Inhibition of Mushroom Tyrosinase Activity by Orsellinates

Several applications have been proposed for tyrosinase inhibitors in the pharmaceutical, food bioprocessing, and environmental industries. However, only a few compounds are known to serve as effective tyrosinase inhibitors. This study evaluated the tyrosinase-related activity of resorcinol (1), orcinol (2) lecanoric acid (3), and derivatives of this acid (4-15). Subjected to alcoholysis, lecanoric acid (3), a depside isolated from the lichen Parmotrema tinctorum, produces orsellinic acid (2,4-dihydroxy-6-methylbenzoic acid) (4) and orsellinates (2,4-dihydroxy-6-methyl benzoates) (5-15). At 0.50 mM, methyl (5), ethyl (6), n-propyl (7), tert-butyl (11), and n-cetyl orsellinates (15) acted as tyrosinase activators, whereas n-butyl (8), iso-propyl (9), sec-butyl (10), n-pentyl (12), n-hexyl (13), and n-octyl orsellinates (14) behaved as inhibitors. Tyrosinase inhibition rose with chain elongation-n-butyl (8)

Keywords:

• Biochemistry
• Parmotrema tinctorum
• Mushroom
• Tyrosinase activity
• Chemistry
• Lecanoric acid
• Tyrosinase
• Resorcinol
• Uncompetitive inhibitor
• Orsellinic acid
• Organic chemistry
• Benzoates
• Stereochemistry
• Enzyme
• Depside
• Orcinol

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