Antioxidant activity, anti-tyrosinase activity, molecular docking studies, and molecular dynamic simulation of active compounds found in nipa palm vinegar

Moragot Chatatikun; Aman Tedasen; Nawanwat Chainuwong Pattaranggoon; Wilawan Palachum; Sirithip Chuaijit; Amron Mudpan; Supawita Pruksaphanrat; Sasirat Sohbenalee; Kenshi Yamasaki; Wiyada Kwanhian Klangbud

doi:10.7717/peerj.16494

journal article Open Access Nov 24, 2023

Antioxidant activity, anti-tyrosinase activity, molecular docking studies, and molecular dynamic simulation of active compounds found in nipa palm vinegar

Moragot Chatatikun Aman Tedasen Nawanwat Chainuwong Pattaranggoon Wilawan Palachum

Sirithip Chuaijit Amron Mudpan Supawita Pruksaphanrat Sasirat Sohbenalee Kenshi Yamasaki

Wiyada Kwanhian Klangbud

PeerJ Vol. 11 pp. e16494 · PeerJ

View at Publisher Save 10.7717/peerj.16494

Abstract

Tyrosinase is a key enzyme in melanogenesis and its inhibitors have become increasingly because of their potential activity as hypopigmenting agents which have less side effects. Nipa palm vinegar is an aqueous product that is normally used as a food supplement. The aim of this study was to study the determination of antioxidant activity and tyrosinase inhibitory activities of aqueous extract of original nipa palm vinegar (AE O-NPV), nipa palm vinegar powder (NPV-P) and aqueous extract of nipa palm vinegar powder (AE NPV-P) were examined. Nipa palm vinegars were evaluated the phenolic and flavonoid content, and the active compounds which were submitted to molecular docking and molecular dynamic simulation, chemoinformatics, rule of five, skin absorption and toxicity. The highest phenolic and flavonoid contents in the AE O-NPV were 2.36 ± 0.23 mg gallic acid equivalents/g extract and 5.11 ± 0.59 mg quercetin equivalents/g, and the highest ABTS radical cation scavenging activity was also found. The AE O-NPV, NPV-P and AE NPV-P showed anti-mushroom tyrosinase activity. The HPLC analysis showed that there were vanillic acid and three flavonoids (catechin, rutin and quercetin). The molecular docking study revealed that the binding of the vanillic acid and three flavonoids occurred in the active site residues (histidine and other amino acids). Moreover, the number of hydrogen bond acceptors/donors, solubility, polar surface area and bioavailability score of the vanillic acid and three flavonoids were acceptable compared to Lipinski’s Rule of Five. The molecular dynamic simulation showed that vanillic acid interacts with HIS284 through π–π stacking hydrophobic interactions and forms a metal-acceptor interaction with the copper molecule at the tyrosinase active site. All compounds revealed good skin permeability and nontoxicity. Nipa palm vinegar could be a promising source of a new ingredient for tyrosinase inhibition for cosmetics or pharmaceutical products.

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Details

Published: Nov 24, 2023
Vol/Issue: 11
Pages: e16494
License: View

Authors

M

Moragot Chatatikun

Department of Medical Technology, School of Allied Health Sciences, Walailak University, Thasala, Nakhon Si Thammarat, Thailand; Center of Excellence Research of Melioidosis and Microorganisms, Walailak University, Thasala, Nakhon Si Thammarat, Thailand

A

Aman Tedasen

Department of Medical Technology, School of Allied Health Sciences, Walailak University, Thasala, Nakhon Si Thammarat, Thailand; Research Excellence Center of Innovation and Health Products, Walailak University, Thasala, Nakhon Si Thammarat, Thailand

N

Nawanwat Chainuwong Pattaranggoon

Program in Bioinformatics and Computational Biology, Chulalongkorn University, Bangkok, Thailand; Faculty of Medical Technology, Rangsit University, Muang Pathumthani, Pathumthani, Thailand

W

Wilawan Palachum

Department of Medical Technology, School of Allied Health Sciences, Walailak University, Thasala, Nakhon Si Thammarat, Thailand; Center of Excellence Research of Melioidosis and Microorganisms, Walailak University, Thasala, Nakhon Si Thammarat, Thailand

S

Sirithip Chuaijit

School of Medicine, Walailak University, Thasala, Nakhon Si Thammarat, Thailand

A

Amron Mudpan

Department of Medical Technology, School of Allied Health Sciences, Walailak University, Thasala, Nakhon Si Thammarat, Thailand

S

Supawita Pruksaphanrat

Department of Medical Technology, School of Allied Health Sciences, Walailak University, Thasala, Nakhon Si Thammarat, Thailand

S

Sasirat Sohbenalee

Department of Medical Technology, School of Allied Health Sciences, Walailak University, Thasala, Nakhon Si Thammarat, Thailand

K

Kenshi Yamasaki

Department of Dermatology, Graduate School of Medicine, Tohoku University, Sendai, Japan

W

Wiyada Kwanhian Klangbud

Department of Medical Technology, School of Allied Health Sciences, Walailak University, Thasala, Nakhon Si Thammarat, Thailand; Center of Excellence Research of Melioidosis and Microorganisms, Walailak University, Thasala, Nakhon Si Thammarat, Thailand

Cite This Article

Moragot Chatatikun, Aman Tedasen, Nawanwat Chainuwong Pattaranggoon, et al. (2023). Antioxidant activity, anti-tyrosinase activity, molecular docking studies, and molecular dynamic simulation of active compounds found in nipa palm vinegar. PeerJ, 11, e16494. https://doi.org/10.7717/peerj.16494

Antioxidant activity, anti-tyrosinase activity, molecular docking studies, and molecular dynamic simulation of active compounds found in nipa palm vinegar

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