Paspalines C–D and Paxillines B–D: New Indole Diterpenoids from Penicillium brefeldianum WZW-F-69
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Elucidation of the New Compounds
2.2. Bioactivities of Compounds
3. Materials and Methods
3.1. General Apparatus
3.2. Fungal Material
3.3. Fermentation and Extraction
3.4. Isolation and Purification
3.5. Antimicrobial Activity
3.6. Cytotoxic Activity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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No. | 1 | 2 | ||
---|---|---|---|---|
1H | 13C | 1H | 13C | |
1 | 7.74, s | 7.77, s | ||
2 | 150.8, C | 150.6, C | ||
3 | 53.1, C | 53.1, C | ||
4 | 39.3, C | 39.3, C | ||
5 | 1.94, dd (11.3, 5.8) 1.62, m | 33.6, CH2 | 2.05, dd (13.7,4.6) 2.01, dd (12.5, 5.4) | 33.1, CH2 |
6 | 1.89, dd (14.7, 2.7) 1.87, m | 26.9, CH2 | 1.90, m | 23.8, CH2 |
7 | 3.59, dd (9.8, 5.9) | 72.8, CH | 4.80, dd (10.2, 5.9) | 75.5, CH |
9 | 3.68, dd (8.3, 4.6) | 84.1, CH | 3.57, dd (8.5, 4.3) | 83.6, CH |
10 | 1.34, dd (12.1, 5.6) 1.32, m | 22.2, CH2 | 1.59, m | 22.6, CH2 |
11 | 1.71, td (12.9, 3.0) 1.41, m | 33.9, CH2 | 1.55, m 1.32, m | 34.4, CH2 |
12 | 39.3, C | 40.2, C | ||
13 | 1.69, s | 41.4, CH | 1.78, dd (12.7, 3.1) | 40.4, CH |
14 | 1.81, d (12.6) 1.64, brs | 25.2, CH2 | 1.82, m 1.65, td (12.9, 4.1) | 25.1, CH2 |
15 | 1.71, m 1.49, td (12.4, 4.4) | 23.0, CH2 | 1.59, m | 22.6, CH2 |
16 | 2.78, m | 47.8, CH | 2.78, m | 48.7, CH |
17 | 2.70, dd (13.2, 6.5) 2.35, dd (13.2, 10.6) | 27.5, CH2 | 2.70, dd (13.2, 6.4) 2.36, dd (13.2, 10.6) | 27.5, CH2 |
18 | 118.4, C | 118.3, C | ||
19 | 125.4, C | 125.1, C | ||
20 | 7.45, ddd (6.6, 3.2, 1.0) | 118.3, CH | 7.44, m | 118.4, CH |
21 | 7.09, m | 119.6, CH | 7.09, m | 119.6, CH |
22 | 7.10, m | 120.5, CH | 7.09, m | 120.5, CH |
23 | 7.32, ddd (6.4, 2.5, 0.8) | 111.4, CH | 7.32, m | 111.5, CH |
No. | 3 | 4 | 5 | |||
---|---|---|---|---|---|---|
1H | 13C | 1H | 13C | 1H | 13C | |
1 | 7.78, s | 7.70, s | 7.79, s | |||
2 | 151.0, C | 151.9, C | 149.3, C | |||
3 | 50.5, C | 50.7, C | 50.5, C | |||
4 | 43.1, C | 43.1, C | 42.4, C | |||
5 | 2.80, td (13.5, 4.9) 1.49, m | 28.1, CH | 2.78, td (13.7, 4.4) 1.47, m | 28.0, CH | 2.15, td (13.7, 6.4) 1.58, m | 31.4, CH |
6 | 2.31, m 1.95, m | 28.3, CH2 | 2.31, m 1.93, m | 28.3, CH2 | 2.44, m 1.90, dd (14.6, 4.3) | 28.8, CH2 |
7 | 4.84, m | 72.9, CH | 4.84, m | 72.9, CH | 96.5, C | |
9 | 4.85, brs | 80.4, CH | 4.85, brs | 80.4, CH | 4.06, s | 76.9, CH |
10 | 195.3, C | 195.3, C | 198.5, C | |||
11 | 5.85, d (2.1) | 120.1, CH | 5.84, d (2.0) | 120.1, CH | 5.81, d (2.0) | 122.1, CH |
