3-6′ | 1.21, d, (4.1) | 19.1, CH3 | 1.22, d, (6.5) | 18.9, CH3 | 1.14, d, (6.5) | 19.2, CH3 | 1.25, d, (6.5) | 18.9, CH3 |
1″ | 5.69, d, (3.5) | 100.1, CH | 5.77, d, (4.5) | 100.5, CH | ||||
2″ | 4.29, brs | 72.1, CH | 4.34, m | 72.2, CH | ||||
3″ | 4.19, brs | 70.1, CH | 4.24, dd, (6.2, 2.7) | 70.4, CH | ||||
4″ | 4.21, brs | 86.4, CH | 4.28, dd, (6.2, 2.7) | 86.5, CH | ||||
5″ | 3.78, d, (11.6); 3.74, d, (11.6) | 62.3, CH2 | 3.89, dd, (12.1, 3.1); 3.81, dd, (12.1, 3.1) | 62.5, CH2 | ||||
8-OH | 11.13, s | 10.86, s | 11.10, s |
2.2. Bioactivity Results
Compounds | Inhibition Zone (mm) | ||
---|---|---|---|
C. gleosporioides Penz | C. gleosporioides (Penz) Sacc. | B. cinerea Pers | |
(−)-asperentin (4) | 19.7 ± 0.58 | 13.3 ± 3.40 | 1.67 ± 1.11 |
amphotericin B | 15.7 ± 1.25 | 16.0 ±1.41 | 11.0 ± 0.82 |
3. Experimental Section
3.1. General Experimental Procedures
3.2. Fungi Materials
3.3. Extraction and Purification
3.4. Acid Hydrolysis and Stereochemistry Determination of the Ribofuranose of 6-O-α-d-Ribosyl Asperentin (1)
3.5. Anti-Crop Pathogens Test
4. Conclusion
Supplementary Files
Supplementary File 1Acknowledgments
Author Contributions
Conflicts of Interest
References
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Tang, Q.; Guo, K.; Li, X.-Y.; Zheng, X.-Y.; Kong, X.-J.; Zheng, Z.-H.; Xu, Q.-Y.; Deng, X. Three New Asperentin Derivatives from the Algicolous Fungus Aspergillus sp. F00785. Mar. Drugs 2014, 12, 5993-6002. https://doi.org/10.3390/md12125993
Tang Q, Guo K, Li X-Y, Zheng X-Y, Kong X-J, Zheng Z-H, Xu Q-Y, Deng X. Three New Asperentin Derivatives from the Algicolous Fungus Aspergillus sp. F00785. Marine Drugs. 2014; 12(12):5993-6002. https://doi.org/10.3390/md12125993
Chicago/Turabian StyleTang, Qian, Kai Guo, Xiao-Yang Li, Xiu-Ying Zheng, Xiang-Jian Kong, Zhong-Hui Zheng, Qing-Yan Xu, and Xianming Deng. 2014. "Three New Asperentin Derivatives from the Algicolous Fungus Aspergillus sp. F00785" Marine Drugs 12, no. 12: 5993-6002. https://doi.org/10.3390/md12125993