Anabaenopeptins from Nostoc edaphicum CCNP1411
Abstract
:1. Introduction
2. Materials and Methods
2.1. NRPS Alignment
2.2. Extraction and Isolation of Anabaenopeptins
2.3. LC-MS/MS Analysis
2.4. NMR Analysis
2.5. Enzymatic Assays
3. Results
3.1. Anabaenopeptin Nonribosomal Peptide Synthetase (NRPS) Gene Cluster
3.2. Identification of AP Structures
3.3. Enzymatic Assays
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Species | Strain | Place of Isolation | References |
---|---|---|---|
Nostoc sp. | CENA543 | Brazilian saline–alkaline lake, Nhecolândia, Pantanal | [4] |
Nostoc sp. | Great Hungarian Plain | [5] | |
N. punctiforme | KVS11 | Blassia pusilla (lichen) Norway | [55] |
N. insulare | CBT163 | [56] | |
Nostoc sp. | CBT599 | [56] | |
Nostoc sp. | CENA352 | Southeastern Brazilian coastal forest | [7] |
N. punctiforme | PCC73102 | Plant symbiont | [6] |
Nostoc sp. | ATCC53789 | Macrozamia sp. | [56] |
N. calcicola | CB158 | Scotland, Arron Island (lichen) | [56] |
Nostoc sp. | CENA358 | [7] |
Locus_Tag | Gene | Bp | Domain Organisation | ||||
---|---|---|---|---|---|---|---|
HUN01_12160 | aptA[fragment 1] | A | PCP | ||||
aptA[fragment 2] | 6957 | C | A | PCP | E | ||
HUN01_12150 | aptB | 3231 | C | A | PCP | ||
HUN01_12145 | aptC[fragment 1] | C | A | PCP | |||
aptC[fragment 2] | 7947 | C | A | M | PCP | ||
HUN01_12140 | aptD | 4215 | D | C | A | PCP |
Proposed AA Activated | Residue Position According to GrsA Phe Numbering | |||||||||
---|---|---|---|---|---|---|---|---|---|---|
235 | 236 | 239 | 278 | 299 | 301 | 322 | 330 | 331 | ||
aptA[fragment 1] | Leu/Ile/Val | D | A | F | F | L | G | [A] | T | F |
aptA[fragment 2] | Lys | D | [T] | E | [Q] | I | G | S | [I] | I |
aptB | Leu* | D | A | [L] | F | L | G | [A] | V | F |
aptC[fragment 1] | Phe | D | L | [G] | T | I | G | [C] | V | I |
aptC[fragment 2] | Asn | D | [A] | T | K | V | G | E | V | G |
aptD | Phe | D | A | W | T | [V] | A | G | V | C |
Name | Calculated MW | [M+H]+ m/z | Amino Acid Sequence | ||||||
---|---|---|---|---|---|---|---|---|---|
1 | 2 | 3 | 4 | 5 | 6 | ||||
AP806Ne | 806.43 | 807.43 | Val | CO | Lys | Leu* | Hph | Asn | Phe |
AP820Ne | 820.45 | 821.44 | Val | CO | Lys | Leu* | Hph | MeAsn | Phe |
AP SA6 | 834.46 | 835.47 | Leu* | CO | Lys | Leu* | Hph | MeAsn | Phe |
AP836Ne | 836.44 | 837.50 | Val | CO | Lys | Leu* | Hty | MeAsn | Phe |
Residue | Position | δH (J in Hz) | Residue | Position | δH (J in Hz) |
---|---|---|---|---|---|
Val | NH 1 2 3 4 | 6.62 (d, 6.7) 3.85 (m) 1.53 (m) 1.11 (d, 6.7) 1.02 (d, 6.9) | Hph | NH 1 2 3 4/4′ 5/5′ 6 | 8.82 (d, 3.9) 4.03 (t, 7.7) 2.73, 2.61 1.72 (m) 7.11 (m) 7.32 (d, 7.3) 7.27 (m) |
Lys | NH 1 2 3 4 5 ε-NH | 7.49 (d, 6.1) 3.53 (m) 1.42 (m) 1.33 (m) 1.42 (m) 2.69 (m) 6.05 (m) | N-MeAsn | N-CH31 2 δ-NH2 | 1.81 (s) 5.33 (dd, 9.8, 3.3) 2.41, 2.35 (m) 7.49, 7.03 (m) |
Leu* | NH 1 2 3 4 5 | 7.06 (m) 3.96 (d, 6.6) 1.50 (m) 1.73 (m) 0.95 (m) 0.77 (dd, 6.8, 2.3) | Phe | NH 1 2 3/3′ 4/4′ 5 | 9.02 (d, 8.9) 4.32 (m) 3.30, 2.77 (m) 7.01 (m) 7.19 (d, 7.6) 7.15 (m) |
Name | Enzyme Inhibition (IC50 [µM]) | ||||
---|---|---|---|---|---|
TRY | CHY | E | CPA | Thr | |
AP SA6 | – | – | 5.5 | 4.5 | * |
AP820Ne | – | – | 22.7 | 3.5 | ** |
AP806Ne | – | – | – | 21.1 | * |
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Konkel, R.; Grabski, M.; Cegłowska, M.; Wieczerzak, E.; Węgrzyn, G.; Mazur-Marzec, H. Anabaenopeptins from Nostoc edaphicum CCNP1411. Int. J. Environ. Res. Public Health 2022, 19, 12346. https://doi.org/10.3390/ijerph191912346
Konkel R, Grabski M, Cegłowska M, Wieczerzak E, Węgrzyn G, Mazur-Marzec H. Anabaenopeptins from Nostoc edaphicum CCNP1411. International Journal of Environmental Research and Public Health. 2022; 19(19):12346. https://doi.org/10.3390/ijerph191912346
Chicago/Turabian StyleKonkel, Robert, Michał Grabski, Marta Cegłowska, Ewa Wieczerzak, Grzegorz Węgrzyn, and Hanna Mazur-Marzec. 2022. "Anabaenopeptins from Nostoc edaphicum CCNP1411" International Journal of Environmental Research and Public Health 19, no. 19: 12346. https://doi.org/10.3390/ijerph191912346