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.

中文翻译：

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忍冬（Empetrum nigrum var。）双联苄的分离，合成及生物学活性。日本

从黑胡椒（Emppetrum nigrum var）的叶中分离出联苄基4-（2-羟基苯乙基）-2，6-二甲氧基苯酚。从立山山收集的日本药材。日本岩雷鸟经常吃这种植物的叶子和果实。联苄的结构通过NMR光谱分析确认并充分表征。该化合物的合成是通过将2-羟基苯基乙酸与丁香醛偶联，所得异金酮的脱羧以及相应的二苯乙烯中双键的氢化而完成的。该化合物对人癌细胞（HCT116和Hela细胞）和白血病细胞（HL-60细胞）显示出细胞毒活性。本研究表明该植物可作为具有生物活性的天然产物的来源。还，