Influence of plasma-activated compounds on melanogenesis and tyrosinase activity

Abstract

Many organic chemists around the world synthesize medicinal compounds or extract multiple compounds from plants in order to increase the activity and quality of medicines. In this work, we synthesized new eugenol derivatives (ED) and then treated them with an N2 feeding gas atmospheric pressure plasma jet (APPJ) to increase their utility. We studied the tyrosinase-inhibition activity (activity test) and structural changes (circular dichroism) of tyrosinase with ED and plasma activated eugenol derivatives (PAED) in a cell-free environment. Later, we used docking studies to determine the possible interaction sites of ED and PAED compounds with tyrosinase enzyme. Moreover, we studied the possible effect of ED and PAED on melanin synthesis and its mechanism in melanoma (B16F10) cells. Additionally, we investigated the structural changes that occurred in activated ED after plasma treatment using nuclear magnetic resonance (NMR). Hence, this study provides a new perspective on PAED for the field of plasma medicine.

Comparative Study of Curcumin and Its Hydrogenated Metabolites, Tetrahydrocurcumin, Hexahydrocurcumin, and Octahydrocurcumin, on Melanogenesis in B16F10 and MNT-1 Cells

“…Similar findings were also noted with the compounds methyl cinnamate (structurally similar to curcumin) and methyl 3-phenylpropionate, where authors noted that the latter compound inhibited monophenolase activity with no effects on diphenolase activity but stimulated melanogenesis in cell cultures [40]. Another study also reported a similar observation in which the authors noted the inhibition of mushroom tyrosinase activity but the stimulation of melanogenesis in B16F10 cells by plasma-activated compounds [41]. This discrepancy can be explained by the differences between mushroom tyrosinase and human tyrosinase [42]; it has been reported that results from the mushroom tyrosinase assay may not be a true indicator of response from cellular melanin levels [43].…”

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

“…Rather low IC50 values have been determined also for resveratrol derivatives such as (E)-2,3-bis(4-hydroxyphenyl)acrylonitrile (IC50 = 5.06 μM) [169] and dihydrooxyresveratrol glucosides [170] (Figure 19). As to other natural phenol-inspired synthetic compounds [157][158][159][160][161], the best results have been reported for a carvacrol derivative containing a 3,5-dihydroxyphenyl moiety (IC 50 = 0.0167 µM) [159] ( Figure 19). Good inhibition properties have been exhibited also by some rhododendrol glycosides (IC 50 = 0.56-9.15 µM) [160] and eugenol derivatives (IC 50 ca.…”

“…Good inhibition properties have been exhibited also by some rhododendrol glycosides (IC50 = 0.56-9.15 μM) [160] and eugenol derivatives (IC50 ca. 8 μM) [161] (Figure 19).…”

“…Good inhibition properties have been exhibited also by some rhododendrol glycosides (IC 50 = 0.56-9.15 µM) [160] and eugenol derivatives (IC 50 ca. 8 µM) [161] (Figure 19). Coumarins are another class of compounds able to efficiently inhibit mushroom tyrosinase [171][172][173][174].…”

Intracellular responses to reactive oxygen and nitrogen species, and lipid peroxidation in apoptotic cells cultivated in plasma-activated medium

“…These aqueous reactions produce other relatively long‐lived RONS, such as hydrogen peroxide (H 2 O 2 ), nitrates (), and nitrites () . RONS are involved in biological dysfunction, oxidative damage, cell destruction, and the activation of cell death pathways, and are believed to act as moderators or effectors in cell signaling cascades. We previously reported that N‐acetyl cysteine, an intracellular RONS scavenger, cancels the antitumor effect, that is, inhibits the anti‐proliferative effect of PAM .…”