TY - JOUR
T1 - Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. Japonicum
AU - Oka, Sayuki
AU - Kuniba, Ryo
AU - Tsuboi, Nozomi
AU - Tsuchida, Sayaka
AU - Ushida, Kazunari
AU - Tomoshige, Shusuke
AU - Kuramochi, Kouji
N1 - Funding Information:
The leaves and stems of Empetrum nigrum var. japonicum were collected in Mt. Tateyama with permissions from Ministry of the Environment of Japan (No. 1,605,111), Forestry Agency of Japan (No.172 and No. 320 in 2016), and Toyama prefecture (No. 117) in accordance with the Environment Research and Technology Development Fund (4–1604).
Funding Information:
This research was supported by the Environment Research and Technology Development Fund [ERTDF/No. 4-1604 and 4-1903] of the Environmental Restoration and Conservation Agency of Japan. This research was supported by the Environment Research and Technology Development Fund [ERTDF/No. 4-1604 and 4-1903] of the Environmental Restoration and Conservation Agency of Japan.
Publisher Copyright:
© 2019 Japan Society for Bioscience, Biotechnology, and Agrochemistry
PY - 2020
Y1 - 2020
N2 - 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.
AB - 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.
KW - Bibenzyl
KW - Biological activity
KW - Isolation
KW - Synthesis
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U2 - 10.1080/09168451.2019.1662279
DO - 10.1080/09168451.2019.1662279
M3 - Article
C2 - 31794330
AN - SCOPUS:85076104618
SN - 0916-8451
VL - 84
SP - 31
EP - 36
JO - Bioscience, Biotechnology and Biochemistry
JF - Bioscience, Biotechnology and Biochemistry
IS - 1
ER -
