Five Tetramic Acid Derivatives Isolated from the Iranian Fungus Colpoma quercinum CCTU A372
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Experiment
2.2. Fungal Material and Morphological Analysis
2.3. Molecular Analysis, Sequencing, and Phylogenetic Analysis
2.4. Scale-up Production, Extraction, and Isolation
2.5. Antimicrobial Activity Assay
2.6. Cytotoxicity Assay
3. Results and Discussion
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Pos. | 1 | 2 | 3 | |||
---|---|---|---|---|---|---|
δH, m (J in Hz) | δC, Type | δH, m (J in Hz) | δC, Type | δH, m (J in Hz) | δC, Type | |
1 | - | 200.7, C | - | 200.1, C | - | 177.3, C |
2 | - | 51.7, C | - | 49.8, C | - | 46.5, C |
3 | 1.91, m | 41.3, CH | 2.17, m | 40.1, CH | 1.35, m | 44.2, CH |
4 | 1.96; 0.98, m | 30.0, CH2 | 2.11; 1.02, m | 30.0, CH2 | 1.68; 1.21, m | 28.5, CH2 |
5 | 1.80; 1.08, m | 37.6, CH2 | 1.15, m | 37.3, CH2 | 1.79; 0.86, m | 37.2, CH2 |
6 | 1.54, m | 35.1, CH | 1.52, m | 35.3, CH | 1.45, m | 34.0, CH |
7 | 1.83; 0.81, m | 43.4, CH2 | 1.72; 0.96, m | 42.6, CH2 | 1.83; 0.74, m | 43.9, CH2 |
8 | 1.85, m | 41.5, CH | 1.80, m | 42.4, CH | 1.86, m | 38.8, CH |
9 | 5.37, s | 130.0, CH | 5.20, s | 128.8, CH | 5.39, s | 130.5, CH |
10 | - | 132.7, C | - | 132.8, C | - | 131.5, C |
11 | 3.02, s (br) | 49.8, CH | 2.24, s (br) | 53.0, CH | 2.18, d (4.04) | 48.4, CH |
12 | 1.41, s | 16.0, CH3 | 1.38, s | 14.7, CH3 | 1.11, s | 19.5, CH3 |
13 | 2.02, t (7.6) | 37.8, CH | 2.92, m | 50.2, CH | 2.53, m | 32.2, CH |
14 | 4.65, d (8.6) | 77.1, CH | 1.86, 1.17, m | 29.5, CH2 | 4.89, d (1.3) | 83.0, CH |
15 | - | 174.3, C | 0.72, t (7.2) | 13.7, CH3 | - | 174.4, C |
16 | 0.93, d (7.0) | 23.1, CH3 | 0.92, d (7.0) | 23.1, CH3 | 0.91, d (7.0) | 22.8, CH3 |
17 | 1.78, s | 24.4, CH3 | 1.77, s | 15.5, CH3 | 1.66, s | 21.8, CH3 |
18 | - | 172.5, C | - | 177.5, C | 1.18, d (7.0) | 15.5, CH3 |
19 | 2.08, s | 21.3, CH3 | - | - | - | - |
20 | 1.01, d (7.7) | 17.4, CH3 | - | - | - | - |
1′ | - | - | - | - | - | - |
2′ | - | n.d | - | n.d | - | - |
3′ | - | n.d | - | n.d | - | - |
4′ | - | 194.9, C | - | 194.5, C | - | - |
5′ | 3.73, s (br) | 62.8, CH | 3.74, m | 62.9, CH | - | - |
6′ | 1.33, d (7.0) | 15.4, CH3 | 1.34, br | 15.5, CH3 | - | - |
7′ | 2.99, s | 27.2, CH3 | 3.01, s | 27.1, CH3 | - | - |
Pos. | 4 | 5 | ||
---|---|---|---|---|
δH, m (J in Hz) | δC, Type | δH, m (J in Hz) | δC, Type | |
1 | - | 186.0, C | - | 184.4, C |
2 | - | 130.4. C | - | 128.6, C |
3 | 6.98, t (7.2) | 146.9, CH | 7.64, d (9.2) | 143.7, CH |
4 | 2.32, m | 27.7, CH2 | 6.53, dd, (15.0, 11.0) | 125.9, CH |
5 | 1.54; 1.40, m | 36.3, CH2 | 6.15, dd (15.0, 7.7) | 151.9, CH |
6 | 1.63, m | 34.4, CH | 2.45, dt (14.0, 7.0 (2x)) | 39.5, CH |
7 | 2.15; 1.99, m | 41.4, CH2 | 2.15; 2.33, m | 41.2, CH2 |
8 | 5.60, dt (15.0, 10.0) | 127.6, C | 5.58, m | 126.8, CH |
