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Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata

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Natural Products and Bioprospecting 2021年第1期11卷 31-50页

作者： Yanan Wang Min Zhang Xue Zhou Chengbo Xu Chenggen Zhu Yuhe Yuan Naihong Chen Yongchun Yang Qinglan Guo Jiangong Shi State Key Laboratory of Bioactive Substance and Function of Natural Medicines Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

From an aqueous extract of“tian ma”(the steamed and dried rhizomes of Gastrodia elata),ten new compounds gastrodiben-zins A−D(1−4)and gastrotribenzins A−F(5−10),along with known analogues(11−20),having structure features coupling between two and three p-hydroxybenzyl-derived units via carbon-and/or ether-bonds,were isolated and characterized by spectroscopic data ***,the new compounds 5a,6a,8a,22,and 23,as well as the known derivatives 13a,14a,15,17−21,24,25,and p-hydroxybenzyl aldehyde were isolated and identified from a refluxed aqueous solution of p-hydroxybenzyl *** of 5a and 6a in methanol and ethylation of 6a,8a,13a,and 14a in ethanol produced 5 and 6 and 7,8,13,and 14,*** ultra-performance liquid chromatography high-resolution electrospray ioniza-tion mass spectrometry(UPLC-HRESIMS)analysis of the refluxed solutions of p-hydroxybenzyl alcohol and the refluxed extracts of the fresh *** rhizome and“tian ma”extracts indicated consistent production and variation of the dimeric and trimeric derivatives of p-hydroxybenzyl alcohol upon extracting solvents and refluxing *** various assays,the dimeric and trimeric derivatives showed more potent activities than p-hydroxybenzyl alcohol itself and gastrodin,which are the main known active constituents of“tian ma”.These results revealed for the first time that the more effective dimers and trimers can be produced through condensation of the co-occurring p-hydroxybenzyl alcohol during processing and decocting of the *** rhizomes,demonstrating insights into medicinal chemistry behind application protocols of traditional Chinese medicines.

关键词： Orchidaceae Gastrodia elata p-Hydroxybenzyl alcohol dimer p-Hydroxybenzyl alcohol trimer gastrodibenzins Gastrotribenzins Medicinal chemistry behind Chinese medicines

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