Total Syntheses and Anti-Inflammatory Studies of Three Natural Coumarins: Glycycoumarin, Glycyrin, and 3-O-Methylglycyrol
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of Natural Coumarins 1–3
2.2. Anti-Inflammatory Activity of Natural Coumarins 1–3
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Synthesis and Characterization of the Compounds
3.2.1. 2-(2-Bromo-4-hydroxyphenyl)-2-hydroxyacetic Acid (6)
3.2.2. 2-(2-Bromo-4-hydroxyphenyl)acetic Acid (7)
3.2.3. 2-(2,4-Dihydroxyphenyl)acetic Acid (8)
3.2.4. 2-Hydroxy-4,6-bis(methoxymethoxy)benzaldehyde (10)
3.2.5. 2-Methoxy-4,6-bis(methoxymethoxy)benzaldehyde (11)
3.2.6. 2-Hydroxy-6-methoxy-4-(methoxymethoxy)benzaldehyde (12)
3.2.7. 2-Methoxy-4-(methoxymethoxy)-6-((3-methylbut-2-en-1-yl)oxy)benzaldehyde (14)
3.2.8. 6-Hydroxy-2-methoxy-4-(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)benzaldehyde (15)
3.2.9. 4-(7-Acetoxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-2-oxo-2H-chromen-3-yl)-1,3-phenylene Diacetate (16)
3.2.10. Glycycoumarin (1)
3.2.11. 2-Hydroxy-4,6-dimethoxybenzaldehyde (17)
3.2.12. 2,4-Dimethoxy-6-((3-methylbut-2-en-1-yl)oxy)benzaldehyde (18)
3.2.13. 6-Hydroxy-2,4-dimethoxy-3-(3-methylbut-2-en-1-yl)benzaldehyde (19)
3.2.14. 4-(5,7-Dimethoxy-6-(3-methylbut-2-en-1-yl)-2-oxo-2H-chromen-3-yl)-1,3-phenylene Diacetate (20)
3.2.15. Glycyrin (2)
3.2.16. 3-O-Methylglycyrol (3)
3.2.17. Cell Culture
3.2.18. Cell Viability Assay
3.2.19. NO Determination
3.2.20. Real-Time Quantitative PCR
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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No. | Natural Product (δ1) 1 | Synthetic Sample (δ1) 1 | ∆ = δ1 − δ2 |
---|---|---|---|
2 | 159.9 | 160.0 | −0.1 |
3 | 120.3 | 120.3 | 0 |
4 | 136.3 | 136.4 | −0.1 |
4a | 106.1 | 106.2 | −0.1 |
5 | 158.3 | 158.3 | 0 |
6 | 113.4 | 113.4 | 0 |
7 | 159.2 | 159.2 | 0 |
8 | 97.8 | 97.9 | −0.1 |
8a | 152.9 | 152.9 | 0 |
1′ | 118.3 | 118.3 | 0 |
2′ | 155.9 | 156.0 | −0.1 |
3′ | 102.6 | 102.6 | 0 |
4′ | 155.2 | 155.2 | 0 |
5′ | 105.8 | 106.1 | −0.3 |
6′ | 131.5 | 131.5 | 0 |
1″ | 22.2 | 22.3 | −0.1 |
2″ | 122.6 | 122.6 | 0 |
3″ | 130.6 | 130.7 | −0.1 |
4″ | 17.7 | 17.7 | 0 |
5″ | 25.4 | 25.4 | 0 |
-OCH3 | 62.7 | 62.8 | −0.1 |
No. | Natural Product (δ1) 1 | Synthetic Sample (δ1) 1 | ∆ = δ1 − δ2 | Natural Product (δ1) 1 | Synthetic Sample (δ1) 1 | ∆ = δ1 − δ2 |
