Oxandrastins: Antibacterial Meroterpenes from an Australian Mud Dauber Wasp Nest-Associated Fungus, Penicillium sp. CMB-MD14
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Fungal Isolation
3.3. Fungal Taxonomy
3.4. Global Natural Product Social (GNPS) Molecular Networking
3.5. Extraction and Fractionation of an ISP-2 Agar Cultivation of CMB-MD14
3.6. Extraction and Fractionation of a Rice Cultivation of CMB-MD14
3.7. Metabolite Characterization
3.8. Hydrolysis of Oxandrastin B (2) to Oxandrastin D (4)
3.9. Antibiotic Assays
3.10. Cytotoxicity Assays
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Position | δH, Mult (J in Hz) | |||
---|---|---|---|---|
(1) | (2) | (3) | (4) | |
1 | α. 1.82, dd (12.3, 4.2) | α. 1.81, dd (12.3, 4.1) | α. 1.72, dd (12.0, 4.1) | α. 1.71, dd (12.0, 4.1) |
β. 1.27, dd (12.3, 12.3) | β. 1.14, dd (12.3, 12.1) | β. 1.36, dd (12.1, 12.0) | β. 1.17, dd (12.1, 12.0) | |
2 | 5.25, ddd (12.3, 4.2, 2.4) | 4.07, ddd (12.1, 4.1, 2.8) | 5.17, ddd (12.1, 4.1, 2.7) | 3.94, ddd (11.9, 4.3, 3.0) |
3 | 4.96, d (2.4) | 4.91, d (2.8) | 3.44, d (2.7) | 3.32, d (3.0) A |
5 | 1.40, dd (12.1, 2.2) | 1.33, dd (12.1, 2.9) | 1.45, dd (12.1, 2.0) | 1.39, dd (11.7, 2.7) |
6 | α. 1.56, ddd (13.3, 12.9, 3.0) | α. 1.53, ddd (12.8, 12.4, 3.1) | α. 1.52, ddd (13.1, 12.8, 3.1) | α. 1.51, ddd (12.8, 12.4, 3.2) |
β. 1.52, m | β. 1.49, m | β. 1.46, m | β. 1.48, m | |
7 | α. 2.13, br d (13.4) | α. 2.11, ddd (12.8, 3.2, 3.1) | α. 2.09, ddd (13.1, 3.1, 2.4) | α. 2.07, ddd (13.2, 3.0, 2.8) |
β. 2.77, m | β. 2.75, ddd (12.8, 12.4, 5.0) | β. 2.76, ddd (13.1, 12.8, 4.4) | β. 2.74, m | |
9 | 1.88, br s | 1.85, br s | 1.86, br s | 1.82, br s |
11 | 5.40, br s | 5.44, br s | 5.39, br s | 5.44, br s |
2-COCH3 | 1.92, s | - | 2.03, s | - |
3-COCH3 | 2.07, s | 2.07, s | - | - |
4-CH3 (α) | 1.00, s | 0.959, s | 0.91, s | 0.86, s |
4-CH3 (β) | 0.90, s | 0.88, s | 0.99, s | 0.99, s |
8-CH3 | 1.31, s | 1.30, s | 1.29, s | 1.28, s |
10-CH3 | 1.03, s | 0.99, s | 1.00, s | 0.95, s |
12-CH3 | 1.80, s | 1.80, br s | 1.78, br s | 1.79, br s |
13-CH3 | 1.18, s | 1.18, s | 1.17, s | 1.17, s |
14-CO2CH3 | 3.57, s | 3.56, s | 3.56, s | 3.56, s |
16-CH3 | 1.60, s | 1.59, s | 1.57, s | 1.57, s |
Position | δC, Type | |||||||
---|---|---|---|---|---|---|---|---|
(1) | (2) | (3) | (4) | |||||
1 | 39.6 | CH2 | 42.8 | CH2 | 38.8 | CH2 | 42.2 | CH2 |
2 | 69.4 | CH | 65.6 | CH | 71.9 | CH | 67.0 | CH |
3 | 78.5 | CH | 81.6 | CH | 77.2 | CH | 79.7 | CH |
4 | 39.3 | C | 39.4 | C | 40.0 | C | 39.6 | C |
5 | 50.0 | CH | 49.9 | CH | 48.4 | CH | 48.3 | CH |
6 | 18.6 | CH2 | 18.6 | CH2 | 18.7 | CH2 | 18.8 | CH2 |
7 | 34.1 | CH2 | 34.1 | CH2 | 34.2 | CH2 | 34.3 | CH2 |
8 | 43.5 | C | 43.5 | C | 43.5 | C | 43.6 | C |
9 | 54.5 | CH | 54.6 | CH | 54.6 | CH | 54.6 | CH |
10 | 39.5 | C | 39.4 | C | 39.4 | C | 39.2 | C |
