Correlation between the Potency of Flavonoids on Mushroom Tyrosinase Inhibitory Activity and Melanin Synthesis in Melanocytes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Inhibitory Effect of Flavonoids on the o-Diphenolase Activity of Mushroom Tyrosinase
2.2. Inhibitory Effect of Flavonoids on the o-Diphenolase Activity of Murine Tyrosinase
2.3. Effects of the Flavonoids on Cell Viability and Melanogenesis of B16-F10 Melanoma Cells
3. Materials and Methods
3.1. Chemicals
3.2. Mushroom Tyrosinase Inhibitory Assay
3.3. Cell Cultures
3.4. Murine Tyrosinase Inhibitory Assay
3.5. Cell Viability and Total Melanin Content Assay
4. Conclusions
Author Contributions
Acknowledgments
Conflicts of Interest
References
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Sample Availability: All samples are available from the authors. |
No. | Isoflavones | R5 | R6 | R7 | R2′ | R3′ | R4′ | R5′ | |
1 | Formononetin | H | H | OH | H | H | OMe | H | |
2 | Calycosin | H | H | OH | H | OH | OMe | H | |
3 | Biochanin A | OH | H | OH | H | H | OMe | H | |
4 | Genistein | OH | H | OH | H | H | OH | H | |
5 | Khrinone B | OH | H | OH | OH | H | OMe | OH | |
6 | 3′-O-Methylorobol | OH | H | OH | H | OMe | OH | H | |
7 | Khrinone C | OH | H | OH | OMe | OH | OMe | H | |
8 | Tectorigenin | OH | OMe | OH | H | H | OH | H | |
9 | Cajanin | OH | H | OMe | OH | H | OH | H | |
No. | Isoflavanones | R5 | R6 | R7 | R2′ | R3′ | R4′ | R5′ | |
10 | (3R)-7,3′-Dihydroxy-4′-methoxy-isoflavanone | H | H | OH | H | OH | OMe | H | |
11 | Onogenin | H | H | OH | OMe | H | OCH2O | ||
12 | Dalparvin | H | H | OH | OMe | H | OMe | OH | |
13 | Dalparvin B | H | H | OH | OH | OMe | OMe | H | |
14 | (3S)-Sativanone | H | H | OH | OMe | H | OMe | H | |
15 | (3R,S)-3′-O-Methylviolanone | H | H | OH | OMe | OMe | OMe | H | |
16 | (3R,S)-Kenusanone G | OH | H | OH | H | OH | OMe | H | |
17 | (3S)-Secundiflorol H | OH | H | OH | OMe | OH | OMe | H | |
18 | Dalparvin A | OH | H | OH | OMe | H | OMe | OH | |
No. | Isoflavans | R6 | R7 | R8 | R2′ | R3′ | R4′ | R5′ | |
19 | (3R)-Vestitol | H | OH | H | OH | H | OMe | H | |
20 | (3R)(+)-Mucronulatol | H | OH | H | OMe | OH | OMe | H | |
21 | (3R,S)-3′-Hydroxy-8-methoxy vestitol | H | OH | OMe | OH | OH | OMe | H | |
22 | Duartin | H | OH | OMe | OMe | OH | OMe | H | |
23 | (3S)-8-Demethylduartin | H | OH | OH | OMe | OH | OMe | H | |
No. | Flavanones | R3 | R5 | R6 | R7 | R4′ | R5′ | R6′ | |
24 | (2S)-Liquiritigenin | H | H | H | OH | OH | H | H | |
25 | (2S)-Naringenin | H | OH | H | OH | OH | H | H | |
26 | Alpinetin | H | OMe | H | OH | H | H | H | |
No. | Pterocarpan | R5 | R6 | R7 | R2′ | R3′ | R4′ | R5′ | |
