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.
Highlights
Marine algae are widely used in a variety of cuisines [1] and are preferred by a growing number of consumers for their functional and nutraceutical properties [2,3]
Melanogenesis describes the production of distinct melanin pigments by specialized cells called melanocytes, which are found within membrane-bound organelles known as melanosomes [10]
Dulbecco’s modified Eagle’s medium (DMEM), fetal bovine serum (FBS), and penicillin-streptomycin were purchased from Gibco-BRL Life Technologies (Grand Island, NY, USA)
Summary
Marine algae are widely used in a variety of cuisines [1] and are preferred by a growing number of consumers for their functional and nutraceutical properties [2,3]. The pharmaceutical industry has developed a strong interest in algae [4,5], as have cosmetologists [6]. A major concern among the latter is hyperpigmentation, which is an abnormal darkening of the skin associated with excessive melanin production [7,8]. Melanin is a pigment responsible for the photo-protective effect of skin, overproduction may lead to skin disorders [9]. Because tyrosinase is a rate-limiting step in melanin formation, identification of a strong tyrosinase inhibitor would be of significant value to hyperpigmentation research. Melanogenesis describes the production of distinct melanin pigments by specialized cells called melanocytes, which are found within membrane-bound organelles known as melanosomes [10]
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