12 | 166.1, C | 166.1, C | 165.1, C | |||
13 | 77.5, C | 77.5, C | 2.83, m | 42.0, CH | ||
14 | 2.08, m 1.66, m | 34.4, CH2 | 2.07, m 1.67, m | 34.4, CH2 | 1.72, m 1.52, m | 25.5, CH2 |
15 | 2.07, m | 20.9, CH2 | 2.05, m 1.80, m | 20.9, CH2 | 1.86, m | 24.1, CH2 |
16 | 2.89, d (2.8) | 49.6, CH | 2.85, m | 49.6, CH | 2.85, m | 49.0, CH |
17 | 2.91, d (6.2) 2.62, m | 29.0, CH2 | 2.74, dd (13.0, 6.3) 2.45, dd (13.2, 10.9) | 27.2, CH2 | 2.74, dd (13.4, 6.4) 2.45, m | 27.3, CH2 |
18 | 116.9, C | 117.1, C, | 118.4, C | |||
19 | 124.4, C | 125.6, C | 125.0, C | |||
20 | 133.1, C | 7.25 (brs) | 117.6, CH | 7.47, dd (6.8, 2.2) | 118.5, CH | |
21 | 6.88, dt (7.3, 0.8) | 119.0, CH | 133.3, C | 7.12, m | 120.8, CH | |
22 | 7.03, dd (8.1, 7.3) | 121.0, CH | 6.94, dd (8.2, 1.7) | 121.4, CH | 7.12, m | 119.8, CH |
23 | 7.17, dd (8.1, 1.0) | 109.3, CH | 7.23, dd (8.1, 1.0) | 111.3, CH | 7.33, dd (6.8, 2.2) | 111.4, CH |
24 | 139.7, C | 138.2, C | 140.0, C | |||
25 | 1.34, s | 16.2, CH3 | 1.33, s | 16.2, CH3 | 1.12, s | 14.7, CH3 |
26 | 1.08, s | 19.8, CH3 | 1.05, s | 19.7, CH3 | 1.03, s | 15.9, CH3 |
27 | 81.9, C | 81.9, C | 72.4, C | |||
28 | 1.46, s | 22.8, CH3 | 1.46, s | 22.8, CH3 | 1.29, s | 24.0, CH3 |
29 | 1.68, s | 23.8, CH3 | 1.68, s | 23.8, CH3 | 1.35, s | 26.7, CH3 |
30 | 170.8, C | 170.8, C | 3.40, s | 49.1, CH3 | ||
31 | 2.06, s | 22.3, CH3 | 2.06, s | 22.3, CH3 | ||
32 | 3.64, d (7.3) | 32.0, CH2 | 3.43, d (7.3) | 34.5, CH2 | ||
33 | 5.43, m | 123.7, CH | 5.40, m | 124.6, CH | ||
34 | 131.8, C | 131.4, C | ||||
35 | 1.76, s | 25.8, CH3 | 1.76, s | 25.8, CH3 | ||
36 | 1.77, s | 17.8, CH3 | 1.77, s | 17.8, CH3 |
HepG-2 | U2OS | MCF 7 | JeKo-1 | HL-60 | |
---|---|---|---|---|---|
Compound 1 | 55.1 | 56.1 | 56.4 | 71.2 | 65.8 |
Compound 6 | 52.4 | 83.4 | 47.5 | 72.4 | 60.3 |
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Lin, W.; Li, H.; Wu, Z.; Su, J.; Zhang, Z.; Yang, L.; Deng, X.; Xu, Q. Paspalines C–D and Paxillines B–D: New Indole Diterpenoids from Penicillium brefeldianum WZW-F-69. Mar. Drugs 2022, 20, 684. https://doi.org/10.3390/md20110684
Lin W, Li H, Wu Z, Su J, Zhang Z, Yang L, Deng X, Xu Q. Paspalines C–D and Paxillines B–D: New Indole Diterpenoids from Penicillium brefeldianum WZW-F-69. Marine Drugs. 2022; 20(11):684. https://doi.org/10.3390/md20110684
Chicago/Turabian StyleLin, Weiwen, Hanpeng Li, Zhiwen Wu, Jingyi Su, Zehong Zhang, Li Yang, Xianming Deng, and Qingyan Xu. 2022. "Paspalines C–D and Paxillines B–D: New Indole Diterpenoids from Penicillium brefeldianum WZW-F-69" Marine Drugs 20, no. 11: 684. https://doi.org/10.3390/md20110684