---|---|---|---|---|---|---|
2 | 160.9 | 160.9 | 0 | 157.9 | 157.9 | 0 |
3 | 121.8 | 121.9 | −0.1 | 103.4 | 103.4 | 0 |
4 | 136.4 | 136.6 | −0.2 | 158.3 | 158.3 | 0 |
4a | 107.5 | 107.5 | 0 | 101.3 | 101.3 | 0 |
5 | 155.0 | 155.0 | 0 | 153.6 | 153.6 | 0 |
6 | 119.6 | 119.6 | 0 | 121.0 | 121.0 | 0 |
7 | 158.9 | 159.0 | −0.1 | 161.0 | 161.0 | 0 |
8 | 95.6 | 95.7 | −0.1 | 97.0 | 96.9 | −0.1 |
8a | 153.7 | 153.8 | −0.1 | 153.8 | 153.8 | 0 |
1′ | 113.7 | 113.7 | 0 | 114.6 | 114.6 | 0 |
2′ | 156.5 | 156.6 | −0.1 | 156.7 | 156.7 | 0 |
3′ | 103.1 | 103.2 | −0.1 | 99.0 | 99.0 | 0 |
4′ | 160.3 | 160.4 | −0.1 | 157.6 | 157.6 | 0 |
5′ | 106.7 | 106.7 | 0 | 114.6 | 114.6 | 0 |
6′ | 132.0 | 132.1 | −0.1 | 121.1 | 121.1 | 0 |
1″ | 22.7 | 22.7 | 0 | 22.5 | 22.4 | 0.1 |
2″ | 122.7 | 122.8 | −0.1 | 122.6 | 122.6 | 0 |
3″ | 131.5 | 131.6 | −0.1 | 131.8 | 131.8 | 0 |
4″ | 18.1 | 18.2 | −0.1 | 18.1 | 18.2 | −0.1 |
5″ | 25.8 | 25.9 | −0.1 | 25.9 | 25.9 | 0 |
-OCH3 | 63.4 | 63.4 | 0 | 57.0 | 57.0 | 0 |
-OCH3 | 56.8 | 56.9 | −0.1 | 63.0 | 63.0 | 0 |
Name | Sequence (5′-3′) |
---|---|
TNF | Forward 5′- GCCTCTTCTCATTCCTGCTTGTGG -3′ |
Reverse 5′- GTGGTTTGTGAGTGTGAGGGTCTG -3′ | |
IL-6 | Forward 5′- CTTCTTGGGACTGATGCTGGTGAC -3′ |
Reverse 5′- AGGTCTGTTGGGAGTGGTATCCTC -3′ | |
IL-1β | Forward 5′- TCGCAGCAGCACATCAACAAGAG -3′ |
Reverse 5′- AGGTCCACGGGAAAGACACAGG -3′ | |
GAPDH | Forward 5′- GGCAAATTCAACGGCACAGTCAAG -3′ |
Reverse 5′- TCGCTCCTGGAAGATGGTGATGG -3′ |
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Peng, T.; Long, B.; Yang, X.; Wang, N.; Wang, X.; He, Y.; Dong, H. Total Syntheses and Anti-Inflammatory Studies of Three Natural Coumarins: Glycycoumarin, Glycyrin, and 3-O-Methylglycyrol. Molecules 2024, 29, 3942. https://doi.org/10.3390/molecules29163942
Peng T, Long B, Yang X, Wang N, Wang X, He Y, Dong H. Total Syntheses and Anti-Inflammatory Studies of Three Natural Coumarins: Glycycoumarin, Glycyrin, and 3-O-Methylglycyrol. Molecules. 2024; 29(16):3942. https://doi.org/10.3390/molecules29163942
Chicago/Turabian StylePeng, Ting, Bin Long, Xiuli Yang, Na Wang, Ximeng Wang, Yujiao He, and Hongbo Dong. 2024. "Total Syntheses and Anti-Inflammatory Studies of Three Natural Coumarins: Glycycoumarin, Glycyrin, and 3-O-Methylglycyrol" Molecules 29, no. 16: 3942. https://doi.org/10.3390/molecules29163942