New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157
Abstract
:1. Introduction
2. Results
2.1. Taxonomy and Phylogenetic Analysis of the Strain M-157
2.2. Isolation and Structural Elucidation of Compounds 1–3
3. Discussion
4. Materials and Methods
4.1. General Experimental Procedures
4.2. Taxonomic Identification of the Producing Microorganism
4.3. Fermentation of the Producing Microorganism
4.4. Extraction and Bioassay-Guided Isolation
4.5. Hydrolysis and Marfey’s Analysis of Compounds 1 and 2
4.6. Oxidation of Compound 3 with Performic Acid and Marfey’s Analysis
4.7. Antibacterial Activity Assays
4.8. Cytotoxicity Assays
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Position | 1 | 2 | ||
---|---|---|---|---|
δC, Type | δH (J in Hz) | δC, Type * | δH (J in Hz) | |
1 | 167.8, C | 168.7, C | ||
2 | 134.6, C | 135.4, C | ||
3 | 153.1, C | 153.4, C | ||
4 | 120.3, CH | 7.89, s | 120.4, CH | 7.87, s |
5 | 131.6, CH | 131.7, CH | ||
6 | 126.7, CH | 7.91, dd (7.6, 1.8) | 127.0, CH | 7.91, d (7.6, 1.7) |
7 | 128.9, CH 127.8, CH | 7.63, m | 129.2, CH 128.0, CH | 7.65, m |
8 | 7.66, m | 7.67, m | ||
9 | 129.0, CH | 8.05, d (8.3) | 129.4, CH | 8.05, d (8.0) |
10 | 140.8, C | 141.2, C | ||
3-OH | 12.01, s | 12.05, s | ||
1′ | 171.1, C | 172.7, C | ||
2′ | 54.6, CH | 4.61, ddd (8.1, 4.2, 3.3) | 52.3, CH | 4.53, ddd (8.6, 8.0, 3.7) |
3′ | 60.8, CH2 | 3.98, dd (11.2, 4.2) 3.89, dd (11.2, 3.3) | 26.5, CH2 | 2.22, m 2.11, m |
4′ | - | - | 31.6, CH2 | 2.22, m, 2H |
5′ | 173.8, C | |||
NH | 9.19, d (8.1) | 9.53, d (8.8) | ||
COOH | 13.11, br s | - | ||
NH2 | - | 7.32, br s/6.80, br s |
Position | 3 | 6 | ||
---|---|---|---|---|
δC, Type * | δH (J in Hz) | δC, Type * | δH (J in Hz) | |
1 | 159.1, C | 159.1, C | ||
2 | 134.5, C | 134.1, C | ||
3 | 150.2, C | 150.2, C | ||
4 | 119.8, CH | 7.96, br s | 119.7, CH | 7.92, br s |
5 | 130.4, C | 130.4, C | ||
6 | 127.0, CH | 7.89, dd (7.4, 1.8) | 127.0, CH | 7.89, dd (7.1, 1.6) |
7 | 128.9, CH 128.0, CH | 7.59, m | 128.9, CH 128.0, CH | 7.59, ddd (7.1, 6.8, 1.4) |
8 | 7.63, m | 7.62, ddd (8.1, 6.8, 1.6) | ||
9 | 129.4, CH | 8.03, br d (7.8) | 129.4, CH | 8.00, br d (8.1) |
10 | 142.5, C | 142.4, C | ||
3-OH | 10.61, s | 10.45, s | ||
1′ | 159.2, C | 159.2, C | ||
2′ | 136.2, C | 136.0, C | ||
3′ | 143.6, CH | 8.96, s | 143.8, CH | 8.90, s |
1″ | 172.0, C | 172.0, C | ||
2″ | 55.3, CH | 4.58, m | 51.6, CH | 4.79, ddd (8.5, 4.5, 4.3) |
3″ | 25.6, CH2 | 3.08, m 2.96, m | 39.3, CH2 | 3.38, m 3.19, dd (12.6, 4.5) |
NH | 9.20, d (8.5) | |||
COOH | 13.09, br s |
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Ortiz-López, F.J.; Alcalde, E.; Sarmiento-Vizcaíno, A.; Díaz, C.; Cautain, B.; García, L.A.; Blanco, G.; Reyes, F. New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157. Mar. Drugs 2018, 16, 371. https://doi.org/10.3390/md16100371
Ortiz-López FJ, Alcalde E, Sarmiento-Vizcaíno A, Díaz C, Cautain B, García LA, Blanco G, Reyes F. New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157. Marine Drugs. 2018; 16(10):371. https://doi.org/10.3390/md16100371
Chicago/Turabian StyleOrtiz-López, Francisco Javier, Elsa Alcalde, Aida Sarmiento-Vizcaíno, Caridad Díaz, Bastien Cautain, Luis A. García, Gloria Blanco, and Fernando Reyes. 2018. "New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157" Marine Drugs 16, no. 10: 371. https://doi.org/10.3390/md16100371