Abstract

Preparation of urushiol derivatives was carried out in response to the drug industry’s increasing demand for new synthetic anticancer agents. Urushiol methylene acetal derivatives were synthesized in high yields by reaction of urushiol with methylene chloride under the catalytic action of NaOH. Four kinds of urushiol methylene acetal monomers were separated by silica-gel column and preparative HPLC, and their structures were elucidated by extensive spectroscopic methods, including 1D-NMR and 2D-NMR (1H,13C-NMR,1H-1HCOSY, HSQC, and HMBC) as well as TOF-MS. They were identified as 3-[pentadecyl] benzene methylene ether (compound 1), 3-[8′-pentadecatrienyl] benzene methylene ether (compound 2), 3-[8′,11′-pentadecatrienyl] benzene methylene ether (compound 3), and 3-[8′,11′,14′-pentadecatrienyl] benzene methylene ether (compound 4). This research provides a theoretical reference for exploration of these interesting and potentially bioactive compounds.

Highlights

  • Urushiols are major components of the sap of the lacquer tree (Rhus verniciflua Stokes, Anacardiaceae) that is widely cultivated in northeastern Asian countries including China, Korea, and Japan [1]

  • Studies showed that acetal derivatives of phenolic compounds have prominent antioxidant, antimicrobial, and anticancer activities, and the acetal-type groups have the advantages of including simultaneous protection of two hydroxyls and easy removal of a partial deprotection [8, 9], but, till there has been no report about the preparation of acetal derivatives of urushiol and its monomers

  • In view of the research status of urushiol and the great potential of urushiol as a potent material in new drug research and development, our study was aimed at synthesizing urushiol methylene acetal derivatives, separating urushiol methylene acetal monomers of various unsaturated degrees, and characterizing their structures

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Summary

Introduction

Urushiols are major components of the sap of the lacquer tree (Rhus verniciflua Stokes, Anacardiaceae) that is widely cultivated in northeastern Asian countries including China, Korea, and Japan [1]. It is thought that the phenolic hydroxyl group of urushiol is the main cause of allergic reaction and polymerization [5]. Studies showed that acetal derivatives of phenolic compounds have prominent antioxidant, antimicrobial, and anticancer activities, and the acetal-type groups have the advantages of including simultaneous protection of two hydroxyls and easy removal of a partial deprotection [8, 9], but, till there has been no report about the preparation of acetal derivatives of urushiol and its monomers. In view of the research status of urushiol and the great potential of urushiol as a potent material in new drug research and development, our study was aimed at synthesizing urushiol methylene acetal derivatives, separating urushiol methylene acetal monomers of various unsaturated degrees, and characterizing their structures. Our studies provide potentially important information for further development of new urushiol derivatives and provide new leading compounds for the research on clinical drugs

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