11 | 125.6 | CH | 125.9 | CH | 126.0 | CH | 126.4 | CH |
12 | 137.2 | C | 136.9 | C | 136.7 | C | 136.3 a | C |
13 | 58.6 a | C | 58.4 a | C | 58.4 | C | 58.8 a | C |
14 | 68.9 a | C | 68.9 a | C | 68.8 | C | 68.8 a | C |
15 | ND | C | ND | C | ND | C | ND | C |
16 | 114.8 | C | 114.6 | C | 114.8 | C | 114.9 a | C |
17 | ND | C | 201.8 a | C | 202.3 a | C | ND | C |
2-COCH3 | 172.3 | C | - | - | 172.7 | C | - | - |
2-COCH3 | 21.1 | CH3 | - | - | 21.3 | CH3 | - | - |
3-COCH3 | 172.6 | C | 173.1 | C | - | - | - | - |
3-COCH3 | 20.9 | CH3 | 21.2 | CH3 | - | - | - | - |
4-CH3 (α) | 21.7 | CH3 | 21.9 | CH3 | 22.0 | CH3 | 22.1 | CH3 |
4-CH3 (β) | 28.2 | CH3 | 28.3 | CH3 | 29.1 | CH3 | 29.2 | CH3 |
8-CH3 | 18.3 | CH3 | 18.4 | CH3 | 18.3 | CH3 | 18.4 | CH3 |
10-CH3 | 18.4 | CH3 | 18.5 | CH3 | 18.5 | CH3 | 18.7 | CH3 |
12-CH3 | 19.9 | CH3 | 19.9 | CH3 | 19.9 | CH3 | 19.9 | CH3 |
13-CH3 | 16.2 | CH3 | 16.2 | CH3 | 16.2 | CH3 | 16.2 | CH3 |
14-CO2CH3 | 172.0 | C | 172.0 | C | 172.1 | C | 172.1 | C |
14-CO2CH3 | 52.2 | CH3 | 52.2 | CH3 | 52.1 | CH3 | 52.1 | CH3 |
16-CH3 | 6.4 | CH3 | 6.4 | CH3 | 6.4 | CH3 | 6.4 | CH3 |
Position | δH, Mult (J in Hz) | δC | Type |
---|---|---|---|
1 | 5.21, br s | 69.9 | CH2 |
2 | - | 171.9 | C |
3 | - | 108.4 | C |
4 | - | 156.7 | C |
5 | - | 117.5 | C |
6 | - | 160.0 | C |
7 | - | 116.2 | C |
8 | - | 147.6 | C |
9 | - | 77.6 | C |
10 | a. 2.33, dd (15.7, 2.0) | 43.4 | CH2 |
b. 2.16, dd (15.7, 4.3) | |||
11 | 4.16, dd (3.9, 2.0) | 69.7 | CH |
12 | - | 87.5 | C |
13 | - | 87.0 | C |
14 | - | 120.1 | C |
15 | 3.71, dd (10.5, 5.9) | 68.8 | CH |
16 | a. 2.18, dd (13.9, 5.9) | 40.5 | CH2 |
b. 1.68, dd (13.9, 10.5) | |||
17 | - | 44.6 | C |
18 | 2.40, d (8.1) | 39.4 | CH |
19 | a. 3.01, d (18.6) | 19.2 | CH2 |
b. 2.94, dd (18.6, 8.1) | |||
7-CH3 | 2.07, s | 10.8 | CH3 |
9-CH3 | 1.23, s | 28.3 | CH3 |
13-CH3(a) | 1.52, s | 29.3 | CH3 |
13-CH3(b) | 1.63, s | 26.7 | CH3 |
17-CH3 | 1.03, s | 18.8 | CH3 |
4-OCH3 | 4.06, s | 62.4 | CH3 |
14-OCH3 | 3.41, s | 49.3 A | CH3 |
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Elbanna, A.H.; Khalil, Z.G.; Capon, R.J. Oxandrastins: Antibacterial Meroterpenes from an Australian Mud Dauber Wasp Nest-Associated Fungus, Penicillium sp. CMB-MD14. Molecules 2021, 26, 7144. https://doi.org/10.3390/molecules26237144
Elbanna AH, Khalil ZG, Capon RJ. Oxandrastins: Antibacterial Meroterpenes from an Australian Mud Dauber Wasp Nest-Associated Fungus, Penicillium sp. CMB-MD14. Molecules. 2021; 26(23):7144. https://doi.org/10.3390/molecules26237144
Chicago/Turabian StyleElbanna, Ahmed H., Zeinab G. Khalil, and Robert J. Capon. 2021. "Oxandrastins: Antibacterial Meroterpenes from an Australian Mud Dauber Wasp Nest-Associated Fungus, Penicillium sp. CMB-MD14" Molecules 26, no. 23: 7144. https://doi.org/10.3390/molecules26237144