27 | (6aR,11aR)-3,8-Dihydroxy-9-methoxy pterocarpan | H | H | OH | H | OH | OMe | H |
No. | Compound | Mushroom Tyrosinase Inhibition | |
---|---|---|---|
% Inhibition (at 200 μM) | IC50 (μM) | ||
(control) | Oxyresveratrol | 98.4 ± 1.1 | 0.19 ± 0.1 |
(control) | Kojic acid | 93.4 ± 1.7 | 16.8 ± 4.6 |
27 | (6aR,11aR)-3,8-Dihydroxy-9-methoxy pterocarpan | 84.6 ± 0.6 | 16.7 ± 5.0 |
5 | Khrinone B | 72.7 ± 2.2 | 54.0 ± 6.0 |
21 | (3RS)-3′-Hydroxy-8-methoxy vestitol | 64.1 ± 1.3 | 67.8 ± 5.8 |
9 | Cajanin | 65.0 ± 1.6 | 67.9 ± 6.2 |
10 | (3R)-7,3′-Dihydroxy-4′-methoxy-isoflavanone | 52.1 ± 0.4 | 176.7 ± 16.3 |
24 | (2S)-Liquiritigenin | 52.1 ± 1.4 | 178.1 ± 14.0 |
20 | (3R)(+)-Mucronulatol | 48.3 ± 1.6 | 228.9 ± 22.2 |
17 | (3S)-Secundiflorol H | 44.0 ± 3.7 | 278.1 ± 54.5 |
26 | Alpinetin | 36.9 ± 0.5 | 450.0 ± 48.5 |
19 | (3R)-Vestitol | 35.6 ± 2.2 | 473.0 ± 60.9 |
12 | Dalparvin | 31.6 ± 0.5 | 906.1 ± 43.6 |
6 | 3′-O-Methylorobol | 14.3 ± 1.1 | N.D. |
3 | Biochanin A | 9.2 ± 0.4 | N.D. |
1 | Formononetin | 10% (at 300 μM) | N.D. |
7 | Khrinone C | 2% (at 300 μM) | N.D. |
2 | Calycosin | 0% (at 300 μM) | N.D. |
11 | Onogenin | 0% (at 300 μM) | N.D. |
15 | (3R,S)-3′-O-Methylviolanone | 0% (at 300 μM) | N.D. |
13 | Dalparvin B | 4% (at 500 μM) | N.D. |
14 | (3S)-Sativanone | 13% (at 500 μM) | N.D. |
16 | (3R,S)-Kenusanone G | 0% (at 500 μM) | N.D. |
18 | Dalparvin A | 0% (at 500 μM) | N.D. |
22 | Duartin | 0% (at 500 μM) | N.D. |
4 | Genistein | S* | N.D. |
8 | Tectorigenin | S* | N.D. |
23 | (3S)-8-Demethylduartin | S* | N.D. |
25 | (2S)-Naringenin | S* | N.D. |
No. | Isoflavones | Murine Tyrosinase Inhibition, % (at 200 μM) | 15 μM | 30 μM | ||
---|---|---|---|---|---|---|
% Melanin Content | % Cell Viability | % Melanin Content | % Cell Viability | |||
1 | Formononetin | - | 133.8 ± 2.7 | 96.0 ± 3.3 | 155.3 ± 15.4 | 92.8 ± 9.4 |
2 | Calycosin | - | 142.8 ± 8.2 | 99.1 ± 9.2 | 196.6 ± 6.4 | 101.3 ± 1.9 |
3 | Biochanin A | - | 165.2 ± 5.9 | 103.4 ± 4.5 | 168.0 ± 5.1 | 102.2 ± 4.8 |
4 | Genistein | 9.9 ± 3.1 | 165.1 ± 1.6 | 128.2 ± 3.5 | 191.7 ± 13.9 | 93.8 ± 5.7 |
5 | Khrinone B | 10.1 ± 3.0 | 84.1 ± 5.3 | 95.1 ± 5.4 | 34.7 ± 12.3 | 62.3 ± 15.1 |
6 | 3′-O-Methylorobol | - | 170.1 ± 10.5 | 106.6 ± 6.2 | 215.7 ± 15.7 | 101.5 ± 2.7 |
7 | Khrinone C | - | 107.6 ± 0.8 | 93.3 ± 2.0 | 154.0 ± 9.9 | 93.4 ± 2.0 |
8 | Tectorigenin | 10.2 ± 2.9 | 127.6 ± 2.8 | 129.7 ± 3.4 | 152.1 ± 4.7 | 119.3 ± 1.3 |
9 | Cajanin | 9.2 ± 1.5 | 65.8 ± 7.5 | 101.5 ± 6.6 | 61.6 ± 8.9 | 107.2 ± 3.3 |
No. | Isoflavanones | |||||
10 | (3R)-7,3′-Dihydroxy-4′-methoxy-isoflavanone | - | 95.1 ± 3.0 | 94.9 ± 3.9 | 95.2 ± 2.7 | 96.5 ± 3.9 |
11 | Onogenin | - | 133.5 ± 4.6 | 100.0 ± 5.0 | 169.8 ± 15.4 | 92.0 ± 2.0 |
