Sulfated Aeruginosins from Lake Kinneret: Microcystis Bloom, Isolation, Structure Elucidation, and Biological Activity
Abstract
:1. Introduction
2. Results
3. Materials and Methods
3.1. General Experimental Procedure
3.2. Biological Material
3.3. Isolation Procedure
3.4. Physical Data of the Compounds
3.5. Determination of the Absolute Configuration of the Amino Acids by Marfey’s Method [30]
3.6. Determination of Absolute Configuration of the Hydroxy Acids
3.7. Protease Inhibition Assays
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Position | δC mult. | δH mult. (J in Hz) | HMBC Correlation | COSY Correlation | TOCSY Correlation | ROESY Correlation |
---|---|---|---|---|---|---|
Hpla 1 | 173.2, C | Phe-2,2-NH, Hpla-2,3a,3b | ||||
2 | 72.3, CH | 3.99, dd (7.9, 3.2) | Hpla-3 | Hpla-3a,3b | Hpla-3a,3b | Phe-2-NH, Hpla-3a,3b,5,5′ |
2-OH | 5.75, brm | |||||
3a 3b | 39.6, CH2 | 2.81, dd (14.1, 3.5) 2.55, dd (14.1, 8.0) | Hpla-5,5′ | Hpla-2,3b Hpla-2,3a | Hpla-2,3b Hpla-2,3a | ChoiSul-2, Hpla-2,3b, 5,5′ Hpla-2,3a, 5,5′ |
4 | 128.5, C | Hpla-2,3a, 3b,6,6′, | ||||
5,5′ | 130.6, CH × 2 | 6.98, d (8.4) | Hpla-3a, 3b,5′,5 | Hpla-6,6′ | Hpla-6,6′ | Hpla-2, 2.81, 2.55 |
6,6′ | 114.9, CH × 2 | 6.64, d (8.4) | Hpla-6′,6 | Hpla-5,5′ | Hpla-5,5′ | Phe-5,5′ |
7 | 155.9, C | Hpla-5,5′, 6,6′ | ||||
Phe 1 | 169.0, C | Phe-2,2-NH,3a,3b, ChoiSul-7a | ||||
2 | 51.5, CH | 4.64, q (7.1) | Phe-2-NH, 3a,3b | Phe-2-NH, 3a,3b | Phe-2-NH, 3a,3b | Phe-2-NH, 3a,3b,5,5′, ChoiSul-7eq,7a |
2-NH | 7.62, d (7.1) | Phe-2 | Phe-2,3a, 3b | Phe-2,3a, 3b, Hpla-2 | ||
3a 3b | 38.3, CH2 | 2.85, dd (13.2, 6.4) 2.76, dd (13.2, 8.1) | Phe-2-NH, 5,5′ | Phe-2,3b Phe-2,3a | Phe-2, 2-NH,3b Phe-2, 2-NH,3b | Phe-2, 2-NH,3b,5,5′, ChoiSul-7a Phe-2, 2-NH,3b,5,5′, ChoiSul-7a |
4 | 136.4, C | Phe-2,3a, 3b,6,6′ | ||||
5,5′ | 129.7, CH × 2 | 7.10, d (7.3) | Phe-3a,3b 5′,5 | Phe-6,6′, | Phe-6,6′, | Phe-2,3a, 3b, ChoiSul-2,7a |
6,6′ | 128.4, CH × 2 | 7.26, t (7.3) | Phe-6′,6 | Phe-5,5′,7 | Phe-5,5′,7 | ChoiSul-2 |
7 | 126.7, CH | 7.20, t (7.3) | Phe-5,5′ | Phe-6,6′ | Phe-6,6′ | |
ChoiSul 1 | 171.5, C | Agm-1-NH,1, ChoiSul-2,3pa | ||||
2 | 59.9, CH | 4.05, t (9.1) | ChoiSul-7a | ChoiSul-3pa, 3pe | ChoiSul-3pa, 3pe,3a,7pe, 7a | Agm-1-NH, Phe-5,5′,6,6′, ChoiSul-3pe, 3a |
