The Cytochalasins and Polyketides from a Mangrove Endophytic Fungus Xylaria arbuscula QYF
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Identification
2.2. Antimicrobial Activity Assays
2.3. Cytotoxic Activity Assays
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Fungal Material
3.3. Fermentation, Extraction, and Isolation
3.4. ECD and Optical Rotation Computation Methods
3.5. Antimicrobial Assays
3.6. Cytotoxic Assays
3.7. Preparation of MTPA Esters of 7 by the Modified Mosher Ester Method
3.8. X-ray Crystallographic Analyses
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Position | 1 a | 2 b | ||
---|---|---|---|---|
δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | |
1 | 176.7, C | 174.6, C | ||
3 | 61.8, CH | 3.36, m | 60.6, CH | 3.35, m |
4 | 50.3, CH | 2.52, br.s | 50.3, CH | 2.50, overlapped |
5 | 134.9, C | 128.9, C | ||
6 | 137.0, C | 137.6, C | ||
7 | 83.0, CH | 4.07, d (10.0) | 83.2, CH | 4.11, d (10.2) |
8 | 44.8, CH | 3.09, t (10.2) | 44.6, CH | 3.00, overlapped |
9 | 54.4, C | 53.3, C | ||
10 | 44.7, CH2 | α: 2.85, dd (13.2, 9.9) β: 3.06, dd (13.2, 5.3) | 44.4, CH2 | 2.98, overlapped |
11 | 16.7, CH3 | 1.19, s | 17.4, CH3 | 1.46, s |
12 | 58.7, CH2 | α: 4.04, d (11.5) β: 4.22, d (11.5) | 14.2, CH3 | 1.75, s |
13 | 131.0, CH | 5.69, dd (15.5, 10.0) | 132.3, CH | 6.01, dd (15.7, 10.4) |
14 | 134.1, CH | 5.34, ddd (15.4, 10.7, 5.0) | 131.3, CH | 5.95, overlapped |
15 | 39.6, CH2 | α: 2.04, m β: 2.40, m | 38.3, CH2 | α: 2.02, m β: 2.52, overlapped |
16 | 43.4, CH | 2.85, m | 42.3, CH | 2.72, m |
17 | 211.6, C | 210.2, C | ||
18 | 79.4, C | 77.8, C | ||
19 | 129.4, CH | 5.29, dd (15.4, 2.0) | 127.9, CH | 5.16, dd (15.7, 2.4) |
20 | 133.0, CH | 5.96, overlapped | 131.9, CH | 5.34, m |
21 | 76.5, CH | 5.91, overlapped | 75.2, CH | 5.94, overlapped |
22 | 19.8, CH3 | 1.15, d (6.8) | 19.5, CH3 | 1.21, d (6.8) |
23 | 24.6, CH3 | 1.50, s | 24.4, CH3 | 1.52, s |
24 | 172.1, C | 170.2, C | ||
25 | 20.7, CH3 | 2.33, s | 21.1, CH3 | 2.32, s |
1′ | 138.9, C | 137.6, C | ||
2′/6′ | 129.8, CH | 7.32, d (7.0) | 129.0, CH | 7.32, d (7.7) |
3′/5′ | 130.7, CH | 7.25, m | 129.2, CH | 7.19, m |
4′ | 128.0, CH | 7.26, m | 127.2, CH | 7.25, m |
Position | 3 a | 4 b | ||
---|---|---|---|---|
δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | |
1 | 175.1, C | 177.1, C | ||
3 | 61.2, CH | 3.49, m | 62.1, CH | 3.29, m |
4 | 50.7, CH | 2.91, m | 50.2, CH | 2.45, m |
5 | 154.5, C | 129.6, C | ||
6 | 136.3, C | 131.2, C | ||
7 | 199.7, C | 70.1, CH | 3.72, d (10.4) | |
8 | 53.2, CH | 3.58, d (9.7) | 43.3, CH | 2.84, overlapped |
9 | 54.2, C | 50.6, C | ||
10 | 44.9, CH2 | α: 2.98, dd (13.2, 9.9) β: 3.14, dd (13.2, 5.2) | 45.0, CH2 | α: 2.85, overlapped β: 3.00, dd (13.2, 5.4) |
11 | 18.0, CH3 | 1.40, s | 17.2, CH3 | 1.04, s |
12 | 56.0, CH2 | α: 4.04, d (11.5) β: 4.25, d (11.5) | 14.4, CH3 | 1.61, s |
13 | 130.4, CH | 5.35, dd (15.7, 10.4) | 132.1, CH | 5.82, overlapped |
14 | 128.2, CH | 5.86, overlapped | 134.8, CH | 5.19, m |
15 | 39.4, CH2 | α: 2.02, m β: 2.42, m | 38.7, CH2 | α: 1.97, m β: 2.32, m |
16 | 43.3, CH | 2.87, m | 47.8, CH | 2.65, m |
17 | 211.9, C | 210.4, C | ||
18 | 79.5, C | 45.9, CH2 | α: 2.88, overlapped β: 3.26, m | |
19 | 131.7, CH | 5.81, overlapped | 117.9, CH | 5.25, m |
20 | 135.1, CH | 5.21, m | 135.3, CH | 5.85, m |
21 | 75.9, CH | 5.98, t (2.4) | 76.8, CH | 5.81, overlapped |
