Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from Perilla frutescens
Abstract
:1. Introduction
2. Results
2.1. Structural Elucidation of the Isolated Compounds
2.2. Physicochemical Properties and Spectroscopic Data of Compounds 1 and 2
2.3. Effects of Compounds (+)-1 and (−)-1 on Cell Viability of RAW 264.7 Macrophages
2.4. Effects of Compounds (+)-1 and (−)-1 on NO Production in RAW 264.7 Macrophages
2.5. Effects of Compound (+)-1 on TNF-α and IL-6 Production in RAW 264.7 Macrophages
2.6. Effects of Compound (+)-1 on iNOS and COX-2 Protein Expression in RAW 264.7 Macrophages
3. Discussion
4. Materials and Methods
4.1. Plant Material
4.2. Extraction and Isolation
4.3. Cell Culture
4.4. Cell Viability Assay
4.5. NO Production Assay
4.6. Cytokines Production Assays
4.7. Western Blot Analysis
4.8. Statistical Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
Abbreviations
References
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Position | Compound 1 | Compound 2 | ||
---|---|---|---|---|
δH | δC | δH | δC | |
1 | 121.0 | 124.0 | ||
2 | 152.4 | 151.8 | ||
3 | 6.44 s | 98.0 | 6.46 s | 98.0 |
4 | 146.5 | 147.7 | ||
5 | 141.8 | 143.2 | ||
6 | 6.38 s | 113.5 | 6.95 s | 112.3 |
7 | 4.40 t (9.6) | 39.2 | 3.26 t (overlapped) | 45.5 |
8 | 2.39 m | 39.6 | 1.76 m | 43.6 |
9 | 0.66 d (7.2) | 15.1 | 1.18 d (6.0) | 19.2 |
1′ | 122.5 | 124.0 | ||
2′ | 152.0 | 151.8 | ||
3′ | 6.30 s | 98.2 | 6.46 s | 98.0 |
4′ | 147.9 | 147.7 | ||
5′ | 143.1 | 143.2 | ||
6′ | 6.80 brs | 111.5 | 6.95 s | 112.3 |
7′ | 3.55 t (9.6) | 44.2 | 3.26 t (overlapped) | 45.5 |
8′ | 2.49 m | 41.3 | 1.76 m | 43.6 |
9′ | 1.28 d (6.6) | 20.1 | 1.18 d (6.0) | 19.2 |
OMe-2 | 3.75 s | 57.3 | 3.69 s | 56.7 |
OMe-4 | 3.80 s | 56.1 | 3.85 s | 56.3 |
OMe-5 | 3.37 s | 56.1 | 3.87 s | 56.9 |
OMe-2′ | 3.39 s | 56.0 | 3.69 s | 56.7 |
OMe-4′ | 3.80 s | 56.3 | 3.85 s | 56.3 |
OMe-5′ | 3.84 s | 57.2 | 3.87 s | 56.9 |
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Zuo, J.; Zhang, T.-H.; Xiong, L.; Huang, L.; Peng, C.; Zhou, Q.-M.; Dai, O. Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from Perilla frutescens. Molecules 2022, 27, 6102. https://doi.org/10.3390/molecules27186102
Zuo J, Zhang T-H, Xiong L, Huang L, Peng C, Zhou Q-M, Dai O. Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from Perilla frutescens. Molecules. 2022; 27(18):6102. https://doi.org/10.3390/molecules27186102
Chicago/Turabian StyleZuo, Jing, Tian-Hao Zhang, Liang Xiong, Lu Huang, Cheng Peng, Qin-Mei Zhou, and Ou Dai. 2022. "Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from Perilla frutescens" Molecules 27, no. 18: 6102. https://doi.org/10.3390/molecules27186102
APA StyleZuo, J., Zhang, T. -H., Xiong, L., Huang, L., Peng, C., Zhou, Q. -M., & Dai, O. (2022). Two Pairs of 7,7′-Cyclolignan Enantiomers with Anti-Inflammatory Activities from Perilla frutescens. Molecules, 27(18), 6102. https://doi.org/10.3390/molecules27186102