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 ultra-performance 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.

Graphic Abstract

中文翻译：

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天麻素 天麻素衍生物。

 抽象的

9个新的天麻素衍生物，包括7个对羟基苄基修饰的天麻素醚( 1 – 7 )、6′- O-乙酰天麻素( 8 )和4-[ α - d -吡喃葡萄糖基-(1 →6)- β - d -从天麻（“天麻”）根茎的水提取物中分离出吡喃葡萄糖氧基]苯甲醇（ 9 ）以及七种已知衍生物。它们的结构通过光谱和化学方法以及单晶X射线衍射测定。通过在H ₂ O中回流天麻素和对羟基苯甲醇，也从反应混合物中分离出化合物1 – 4、7、10和11。由于天麻素和对羟基苯甲醇都存在于植物中，因此反应结果为当“天麻”单独煎煮或与中药配方中的成分一起煎煮时，潜在有效/毒性成分的产生和增加/减少，尽管在初步的细胞分析中，分离物在浓度为 10 μM 时没有活性。此外，使用超高效液相色谱高分辨率电喷雾电离质谱 (UPLC-HRESIMS)，在不同类型样品的新鲜制备的提取物中可检测到4 、 7 、 10和11以及成分变化，包括冻干的新鲜G. elata根茎。

 图文摘要