Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. Japonicum

Sayuki Oka, Ryo Kuniba, Nozomi Tsuboi, Sayaka Tsuchida, Kazunari Ushida, Shusuke Tomoshige, Kouji Kuramochi

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)


4-(2-Hydroxyphenethyl)-2,6-dimethoxyphenol, a bibenzyl, was isolated from the leaves of Empetrum nigrum var. japonicum, collected from Mount Tateyama. Japanese rock ptarmigans frequently eat the leaves and fruits of this plant. The structure of the bibenzyl was confirmed by NMR spectroscopic analysis and fully characterized. A synthesis of this compound was accomplished by coupling 2-hydroxyphenylacetic acid with syringaldehyde, decarboxylation of the resultant isoaurones, and hydrogenation of the double bond in the corresponding stilbene. This compound displayed cytotoxic activity against human cancer cells (HCT116 and Hela cells) and leukemia cells (HL-60 cells). The present study suggests that this plant serves as a source of biologically active natural products. Also, our findings provide information on the secondary metabolites in the diet of Japanese rock ptarmigans.

Original languageEnglish
Pages (from-to)31-36
Number of pages6
JournalBioscience, Biotechnology and Biochemistry
Issue number1
Publication statusPublished - 2020


  • Bibenzyl
  • Biological activity
  • Isolation
  • Synthesis


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