A novel ring-expanded product with enhanced tyrosinase inhibitory activity from classical Fe-catalyzed oxidation of rosmarinic acid, a potent antioxidative Lamiaceae polyphenol

作者：Fujimoto Aya; Shingai Yoshimi; Nakamura Mitsuhiro; Maekawa Tomomi; Sone Yoshiaki; Masuda Toshiya^*

来源：Bioorganic & Medicinal Chemistry Letters, 2010, 20(24): 7393-7396.

DOI：10.1016/j.bmcl.2010.10.040

• Rosmarinic acid
• Polyphenol
• Antioxidant
• Tyrosinase inhibitory activity
• Fe-catalyzed oxidation
• Structure determination

The iron-ion catalyzed oxidation of the ethanol solution of rosmarinic acid, a potent antioxidant polyphenol of Lamiaceae (Labiatae) plants, afforded a highly tyrosinase-inhibitory active product. The structure of the active product in the oxidation product mixture was determined using extensive NMR spectroscopy to have a novel oxygen-containing seven-membered ring system. The formation mechanism of the unique ring structure from the catechol part of the rosmarinic acid was proposed.

• 出版日期2010-12-15