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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crinformauk:10.1080/09168451.2019.1662279 2024-10-13T14:06:57+00:00 Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. japonicum Oka, Sayuki Kuniba, Ryo Tsuboi, Nozomi Tsuchida, Sayaka Ushida, Kazunari Tomoshige, Shusuke Kuramochi, Kouji 2020 http://dx.doi.org/10.1080/09168451.2019.1662279 http://academic.oup.com/bbb/article-pdf/84/1/31/36834303/bbb0031.pdf en eng Informa UK Limited https://academic.oup.com/journals/pages/open_access/funder_policies/chorus/standard_publication_model Bioscience, Biotechnology, and Biochemistry volume 84, issue 1, page 31-36 ISSN 0916-8451 1347-6947 journal-article 2020 crinformauk https://doi.org/10.1080/09168451.2019.1662279 2024-09-23T04:17:57Z 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. Article in Journal/Newspaper Empetrum nigrum Informa Bioscience, Biotechnology, and Biochemistry 84 1 31 36 |
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English |
description |
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. |
format |
Article in Journal/Newspaper |
author |
Oka, Sayuki Kuniba, Ryo Tsuboi, Nozomi Tsuchida, Sayaka Ushida, Kazunari Tomoshige, Shusuke Kuramochi, Kouji |
spellingShingle |
Oka, Sayuki Kuniba, Ryo Tsuboi, Nozomi Tsuchida, Sayaka Ushida, Kazunari Tomoshige, Shusuke Kuramochi, Kouji Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. japonicum |
author_facet |
Oka, Sayuki Kuniba, Ryo Tsuboi, Nozomi Tsuchida, Sayaka Ushida, Kazunari Tomoshige, Shusuke Kuramochi, Kouji |
author_sort |
Oka, Sayuki |
title |
Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. japonicum |
title_short |
Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. japonicum |
title_full |
Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. japonicum |
title_fullStr |
Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. japonicum |
title_full_unstemmed |
Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. japonicum |
title_sort |
isolation, synthesis, and biological activities of a bibenzyl from empetrum nigrum var. japonicum |
publisher |
Informa UK Limited |
publishDate |
2020 |
url |
http://dx.doi.org/10.1080/09168451.2019.1662279 http://academic.oup.com/bbb/article-pdf/84/1/31/36834303/bbb0031.pdf |
genre |
Empetrum nigrum |
genre_facet |
Empetrum nigrum |
op_source |
Bioscience, Biotechnology, and Biochemistry volume 84, issue 1, page 31-36 ISSN 0916-8451 1347-6947 |
op_rights |
https://academic.oup.com/journals/pages/open_access/funder_policies/chorus/standard_publication_model |
op_doi |
https://doi.org/10.1080/09168451.2019.1662279 |
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Bioscience, Biotechnology, and Biochemistry |
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84 |
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1 |
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31 |
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36 |
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1812813205384200192 |