Polyketides from the Mangrove-Derived Endophytic Fungus Cladosporium cladosporioides
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
3.5. X-Ray Crystallographic Analysis of Compounds 3 and 6
3.6. Acetylation of Compounds 3 and 4
3.7. Antimicrobial Assay
3.8. Enzyme inhibitory Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Pos. | 1 | 2 | 7 | ||||
---|---|---|---|---|---|---|---|
a δH (J in Hz) | b δH (J in Hz) | d δC | b δH (J in Hz) | e δC | c δH (J in Hz) | f δC | |
1 | 172.3, C | 172.2, C | 174.7, C | ||||
2 | α 2.40, ddd (13.0, 5.6, 3.9) β 1.93, ddd (13.1, 11.0, 4.4) | α 2.40, ddd (13.0, 5.6, 3.9) β 1.93, ddd (13.1, 11.0, 4.4) | 35.2, CH2 | α 2.25, m (overlap) β 2.16, m | 31.8, CH2 | α 3.23, dd (18.5, 8.5) β 2.90, dd (18.5, 1.7) | 43.0, CH2 |
3 | 1.56, m (overlap) | 1.56, m (overlap) | 18.2, CH2 | α 1.67, m (overlap) β 1.54, m | 19.9, CH2 | 4.72, dd (8.5, 1.7) | 65.7, CH |
4 | 1.43, m (overlap) | 1.43, m (overlap) | 32.9, CH2 | α 1.41, m β 0.97, m | 30.0, CH2 | 209.3, C | |
5 | 3.51, m | 3.51, m | 70.2, CH | 3.48, m | 65.4, CH | 4.31, d (5.4) | 76.3, CH |
6 | α 1.60, m (overlap) β 1.35, m (overlap) | α 1.60, m (overlap) β 1.35, m (overlap) | 32.6, CH2 | α 1.63, m (overlap) β 1.30, m | 33.7, CH2 | α 1.97, m β 1.76, m | 30.7, CH2 |
7 | α 2.17, m β 1.72, m | α 2.17, m β 1.72, m | 28.6, CH2 | α 2.05, m β 1.91, m | 27.7, CH2 | α 1.45, m (overlap) β 1.18, m (overlap) | 20.8, CH2 |
8 | 5.34, ddd (15.3, 10.7, 2.8) | 5.34, ddd (15.3, 10.7, 2.8) | 135.2, CH | 5.26, m | 132.7, CH | α 1.60, m (overlap) β 1.31, m (overlap) | 26.9, CH2 |
9 | 5.20, ddd (15.3, 10.1, 4.1) | 5.20, ddd (15.3, 10.1, 4.1) | 125.6, CH | 5.11, m | 126.7, CH | α 1.51, m (overlap) β 1.10, m (overlap) | 22.7, CH2 |
10 | α 2.25, m β 2.06, m | α 2.25, m β 2.06, m | 40.3, CH2 | α 2.29, m (overlap) β 1.99, m (overlap) | 40.3, CH2 | α 1.69, m (overlap) β 1.39, m (overlap) | 33.5, CH2 |
11 | 4.84, m | 4.84, m | 68.3, CH | 5.02, m | 67.8, CH | 4.88, m | 75.2, CH |
12 | 1.17, d (6.3) | 1.17, d (6.3) | 20.4, CH3 | 1.15, d (6.3) | 20.2, CH3 | 1.25, d (6.2) | 19.3, CH3 |
3-OH | 3.19, s | ||||||
5-OH | 4.39, brs | 4.39, brs | 4.28, brs | 3.03, s |
Pos. | 3 | 4 | 5 | 6 | ||||||
---|---|---|---|---|---|---|---|---|---|---|
a δH (J in Hz) | b δH (J in Hz) | d δC | e δC | c δH (J in Hz) | f δC | a δH (J in Hz) | d δC | a δH (J in Hz) | d δC | |
1 | 175.5, C | 175.8, C | 175.5, C | 169.7, C | 173.2, C | |||||
2 | α 2.85, dd (17.7, 6.4) β 2.25, dd (17.7, 3.2) | α 2.78, dd (18.0, 6.7) β 2.47, dd (18.0, 3.7) | 37.0, CH2 | 37.8, CH2 | α 2.85, dd (17.7, 6.4) β 2.25, dd (17.7, 3.2) | 37.0, CH2 | 6.37, d (5.4) | 118.4, CH | 6.21, d (5.6) | 121.1, CH |
3 | 4.09, m | 4.22, m | 70.1, CH | 71.7, CH | 4.09, m | 70.1, CH | 7.80, d (5.4) | 145.1, CH | 7.71, d (5.6) | 156.6, CH |
