Inhibitory Effects of Quercetin and Kaempferol as two Propolis Derived Flavonoids on Tyrosinase Enzyme

Abstract

Background: Tyrosinase is a copper-containing enzyme, which is widely distributed in microorganisms, animals and plants. It is also a key enzyme in melanin biosynthesis, which plays a crucial role in determining the color of mammalian skin and hair. In addition, unfavorable enzymatic browning of plant-derived foods by tyrosinase causes a decrease in nutritional quality and economic loss of food products. Objectives: In the present study the activity of this enzyme was examined against quersetin and kaempferol as two potentially flavonoid inhibitors. Materials and Methods: In this work, the effects of quercetin and kaempferol as propolis-derived compounds on activity of mushroom tyrosinase (MT) were studied. These flavonoids showed inhibitory activity on catecholase and cresolase reactions in presence of caffeic acid and p-comaric acid, respectively. The inhibition mode of quercetin and kaempferol were competitive towards both catecholase and cresolase activities of the enzyme. Results: The inhibition constants (Ki) were determined as 0.072 and 0.112 mM for catecholase activity, and 0.016 and 0.06 mM for cresolase activity, respectively. Conclusions: In general, quercetin and kaempferol can be used as good candidates in melanogenesis inhibition. Moreover they should be considered as good blockers of enzyme activity in hyper pigmentation and clinical application.

Screening of Peruvian Medicinal Plants for Tyrosinase Inhibitory Properties: Identification of Tyrosinase Inhibitors in Hypericum laricifolium Juss

“…In previous studies on flavonoids, compounds such as quercetin and kaempferol were shown to interfere with the activity of tyrosinase through chelation of copper in its active site [ 28 ]. It has been demonstrated that quercetin and kaempferol can suppress melanogenesis, directly inhibiting tyrosinase activity or reducing tyrosinase expression [ 45 ]. In our study, quercetin proved to be a good tyrosinase inhibitor, while kaempferol was a weaker inhibitor than arbutin.…”

Green tea extract as an anti‐browning agent for cloudy apple juice

“…Additionally, it was found that flavonoids containing the C4‐keto group or free hydroxyl group at the C3 position, e.g. quercetin and kaempferol, are also very effective tyrosinase inhibitors …”

In silico assessment of the inhibitory effect of four flavonoids (Chrysin, Naringin, Quercetin, Kaempferol) on tyrosinase activity using the MD simulation approach

“…The enzyme has molecular weight of 120 kDa with two heavy (H) and two light (L) subunits of 43 and 14 kDa, respectively. Subunit H, contrary to subunit L, consists of an active site for copper ions (Hassani et al, 2018;Taherkhani and Gheibi, 2014). The enzyme has multiple catalytic functions, including mono-oxygenase (cresolase) activity (hydroxylation of monophenols to o-diphenols) and catechol oxidase activity (oxidation of o-diphenols to o-quinone) (Yin et al, 2011).…”

“…Quinines can react with proteins and amino acids to form black or brown products (Sugumaran and Barek, 2016) or evolve chemically to form polyphenolic compounds or melanin (Gheibi et al, 2016;Ullah et al, 2016). Moreover, tyrosinase plays a key role in different processes such as melanin production in the skin, wound healing, agriculture, and cosmetic industry (Choi and Shin, 2016;Popoola et al, 2015;Taherkhani and Gheibi, 2014). The overactivity of the enzyme in the skin may lead to melanin overproduction and multiple skin disorders, including hyperpigmentation, depigmentation, and even melanoma (Choi and Shin, 2016;Popoola et al, 2015;Taherkhani and Gheibi, 2014).…”

“…Moreover, tyrosinase plays a key role in different processes such as melanin production in the skin, wound healing, agriculture, and cosmetic industry (Choi and Shin, 2016;Popoola et al, 2015;Taherkhani and Gheibi, 2014). The overactivity of the enzyme in the skin may lead to melanin overproduction and multiple skin disorders, including hyperpigmentation, depigmentation, and even melanoma (Choi and Shin, 2016;Popoola et al, 2015;Taherkhani and Gheibi, 2014). Among the various sources of tyrosinase, mushroom tyrosinase from Agaricus bisporus is a major and commercial source with high homology compared to human tyrosinase (Zolghadri et al, 2019).…”