Anti-Inflammatory Phenolic Acid Esters from the Roots and Rhizomes of Notopterygium incisium and Their Permeability in the Human Caco-2 Monolayer Cell Model
Abstract
:1. Introduction
2. Results and Discussion
2.1. Extraction and Isolation
2.2. Structural Elucidation of Isolated Compounds 1–9
2.3. Transport of Phenolic Acid Esters 1–9 in the Human Intestinal Caco-2 Cell Monolayer Model
2.4. Inhibitory Activity of Compounds 1–9 on NO Production
3. Experimental Section
3.1. Plant Material
3.2. Chemicals and Reagents
3.3. Instrumental Analyses
3.4. Cell Culture
3.5. Caco-2 Cell Permeability
3.6. NO Inhibitory Assay
3.7. Statistical Analysis
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–9 are not available from the authors. |
No. | 1 | No. | 8 | ||
---|---|---|---|---|---|
δH (J in Hz) | δC (mult.) a | δH (J in Hz) | δC (mult.) a | ||
1 | – | 127.1, C | 1 | – | 127.1, C |
2 | 7.03, d (1.7) | 109.3, CH | 2 | 7.02, d (2.1) | 109.4, CH |
3 | – | 146.7, C | 3 | – | 146.8, C |
4 | – | 147.9, C | 4 | – | 148.0, C |
5 | 6.92, d (8.1) | 114.7, CH | 5 | 6.92, d, 8.2 | 114.8, CH |
6 | 7.07, dd (8.1, 1.7) | 123.0, CH | 6 | 7.07, dd (8.2, 2.1) | 123.1, CH |
7 | 7.61, d (15.9) | 144.7, CH | 7 | 7.60, d (15.9) | 144.9, CH |
8 | 6.29, d, (15.9) | 115.7, CH | 8 | 6.27, d (15.9) | 115.6, CH |
9 | – | 167.3, C | 9 | – | 167.2, C |
3-OCH3 | 3.93, s | 55.9, CH3 | 3-OCH3 | 3.93, s | 56.0, CH3 |
4-OH | 5.84, s | – | 4-OH | 5.86, s | – |
1′ | 4.17, t (7.1) | 64.2, CH2 | 1′ | – | 130.0, C |
2′ | 2.41, q (6.9) | 27.6, CH2 | 2′, 6′ | 7.18, d (8.8) | 129.9, CH |
3′ | 5.16, t (7.6) | 117.7, CH | 3′, 5′ | 6.86, d (8.8) | 114.0, CH |
4′ | – | 140.2, C | 4′ | – | 158.4, C |
5′ | 2.02, q (7.5) | 32.4, CH2 | 7′ | 2.96, t (7.0) | 34.4, CH2 |
6′ | 1.00, t (7.5) | 12.7, CH3 | 8′ | 4.38, t (7.0) | 65.2, CH2 |
7′ | 1.65, s | 16.1, CH3 | 4′-OCH3 | 3.79, s | 55.3, CH3 |
No. | Papp AP→BL b (×10−6 cm/s) | Papp BL→AP c (×10−6 cm/s) | Efflux Ratio d | MW | Log D (pH = 7.35) |
---|---|---|---|---|---|
1 | 0.50 ± 0.12 | 0.62 ± 0.12 | 1.24 | 290 | 4.59 |
2 | 18.04 ± 1.63 | 13.45 ± 0.63 | 0.75 | 228 | 3.56 |
3 | <0.05 | <0.02 | – | 284 | 5.79 |
4 | 0.36 ± 0.04 | 0.05 ± 0.01 | 0.15 | 272 | 3.74 |
5 | 0.08 ± 0.02 | 0.13 ± 0.02 | 1.69 | 330 | 4.57 |
6 | 17.59 ± 2.27 | 13.85 ± 2.74 | 0.79 | 236 | 3.35 |
7 | <0.02 | <0.01 | – | 614 | 9.97 |
8 | 2.21 ± 0.07 | 2.55 ± 0.44 | 1.15 | 328 | 3.67 |
9 | 0.66 ± 0.16 | 0.70 ± 0.18 | 1.06 | 298 | 3.89 |
No. | IC50 (μM) | No. | IC50 (μM) | No. | IC50 (μM) |
---|---|---|---|---|---|
1 | 1.01 ± 0.08 *** | 5 | 4.63 ± 1.73 * | 10 | 67.94 ± 0.91 |
2 | 53.69 ± 4.13 | 6 | 12.62 ± 2.80 | 11 | >200 |
3 | 70.50 ± 25.86 | 8 | 2.47 ± 0.64 *** | L-NIL | 9.37 ± 1.57 |
4 | 11.11 ± 1.43 | 9 | 2.73 ± 0.58 *** |
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Wu, X.-W.; Wei, W.; Yang, X.-W.; Zhang, Y.-B.; Xu, W.; Yang, Y.-F.; Zhong, G.-Y.; Liu, H.-N.; Yang, S.-L. Anti-Inflammatory Phenolic Acid Esters from the Roots and Rhizomes of Notopterygium incisium and Their Permeability in the Human Caco-2 Monolayer Cell Model. Molecules 2017, 22, 935. https://doi.org/10.3390/molecules22060935
Wu X-W, Wei W, Yang X-W, Zhang Y-B, Xu W, Yang Y-F, Zhong G-Y, Liu H-N, Yang S-L. Anti-Inflammatory Phenolic Acid Esters from the Roots and Rhizomes of Notopterygium incisium and Their Permeability in the Human Caco-2 Monolayer Cell Model. Molecules. 2017; 22(6):935. https://doi.org/10.3390/molecules22060935
Chicago/Turabian StyleWu, Xiu-Wen, Wei Wei, Xiu-Wei Yang, You-Bo Zhang, Wei Xu, Yan-Fang Yang, Guo-Yue Zhong, Hong-Ning Liu, and Shi-Lin Yang. 2017. "Anti-Inflammatory Phenolic Acid Esters from the Roots and Rhizomes of Notopterygium incisium and Their Permeability in the Human Caco-2 Monolayer Cell Model" Molecules 22, no. 6: 935. https://doi.org/10.3390/molecules22060935