Sequential injection spectrophotometric system for evaluation of mushroom tyrosinase-inhibitory activity

Tyrosinase Inhibitory Activity of Flavonoids from Artocarpus Lowii King

Jurnal Teknologi ◽

10.11113/jt.v71.2711 ◽

2014 ◽

Vol 71 (1) ◽

Author(s):

Shajarahtunnur Jamil ◽

Siti Awanis Abdullah ◽

Siti Mariam Abdul Lathiff ◽

Hasnah Mohd Sirat

Keyword(s):

Inhibitory Activity ◽

Kojic Acid ◽

Mushroom Tyrosinase ◽

Tyrosinase Inhibitory Activity ◽

Crude Extracts ◽

Ic50 Value ◽

Microplate Reader

Tyrosinase inhibitory activity was studied on the crude extracts and flavonoids successfully isolated from the leaves and heartwoods of Artocarpus lowii King. The flavonoids were fully characterized spectroscopically as isobavachalcone (1), 4-hydroxyonchocarpin (2), 2',4'-dihydroxy-4-methoxy-3'-prenyldihydrochalcone (3), 2',4'-dihydroxy-3,4-(2",2"-dimethylchromeno)-3'-prenyldihydrochalcone (4), artocarpin (5), cycloheterophyllin (6) and 4',5-dihydroxy-6,7-(2,2-dimethylpyrano)-2'-methoxy-8-γ,γ-dimethyl allylflavone (7). Tyrosinase inhibitory activity of the samples was determined against mushroom tyrosinase using ELISA microplate reader. Cycloheterophyllin (6) exhibited an excellent inhibitory activity against mushroom tyrosinase comparable to the standard kojic acid with the IC50 value of 52.5 µg/mL (88.3%).

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Mushroom Tyrosinase Inhibitory Activity of Esculetin Isolated from Seeds ofEuphorbia lathyrisL.

Bioscience Biotechnology and Biochemistry ◽

10.1271/bbb.67.631 ◽

2003 ◽

Vol 67 (3) ◽

pp. 631-634 ◽

Cited By ~ 134

Author(s):

Yukimitsu MASAMOTO ◽

Hideya ANDO ◽

Yoshiyuki MURATA ◽

Yasuaki SHIMOISHI ◽

Mikiro TADA ◽

...

Keyword(s):

Inhibitory Activity ◽

Mushroom Tyrosinase ◽

Tyrosinase Inhibitory Activity

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Mushroom tyrosinase inhibitory activity and major fatty acid constituents of Amazonian native flora oils

Brazilian Journal of Pharmaceutical Sciences ◽

10.1590/s1984-82502012000300006 ◽

2012 ◽

Vol 48 (3) ◽

pp. 399-404 ◽

Cited By ~ 8

Author(s):

Raquel da Silva Teixeira ◽

Paula Rafaela Rocha ◽

Hudson Caetano Polonini ◽

Marcos Antônio Fernandes Brandão ◽

Maria das Graças Afonso Miranda Chaves ◽

...

Keyword(s):

Fatty Acid ◽

Inhibitory Activity ◽

Major Fatty Acid ◽

Mushroom Tyrosinase ◽

Melanin Biosynthesis ◽

Tyrosinase Inhibitory Activity ◽

Native Flora ◽

Global Trend ◽

Main Components

In order to treat hyperpigmentation-related problems, there has been a global trend in developing cosmetics claiming to have skin-whitening properties, which act by inhibiting melanin biosynthesis. The objective of this work was to evaluate the in vitro mushroom tyrosinase inhibitory activity of five Amazonian native flora oils, and so to verify the possibility of their incorporation into cosmetic products. In addition, the fatty acid composition of the essential oils was determined by gas chromatography-flame ionisation detection in order to determine the main components of these oils. The tyrosinase inhibitory activity of the tested oils was found to be in the following order: açaí (IA50 = 66.08 µg mL-1) > tucumã > patauá > pracaxi > castanha do Brasil. This study suggests that açaí oil has great potential in the treatment of hyperpigmentation and other related disorders, due to its considerable tyrosinase inhibitory activity.

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Molecular Docking, Synthesis, and Tyrosinase Inhibition Activity of Acetophenone Amide: Potential Inhibitor of Melanogenesis

BioMed Research International ◽

10.1155/2022/1040693 ◽

2022 ◽

Vol 2022 ◽

pp. 1-10

Author(s):

Yasir Nazir ◽

Hummera Rafique ◽

Sadia Roshan ◽

Shazia Shamas ◽

Zaman Ashraf ◽

...

Keyword(s):

Hydrogen Bond ◽

Cinnamic Acid ◽

Inhibitory Activity ◽

Reversible Inhibitor ◽

Binding Modes ◽

Mushroom Tyrosinase ◽

Cinnamic Acids ◽

Tyrosinase Inhibitory Activity ◽

In Silico Docking

Tyrosinase and its related proteins are responsible for pigmentation disorders, and inhibiting tyrosinase is an established strategy to treat hyperpigmentation. The carbonyl scaffolds can be effective inhibitors of tyrosinase activity, and the fact that both benzoic and cinnamic acids are safe natural substances with such a scaffolded structure, it was speculated that hydroxyl-substituted benzoic and cinnamic acid derivatives may exhibit potent tyrosinase inhibitory activity. These moieties were incorporated into new chemotypes that displayed in vitro inhibitory effect against mushroom tyrosinase with a view to explore antimelanogenic ingredients. The most active compound, 2-((3-acetylphenyl)amino)-2-oxoethyl(E)-3-(2,4-dihydroxyphenyl)acrylate (5c), inhibited mushroom tyrosinase with an IC50 of 0.0020 ± 0.0002 μ M , while 2-((3-acetylphenyl)amino)-2-oxoethyl 2,4-dihydroxybenzoate (3c) had an IC50 of 27.35 ± 3.6 μ M in comparison to the positive control arbutin and kojic acid with a tyrosinase inhibitory activity of IC50 of 191.17 ± 5.5 μ M and IC50 of 16.69 ± 2.8 μ M , respectively. Analysis of enzyme kinetics revealed that 5c is a competitive and reversible inhibitor with dissociation constant (Ki) value 0.0072 μM. In silico docking studies with mushroom tyrosinase (PDB ID 2Y9X) predicted possible binding modes in the enzymatic pocket for these compounds. The orthohydroxyl of the cinnamic acid moiety of 5c is predicted to form hydrogen bond with the active site side chain carbonyl of Asn 260 (2.16 Å) closer to the catalytic site Cu ions. The acetyl carbonyl is picking up another hydrogen bond with Asn 81 (1.90 Å). The inhibitor 5c passed the panassay interference (PAINS) alerts. This study presents the potential of hydroxyl-substituted benzoic and cinnamic acids and could be beneficial for various cosmetic formulations.

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