9 | 6.05, d (15.0) | 137.8, CH | 6.07, d (15.0) | 138.2, CH |
10 | - | 135.6, C | - | 135.6, C |
11 | 5.37, d (10.0) | 131.2, CH | 5.39, d (10.0) | 131.7, CH |
12 | 3.05, ddd (10.0, 7.0, 4.0) | 37.9, CH | 3.03, m | 37.9, CH |
13 | 4.06, d (4.0) | 75.7, CH | 4.06, d (4.0) | 75.7, CH |
14 | - | 177.1, C | - | 177.1, C |
15 | 1.09, d (7.0) | 18.1, CH3 | 1.09, d (7.0)ov | 18.1, CH3 |
16 | 1.74, d (1.1) | 13.1, CH3 | 1.74, d (1.0) | 13.1, CH3 |
17 | 0.93, d (7.0) | 20.0, CH3 | 1.08, d (7.0)ov | 20.1, CH3 |
18 | 1.90, s | 12.6, CH3 | 1.99, s | 12.8, CH3 |
1′ | - | - | - | - |
2′ | - | 174.9, C | - | 175.2, C |
3′ | - | n.d | - | n.d |
4′ | - | 195.8, C | - | 196.1, C |
5′ | 3.80, q (6.9) | 63,1, CH | 3.80, q (6.9) | 63.3, CH |
6′ | 2.97, s | 27.0, CH3 | 2.98, s | 27.0, CH3 |
7′ | 1.34, d (7.0) | 15.5, CH3 | 1.35, d (7.0) | 15.5, CH3 |
Microorganism | 1 | 2 | 3 | 4 | 5 | Ref |
---|---|---|---|---|---|---|
MIC (µg/mL) | (µg/mL) | |||||
Bacillus subtilis DSM 10 | n.i | 67 | n.i | n.i | n.i | 8.3 a |
Staphylococcus aureus DSM 346 | n.i | n.1 | n.i | n.i | n.i | 1.7 a |
Mucor hiemalis DSM 2656 | n.i | 67 | n.i | n.i | n.i | 4.2 b |
Pichia anomala DSM 6766 | n.i | n.i | n.i | n.i | n.i | 4.2 b |
Rhodotorula glutinis DSM 10134 | n.i | n.i | n.i | n.i | n.i | 1.0 b |
Acinetobacter baumanii DSM 30008 | n.i | n.i | n.i | n.i | n.i | 0.26 c |
Escherichia coli | n.i | n.i | n.i | n.i | n.i | 1.7 d |
Cell lines | IC50 (µM) | Ref e (µM) | ||||
mouse fibroblast L-929 | n.d | 57.5 | n.d | n.d | n.d | 8.3 × 10−4 |
endocervical adenocarcinoma KB-3.1 | n.d | 5.7 | n.d | n.d | n.d | 5.3 × 10−5 |
human breast adenocarcinoma MCF-7 | n.t | 7.9 | n.t | n.t | n.t | 7.1 × 10−5 |
human lung carcinoma A-549 | n.t | 16.5 | n.t | n.t | n.t | 5.5 × 10−5 |
human prostate cancer PC-3 | n.t | 17.9 | n.t | n.t | n.t | 2.7 × 10−4 |
ovarian carcinoma SK-OV-3 | n.t | 8.1 | n.t | n.t | n.t | 2.4 × 10−4 |
squamous cell carcinoma A-431 | n.t | 6.2 | n.t | n.t | n.t | 8.3 × 10−5 |
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Primahana, G.; Narmani, A.; Surup, F.; Teponno, R.B.; Arzanlou, M.; Stadler, M. Five Tetramic Acid Derivatives Isolated from the Iranian Fungus Colpoma quercinum CCTU A372. Biomolecules 2021, 11, 783. https://doi.org/10.3390/biom11060783
Primahana G, Narmani A, Surup F, Teponno RB, Arzanlou M, Stadler M. Five Tetramic Acid Derivatives Isolated from the Iranian Fungus Colpoma quercinum CCTU A372. Biomolecules. 2021; 11(6):783. https://doi.org/10.3390/biom11060783
Chicago/Turabian StylePrimahana, Gian, Abolfazl Narmani, Frank Surup, Rémy Bertrand Teponno, Mahdi Arzanlou, and Marc Stadler. 2021. "Five Tetramic Acid Derivatives Isolated from the Iranian Fungus Colpoma quercinum CCTU A372" Biomolecules 11, no. 6: 783. https://doi.org/10.3390/biom11060783