Bioactive Phenylpropanoid Glycosides from Tabebuia avellanedae
Abstract
:1. Introduction
2. Results and Discussion
2.1. Isolation and Chemistry
No. | 1 | 2 | 3 | |||
---|---|---|---|---|---|---|
δ 1H | δ 13C | δ 1H | δ 13C | δ 1H | δ 13C | |
1 | 3.91 (1H, m), 4.04 (1H, m) | 72.3 | 3.71 (1H, m), 4.04 (1H, m) | 72.3 | 3.71 (1H, m), 3.96 (1H, m) | 72.4 |
2 | 2.78 (2H, m) | 36.5 | 2.78 (2H, m) | 36.6 | 2.78 (2H, m) | 36.6 |
3 | 131.4 | 131.4 | 131.2 | |||
4 | 6.68 (1H, d, J = 2.4) | 117.1 | 6.68 (1H, d, J = 2.4) | 117.1 | 6.68 (1H, d, J = 2.4) | 117.0 |
5 | 146.1 | 146.1 | 146.1 | |||
6 | 144.6 | 144.6 | 144.7 | |||
7 | 6.66 (1H, d, J = 8.2) | 116.2 | 6.66 (1H, d, J = 7.9) | 116.3 | 6.66 (1H, d, J = 8.3) | 116.2 |
8 | 6.55 (1H, dd, J = 2.4, 8.2) | 121.2 | 6.56 (1H, dd, J = 2.4, 7.9) | 121.2 | 6.55 (1H, dd, J = 2.4, 8.2) | 121.2 |
1′ | 4.36 (1H, d, J = 7.9) | 104.2 | 4.37 (1H, d, J = 7.6) | 104.1 | 4.39 (1H, d, J = 7.5) | 104.2 |
2′ | 3.52 (1H, m) | 76.0 | 3.54 (1H, m) | 76.0 | 3.80 (1H, m) | 73.0 |
3′ | 3.81 (1H, m) | 81.6 | 3.85 (1H, m) | 79.9 | 3.82 (1H, m) | 81.3 |
4′ | 4.91 (1H, m) | 70.4 | 4.95 (1H, m) | 70.4 | 4.97 (1H, m) | 70.3 |
5′ | 3.38 (1H, m) | 76.2 | 3.42 (1H, m) | 76.4 | 3.39 (1H, m) | 76.0 |
6′ | 3.50 (1H, dd, J = 5.5, 9.6), 3.62 (1H, br d J = 9.6) | 62.3 | 3.52 (1H, m), 3.63 (1H, br d, J = 5.8) | 62.3 | 4.19 (1H, m), 4.21 (1H, m) | 63.3 |
1′′ | 5.18 (1H, d, J = 1.3) | 103.0 | 5.34 (1H, d, J = 1.3) | 102.0 | 5.18 (1H, d, J = 1.3) | 103.1 |
2′′ | 3.72 (1H, m) | 72.2 | 3.91 (1H, m) | 72.2 | 3.91 (1H.m) | 72.3 |
3′′ | 3.57 (1H, m) | 72.0 | 3.70 (1H, m) | 69.8 | 3.56 (1H, m) | 72.0 |
4′′ | 3.28 (1H, m) | 73.7 | 3.55 (1H, m) | 75.9 | 3.28 (1H, m) | 73.7 |
5′′ | 3.55 (1H, m) | 70.5 | 3.78 (1H, m) | 67.5 | 3.55 (1H, m) | 70.4 |
6′′ | 1.09 (3H, d, J = 6.2) | 18.4 | 1.02 (3H d, J = 6.2) | 18.1 | 1.08 (3H, d, J = 6.2) | 18.4 |
1′′′ | 168.3 | 168.3 | 168.0 | |||
2′′′ | 6.26 (1H, d, J = 16.2) | 114.6 | 6.25 (1H, d, J = 15.8) | 114.6 | 6.26 (1H, d, J = 16.2) | 114.4 |
3′′′ | 7.58 (1H, d, J = 16.2) | 147.9 | 7.58 (1H, d, J = 15.8) | 148.1 | 7.59 (1H, d, J = 16.2) | 148.2 |