12 | Dalparvin | - | 133.8 ± 9.7 | 117.1 ± 8.9 | 199.6 ± 12.1 | 99.7 ± 6.7 |
13 | Dalparvin B | 9.8 ± 2.8 | 102.0 ± 2.7 | 82.3 ± 5.4 | 99.1 ± 2.3 | 74.1 ± 6.4 |
14 | (3S)-Sativanone | 9.5 ± 1.6 | 124.2 ± 4.3 | 106.7 ± 10.6 | 127.6 ± 6.0 | 64.3 ± 23.7 |
15 | (3R,S)-3′-O-Methylviolanone | - | 143.3 ± 8.4 | 74.2 ± 7.8 | 157.2 ± 11.5 | 72.9 ± 6.2 |
16 | (3R,S)-Kenusanone G | - | 132.6 ± 5.1 | 124.0 ± 1.7 | 158.5 ± 13.5 | 102.2 ± 2.8 |
17 | (3S)-Secundiflorol H | - | 117.6 ± 17.7 | 109.4 ± 6.6 | 146.4 ± 6.1 | 102.7 ± 4.1 |
18 | Dalparvin A | - | 132.0 ± 4.4 | 105.4 ± 4.8 | 184.2 ± 10.6 | 100.4 ± 7.1 |
No. | Isoflavans | |||||
19 | (3R)-Vestitol | 12.4 ± 3.3 | 186.1 ± 1.6 | 142.1 ± 3.0 | 232.0 ± 9.3 | 119.7 ± 4.1 |
20 | (3R)(+)-Mucronulatol | 12.8 ± 2.1 | 178.6 ± 15.9 | 103.6 ± 6.9 | 263.7± 8.2 | 102.5 ± 2.7 |
21 | (3RS)-3′-Hydroxy-8-methoxy Vestitol | 11.4 ± 2.5 | 97.0 ± 6.3 | 102.9 ± 1.0 | 36.3 ± 0.1 | 62.4 ± 3.2 |
22 | Duartin | - | 301.1 ± 2.3 | 139.9 ± 7.5 | 326.8 ± 2.1 | 94.4 ± 2.8 |
23 | (3S)-8-Demethylduartin | - | 87.8 ± 2.0 | 93.5 ± 3.0 | 72.7 ± 4.3 | 98.3 ± 5.4 |
No. | Flavanones | |||||
24 | (2S)-Liquiritigenin | 13.2 ± 2.7 | 102.9 ± 5.5 | 98.9 ± 10.7 | 124.5 ± 2.0 | 100.0 ± 3.5 |
25 | (2S)-Naringenin | - | 132.5 ± 14.5 | 94.3 ± 2.0 | 152.1 ± 3.8 | 98.1 ± 0.5 |
26 | Alpinetin | - | 89.7 ± 0.4 | 77.0 ± 12.7 | 92.3 ± 1.6 | 77.1 ± 10.2 |
No. | Pterocarpan | |||||
27 | (6aR,11aR)-3,8-Dihydroxy-9-methoxy pterocarpan | 29.2 ± 2.9 | 41.9 ± 0.4 | 105.7 ± 4.9 | 53.5 ± 0.4 | 14.5 ± 0.9 |
Others | ||||||
Control | Kojic acid | 73.8 ± 1.0 | 68.9 ± 5.2 | 98.9 ± 4.7 | 74.2 ± 5.8 | 99.6 ± 2.3 |
Control | Oxyresveratrol | 99.4 ± 1.0 | 24.3 ± 1.1 | 117.2 ± 2.2 | 28.4 ± 1.7 | 118.1 ± 5.1 |
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Promden, W.; Viriyabancha, W.; Monthakantirat, O.; Umehara, K.; Noguchi, H.; De-Eknamkul, W. Correlation between the Potency of Flavonoids on Mushroom Tyrosinase Inhibitory Activity and Melanin Synthesis in Melanocytes. Molecules 2018, 23, 1403. https://doi.org/10.3390/molecules23061403
Promden W, Viriyabancha W, Monthakantirat O, Umehara K, Noguchi H, De-Eknamkul W. Correlation between the Potency of Flavonoids on Mushroom Tyrosinase Inhibitory Activity and Melanin Synthesis in Melanocytes. Molecules. 2018; 23(6):1403. https://doi.org/10.3390/molecules23061403
Chicago/Turabian StylePromden, Worrawat, Wittawat Viriyabancha, Orawan Monthakantirat, Kaoru Umehara, Hiroshi Noguchi, and Wanchai De-Eknamkul. 2018. "Correlation between the Potency of Flavonoids on Mushroom Tyrosinase Inhibitory Activity and Melanin Synthesis in Melanocytes" Molecules 23, no. 6: 1403. https://doi.org/10.3390/molecules23061403