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Tyrosinase Inhibitors of Pulsatilla cernua Root-Derived Materials
- Source :
- Journal of Agricultural and Food Chemistry. 50:1400-1403
- Publication Year :
- 2002
- Publisher :
- American Chemical Society (ACS), 2002.
-
Abstract
- The inhibition of mushroom tyrosinase by Pulsatilla cernua root-derived materials was evaluated. The bioactive components of Pulsatilla cernua root were characterized by spectroscopic analyses as 3,4-dihydroxycinnamic acid and 4-hydroxy-3-methoxycinnamic acid, which exhibited potent antityrosinase activity. The ID50 values of 3,4-dihydroxycinnamic acid and 4-hydroxy-3-methoxycinnamic acid were 0.97 and 0.33 mM, respectively. The compounds isolated from Pulsatilla cernua roots exhibited noncompetitive inhibition against oxidation of L-DOPA by mushroom tyrosinase. This activity was compared with that of three cinnamic acid derivatives and four well-known tyrosinase inhibitors. The ID50 of 4-hydroxy-3-methoxycinnamic acid exhibited superior activity relative to anisaldehyde, anisic acid, benzoic acid, benzaldehyde, cinnamic acid, and cinnamaldehyde; but antityrosinase inhibitors and cinnamic acid derivatives, except for cinnamyl alcohol, were slightly more effective than 3,4-dihydroxycinnamic acid. In the case of benzaldehyde and cinnamaldehyde, the aldehyde group is, apparently, a key group in eliciting potent inhibitory activity, whereas anisaldehyde is more effective than anisic acid. Methoxy substitutions, such as 2-methoxycinnamic acid, 3-methoxycinnamic acid, and 4-methoxycinnamic acid, enhanced inhibition of tyrosinase activity. As a naturally occurring tyrosinase inhibitor, 3,4-dihydroxycinnamic acid and 4-hydroxy-3-methoxycinnamic acid may be useful as new agents to inhibit the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) by mushroom tyrosinase.
- Subjects :
- Magnetic Resonance Spectroscopy
Coumaric Acids
Monophenol Monooxygenase
Tyrosinase
General Chemistry
Plant Roots
Mass Spectrometry
Cinnamic acid
Cinnamaldehyde
Levodopa
Benzaldehyde
chemistry.chemical_compound
Caffeic Acids
Non-competitive inhibition
chemistry
Organic chemistry
Phenols
Enzyme Inhibitors
Agaricales
General Agricultural and Biological Sciences
Oxidation-Reduction
Ranunculaceae
Benzoic acid
Anisic acid
Subjects
Details
- ISSN :
- 15205118 and 00218561
- Volume :
- 50
- Database :
- OpenAIRE
- Journal :
- Journal of Agricultural and Food Chemistry
- Accession number :
- edsair.doi.dedup.....7df83ba2200ff075eb2d4805efb366df