Study of the UV Light Conversion of Feruloyl Amides from Portulaca oleracea and Their Inhibitory Effect on IL-6-Induced STAT3 Activation
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Elucidation of the Isolated Compounds
2.2. Conversion Study of Compounds 1–10
2.3. Activity of Isolated Compounds
3. Materials and Methods
3.1. Plant Material
3.2. General Procedure
3.3. Isolation and Purification Procedures
3.4. Stability and Conversion Testing of Cis and trans-Feruloyl Amides
3.5. Cell Culture
3.6. Reagents and Chemicals
3.7. Establishment of the Stable Cell Line Expressing pStat3-Luc
3.8. IL-6-Induced STAT3 Activation
3.9. Cell Viability Assay
3.10. Western Blot Analysis
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Positions | 5 (cis, Z) | 6 (trans, E) | 9 (cis, Z) | 10 (trans, E) | ||||
---|---|---|---|---|---|---|---|---|
δH | δc | δH | δc | δH | δc | δH | δc | |
1 | - | 128.0 | - | 127.6 | - | 126.6 | - | 128.5 |
2 | 7.34 (d, 2.0) 2 | 116.2 | 7.07 (d, 2.0) | 111.6 | 7.38 (d, 1.8) | 112.7 | 7.09 (d, 1.8) | 111.8 |
3 | - | 149.3 | - | 149.4 | - | 147.4 | - | 149.2 |
4 | - | 149.8 | - | 149.4 | - | 148.2 | - | 150.1 |
5 | 6.69 (d, 8.0) | 114.0 | 6.74 (d, 8.0) | 117.0 | 6.72 (d, 8.4) | 115.9 | 6.77 (d, 7.8) | 116.7 |
6 | 6.90 (dd, 8.0, 2.0) | 125.2 | 6.98 (dd, 8.0, 2.0) | 123.6 | 6.91 (dd, 8.4, 1.8) | 123.8 | 7.00 (d, 7.8) | 123.5 |
7 | 6.57 (d, 13.2) | 138.6 | 7.41 (d, 15.6) | 142.4 | 6.59 (d, 12.6) | 137.7 | 7.42 (d, 15.6) | 142.5 |
8 | 5.78 (d, 13.2) | 121.2 | 6.36 (d, 15.6) | 118.3 | 5.79 (d, 12.6) | 118.6 | 6.45 (d, 15.6) | 118.9 |
9 | - | 170.6 | - | 169.5 | - | 169.2 | - | 169.8 |
1′ | - | 131.3 | - | 131.4 | - | 133.9 | - | 135.7 |
2′ | 6.45 (s) | 107.1 | 6.50 (s) | 106.9 | 6.93 (d, 1.8) | 109.4 | 6.97 (d, 1.8) | 111.1 |
3′ | - | 149.3 | - | 151.5 | - | 147.6 | - | 149.6 |
4′ | - | 135.2 | - | 135.2 | - | 145.9 | - | 147.4 |
5′ | - | 149.0 | - | 149.9 | 6.69 (d, 8.4) | 114.4 | 6.75 (d, 7.8) | 116.2 |
6′ | 6.45 (s) | 107.0 | 6.50 (s) | 107.2 | 6.76 (dd, 8.4, 1.8) | 118.6 | 6.81 (dd, 7.8, 1.8) | 120.2 |
7′ | 2.70 (t, 7.2) | 36.6 | 2.75 (t, 7.2) | 36.8 | 4.66 (dd, 7.8, 4.8) | 72.2 | 4.71 (dd, 7.8, 4.8) | 73.8 |
8′ α | 3.42 (t, 7.6) | 42.4 | 3.47 (t, 7.6) | 42.6 | 3.39 (dd, 13.8, 5.4) | 46.8 | 3.43 (dd, 13.8, 5.4) | 50.0 |
8′ β | 3.42 (t, 7.6) | 42.4 | 3.47 (t, 7.6) | 42.6 | 3.46 (dd, 13.2, 7.8) | 46.8 | 3.52 (dd, 13.2, 7.8) | 50.0 |
3-OCH3 | 3.75 (s) | 56.8 | 3.80 (s) | 56.9 | 3.79 (s) | 55.0 | 3.82 (s) | 55.6 |
3′-OCH3 | 3.75 (s) | 56.8 | 3.80 (s) | 56.9 | 3.80 (s) | 55.0 | 3.84 (s) | 55.5 |
5′-OCH3 | 3.79 (s) | 56.4 | 3.85 (s) | 56.5 | - | - | - | - |
Compounds | IC50 (μM) |
---|---|
N-cis-feruloyltyramine (1) | 19.3 |
N-trans-feruloyltyramine (2) | 5.6 |
Converted mixture (1 + 2) | 15.2 |
N-cis-feruloyl-3′-methoxytyramine (3) | 16.2 |
N-trans-feruloyl-3′-methoxytyramine (4) | 6.0 |
Converted mixture (3 + 4) | 6.5 |
N-cis-hibiscusamide (5) | 6.7 |
N-trans-hibiscusamide (6) | 0.2 |
Converted mixture (5 + 6) | 5.9 |
(7′S)-N-cis-feruloyloctopamine (7) | 19.5 |
(7′S)-N-trans-feruloyloctopamine (8) | 2.6 |
Converted mixture (7 + 8) | 6.7 |
(7′S)-N-cis-feruloylnormetanephrine (9) | 28.6 |
(7′S)-N-trans-feruloylnormetanephrine (10) | 13.0 |
Converted mixture (9 + 10) | 13.7 |
Oleanolic acid acetate 1 | 0.7 |
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Hwang, J.T.; Kim, Y.; Jang, H.-J.; Oh, H.-M.; Lim, C.-H.; Lee, S.W.; Rho, M.-C. Study of the UV Light Conversion of Feruloyl Amides from Portulaca oleracea and Their Inhibitory Effect on IL-6-Induced STAT3 Activation. Molecules 2016, 21, 865. https://doi.org/10.3390/molecules21070865
Hwang JT, Kim Y, Jang H-J, Oh H-M, Lim C-H, Lee SW, Rho M-C. Study of the UV Light Conversion of Feruloyl Amides from Portulaca oleracea and Their Inhibitory Effect on IL-6-Induced STAT3 Activation. Molecules. 2016; 21(7):865. https://doi.org/10.3390/molecules21070865
Chicago/Turabian StyleHwang, Joo Tae, Yesol Kim, Hyun-Jae Jang, Hyun-Mee Oh, Chi-Hwan Lim, Seung Woong Lee, and Mun-Chual Rho. 2016. "Study of the UV Light Conversion of Feruloyl Amides from Portulaca oleracea and Their Inhibitory Effect on IL-6-Induced STAT3 Activation" Molecules 21, no. 7: 865. https://doi.org/10.3390/molecules21070865