Cytotoxic Polyketides from the Deep-Sea-Derived Fungus Engyodontium album DFFSCS021
Abstract
:1. Introduction
2. Results and Discussion
Position | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 |
---|---|---|---|---|---|---|---|---|
δH (J) | δH (J) | δH (J) | δH (J) | δH (J) | δH (J) | δH (J) | δH (J) | |
1 | 3.84, d (6.0) | 3.78, d (5.5) | 3.62, d (3.5) | 3.60, d (4.5) | 3.63, d (6.0) | 4.03, d (10.0) | ||
2 | 4.11, ddd (3.5, 6.0, 9.5) | 3.99, br t (5.5) | 4.14, ddd (2.5, 3.5, 6.0) | 4.15, br t (4.5) | 3.99, dd (1.5, 6.0) | 5.01, br d (10.0) | ||
3 | 7.79, d (9.0) | 8.06, d (9.0) | 1.84, m 2.01, m | 4.04, ddd (4.5, 5.0, 5.5) | 1.80, m 1.90, m | 3.96, ddd (3.5, 4.5, 4.5) | 3.92, ddd (1.5, 4.5, 6.5) | 6.49, d (2.0) |
4 | 7.82, d (8.5) | 7.84, d (9.0) | 2.73–2.89, m | 3.10, dd (4.0, 18.5) | 2.73–2.87, m | 3.03, dd (4.5, 18.5) | 3.07, dd (4.5, 18.5) | 6.36, d (2.0) |
2.60, dd (5.0, 18.5) | 2.70, dd (3.5, 18.5) | 2.79, dd (6.5, 18.5) | ||||||
5 | 7.02, s | 7.05, s | 6.96, s | 6.89, s | 6.98, s | 6.98, s | 6.98, s | 6.98, s |
7 | 6.77, s | 6.81, s | 6.73, s | 6.65, s | 6.74, s | 6.74, s | 6.74, s | 6.75, s |
15 | 3.87, s | 3.95, s | 3.60, s | 3.60, s | 3.64, s | 3.65, s | 3.65, s | 3.58, s |
16 | 4.60, s | 4.62, d (4.5) | 4.56, s | 2.37, s | 4.58, s | 4.56, s | 4.56, s | 4.56, s |
2-OH | 5.49, brs | 5.90, brs | ||||||
8-OH | 12.11, s | 11.88, brs | 12.29, s | 12.29, s | 12.41, brs | 12.25, brs | 12.39, s | |
16-OH | 5.58, t (4.5) | 5.50, brs | 5.50, brs | |||||
8-OCH3 | 3.88, s |
Position | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 |
---|---|---|---|---|---|---|---|---|
δC | δC | δC | δC | δC | δC | δC | δC | |
1 | 120.3, C | 131.0, C | 43.5, CH | 42.3, CH | 46.2, CH | 43.5, CH | 44.6, CH | 41.7, CH |
2 | 154.4, C | 125.5, C | 65.1, CH | 68.1, CH | 65.4, CH | 66.3, CH | 65.8, CH | 65.9, CH |
3 | 121.3, CH | 136.4, CH | 26.1, CH2 | 66.1, CH | 26.1,CH2 | 69.8, CH | 69.9, CH | 145.0, CH |
4 | 120.8, CH | 121.3, CH | 25.7, CH2 | 32.8, CH2 | 23.8, CH2 | 32.9, CH2 | 33.4, CH2 | 119.7, CH |
5 | 103.9, CH | 104.1, CH | 103.8, CH | 107.2, CH | 103.9, CH | 103.9, CH | 103.9, CH | 104.1, CH |
6 | 155.5, C | 154.8, C | 155.5, C | 147.2, C | 152.3, C | 152.1, C | 152.3, C | 152.2, C |
7 | 107.2, CH | 107.8, CH | 107.7, CH | 111.4, CH | 107.8, CH | 107.9, CH | 107.9, CH | 108.3, C |
8 | 160.2, C | 160.4, C | 159.3, C | 159.2, C | 159.3, C | 159.4, C | 159.3, C | 159.3, C |
9 | 180.2, C | 179.2, C | 181.1, C | 180.7, C | 181.2, C | 180.1, C | 180.8, C | 180.0, C |
10 | 117.1, C | 118.0, C | 113.9, C | 113.1, C | 113.1, C | 112.7, C | 113.0, C | 111.0, C |
11 | 152.0, C | 154.3, C | 166.9, C | 164.1, C | 166.7, C | 164.3, C | 164.8, C | 160.4, C |
12 | 156.2, C | 155.3, C | 152.2, C | 155.6, C | 155.5, C | 155.7, C | 155.7, C | 154.9, C |
13 | 107.0, C | 106.9, C | 107.9, C | 107.2, C | 107.9, C | 107.8, C | 107.9, C | 108.3, C |
