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

ABSTRACT 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 spectroscopi...

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Bibliographic Details
Published in:Bioscience, Biotechnology, and Biochemistry
Main Authors: Oka, Sayuki, Kuniba, Ryo, Tsuboi, Nozomi, Tsuchida, Sayaka, Ushida, Kazunari, Tomoshige, Shusuke, Kuramochi, Kouji
Format: Article in Journal/Newspaper
Language:English
Published: Informa UK Limited 2020
Subjects:
Organic Chemistry
Molecular Biology
Applied Microbiology and Biotechnology
General Medicine
Biochemistry
Analytical Chemistry
Biotechnology
Empetrum nigrum
Online Access:http://dx.doi.org/10.1080/09168451.2019.1662279
http://academic.oup.com/bbb/article-pdf/84/1/31/36834303/bbb0031.pdf
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Summary:ABSTRACT 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.

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