The Luteolinidin and Petunidin 3-O-Glucoside: A Competitive Inhibitor of Tyrosinase

Abstract

The enzyme tyrosinase plays a key role in the early stages of melanin biosynthesis. This study evaluated the inhibitory activity of anthocyanidin (1) and anthocyanins (2–6) on the catalytic reaction. Of the six derivatives examined, 1–3 showed inhibitory activity with IC50 values of 3.7 ± 0.1, 10.3 ± 1.0, and 41.3 ± 3.2 μM, respectively. Based on enzyme kinetics, 1–3 were confirmed to be competitive inhibitors with Ki values of 2.8, 9.0, and 51.9 μM, respectively. Molecular docking analysis revealed the formation of a binary encounter complex between 1–3 and the tyrosinase catalytic site. Luteolinidin (1) and petunidin 3-O-glucoside (2) may serve as tyrosinase inhibitors to block melanin production.

High-resolution metabolite imaging: luteolinidin accumulates at the host-cyanobiont interface during cold-acclimation inAzollasymbioses

“…Apigenidin was more predominant in the leaf tips and parenchyma whilst luteolinidin was more epidermis-specific ( Figure 4A-C ). Apigenidin could therefore be scavenging ROS in the photosynthetically active parenchyma, whilst luteolinidin may prevent blue/green light from reaching the parenchyma and, in addition, inhibit microbial infection of the plant surface by specifically inhibiting tyrosinase activity (Panis et al, 2021; Yang et al, 2022).…”

Isolation, Purification and Tyrosinase Inhibitory Activity of Anthocyanins and Their Novel Degradation Compounds from Solanum tuberosum L.

“…Molecules 2024, 29, x FOR PEER REVIEW 3 of 18 inhibitory activity with an IC50 value of 10.3 ± 1.0 μM [29]. Additionally, anthocyanins from Hibiscus syriacus L. inhibit melanogenesis by activating the extracellular regulated protein kinases signaling pathway [30].…”

“…had inhibitory effect on tyrosinase monophenolase (IC 50 = 1.483 ± 0.058 mg mL −1 ), and the maximum inhibitory activity of the purified anthocyanins (3.00 mg mL −1 ) on tyrosinase diphenolase was 42.16% ± 0.77% [28]. Petunidin 3-O-glucoside may act as a tyrosinase inhibitor to block melanin production, and its IC 50 value was 10.3 ± 1.0 µM [29]. As shown in Table 4 and Figure 3A, regarding the tyrosinase activity of petanin and its degradation compounds, petanin and 4-O-(p-coumaryl) rhamnose were shown to be significantly different (p < 0.01).…”

“…had inhibitory effects on tyrosinase monophenolase (IC 50 = 1.483 ± 0.058 mg mL −1 ), and the type of inhibition was competitive (K i = 39.83 ± 1.4 mg mL −1 ) [28]. Moreover, petunidin 3-O-glucoside may act as a tyrosinase inhibitor to block melanin production, and has inhibitory ratios exceeding 55% of the control value at 50 µM, showing dose-dependent inhibitory activity with an IC 50 value of 10.3 ± 1.0 µM [29]. Additionally, anthocyanins from Hibiscus syriacus L. inhibit melanogenesis by activating the extracellular regulated protein kinases signaling pathway [30].…”