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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Main Authors:	Akhtar, Muhammad Nadeem, Seema, Zareen, Nurshafika, Sakeh, Gul, Sana, Syed Adnan, Ali Shah, Syahida, Ahmad
Format:	Article
Language:	English
Published:	Elsevier Ltd 2015
Subjects:	QD Chemistry
Online Access:	http://umpir.ump.edu.my/id/eprint/8033/ http://umpir.ump.edu.my/id/eprint/8033/ http://umpir.ump.edu.my/id/eprint/8033/ http://umpir.ump.edu.my/id/eprint/8033/1/fist-2015-nadeem-Design%20and%20synthesis%20of%20chalcone%20derivative1.pdf

id	ump-8033
recordtype	eprints
spelling	ump-80332018-04-18T04:03:30Z 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 http://dx.doi.org/10.1016/j.molstruc.2014.12.073 DOI: 10.1016/j.molstruc.2014.12.073
repository_type	Digital Repository
institution_category	Local University
institution	Universiti Malaysia Pahang
building	UMP Institutional Repository
collection	Online Access
language	English
topic	QD Chemistry
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
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. 50
format	Article
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
title	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_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_sort	design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship
publisher	Elsevier Ltd
publishDate	2015
url	http://umpir.ump.edu.my/id/eprint/8033/ http://umpir.ump.edu.my/id/eprint/8033/ http://umpir.ump.edu.my/id/eprint/8033/ http://umpir.ump.edu.my/id/eprint/8033/1/fist-2015-nadeem-Design%20and%20synthesis%20of%20chalcone%20derivative1.pdf
first_indexed	2023-09-18T22:05:17Z
last_indexed	2023-09-18T22:05:17Z
_version_	1777414666970988544

Design and Synthesis of Chalcone Derivatives as Potent Tyrosinase Inhibitors and Their Structural Activity Relationship

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