3pe b 3pa b | 30.6, CH2 | 1.89, m 1.66, m | ChoiSul-2,7a | ChoiSul-3pa, 3a ChoiSul-3pe, 3a | ChoiSul-3pa, 3a,5a, ChoiSul-3pe, 3a | ChoiSul-2,3pa,3a ChoiSul-3pe |
3a | 35.8, CH | 1.58, m | ChoiSul-7a | ChoiSul-3pe, 3pa,4a,7a, | ChoiSul-3pe,7a | |
4a 4b | 19.4, CH2 | 1.71, m 1.29, m | ChoiSul-3a,4b ChoiSul-3a,4a | ChoiSul-7a | ||
5a 5b | 23.7, CH2 | 1.70, m 1.28, m | ChoiSul-5b,7pe ChoiSul-5a | ChoiSul-5b ChoiSul-5a | ||
6 | 70.9, CH | 4.29, brs | ChoiSul-5b | ChoiSul-5a,5b, 7pe,7pa | ChoiSul-5pe, 5b,7pe,7pa, 7a | Phe-3a, ChoiSul-5a,5b,7pe,7pa |
7pe b 7pa b | 31.3, CH2 | 2.27, m 1.49, m | ChoiSul-5pe, 7pa ChoiSul-7pe | ChoiSul-3pe, 7pa ChoiSul-3pe, 7pe | Phe-2, ChoiSul-6,7pa,7a, ChoiSul-6,7pe | |
7a | 54.3, CH | 3.66, dt (11.1, 5.8) | ChoiSul-3pe,3a | ChoiSul-3a, 7pe,7pa | ChoiSul-2,3a, 3pa,6,7pe, 7pa | Phe-2,5,5′, ChoiSul-3a,4a,7pe |
Agm-1-NH | 7.68, t (5.0) | Agm-1 | Agm-1, 1.41 | ChoiSul-2, Agm-1, 2 | ||
1 | 38.1, CH2 | 3.02, m | Agm-1-NH | Agm-1-NH,2,4-NH | Agm-1-NH,2,4-NH | |
2 | 25.9, CH2 | 1.41, m | Agm-3,4 | Agm-1-NH | ||
3 | 26.3, CH2 | 1.41. m | Agm-2,4 | Agm-4-NH | Agm-1-NH,4-NH | |
4 | 40.4, CH2 | 3.02, m | Agm-1-NH, 12 | Agm-1-NH, 2 | Agm-2,3,4-NH, | |
4-NH | 8.58, brs | Agm-4 | Agm-3,4 | Agm-3,4 | ||
5 | 157.5, C | Agm-4 | ||||
5-NH, NH2 | 8.58, brs 8.69, brs | Agm-4 | Agm-3,4 | Agm-3,4 |
Position | δC mult. | δH mult. (J in Hz) | HMBC Correlation | COSY Correlation | TOCSY Correlation | ROESY Correlation |
---|---|---|---|---|---|---|
Hpla 1 | 173.4, C | Hty-2-NH, Hpla-3a,3b | ||||
2 | 72.3, CH | 4.03, m | Hpla-3a,3b | Hpla-3a,3b | Hpla-3a,3b | |
2-OH | 5.73, brs | Hpla-2,3a,3b | ||||
3 | 39.4, CH2 | 2.86, dd (14.0,3.6) 2.62, dd (14.0,8.1) | Hpla-5,5′ | Hpla-2,3b Hpla-2,3a | ||
4 | 128.5, C | Hpla-3a,3b,6,6′ | ||||
5,5′ | 130.6, CH × 2 | 7.00, d (8.6) | Hpla-3a,3b,5′,5 | Hpla-6,6′ | Hpla-2,3a,3b | |
6,6′ | 114.9, CH × 2 | 6.63, d (8.6) | Hpla-6′,6 | Hpla-5,5′ | ||
7 | 155.9, C | Hpla-5,5′,6,6′ | ||||
Hty 1 | 169.7, C | Hty-2 | ||||
2 | 50.5, CH | 4.49, dt (7.7,5.5) | Hty-3a,3b | Hty-3b,4 | Hpla-2, Hty-3a,4, ChoiSul-5b,7ax,7a | |
2-NH | 7.71, d (7.7) | Hty-2, | Hty-2,4 | Hpla-2,3a,3b Hty-2,3a,3b, ChoiSul-7ax | ||
3a 3b | 34.3, CH2 | 1.77, m 1.69, m | Hty-4 | Hty-2,3b,4 Hty-2,3a,4 | ChoiSul-7a | |
4 | 30.2, CH2 | 2.38, m | Hty-3a,3b | |||
5 | 131.6, C | Hty-4,7,7′, | ||||
6,6′ | 129.1, CH × 2 | 6.94, d (8.6) | Hty-4,6′,6 | Hty-7,7′ | Hty-3a,3b,4 | |
