Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation of the New Compounds
2.2. Biological Activities of the Isolated Compounds
3. Experimental Section
3.1. General Experimental Procedures
3.2. Fungal Material
3.3. Fermentation
3.4. Extraction and Isolation
3.5. Antioxidant and Antimicrobial Assays
3.6. Computational Section
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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No. | 1 a | 2 b | 3 a | |||
---|---|---|---|---|---|---|
δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | |
1 | 128.1, C | 129.1, C | 129.8, C | |||
2 | 128.9, CH | 7.59, s | 130.6, CH | 7.71, s | 133.2, CH | 8.50, s |
3 | 125.8, C | 118.2, C | 121.8, C | |||
4 | 160.8, C | 154.5, C | 159.2, C | |||
5 | 115.0, CH | 6.77, d (9.1) | 115.1, CH | 6.69, d (8.3) | 117.9, CH | 7.72, d (8.4) |
6 | 127.7, CH | 7.58, d (9.1) | 128.0, CH | 7.70, d (8.3) | 129.8, CH | 8.46, d (8.4) |
7 | 196.4, C | 173.4, C | 191.9, CH | 10.64, s | ||
8 | 64.3, CH2 | 4.63, s | ||||
1’ | 28.1, CH2 | 30.3, CH2 | 2.75, dd (7.4, 16.6) 3.03, dd (5.3, 16.6) | 31.4, CH2 | 3.54, dd (7.1, 16.8) 3.85, dd (4.9, 16.8) | |
2’ | 122.7, CH | 3.22, d (7.3) | 68.6, CH | 3.77, dd (5.3, 7.4) | 68.0, CH | 4.54, dd (4.9, 7.1) |
3’ | 131.3, C | 5.29, t (7.3) | 76.6, C | 79.4, C | ||
4’ | 17.6, CH3 | 1.67, s | 19.2, CH3 | 1.26, s | 22.0, CH3 | 2.07, s |
5’ | 25.5, CH3 | 1.70, s | 24.1, CH3 | 1.33, s | 26.2, CH3 | 2.13, s |
Compounds | 4 | 5 | ||
---|---|---|---|---|
2’R | 2’S | 2’R | 2’S | |
calculated OR | −60.9 | +61.0 | −91.3 | +95.5 |
measured OR | −95.0 | −55.0 |
Compounds | Ah | Et | Ec | Ml | Pa | Sa | Vh | Vp | Vv |
---|---|---|---|---|---|---|---|---|---|
1 | 2 | 32 | 32 | 16 | 2 | 8 | 4 | 8 | 32 |
2 | 64 | n.a. | 32 | 32 | 64 | n.a. | n.a. | n.a. | n.a. |
3 | n.a. | n.a. | 64 | 32 | n.a. | n.a. | n.a. | n.a. | n.a. |
4 | n.a. | 32 | n.a. | n.a. | n.a. | 64 | n.a. | n.a. | n.a. |
5 | n.a. | 64 | n.a. | 32 | n.a. | 32 | n.a. | n.a. | n.a. |
6 | 8 | 16 | 16 | n.a. | n.a. | 64 | 32 | 8 | n.a. |
7 | 4 | 16 | 32 | 8 | 16 | 16 | 8 | 8 | 64 |
Chloramphenicol | 1 | 0.5 | 2 | 2 | 1 | 2 | 2 | 4 | 4 |
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Li, H.-L.; Li, X.-M.; Yang, S.-Q.; Meng, L.-H.; Li, X.; Wang, B.-G. Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai. Mar. Drugs 2019, 17, 605. https://doi.org/10.3390/md17110605
Li H-L, Li X-M, Yang S-Q, Meng L-H, Li X, Wang B-G. Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai. Marine Drugs. 2019; 17(11):605. https://doi.org/10.3390/md17110605
Chicago/Turabian StyleLi, Hong-Lei, Xiao-Ming Li, Sui-Qun Yang, Ling-Hong Meng, Xin Li, and Bin-Gui Wang. 2019. "Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai" Marine Drugs 17, no. 11: 605. https://doi.org/10.3390/md17110605
APA StyleLi, H. -L., Li, X. -M., Yang, S. -Q., Meng, L. -H., Li, X., & Wang, B. -G. (2019). Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai. Marine Drugs, 17(11), 605. https://doi.org/10.3390/md17110605