22 | 19.6, CH3 | 1.16, d (6.8) | 18.9, CH3 | 1.08, d (6.9) |
23 | 24.6, CH3 | 1.49, s | 172.2, C | |
24 | 171.9, C | 20.7, CH3 | 2.27, s | |
25 | 20.7, CH3 | 2.36, s | ||
1′ | 138.5, C | 139.0, C | ||
2′/6′ | 130.0, CH | 7.35, d (7.5) | 129.7, CH | 7.30, d (7.6) |
3′/5′ | 130.7, CH | 7.27, m | 130.7, CH | 7.23, m |
4′ | 128.3, CH | 7.29, m | 127.9, CH | 7.22, m |
Position | 5 | 6 | ||
---|---|---|---|---|
δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | |
2 | 171.4, C | 169.7, C | ||
3 | 117.3, C | 98.0, C | ||
4 | 123.6, C | 159.1, C | ||
5 | 126.4, CH | 8.58, d (8.0) | 104.0, CH | 6.41, s |
6 | 125.3, CH | 7.26, t (8.0) | 156.1, C | |
7 | 131.4, CH | 7.40, t (8.0) | 139.4, C | |
8 | 111.3, CH | 7.17, overlapped | 121.4, C | |
9 | 155.4, C | 70.8, CH | 5.12, s | |
10 | 124.4, CH | 7.47, s | 113.8, C | |
11 | 152.0, C | 43.5, CH2 | α: 2.08, dd (12.8, 9.5) β: 2.73, dd (12.8, 6.2) | |
12 | 124.1, CH | 7.17, overlapped | 76.3, CH | 4.39, m |
13 | 112.2, CH | 6.65, d (3.4) | 53.5, CH3 | 3.50, s |
14 | 162.0, C | 22.1, CH3 | 1.38, d (6.2) | |
15 | 57.8, CH2 | 4.74, s |
Position | 7 a | 8 b | ||
---|---|---|---|---|
δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | |
2 | 72.0, CH | 4.31, m | 169.8, C | |
3 | 34.1, CH2 | α: 1.38, m β: 2.11, m | 117.1, CH | 5.73, s |
4 | 67.1, CH | 4.19, br.s | 157.8, C | |
5 | 113.3, C | 39.7, CH2 | 2.51, t (6.5) | |
6 | 197.9, C | 62.7, CH2 | 4.31, t (6.5) | |
7 | 46.7, CH2 | α: 2.45, dd (15.8, 9.0) β: 2.60, dd (15.8, 4.4) | 167.0, C | |
8 | 65.5, CH | 4.15, m | 41.4, CH2 | 3.38, s |
9 | 38.7, CH2 | α: 2.48, dd (17.4, 8.4) β: 2.72, dd (17.4, 5.0) | 166.5, C | |
10 | 174.0, C | 52.7, CH3 | 3.74, s | |
11 | 56.7, CH3 | 3.35, s | 19.0, CH3 | 2.20, s |
12 | 20.8, CH3 | 1.40, d (6.4) |
MIC of Compounds/μM | ||||||||
---|---|---|---|---|---|---|---|---|
1 | 2 | 3 | 10 | 11 | 12 | Amp. 1 | Ket. 2 | |
MRSA | >100 | 25 | 50 | >100 | 50 | 50 | 0.25 | NT |
S. aureus | >100 | 12.5 | >100 | >100 | >100 | >100 | 0.25 | NT |
S. typhimurium | >100 | >100 | 25 | >100 | 25 | >100 | 0.25 | NT |
P. aeruginosa | >100 | 25 | >100 | >100 | >100 | 12.5 | 0.13 | NT |
C. albicans | 25 | 12.5 | >100 | 25 | 50 | 50 | NT | 0.13 |
Compound | MDA-MB-435 | MDA-MB-231 | HCT116 | A549 | SNB19 | PC3 |
---|---|---|---|---|---|---|
1 | >50 | >50 | >50 | >50 | 39.18 ± 0.71 | >50 |
10 | 3.61 ± 1.60 | >50 | >50 | >50 | 23.76 ± 0.54 | >50 |
11 | >50 | >50 | >50 | 20.11 ± 2.71 | >50 | 22.92 ± 0.43 |
Cisplatin 1 | 44.43 ± 3.25 | 38.16 ± 5.93 | 14.68 ± 1.34 | 26.42 ± 7.58 | 26.54 ± 1.53 | 33.00 ± 0.19 |
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Tan, Q.; Ye, X.; Fu, S.; Yin, Y.; Liu, Y.; Wu, J.; Cao, F.; Wang, B.; Zhu, T.; Yang, W.; et al. The Cytochalasins and Polyketides from a Mangrove Endophytic Fungus Xylaria arbuscula QYF. Mar. Drugs 2024, 22, 407. https://doi.org/10.3390/md22090407
Tan Q, Ye X, Fu S, Yin Y, Liu Y, Wu J, Cao F, Wang B, Zhu T, Yang W, et al. The Cytochalasins and Polyketides from a Mangrove Endophytic Fungus Xylaria arbuscula QYF. Marine Drugs. 2024; 22(9):407. https://doi.org/10.3390/md22090407
Chicago/Turabian StyleTan, Qi, Xinyu Ye, Siqi Fu, Yihao Yin, Yufeng Liu, Jianying Wu, Fei Cao, Bo Wang, Tingshun Zhu, Wencong Yang, and et al. 2024. "The Cytochalasins and Polyketides from a Mangrove Endophytic Fungus Xylaria arbuscula QYF" Marine Drugs 22, no. 9: 407. https://doi.org/10.3390/md22090407