Mintaimycins, a Group of Novel Peptide Metabolites from Micromonospora sp. C-3509
Abstract
:1. Introduction
2. Results and Discussion
2.1. Discovery of New Secondary Metaboltes (Mintaimycins) from Micromonospora sp. C-3509
2.2. Structural Elucidation of Mintaimycins (1–4)
2.3. Stereochemistry of Mintaimycins
2.4. Speculation of Pathway for Mintaimycins (1–4) Biosynthesis
2.5. Biological Activities of Mintaimycins
3. Materials and Methods
3.1. General Procedures
3.2. Solid State Fermentation of Micromonospora sp. C-3509
3.3. Extraction and Isolation of Mintaimycins (1–4)
3.4. Stereochemistry of β-Methylphenylalanine (β-MePhe) and Phenylalanine (Phe) Residue in Mintaimycins by Marfey’s Method
3.5. Preparation of (R)- and (S)-MTPA Ester Derivatives of Mintaimycins A1 (1), B (2) and A2 (3) by Mosher’s Method
3.6. Pre-Adipocyte Differentiation Assay
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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Mintaimycin A1 (1) | Mintaimycin B (2) | Mintaimycin A2 (3) | Mintaimycin A3 (4) | |||||
---|---|---|---|---|---|---|---|---|
Position | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) |
1 | 172.5, C | 170.7, C | 171.0, C | 172.5, C | ||||
1-NH | 7.22, d (10.2) | 6.15, d (8.0) | 7.88, d (9.6) | 7.12, d (8.8) | ||||
2 | 60.8, CH | 4.50, dd (10.2, 8.4) | 59.1, CH | 4.50, t (7.2) | 55.0, CH | 4.44, m | 56.6, CH | 4.67, m |
3 | 42.4, CH | 3.19, dq (10.2, 6.6) | 40.5, CH | 3.43, m | 37.5, CH2 | 2.88, dd (15.8, 6.6); 2.80, dd (15.8, 9.0) | 39.6, CH2 | 2.93, dd (11.9, 7.2); 3.10, dd (11.9, 7.2) |
4 | 145.2, C | 141.7, C | 137.9, C | 139.3, C | ||||
5 | 129.2, CH | 7.29, overlap | 127.6, CH | 7.24, overlap | 128.2, CH | 7.25, overlap | 130.8, CH | 7.26, overlap |
6 | 129.9, CH | 7.27, overlap | 128.9, CH | 7.31, t (7.2) | 129.3, CH | 7.25, overlap | 129.7, CH | 7.26, overlap |
7 | 128.0, CH | 7.22, m | 127.2, CH | 7.23, d (7.2) | 126.4, CH | 7.18, m | 127.9, CH | 7.19, overlap |
8 | 129.9, CH | 7.27, overlap | 128.9, CH | 7.31, t (7.2) | 129.3, CH | 7.25, overlap | 129.7, CH | 7.26, overlap |
9 | 129.2, CH | 7.29, overlap | 127.6, CH | 7.24, overlap | 128.2, CH | 7.25, overlap | 130.8, CH | 7.26, overlap |
10 | 20.7, CH3 | 1.29, d (7.2) | 18.2, CH3 | 1.30, d (7.2) | ||||
1′ | 166.4, C | 165.8, C | 164.9, C | 166.5, C | ||||
1′-NH | 7.09, d (8.4) | 5.77, d (7.2) | 8.21, d (8.4) | 7.34, d (8.0) | ||||
2′ | 126.5, CH | 5.76, dt (15.6, 1.2) | 123.7, CH | 5.62, d (15.2); | 125.4, CH | 5.93, d (15.0) | 126.7, CH | 5.98, d (14.4) |
3′ | 143.9, CH | 6.62, td (15.0, 7.8) | 145.1, CH | 6.70, td (15.2, 7.2) | 141.6, CH | 6.53, td (15.0, 7.2) | 144.0, CH | 6.71, dt (14.4, 6.4) |