7,7′ | 115.3, CH × 2 | 6.65, d (8.6) | Hty-7′,7 | Hty-6,6′ | ||
8 | 155.6, C | Hty-6,6′,7,7′ | ||||
ChoiSul 1 | 171.6, C | Hty-2-NH, ChoiSul-2, 3ax | ||||
2 | 60.1, CH | 4.18, dd (9.3,8.8) | ChoiSul-3pe,3pa | ChoiSul-3a,3pe | ChoiSul-3a,3pe, Agm-1-NH | |
3pe b 3pa b | 30.8, CH2 | 2.02, m 1.77, m | ChoiSul-2,7a | ChoiSul-3a ChoiSul-3a | ChoiSul-3pa ChoiSul-3pe | |
3a | 36.0, CH | 2.27, m | ChoiSul-3pa | ChoiSul-3pe,7a,4a,4b | ChoiSul-3pe,4a,4b,7pa | |
4a 4b | 19.6, CH2 | 1.97, m 1.44, m | ChoiSul-3pa,3a,4b,5b ChoiSul-3pa,3a,4a,5b | ChoiSul-4b ChoiSul-4a | ||
5a 5b | 23.9, CH2 | 1.76, m 1.38, m | ChoiSul-4a, 4b,5b,6, ChoiSul-4a,4b,5a,6 | ChoiSul-5b ChoiSul-5a, Hty-2 | ||
6 | 71.1, CH | 4.35, brs | ChoiSul-5a,5b,7pe,7pa | ChoiSul-4a7pe,7pa | ChoiSul-3a,7pe,7pa | |
7pe b 7pa b | 31.5, CH2 | 2.38, m 1.60, brt (12.0) | ChoiSul-6,7pa,7a ChoiSul-6,7pe,7a | Hty-2,2-NH | ||
7a | 54.3, CH | 4.03, m | ChoiSul-3a,7pe,7pa | ChoiSul-7pe,7pa,7a | Hty-2,3b ChoiSul-3pa,7pe,7a | |
Agm 1-NH | 7.71, t (5.5) | Agm-1 | Agm-1,3 | ChoiSul-2, Agm-1,3 | ||
1 | 31.5, CH2 | 3.03, m | Agm-1-NH,2 | |||
2 | 31.5, CH2 | 1.42, m | Agm-1,3 | Agm-1 | ||
3 | 31.5, CH2 | 1.43, m | Agm-1,2,4 | |||
4 | 40.4, CH2 | 3.03, m | Agm-3 | Agm-3 | ||
4-NH | 8.58, t (5.6) | Agm-1 | Agm-1,3 | Agm-1,3 | ||
5 | 157.5, C | Agm-1 | ||||
5-NH2,NH | 7.65, brs |
Position | δC, Mult. | δH, Mult. (J in Hz) | HMBC Correlation | COSY Correlation | TOCSY Correlation | ROESY Correlation |
---|---|---|---|---|---|---|
Hpla b 1 | 172.3, C | Ile-2,2NH, Hpla-2,2-OH,3a,3b | ||||
2 | 71.9, CH | 4.09, m | Hpla-2-OH,3a,3b | Hpla-2-OH,3a,3b | Hpla-2-OH,3a,3b | Hpla-3a,3b |
2-OH | 5.98, d (5.8) | Hpla-2 | Hpla-2,3a,3b | Ile-2-NH, Hpla-3a, 3b | ||
3a 3b | 39.4, CH2 | 2.92, dd (14.0,3.4) 2.70, dd (14.0,7.6) | Hpla-5,9 | Hpla-2,3b Hpla-2,3a | Hpla-2,2-OH,3b Hpla-2,2-OH,3a | Hpla-9 |
4 | 134.0, C | Hpla-3a,3b,8 | ||||
5 | 130.5, CH | 7.22, d (2.1) | Hpla-3a,3pa,8,9 | Hpla-9 | Hpla-8,9 | Hpla-3a,3b |
6 | 123.8, C | Hpla-5,8,9 | ||||
7 | 148.0, C | Hpla-5,8,9 | ||||
8 | 121.3, CH | 7.45, d (8.9) | Hpla-9 | Hpla-5,9 | ||
9 | 128.8, CH | 7.07, dd (8.9,2.1) | Hpla-3a, 3pb,5 | Hpla-5,8 | Hpla-5,8 | Hpla-3b |
Ile 1 | 168.7, C | Ile-2,2-NH | ||||
2 | 51.8, CH | 4.55, dd (9.4,4.2) | Ile-4a,4b,6 | Ile-2-NH,3 | Ile-3 | Choi-7a |
2-NH | 7.37, d (9.4) | Ile-2 | Ile-2,3,6 | Hpla-2-OH, Ile-2 | ||