4 | 4.18, m | 4.31, ddd (8.3, 5.3, 3.0) | 87.5, CH | 88.2, CH | 4.18, ddd (8.1, 5.5, 2.5) | 87.5, CH | 149.4, C | 5.04, d (1.5) | 86.2, CH | |
5 | α 1.56, m β 1.48, m | 1.57, m | 32.1, CH2 | 33.2, CH2 | α 1.57, m β 1.48, m (overlap) | 32.0, CH2 | 5.53, t (7.9) | 117.1, CH | 3.66, m | 69.4, CH |
6 | 1.26, m (overlap) | 1.34, m (overlap) | 25.2, CH2 | 25.7, CH2 | 1.25, m (overlap) | 24.7, CH2 | 2.30, m | 25.8, CH2 | 1.44, m (overlap) | 40.0, CH2 |
7 | 1.33, m (overlap) | 1.41, m (overlap) | 29.0, CH2 | 29.5, CH2 | 1.33, m (overlap) | 28.6, CH2 | 1.44, m | 28.3, CH2 | 1.34, m (overlap) | 32.8, CH2 |
8 | 1.31, m (overlap) | 1.28, m (overlap) | 28.8, CH2 | 29.3, CH2 | 1.31, m (overlap) | 28.5, CH2 | 1.23, m (overlap) | 28.7, CH2 | 1.29, m (overlap) | 29.1, CH2 |
9 | 1.24, m (overlap) | 1.26, m (overlap) | 24.8, CH2 | 25.3, CH2 | 1.24, m (overlap) | 24.6, CH2 | 1.27, m (overlap) | 25.0, CH2 | 1.25, m (overlap) | 25.3, CH2 |
10 | 1.36, m (overlap) | 1.45, m (overlap) | 39.0, CH2 | 39.3, CH2 | 1.45, m (overlap) | 35.2, CH2 | 1.32, m (overlap) | 38.9, CH2 | 1.39, m (overlap) | 39.0, CH2 |
11 | 3.55, m | 3.75, m | 65.7, CH | 68.3, CH | 4.78, m | 70.1, CH | 3.55, m (overlap) | 65.6, CH | 3.55, m | 65.7, CH |
12 | 1.02, d (6.1) | 1.15, d (6.2) | 23.6, CH3 | 23.7, CH3 | 1.15, d (6.3) | 19.7, CH3 | 1.02, d (6.1) | 23.6, CH3 | 1.02, d (6.2) | 23.6, CH3 |
13 | 169.9, C | |||||||||
14 | 1.97, s | 21.0, CH3 | ||||||||
3-OH | 5.49, s | 5.50, d (4.0) | ||||||||
5-OH | 4.95, d (6.3) | |||||||||
11-OH | 4.27, d (4.2) | 3.41, brs | 4.29, d (4.7) |
Strains | Compounds | ||||||
---|---|---|---|---|---|---|---|
1 | 2 | 3 | 4 | 6 | 7 | Positive control | |
E. colib | – | – | – | 32 | 32 | – | 2.0 |
S. aureusb | – | – | 8.0 | – | – | 32 | 1.0 |
E. tardab | – | – | – | – | 32 | – | 0.5 |
E. ictardab | 32 | – | 16 | – | 16 | 4.0 | 0.5 |
G. cingulatec | – | 16 | – | 1.0 | 64 | 1.0 | 0.5 |
B. sorokinianac | – | – | – | 32 | – | – | 0.5 |
P. aeruginosac | 32 | – | 64 | – | – | 32 | 2.0 |
F.oxysporum f. sp. Cucumerinum c | – | – | – | 1.0 | – | – | 0.5 |
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Zhang, F.-Z.; Li, X.-M.; Li, X.; Yang, S.-Q.; Meng, L.-H.; Wang, B.-G. Polyketides from the Mangrove-Derived Endophytic Fungus Cladosporium cladosporioides. Mar. Drugs 2019, 17, 296. https://doi.org/10.3390/md17050296
Zhang F-Z, Li X-M, Li X, Yang S-Q, Meng L-H, Wang B-G. Polyketides from the Mangrove-Derived Endophytic Fungus Cladosporium cladosporioides. Marine Drugs. 2019; 17(5):296. https://doi.org/10.3390/md17050296
Chicago/Turabian StyleZhang, Fan-Zhong, **ao-Ming Li, **n Li, Sui-Qun Yang, Ling-Hong Meng, and Bin-Gui Wang. 2019. "Polyketides from the Mangrove-Derived Endophytic Fungus Cladosporium cladosporioides" Marine Drugs 17, no. 5: 296. https://doi.org/10.3390/md17050296