Generation of Unusual Aromatic Polyketides by Incorporation of Phenylamine Analogues into a C-Ring-Cleaved Angucyclinone
Abstract
:1. Introduction
2. Results and Discussion
2.1. Generation of 3–6 by Nonenzymatic Incorporation of Phenylamine Analogues into C-Ring-Cleaved Angucyclinone 2
2.2. Structural Elucidation of 3–6
2.3. Biological Activity Assays
3. Materials and Methods
3.1. General Experimental Procedures
3.2. The Fermentation and Isolation of 2
3.3. The Conversion of 2 to 3–6
3.4. Biological Activity Assays
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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NO. | 1 | 3 | 4 | 5 | 6 | |||||
---|---|---|---|---|---|---|---|---|---|---|
δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | |
1 | - | 134.8 | - | 134.9 | - | 135.0 | - | 135.2 | - | 134.8 |
2 | 7.27, s | 114.0 | 7.25, s | 113.9 | 7.23, s | 114.2 | 7.26, s | 114.1 | 7.30, s | 114.1 |
3 | - | 134.1 | - | 134.3 | - | 134.0 | - | 134.0 | - | 134.3 |
4 | 7.56, s | 124.1 | 7.55, s | 124.2 | 7.54, s | 124.1 | 7.54, s | 124.0 | 7.55, s | 124.2 |
4a | - | 113.1 | - | 113.1 | - | 113.0 | - | 112.9 | - | 113.1 |
5 | 7.85, d (9.6) | 137.2 | 7.85, d (9.6) | 137.3 | 7.84, d (9.5) | 137.2 | 7.84, d (9.5) | 137.2 | 7.84, d (9.5) | 137.3 |
6 | 6.53, d (9.6) | 132.9 | 6.52, d (9.6) | 132.9 | 6.52, d (9.5) | 132.9 | 6.51, d (9.5) | 132.9 | 6.52, d (9.5) | 132.9 |
6a | - | 180.2 | - | 180.2 | - | 180.2 | - | 180.1 | - | 180.2 |
7 | 4.70, d (11.5) | 55.2 | 4.71, br d (9.7) 2 | 55.1 | 4.65, br d (11.0) | 55.4 | 4.71, br d (11.0) | 55.1 | 4.71, br d 2 | 55.1 |
4.50, d (11.5) | 4.47, dd (12.1, 7.2) | - | 4.47, br dd (11.0, 4.0) | - | 4.46, br dd (11.0, 4.6) | - | 4.47, dd (12.7, 7.4) | - | ||
7a | - | 130.2 | - | 130.3 | - | 130.1 | - | 130.1 | - | 130.2 |
8 | - | 157.1 | - | 157.1 | - | 157.2 | - | 157.1 | - | 157.1 |
9 | 7.02, dd (8.0, 1.0) | 111.9 | 7.02, d (8.0) | 112.1 | 7.02, d (8.0) | 111.9 | 7.04, d 2 (8.0) | 112.0 | 7.03, d (8.5) | 112.1 |
10 | 7.11, t (8.0) | 127.9 | 7.13, t (8.0) | 128.0 | 7.13, t (8.0) | 128.0 | 7.17, t (8.0) | 128.0 | 7.15, t (8.0) | 128.1 |
11 | 6.61, dd (8.0, 1.0) | 122.5 | 6.65, br d (7.6) | 122.5 | 6.62, br d (8.0) | 122.5 | 6.67, br d (8.0) | 122.4 | 6.63, br d (7.6) | 122.5 |
11a | - | 130.9 | - | 130.8 | - | 131.1 | - | 131.1 | - | 130.9 |
12 | - | 145.8 | - | 145.8 | - | 145.9 | - | 146.0 | - | 145.6 |
12a | - | 123.0 | - | 123.1 | - | 123.0 | - | 123.0 | - | 123.1 |
12b | - | 123.3 | - | 123.3 | - | 123.3 | - | 123.2 | - | 123.3 |
13 | 3.85, s | 55.5 | 3.84, s | 55.6 | 3.84, s | 55.6 | 3.85, s | 55.6 | 3.84, s | 55.6 |
14 | 2.51, s | 21.5 | 2.51, s 1 | 21.5 | 2.51, s1 | 21.6 | 2.52, s 1 | 21.5 | 2.51, s 1 | 21.5 |
7-OH | 4.68, br s | 4.70, br s 2 | - | 4.62, br s | - | 4.69, br s | - | 4.70, br s 2 | - | |
1′ | - | 136.0 | - | 136.4 | - | 137.4 | - | 129.7 | - | 135.5 |
2′ | 7.54, br d (8.3) | 127.6 | 7.70, br s | 130.7 | 7.36, br s | 128.3 | 7.18, s 2 | 108.2 | 7.61, s 2 | 130.1 |
3′ | 7.45, br t (7.7) | 129.3 | - | 122.7 | - | 136.7 | - | 147.1 | - | 138.6 |
4′ | 7.41, m | 128.3 | 7.50, d (8.0) | 131.8 | - | 133.6 | - | 147.5 | - | 124.0 |
5′ | 7.45, br t (7.7) | 129.3 | 7.45, m | 129.7 | 7.16, br s 2 | 130.1 | 7.04, d 2 | 108.7 | 7.62, d 2 | 132.8 |
6′ | 7.54, br d (8.3) | 127.6 | 7.29, m | 128.6 | 7.19, br s 2 | 124.9 | 6.98, br s | 121.6 | 7.28, m | 127.0 |
7′ | - | - | 82.4 | 2.28, s | 19.4 | 6.10, br s | 101.9 | 2.32, s | 22.5 | |
6.08, br s | ||||||||||
8′ | - | 4.31, s | 82.2 | 2.21, s | 19.0 | - | - | - | - |
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Xiao, H.; Wang, G.; Wang, Z.; Kuang, Y.; Song, J.; Jin, J.; Ye, M.; Yang, D.; Ma, M. Generation of Unusual Aromatic Polyketides by Incorporation of Phenylamine Analogues into a C-Ring-Cleaved Angucyclinone. Molecules 2021, 26, 1959. https://doi.org/10.3390/molecules26071959
Xiao H, Wang G, Wang Z, Kuang Y, Song J, Jin J, Ye M, Yang D, Ma M. Generation of Unusual Aromatic Polyketides by Incorporation of Phenylamine Analogues into a C-Ring-Cleaved Angucyclinone. Molecules. 2021; 26(7):1959. https://doi.org/10.3390/molecules26071959
Chicago/Turabian StyleXiao, Hua, Guiyang Wang, Zhengdong Wang, Yi Kuang, Juan Song, Jing Jin, Min Ye, Donghui Yang, and Ming Ma. 2021. "Generation of Unusual Aromatic Polyketides by Incorporation of Phenylamine Analogues into a C-Ring-Cleaved Angucyclinone" Molecules 26, no. 7: 1959. https://doi.org/10.3390/molecules26071959