3 | 38.2, CH | 1.52, ddq (4.3,7.1, 6.7) | Ile-2,4a,4b,6 | Ile-2,4a,4b,6 | Ile-2,4a,4b,5,6 | Choi-6-OH |
4a 4b | 26.3, CH2 | 1.14, m 0.99, m | Ile-5,6 | Ile-3,4b,5 Ile-3,4a,5 | Ile-3,4b,5,6 Ile-3,4a,5,6 | Choi-6-OH |
Ile 5 | 12.0, CH3 | 0.88, t (7.5) | Ile-4a,4b | Ile-4a,4b | Ile-2,3,4a,4b,6 | |
Ile 6 | 14.1, CH3 | 0.65, d (6.7) | Ile-2,4a,4b | Ile-3 | Ile-3,4a,4b,5 | |
Choi 1 | 173.6, C | Choi-1- NH2,2,3pe | ||||
1- NH2 | 7.29, d (1.0) 6.83, d (1.0) | Choi-1- NHb Choi-1- NHa | Choi-1- NHb Choi-1- NHa | Choi-2 Choi-2 | ||
2 | 59.7, CH | 4.14, dd (9.6,8.4) | Choi-1- NHb,3pe,7a | Choi-3pa,3pe | Choi-3pa, 3pe,3a,4pa | Choi-3pa,3pe |
3pe c 3pa c | 30.6, CH2 | 1.97, m 1.79, ddq (12.5,9.8,7.8) | Choi-2,3pe,7a | Choi-2,3pe, 3a Choi-2,3pa,3a | Choi-2,3pe, 3a Choi-2,3pa,3a | |
3a | 36.3, CH | 2.24, ddq (12.9,7.1,6.0) | Choi-2,3pe, 3pa,4pa | Choi-3pe,3pa, 4pe,4pa,7a | Choi-2,3pe, 3pa,4pa,6,7pe, 7pa | |
4pe c 4pa c | 19.2, CH2 | 2.02, m 1.41, m | Choi-3a,4pa Choi-3a,4pe | Choi-3pe,3pa,3a,4pa Choi-3pe,3pa,3a,4pe | ||
5 | 26.2, CH2 | 1.42, m | Choi-3a,7pa | Choi-4pe,6 | ||
6 | 64.1, CH | 3.90, brs | Choi-4pa,6-OH,7pe | Choi-4pa,6-OH,7pe,7pa | Choi-3pe,3pa, 3a,4pe,4pa,7a | Choi-4pa, 6-OH,7pe |
6-OH | 4.53, d (3.1) | Choi-6 | Choi-4pe,4pa, 5,6,7pe,7pa | Choi-5,6, 7pa, Ile-3,4a | ||
7pe c 7pa c | 33.7, CH2 | 1.96, m 1.69, brtd (11.8, 1.9) | Choi-6-OH | Choi-3a,7pa Choi-3a,7pe | Choi-2,3pe, 3a,4pa,6,7a,7pa Choi-2,3a,5, 6,7a,7pa | |
7a | 54.0, CH | 4.07, m | Choi-4pa, 7pe,7pa | Choi-7pe,7pa | Choi-3a,3pe, 3pa,6,7pe,7pa | Ile-2, Choi-3a,4pa |
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Weisthal Algor, S.; Sukenik, A.; Carmeli, S. Sulfated Aeruginosins from Lake Kinneret: Microcystis Bloom, Isolation, Structure Elucidation, and Biological Activity. Mar. Drugs 2024, 22, 389. https://doi.org/10.3390/md22090389
Weisthal Algor S, Sukenik A, Carmeli S. Sulfated Aeruginosins from Lake Kinneret: Microcystis Bloom, Isolation, Structure Elucidation, and Biological Activity. Marine Drugs. 2024; 22(9):389. https://doi.org/10.3390/md22090389
Chicago/Turabian StyleWeisthal Algor, Shira, Assaf Sukenik, and Shmuel Carmeli. 2024. "Sulfated Aeruginosins from Lake Kinneret: Microcystis Bloom, Isolation, Structure Elucidation, and Biological Activity" Marine Drugs 22, no. 9: 389. https://doi.org/10.3390/md22090389