4′′′ | 127.6 | 127.6 | 127.7 | |||
5′′′ | 7.04 ( 1H, d, J = 1.8 ) | 115.2 | 7.04 (1H, d, J = 1.8) | 115.1 | 7.04 (1H, d, J = 1.8) | 115.2 |
6′′′ | 146.8 | 146.8 | 146.8 | |||
7′′′ | 149.7 | 149.9 | 149.8 | |||
8′′′ | 6.77 (1H, d, J = 8.2) | 116.4 | 6.78 (1H, d, J = 8.2) | 116.5 | 6.77 (1H, d, J = 8.2) | 116.4 |
9′′′ | 6.95 (1H, dd, J = 1.8, 8.2) | 123.2 | 6.95 (1H, dd, J = 1.8, 8.2) | 123.2 | 6.95 (1H, dd, J = 1.8, 8.2) | 123.2 |
No. | 4 | 5 | 6 | |||
---|---|---|---|---|---|---|
δ 1H | δ 13C | δ 1H | δ 13C | δ 1H | δ 13C | |
1 | 3.69 (1H, m), 3.97 (1H, m) | 72.3 | 3.71 (1H, m), 3.93 (1H, m) | 72.4 | 3.69 (1H, m), 3.97 (1H, m) | 72.3 |
2 | 2.77 (2H, m) | 36.6 | 2.77 (2H, m) | 36.6 | 2.77 (2H, m) | 36.6 |
3 | 131.3 | 131.4 | 131.3 | |||
4 | 6.66 (1H, d, J = 2.4) | 117.0 | 6.68 (1H, d, J = 2.4) | 117.0 | 6.66 (1H, d, J = 2.4) | 117.0 |
5 | 146.1 | 146.1 | 146.1 | |||
6 | 144.6 | 144.6 | 144.6 | |||
7 | 6.62 (1H, d, J = 8.2) | 116.3 | 6.66 (1H, d, J = 8.2) | 116.3 | 6.62 (1H, d, J = 8.2) | 116.3 |
8 | 6.52 (1H, dd, J = 2.4, 8.2) | 121.2 | 6.55 (1H, dd, J = 2.4, 8.2) | 121.2 | 6.52 (1H, dd, J = 2.4, 8.2) | 121.2 |
1′ | 4.32 (1H, d, J = 7.9) | 104.3 | 4.31 (1H, d, J = 7.8) | 104.4 | 4.34 (1H, d, J = 7.9) | 104.3 |
2′ | 3.54 (1H, m) | 75.4 | 3.52 (1H, m) | 75.4 | 3.54 (1H, m) | 75.5 |
3′ | 3.52 (1H, m) | 83.9 | 3.54 (1H, m) | 83.3 | 3.55 (1H, m) | 83.1 |
4′ | 3.99 (1H, m) | 70.3 | 4.10 (1H, m) | 70.2 | 3.73 (1H, m) | 72.2 |
5′ | 3.32 (1H, m) | 75.7 | 3.34 (1H, m) | 75.8 | 3.32 (1H, m) | 75.9 |
6′ | 4.35 (1H, dd, J = 5.9, 12.1), 4.49 (1H, dd, J = 2.1, 11.7) | 64.6 | 4.32 (1H, m), 4.47 (1H, dd, J = 2.1, 11.7) | 64.4 | 4.32 (1H, br d, J = 8.5), 4.47 (1H, dd, J = 2.3, 11.7) | 64.6 |
1′′ | 5.17 (1H, d, J = 1.8) | 102.7 | 5.23 (1H, d, J = 1.4) | 102.2 | 5.25 (1H, d, J = 1.8) | 102.3 |
2′′ | 3.71 (1H, m) | 72.2 | 3.90 (1H, m) | 71.1 | 3.89 (1H, m ) | 70.0 |
3′′ | 3.94 (1H, m) | 72.2 | 3.67 (1H, m) | 72.4 | 3.41 (1H, m) | 70.3 |
4′′ | 3.38 (1H, m) | 73.9 | 5.05 (1H, m) | 75.5 | 4.89 (1H, m) | 76.0 |
