Design and Synthesis of Chalcone Derivatives as Potent Tyrosinase Inhibitors and Their Structural Activity Relationship
Browning of fruits and vegetables is a serious issue in the food industry, as it damages the organoleptic properties of the final products. Overproduction of melanin causes aesthetic problems such as melisma, freckles and lentigo. In this study, a series of chalcones (1-10) have been synthesized and...
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| Format: | Article |
| Language: | English |
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Elsevier Ltd
2015
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| Subjects: | |
| Online Access: | http://umpir.ump.edu.my/id/eprint/8033/1/fist-2015-nadeem-Design%20and%20synthesis%20of%20chalcone%20derivative1.pdf |
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| author | Akhtar, Muhammad Nadeem Seema, Zareen Nurshafika, Sakeh Gul, Sana Syed Adnan, Ali Shah Syahida, Ahmad |
| author_facet | Akhtar, Muhammad Nadeem Seema, Zareen Nurshafika, Sakeh Gul, Sana Syed Adnan, Ali Shah Syahida, Ahmad |
| author_sort | Akhtar, Muhammad Nadeem |
| collection | UMP |
| description | Browning of fruits and vegetables is a serious issue in the food industry, as it damages the organoleptic properties of the final products. Overproduction of melanin causes aesthetic problems such as melisma, freckles and lentigo. In this study, a series of chalcones (1-10) have been synthesized and examined for their tryrosinase inhibitory activity. The results showed that flavokawain B (1), flavokawain A (2) and compound 3 were found to be potential tyrosinase inhibitors, indicating IC
14.20 -14.38 M values. This demonstrates that 4-substituted phenolic compound especially at ring A exhibited significant tyrosinase inhibition. Additionally, molecular docking results showed a strong binding affinity for compounds 1-3 through chelation between copper metal and ligands. The detailed molecular docking and SARs studies correlate well with the tyrosinase inhibition studies in vitro. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and single X-ray crystallographic techniques. These findings could lead to design and discovery of new tyrosinase inhibitors to control the melanine overproduction and overcome the economic loss of food industry.
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| first_indexed | 2024-03-06T11:50:41Z |
| format | Article |
| id | UMPir8033 |
| institution | Universiti Malaysia Pahang |
| language | English |
| last_indexed | 2024-03-06T11:50:41Z |
| publishDate | 2015 |
| publisher | Elsevier Ltd |
| record_format | dspace |
| spelling | UMPir80332018-04-18T04:03:30Z http://umpir.ump.edu.my/id/eprint/8033/ Design and Synthesis of Chalcone Derivatives as Potent Tyrosinase Inhibitors and Their Structural Activity Relationship Akhtar, Muhammad Nadeem Seema, Zareen Nurshafika, Sakeh Gul, Sana Syed Adnan, Ali Shah Syahida, Ahmad QD Chemistry Browning of fruits and vegetables is a serious issue in the food industry, as it damages the organoleptic properties of the final products. Overproduction of melanin causes aesthetic problems such as melisma, freckles and lentigo. In this study, a series of chalcones (1-10) have been synthesized and examined for their tryrosinase inhibitory activity. The results showed that flavokawain B (1), flavokawain A (2) and compound 3 were found to be potential tyrosinase inhibitors, indicating IC 14.20 -14.38 M values. This demonstrates that 4-substituted phenolic compound especially at ring A exhibited significant tyrosinase inhibition. Additionally, molecular docking results showed a strong binding affinity for compounds 1-3 through chelation between copper metal and ligands. The detailed molecular docking and SARs studies correlate well with the tyrosinase inhibition studies in vitro. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and single X-ray crystallographic techniques. These findings could lead to design and discovery of new tyrosinase inhibitors to control the melanine overproduction and overcome the economic loss of food industry. 50 Elsevier Ltd 2015 Article PeerReviewed application/pdf en http://umpir.ump.edu.my/id/eprint/8033/1/fist-2015-nadeem-Design%20and%20synthesis%20of%20chalcone%20derivative1.pdf Akhtar, Muhammad Nadeem and Seema, Zareen and Nurshafika, Sakeh and Gul, Sana and Syed Adnan, Ali Shah and Syahida, Ahmad (2015) Design and Synthesis of Chalcone Derivatives as Potent Tyrosinase Inhibitors and Their Structural Activity Relationship. Journal of Molecular Structure, 1085. pp. 97-1. ISSN 0022-2860. (Published) http://dx.doi.org/10.1016/j.molstruc.2014.12.073 DOI: 10.1016/j.molstruc.2014.12.073 |
| spellingShingle | QD Chemistry Akhtar, Muhammad Nadeem Seema, Zareen Nurshafika, Sakeh Gul, Sana Syed Adnan, Ali Shah Syahida, Ahmad Design and Synthesis of Chalcone Derivatives as Potent Tyrosinase Inhibitors and Their Structural Activity Relationship |
| title | Design and Synthesis of Chalcone Derivatives as Potent Tyrosinase Inhibitors and Their Structural Activity Relationship |
| title_full | Design and Synthesis of Chalcone Derivatives as Potent Tyrosinase Inhibitors and Their Structural Activity Relationship |
| title_fullStr | Design and Synthesis of Chalcone Derivatives as Potent Tyrosinase Inhibitors and Their Structural Activity Relationship |
| title_full_unstemmed | Design and Synthesis of Chalcone Derivatives as Potent Tyrosinase Inhibitors and Their Structural Activity Relationship |
| title_short | Design and Synthesis of Chalcone Derivatives as Potent Tyrosinase Inhibitors and Their Structural Activity Relationship |
| title_sort | design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship |
| topic | QD Chemistry |
| url | http://umpir.ump.edu.my/id/eprint/8033/1/fist-2015-nadeem-Design%20and%20synthesis%20of%20chalcone%20derivative1.pdf |
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