Inhibition of Mushroom Tyrosinase Activity by Orsellinates

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  • Lopes Thiago Inácio Barros
    Instituto de Química, Universidade Federal de Mato Grosso do Sul Instituto Federal de Educação Ciência e Tecnologia de Mato Grosso do Sul
  • Coelho Roberta Gomes
    Instituto de Química, Universidade Federal de Mato Grosso do Sul
  • Honda Neli Kika
    Instituto de Química, Universidade Federal de Mato Grosso do Sul

書誌事項

公開日
2018
資源種別
journal article
DOI
  • 10.1248/cpb.c17-00502
公開者
公益社団法人 日本薬学会

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説明

<p>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)<n-pentyl (12)<n-hexyl (13)<n-octyl orsellinates (14)-suggesting that the enzyme site can accept an eight-carbon alkyl chain. A kinetic study of n-octyl orsellinate (14) revealed uncompetitive inhibition of tyrosinase, with an inhibition constant of 0.99 mM.</p>

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