Tyrosinase Inhibitors of Pulsatilla cernua Root-Derived Materials

Abstract

The inhibition of mushroom tyrosinase by Pulsatilla cernua root-derived materials was evaluated. The bioactive components of Pulsatilla cernua root were characterized by spectroscopic analyses as 3,4-dihydroxycinnamic acid and 4-hydroxy-3-methoxycinnamic acid, which exhibited potent antityrosinase activity. The ID50 values of 3,4-dihydroxycinnamic acid and 4-hydroxy-3-methoxycinnamic acid were 0.97 and 0.33 mM, respectively. The compounds isolated from Pulsatilla cernua roots exhibited noncompetitive inhibition against oxidation of L-DOPA by mushroom tyrosinase. This activity was compared with that of three cinnamic acid derivatives and four well-known tyrosinase inhibitors. The ID50 of 4-hydroxy-3-methoxycinnamic acid exhibited superior activity relative to anisaldehyde, anisic acid, benzoic acid, benzaldehyde, cinnamic acid, and cinnamaldehyde; but antityrosinase inhibitors and cinnamic acid derivatives, except for cinnamyl alcohol, were slightly more effective than 3,4-dihydroxycinnamic acid. In the case of benzaldehyde and cinnamaldehyde, the aldehyde group is, apparently, a key group in eliciting potent inhibitory activity, whereas anisaldehyde is more effective than anisic acid. Methoxy substitutions, such as 2-methoxycinnamic acid, 3-methoxycinnamic acid, and 4-methoxycinnamic acid, enhanced inhibition of tyrosinase activity. As a naturally occurring tyrosinase inhibitor, 3,4-dihydroxycinnamic acid and 4-hydroxy-3-methoxycinnamic acid may be useful as new agents to inhibit the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) by mushroom tyrosinase.

Human Tyrosinase Inhibitor in Rum Distillate Wastewater

“…These results indicate that 4'-hydroxy-3'-methoxyl substituted aromatic compounds may play an important role in interacting with the tyrosinase active site. Several 4-hydroxy-3-methoxyl substituted compounds such as 4-hydroxy-3-methoxycinnamic acids have been reported as mushroom tyrosinase inhibitors 22) . However, at another aromatic moiety, the 3,4,5-substituted group, methoxyl and glucosyl substitution decreased activity as assayed by inhibition kinetics.…”

Effects of Dietary Supplementation of Ferulic Acid and .GAMMA.-Oryzanol on Integument Color and Suppression of Oxidative Stress in Cultured Red Sea Bream, Pagrus major

“…It is well-known that melanogenesis is induced by UV light and catalyzed by tyrosinase. FA and OZ are not only effective UV absorbers 6) , but also tyrosinase inhibitors [5][6][7] . Therefore, FA and OZ suppressed dark-color pigmentation in the integument of red sea bream.…”

“…Ferulic acid (FA) and g -oryzanol (OZ), which is a sterol, triterpene alcohol, and higher alcohol esters of ferulic acid, both have antioxidative and melanogenesis-inhibitory activities [5][6][7] . Thus, we attempted to apply FA and OZ supplementation for the improvement of the integument color and suppression of oxidative stress in cultured red sea bream.…”

2,4-Dihydroxycinnamic Esters as Skin Depigmenting Agents

“…The tyrosinase activity was determined using the method described by Masamoto et al with a slight modification. [18][19][20] Mushroom tyrosinase, 3-(3,4-dihydroxyphenyl)-L-alanine (L-dopa) were purchased from Sigma Chemical Co (St. Louis, Mo, USA). The test compound solution was prepared by mixing the compound with DMSO and a 0.1 M phosphate buffer (pH 7.0).…”