New Whitening Constituents from Taiwan-Native Pyracantha koidzumii: Structures and Tyrosinase Inhibitory Analysis in Human Epidermal Melanocytes
Abstract
:1. Introduction
2. Results and Discussion
2.1. New Compounds 9 and 13 Isolated from Pyracantha koidzumii
2.2. Cell Viability of Human Epidermal Melanocytes Treated with Compounds Isolated from Pyracantha koidzumii
2.3. Cellular Tyrosinase-Inhibitory Activity and Melanin Content of the Isolated Compounds in Human Epidermal Melanocytes
2.4. Effects of 3,6-Dihydroxy-2,4-dimethoxy-dibenzofuran (9) and 3,4-Dihydroxy-5-methoxybiphenyl-2′-O-β-d-glucopyranoside (13) on the Expression of Tyrosinase-Related Proteins in Human Epidermal Melanocytes
2.5. Effects of 3,6-Dihydroxy-2,4-dimethoxy-dibenzofuran (9) and 3,4-Dihydroxy-5-methoxybiphenyl-2′-O-β-d-glucopyranoside (13) on the Expression of MITF and PAX3 mRNA in Human Epidermal Melanocytes
2.6. Tyrosinase Kinetic Analysis on 3,4-Dihydroxy-5-methoxybiphenyl-2ʹ-O-β-d-glucopyranoside (13) Treatment of Human Epidermal Melanocytes
3. Experimental Section
3.1. Reagents
3.2. Collection, Extraction, and Isolation
3.2.1. Compound 9
Position | δc | δH (Mult, J in Hz) | HMBC |
---|---|---|---|
1 | 98.3 | 7.21 (1H, s) | C-9a, C-3, C-4a, C-2 |
2 | 147.4 | - | - |
3 | 140.2 | - | - |
4 | 134.7 | - | - |
4a | 144.6 | - | - |
5a | 146.0 | - | - |
6 | 144.1 | - | - |
7 | 113.5 | 6.82 (1H, dd, J = 7.7, 1.0) | C-5a, C-8 |
8 | 111.5 | 7.08 (1H, t, J = 7.7) | C-6, C-9a |
9 | 124.5 | 7.33 (1H, dd, J = 7.7, 1.0) | C-7, C-9a |
9a | 127.9 | - | - |
9b | 117.4 | - | - |
2-OMe | 57.3 | 3.94 (3H, s) | C-2 |
4-OMe | 61.3 | 4.15 (3H, s) | C-4 |
3.2.2. Compound 13
Position | δc | δH (Mult, J in Hz) | HMBC |
---|---|---|---|
1 | 130.6 | - | - |
2 | 111.4 | 6.67 (1H, d, J = 1.8) | C-3, C-4, C-6, C-1′ |
3 | 146.0 | - | - |
4 | 134.6 | - | - |
5 | 149.1 | - | - |
6 | 106.8 | 6.80 (1H, d, J = 1.8) | C-2, C-4, C-5, C-1′ |
1′ | 133.0 | - | - |
2′ | 155.4 | - | - |
3′ | 116.4 | 7.22 (1H, dd, J = 7.6, 1.8) | C-1′, C-2′, C-5′ |
4′ | 129.0 | 7.23 (1H, m) | C-2′, C-5′ |
5′ | 123.4 | 7.02 (1H, m) | C-1′, C-3′, C-4′, C-6′ |
6′ | 131.7 | 7.27 (1H, dd, J = 8.4, 1.4) | C-1, C-2′, C-4′ |
1′′ | 101.8 | 5.03 (1H, d, J = 7.2) | C-2′ |
2′′ | 75.0 | 3.43 (1H, m) | C-1′′ |
3′′ | 78.2 | 3.42 (1H, m) | C-4′′ |
4′′ | 71.3 | 3.34 (1H, m) | C-4′′ |
5′′ | 78.3 | 3.44 (1H, m) | C-4′′, C-3′′ |
6′′ | 62.5 | 3.68 (1H, dd, J = 12.0, 5.4); 3.86 (1H, dd, J = 12.0, 2.1) | C-5′′ |
5-OCH3 | 56.8 | 3.86 (3H, s) | C-5 |
3.3. Cell Culture
3.4. Cell Viability in Human Epidermal Melanocytes
3.5. Tyrosinase Activity in Human Epidermal Melanocytes
3.6. Melanin Contents in Human Epidermal Melanocytes
3.7. Western Blot Analysis
3.8. Real-Time PCR Analysis
3.9. Kinetic Analysis of Cellular Tyrosinase
3.10. Statistical Analysis
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Lin, R.-D.; Chen, M.-C.; Liu, Y.-L.; Lin, Y.-T.; Lu, M.-K.; Hsu, F.-L.; Lee, M.-H. New Whitening Constituents from Taiwan-Native Pyracantha koidzumii: Structures and Tyrosinase Inhibitory Analysis in Human Epidermal Melanocytes. Int. J. Mol. Sci. 2015, 16, 28598-28613. https://doi.org/10.3390/ijms161226115
Lin R-D, Chen M-C, Liu Y-L, Lin Y-T, Lu M-K, Hsu F-L, Lee M-H. New Whitening Constituents from Taiwan-Native Pyracantha koidzumii: Structures and Tyrosinase Inhibitory Analysis in Human Epidermal Melanocytes. International Journal of Molecular Sciences. 2015; 16(12):28598-28613. https://doi.org/10.3390/ijms161226115
Chicago/Turabian StyleLin, Rong-Dih, Mei-Chuan Chen, Yan-Ling Liu, Yi-Tzu Lin, Mei-Kuang Lu, Feng-Lin Hsu, and Mei-Hsien Lee. 2015. "New Whitening Constituents from Taiwan-Native Pyracantha koidzumii: Structures and Tyrosinase Inhibitory Analysis in Human Epidermal Melanocytes" International Journal of Molecular Sciences 16, no. 12: 28598-28613. https://doi.org/10.3390/ijms161226115