A New Tyrosinase Inhibitor from the Red Alga Symphyocladia latiuscula (Harvey) Yamada (Rhodomelaceae)

Abstract

A marine red alga, Symphyocladia latiuscula (Harvey) Yamada (Rhodomelaceae), is a rich source of bromophenols with a wide array of biological activities. This study investigates the anti-tyrosinase activity of the alga. Moderate activity was demonstrated by the methanol extract of S. latiuscula, and subsequent column chromatography identified three bromophenols: 2,3,6-tribromo-4,5-dihydroxybenzyl methyl alcohol (1), 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether (2), and bis-(2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether) (3). Bromophenols 1 and 3 exhibited potent competitive tyrosinase inhibitory activity against l-tyrosine substrates, with IC50 values of 10.78 ± 0.19 and 2.92 ± 0.04 μM, respectively. Against substrate l-3,4-dihydroxyphenylalanine (l-DOPA), compounds 1 and 3 demonstrated moderate activity, while 2 showed no observable effect. The experimental data were verified by a molecular docking study that found catalytic hydrogen and halogen interactions were responsible for the activity. In addition, compounds 1 and 3 exhibited dose-dependent inhibitory effects in melanin and intracellular tyrosinase levels in α-melanocyte-stimulating hormone (α-MSH)-induced B16F10 melanoma cells. Compounds 3 and 1 were the most effective tyrosinase inhibitors. In addition, increasing the bromine group number increased the mushroom tyrosinase inhibitory activity.

Progress of Bromophenols in Marine Algae from 2011 to 2020: Structure, Bioactivities, and Applications

“…A molecular docking study found that catalytic hydrogen bond, hydrogen and halogen interactions contributed to the enzyme inhibition activity (see Section 3 ). In addition, BPs 7.1.1 and 7.1.2 also showed dose-dependent inhibition of tyrosinase expression levels, melanin content, and intracellular tyrosinase activity in B16F10 melanoma cells [ 113 ]. Therefore, the strong tyrosinase inhibitory activity exhibited by these marine BPs isolated from S. latiuscula, suggests these algae as a possible source for depigmenting agents used in cosmetology.…”

“…An inspection of the graphics revealed major interactions to a side-chain nitrogen of Arg221 and to the OH group of Thr263, whereas the remaining interactions are to CH bonds. Docking of 2.1–2.3 has also been done to the oxy-form of Agaricus bisporus tyrosinase [ 113 ]. The interactions are not specified.…”

Anti-Alzheimer’s Disease Activity of Bromophenols from a Red Alga, Symphyocladia latiuscula (Harvey) Yamada

“…S. latiuscula (Harvey) Yamada is a marine red algal species with a high content of bromophenols, 13 and is widely distributed in Korea, Japan, and northern China. As constituents with a highly conserved biosynthetic pathway, bromophenols from S. latiuscula typically contain at least one 2,3,6-tribromo-4,5-dihydroxybenzyl moiety linked with different groups (aconitic acids, diketopiperazines, glutamines, pyrrolidin-2-ones, sulfoxides, sulfones, sulfates, and ureas) and have been reported to exhibit aldose reductase inhibitory, 14 antibacterial, 15 anticancer, 16 antifungal, 17 antiviral, 18 antidiabetic, 19 antityrosinase, 20 and free radical scavenging activities. 21 The presence of a number of electron-donating hydroxyl groups in the 2,3,6-tribromo-4,5-dihydroxybenzyl moiety supports the pronounced antioxidant effect of bromophenols from S. latiuscula .…”

“…21 The presence of a number of electron-donating hydroxyl groups in the 2,3,6-tribromo-4,5-dihydroxybenzyl moiety supports the pronounced antioxidant effect of bromophenols from S. latiuscula . 22,23 We previously isolated three bromophenol derivatives from S. latiuscula and reported their antidiabetic 19 and antityrosinase 20 activities. Recently, S. latiuscula -derived polyphenols showed a neuroprotective effect by ameliorating streptozotocin-induced diabetic peripheral neuropathy in rats.…”

Marine derived tyrosinase inhibitors

“…Symphyocladia latiuscula (Harvey) Yamada (Rhodomelaceae), and sea-red alga which contain bromophenol exhibiting a wide range of biological activities. Paudel et al (2019) investigated the anti-tyrosinase activity of the alga and from three bromophenols isolated from the alga two of them showed an activity against L-tyrosine substrates.…”