Gastrodin Derivatives from Gastrodia elata

doi:10.1007/s13659-019-00224-1

应用天然产物 ›› 2019, Vol. 9 ›› Issue (6): 393-404.DOI: 10.1007/s13659-019-00224-1

• ORIGINAL ARTICLES • 上一篇下一篇

Gastrodin Derivatives from Gastrodia elata

Cheng-Bo Xu, Qing-Lan Guo, Ya-Nan Wang, Sheng Lin, Cheng-Gen Zhu, Jian-Gong Shi

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China

收稿日期:2019-10-14 修回日期:2019-10-24 出版日期:2019-12-24 发布日期:2019-12-11
通讯作者: Jian-Gong Shi
基金资助:
Financial support from the National Natural Science Foundation of China (81630094, 81502942, and 81730093), CAMS Innovation Fund for Medical Science of China (2016-I2M-1-004, 2017-I2M-3-010, and 2016-I2M-1-010), and Drug Innovation Major Project (2018ZX09711001-001-001, China) is gratefully acknowledged.

Gastrodin Derivatives from Gastrodia elata

Cheng-Bo Xu, Qing-Lan Guo, Ya-Nan Wang, Sheng Lin, Cheng-Gen Zhu, Jian-Gong Shi

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China

Received:2019-10-14 Revised:2019-10-24 Online:2019-12-24 Published:2019-12-11
Contact: Jian-Gong Shi
Supported by:
Financial support from the National Natural Science Foundation of China (81630094, 81502942, and 81730093), CAMS Innovation Fund for Medical Science of China (2016-I2M-1-004, 2017-I2M-3-010, and 2016-I2M-1-010), and Drug Innovation Major Project (2018ZX09711001-001-001, China) is gratefully acknowledged.

摘要/Abstract

摘要： Nine new gastrodin derivatives, including seven p-hydroxybenzyl-modified gastrodin ethers (1-7), 6'-O-acetylgastrodin (8), and 4-[α-D-glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]benzyl alcohol (9), together with seven known derivatives, were isolated from an aqueous extract of Gastrodia elata ("tian ma") rhizomes. Their structures were determined by spectroscopic and chemical methods as well as single crystal X-ray diffraction. Compounds 1-4, 7, 10, and 11 were also isolated from a reaction mixture by refluxing gastrodin and p-hydroxybenzyl alcohol in H₂O. As both gastrodin and p-hydroxybenzyl alcohol exist in the plant, the reaction results provide evidence for the production and increase/decrease of potential effective/toxic components when "tian ma" is decocted solely or together with ingredients in Chinese traditional medicine formulations, though the isolates were inactive in the preliminarily cell-based assays at concentrations of 10 μM. Moreover, using ultraperformance liquid chromatography high-resolution electrospray ionization mass spectrometry (UPLC-HRESIMS), 4, 7, 10, and 11, as well as component variations, were detectable in the freshly prepared extracts of different types of samples, including the freeze-dried fresh G. elata rhizomes.

关键词: Orchidaceae, Gastrodia elata Blume, p-Hydroxybenzyl gastrodin ethers, Reaction of gastrodin with p-hydroxybenzyl alcohol, Component variation during decocting

Abstract: Nine new gastrodin derivatives, including seven p-hydroxybenzyl-modified gastrodin ethers (1-7), 6'-O-acetylgastrodin (8), and 4-[α-D-glucopyranosyl-(1→6)-β-D-glucopyranosyloxy]benzyl alcohol (9), together with seven known derivatives, were isolated from an aqueous extract of Gastrodia elata ("tian ma") rhizomes. Their structures were determined by spectroscopic and chemical methods as well as single crystal X-ray diffraction. Compounds 1-4, 7, 10, and 11 were also isolated from a reaction mixture by refluxing gastrodin and p-hydroxybenzyl alcohol in H₂O. As both gastrodin and p-hydroxybenzyl alcohol exist in the plant, the reaction results provide evidence for the production and increase/decrease of potential effective/toxic components when "tian ma" is decocted solely or together with ingredients in Chinese traditional medicine formulations, though the isolates were inactive in the preliminarily cell-based assays at concentrations of 10 μM. Moreover, using ultraperformance liquid chromatography high-resolution electrospray ionization mass spectrometry (UPLC-HRESIMS), 4, 7, 10, and 11, as well as component variations, were detectable in the freshly prepared extracts of different types of samples, including the freeze-dried fresh G. elata rhizomes.

Key words: Orchidaceae, Gastrodia elata Blume, p-Hydroxybenzyl gastrodin ethers, Reaction of gastrodin with p-hydroxybenzyl alcohol, Component variation during decocting

Cheng-Bo Xu, Qing-Lan Guo, Ya-Nan Wang, Sheng Lin, Cheng-Gen Zhu, Jian-Gong Shi. Gastrodin Derivatives from Gastrodia elata[J]. 应用天然产物, 2019, 9(6): 393-404.

Cheng-Bo Xu, Qing-Lan Guo, Ya-Nan Wang, Sheng Lin, Cheng-Gen Zhu, Jian-Gong Shi. Gastrodin Derivatives from Gastrodia elata[J]. Natural Products and Bioprospecting, 2019, 9(6): 393-404.

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Gastrodin Derivatives from Gastrodia elata

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