14 | 166.2, C | 165.7, C | 171.4, C | 170.0, C | 172.0, C | 170.7, C | 172.3, C | 169.7, C |
15 | 52.4, CH3 | 52.9, CH3 | 51.5, CH3 | 51.5, CH3 | 52.0, CH3 | 51.5, CH3 | 51.9, CH3 | 51.5, CH3 |
16 | 62.3, CH2 | 62.2, CH2 | 62.1, CH2 | 21.7, CH3 | 62.2, CH2 | 62.2, CH2 | 62.1, CH2 | 62.1, CH2 |
2-OCH3 | 58.6, OCH3 |
Compound | JH-1,H-2 | JH-2,H-3 | JH-3,H-4 | Orientations of H-1, H-2, H-3 |
---|---|---|---|---|
3 | 6.0 | 3.5, 9.5 | H-1: equatorial, H-2: axial | |
4 | 5.5 | 5.5 | 4.5, 5.0 | H-1: equatorial, H-2: axial, H-3: equatorial |
5 | 3.5 | 2.5, 6.0 | H-1: equatorial, H-2: equatorial | |
6 | 4.5 | 4.5 | 3.5, 4.5 | H-1: equatorial, H-2: axial, H-3: equatorial |
7 | 6.0 | 1.5 | 4.5, 6.5 | H-1: axial, H-2: equatorial, H-3: equatorial |
Compound | Zone of Inhibition (mm) a | MIC (μg/mL) | Cytotoxicity (IC50 μM) | ||||||
---|---|---|---|---|---|---|---|---|---|
E. coli | B. subtilis | E. coli | B. subtilis | U937 | Hela | MCF-7 | HepG2 | Huh7 | |
2 | - b | - | - | - | 55.5 | 96.1 | 172.3 | 73.8 | >300 |
3 | - | - | - | - | 218.4 | >300 | >300 | >300 | >300 |
4 | - | - | - | - | 208.6 | >300 | >300 | >300 | >300 |
5 | - | - | - | - | 15.9 | 205.2 | >300 | >300 | >300 |
6 | - | - | - | - | 192.7 | >300 | >300 | >300 | >300 |
7 | - | - | - | - | 287.2 | >300 | >300 | >300 | >300 |
8 | 13.8 | 16.5 | 64.0 | 32.0 | 4.9 | 24.8 | 38.5 | 60.5 | 53.3 |
10 | - | 10.0 | - | 256.0 | c NT | NT | NT | NT | NT |
12 | - | - | - | - | 75.6 | >300 | >300 | >300 | >300 |
14 | - | - | - | - | 127.0 | >300 | >300 | >300 | >300 |
15 | 11.0 | 14.4 | 64.0 | 64.0 | NT | NT | NT | NT | NT |
16 | 15.8 | 17.5 | 64.0 | 64.0 | 8.8 | 60.0 | 102.2 | 52.7 | 133.3 |
19 | 11.4 | 13.6 | 64.0 | 128.0 | NT | NT | NT | NT | NT |
d Dox | 0.06 | 0.8 | 23.1 | 3.3 | 1.2 | ||||
d PG | 31.8 | 43.3 | 2.0 | 2.0 |
3. Experimental Section
3.1. General Experimental Procedure
3.2. Fungal Material
3.3. Fermentation and Extraction
3.4. Purification
3.5. Cytotoxicity
3.6. Antibacterial Activities
3.7. Barnacle Balanus amphitrite Larval Settlement Bioassays
4. Conclusions
Supplementary Files
Supplementary File 1Acknowledgments
Author Contributions
Conflicts of Interest
References
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Yao, Q.; Wang, J.; Zhang, X.; Nong, X.; Xu, X.; Qi, S. Cytotoxic Polyketides from the Deep-Sea-Derived Fungus Engyodontium album DFFSCS021. Mar. Drugs 2014, 12, 5902-5915. https://doi.org/10.3390/md12125902
Yao Q, Wang J, Zhang X, Nong X, Xu X, Qi S. Cytotoxic Polyketides from the Deep-Sea-Derived Fungus Engyodontium album DFFSCS021. Marine Drugs. 2014; 12(12):5902-5915. https://doi.org/10.3390/md12125902
Chicago/Turabian StyleYao, Qifeng, Jie Wang, Xiaoyong Zhang, Xuhua Nong, Xinya Xu, and Shuhua Qi. 2014. "Cytotoxic Polyketides from the Deep-Sea-Derived Fungus Engyodontium album DFFSCS021" Marine Drugs 12, no. 12: 5902-5915. https://doi.org/10.3390/md12125902