5′′ | 3.41 (1H, m) | 70.0 | 3.44 (1H, m) | 70.0 | 4.26 (1H, m) | 67.4 |
6′′ | 1.23 (3H, d, J = 6.2) | 17.8 | 1.25 (3H, d, J = 7.0) | 17.8 | 1.15 (3H, d, J = 5.9) | 17.6 |
1′′′ | 169.1 | 168.3 | 169.1 | |||
2′′′ | 6.28 (1H, d, J = 15.8) | 114.8 | 6.26 (1H, d, J = 15.8) | 114.6 | 6.28 (1H, d, J = 15.8) | 114.8 |
3′′′ | 7.56 (1H, d, J = 15.8) | 147.2 | 7.58 (1H, d, J = 15.8) | 147.9 | 7.56 (1H, d, J = 15.8) | 147.2 |
4′′′ | 127.6 | 127.6 | 127.6 | |||
5′′′ | 7.03 (1H, d, J = 2.0) | 115.0 | 7.04 (1H, d, J = 2.0) | 115.2 | 7.03 (1H, d, J = 2.0) | 115.0 |
6′′′ | 146.7 | 146.8 | 146.7 | |||
7′′′ | 149.6 | 149.7 | 149.6 | |||
8′′′ | 6.62 (1H, d, J = 8.2) | 116.5 | 6.77 (1H, d, J = 8.2) | 116.4 | 6.62 (1H, d, J = 8.2) | 116.5 |
9′′′ | 6.88 (1H, dd, J = 2.0, 8.2) | 123.1 | 6.95 (1H, dd, J = 2.0, 8.2) | 123.2 | 6.88 (1H, dd, J = 2.0, 8.2) | 123.1 |
2.2. Bioactivity
Compound | IC50 (µM) ± SD |
---|---|
1 | 2.33 ± 0.06 |
2 | 1 ± 0.02 |
3 | 0.66 ± 0.04 |
4 | 1.15 ± 0.04 |
5 | 0.12 ± 0.03 |
6 | 0.24 ± 0.01 |
Ascorbic acid | 3.08 ± 0.06 |
Compound | IC50 (µM) ± SD |
---|---|
1 | 46.27 ± 1.53 |
2 | 43.3 ± 1.79 |
3 | 37.73 ± 2.11 |
4 | 91.7 ± 5.44 |
5 | 22.49 ± 1.65 |
6 | 15.1 ± 2.43 |
Ketoconazole | 6.44 ± 0.56 |
3. Experimental
3.1. General
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Acid Hydrolysis of Compounds 2, 5, 6
3.5. Antioxidant Assay
3.6. Inhibitory Activity on Cytochrome CYP3A4 Enzyme
4. Conclusions
Conflicts of Interest
References
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Suo, M.; Ohta, T.; Takano, F.; Jin, S. Bioactive Phenylpropanoid Glycosides from Tabebuia avellanedae. Molecules 2013, 18, 7336-7345. https://doi.org/10.3390/molecules18077336
Suo M, Ohta T, Takano F, Jin S. Bioactive Phenylpropanoid Glycosides from Tabebuia avellanedae. Molecules. 2013; 18(7):7336-7345. https://doi.org/10.3390/molecules18077336
Chicago/Turabian StyleSuo, Maorong, Tomihisa Ohta, Fumihide Takano, and Shouwen Jin. 2013. "Bioactive Phenylpropanoid Glycosides from Tabebuia avellanedae" Molecules 18, no. 7: 7336-7345. https://doi.org/10.3390/molecules18077336