Cyclodepsipeptides and Other O-Containing Heterocyclic Metabolites from Beauveria felina EN-135, a Marine-Derived Entomopathogenic Fungus
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation of the New Compounds
Position | δH (J in Hz) | δC | Position | δH (J in Hz) | δC |
---|---|---|---|---|---|
HMA1 | - | - | Leu4 | - | - |
CO | - | 169.7 C | CO | - | 171.1 C |
1 | 3.19, m; 2.92, d (13.6) | 37.6 CH2 | α | 4.68, m | 51.9 CH |
2 | 5.63, m | 74.3 CH | β | 2.13, m | 38.6 CH2 |
3 | 2.20, m | 38.0 CH | γ | 2.28, m | 24.1 CH |
4 | 2.03, m; 1.70, m | 24.8 CH2 | δ | 1.48, d (6.8) | 21.1 CH3 |
5 | 1.49, t (6.9) | 11.3 CH3 | δ’ | 1.53, d (6.8) | 18.8 CH3 |
6 | 1.46, d (6.8) | 14.1 CH3 | NH | 9.30, d (6.0) | - |
Gly2 | - | - | Ala5 | - | - |
CO | - | 168.9 C | CO | - | 171.6 C |
α | 4.73, m; 4.64, dd (16.4, 3.4) | 42.4 CH2 | α | 4.84, m | 47.5 CH |
NH | 8.54, br. s | - | β | 1.85, d (7.0) | 17.3 CH3 |
Val3 | - | - | NH | 8.60, d (8.3) | - |
CO | - | 171.7 C | Ala6 | - | - |
α | 4.76, m | 58.1 CH | CO | - | 171.6 C |
β | 2.51, m | 29.9 CH | α | 4.79, m | 48.3 CH |
γ | 1.55, d (7.7) | 22.8 CH3 | β | 1.95, d (7.2) | 16.6 CH3 |
γ’ | 1.51, d (7.7) | 18.6 CH3 | NH | 8.48, d (7.6) | - |
NH | 8.48, d (7.6) | - | - | - | - |
Compound 2 | Compound 3 | |||||
---|---|---|---|---|---|---|
Position | δH (J in Hz) a | δH (J in Hz) b | δC a | Position | δH (J in Hz) b | δC b |
1 | 4.29, d (15.5) 4.00, d (15.5) | 4.43, d (15.8) 4.04, d (15.8) | 62.9 CH2 | 1 | - | 164.1 C |
2 | - | - | 127.3 C | 2 | 6.61, s | 100.0 CH |
3 | - | - | 199.1 C | 3 | - | 128.5 C |
4 | - | - | 76.1 C | 4 | 7.52, s | 119.2 CH |
5 | 3.74, m | 3.91, dd (9.5, 5.3) | 71.4 CH | 5 | - | 135.8 C |
6α 6β | 2.52, m 2.14, m | 2.59, dd (18.1, 5.3) 2.35, dd (18.1, 9.5) | 36.7 CH2 | 6 | 7.24, d (8.4) | 123.1 CH |
7 | - | - | 151.6 C | 7 | 7.39, d (8.4) | 110.2 CH |
8α 8β | 2.07, m 2.20, m | 2.12, dd (18.3, 10.1) 2.24, br. s (18.3) | 36.9 CH2 | 8 | - | 154.2 C |
9 | 3.54, m | 3.60, ddd (10.1, 6.2, 3.5) | 68.6 CH | 9 | - | 68.4 C |
10 | 1.16, d (6.2) | 1.21, d (6.2) | 20.9 CH3 | 10 | 1.61, s | 27.6 CH3 |
11 | 1.08, s | 1.18, s | 18.0 CH3 | 11 | 1.61, s | 27.6 CH3 |
4-OH | 5.05, br. s | - | - | 12 | 4.65, s | 64.1 CH2 |
5-OH | 5.07, d (4.2) | - | - | - | - | - |
2.2. Biological Activities of the Isolated Compounds
3. Experimental Section
3.1. General
3.2. Fungal Material
3.3. Fermentation
3.4. Extraction and Isolation
3.5. X-ray Crystallographic Analysis of Compound 1
3.6. Brine-Shrimp Lethality
3.7. Antimicrobial Assay
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Du, F.-Y.; Li, X.-M.; Zhang, P.; Li, C.-S.; Wang, B.-G. Cyclodepsipeptides and Other O-Containing Heterocyclic Metabolites from Beauveria felina EN-135, a Marine-Derived Entomopathogenic Fungus. Mar. Drugs 2014, 12, 2816-2826. https://doi.org/10.3390/md12052816
Du F-Y, Li X-M, Zhang P, Li C-S, Wang B-G. Cyclodepsipeptides and Other O-Containing Heterocyclic Metabolites from Beauveria felina EN-135, a Marine-Derived Entomopathogenic Fungus. Marine Drugs. 2014; 12(5):2816-2826. https://doi.org/10.3390/md12052816
Chicago/Turabian StyleDu, Feng-Yu, Xiao-Ming Li, Peng Zhang, Chun-Shun Li, and Bin-Gui Wang. 2014. "Cyclodepsipeptides and Other O-Containing Heterocyclic Metabolites from Beauveria felina EN-135, a Marine-Derived Entomopathogenic Fungus" Marine Drugs 12, no. 5: 2816-2826. https://doi.org/10.3390/md12052816
APA StyleDu, F. -Y., Li, X. -M., Zhang, P., Li, C. -S., & Wang, B. -G. (2014). Cyclodepsipeptides and Other O-Containing Heterocyclic Metabolites from Beauveria felina EN-135, a Marine-Derived Entomopathogenic Fungus. Marine Drugs, 12(5), 2816-2826. https://doi.org/10.3390/md12052816