4′ | 42.4, CH2 | 1.97, m | 41.3, CH2 | 2.00, m | 40.6, CH2 | 2.00, m | 42.5, CH2 | 2.05, overlap |
5′ | 29.3, CH | 1.66, m | 27.8, CH | 1.88, m | 27.6, CH | 1.67, m | 29.3, CH | 1.72, m |
6′ | 23.3, CH3 | 0.86, d (6.6) | 22.3, CH3 | 0.87, d (6.4) | 21.6, CH3 | 0.87, d (6.6) | 23.3, CH3 | 0.90, d (6.4) |
7′ | 23.3, CH3 | 0.86, d (6.6) | 22.4, CH3 | 0.87, d (6.4) | 22.3, CH3 | 0.87, d (6.6) | 23.3, CH3 | 0.90, d (6.4) |
1″ | 22.5, CH3 | 1.22, d (6.6) | 21.4, CH3 | 0.94, d (6.4) | 22.0, CH3 | 1.89, d (6.0) | 24.7, CH3 | 1.06, d (6.4) |
2″ | 78.4, CH | 4.28, m | 23.9, CH3 | 0.93, d (6.4) | 76.9, CH | 4.27, m | 67.3, CH | 3.64, overlap |
3″ | 31.7, CH2 | 1.90, m; 1.38, m | 24.8, CH | 1.64, m | 29.8, CH2 | 1.76, m; 1.26, m | 38.5, CH2 | 1.37, m; 1.28, m |
4″ | 20.3, CH2 | 1.98, m; 1.89, m | 19.5, CH2 | 1.99, m; 1.87, m | 18.5, CH2 | 1.83, m; 1.68, m | 24.8, CH2 | 1.86, m; 1.72, m |
5″ | 45.3, CH | 2.77, ddd (9.0, 7.2, 2.4) | 43.8, CH | 2.58, m | 43.5, CH | 2.65, m | 49.4, CH | 2.51, m |
6″ | 75.3, CH | 4.16, ddd (8.4, 6.0, 1.8) | 73.8, CH | 4.11, overlap | 73.0, CH | 3.94, ddd (9.0, 6.6, 1.8) | 76.2, CH | 3.69, m |
7″ | 50.3, CH | 4.03, m | 49.3, CH | 4.10, overlap | 48.2, CH | 3.64, m | 51.3, CH | 3.90, m |
8″ | 43.3, CH2 | 1.79, m; 1.38, m | 40.8, CH2 | 1.55, m; 1.26, m | 41.0, CH2 | 1.46, m; 1.13, m | 39.8, CH2 | 1.38, m |
9″ | 26.2, CH | 1.79, m | 30.3, CH2 | 1.89, m; 1.42, m | 24.1, CH | 1.14, m | 25.5, CH | 1.28, m |
10″ | 23.1, CH3 | 0.95, d (6.6) | 78.0, CH | 4.39, m | 22.4, CH3 | 0.74, d (6.6) | 22.3, CH3 | 0.78, d (6.4) |
11″ | 25.2, CH3 | 0.93, d (6.6) | 22.0, CH3 | 1.31, d (7.2) | 24.2, CH3 | 0.74, d (6.6) | 25.1, CH3 | 0.80, d (6.4) |
12″ | 173.8, C | 173.8, C | 172.9, C | 176.2, C | ||||
13″-OCH3 | 50.9, CH3 | 3.49, s | 52.2, CH3 | 3.63, s |
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Hu, X.; Wang, Y.; Zhao, C.; Li, S.; Hu, X.; You, X.; Shen, J.; Wang, Z.; Hong, B.; Jiang, B.; et al. Mintaimycins, a Group of Novel Peptide Metabolites from Micromonospora sp. C-3509. Molecules 2022, 27, 1150. https://doi.org/10.3390/molecules27041150
Hu X, Wang Y, Zhao C, Li S, Hu X, You X, Shen J, Wang Z, Hong B, Jiang B, et al. Mintaimycins, a Group of Novel Peptide Metabolites from Micromonospora sp. C-3509. Molecules. 2022; 27(4):1150. https://doi.org/10.3390/molecules27041150
Chicago/Turabian StyleHu, Xiaomin, Ying Wang, Chunyan Zhao, Shufen Li, Xinxin Hu, Xuefu You, Jiajia Shen, Zhen Wang, Bin Hong, Bingya Jiang, and et al. 2022. "Mintaimycins, a Group of Novel Peptide Metabolites from Micromonospora sp. C-3509" Molecules 27, no. 4: 1150. https://doi.org/10.3390/molecules27041150