Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata
| Autor: | Min Zhang, Qing-Lan Guo, Yanan Wang, Yongchun Yang, Chengbo Xu, Yu-He Yuan, Xue Zhou, Nai-Hong Chen, Cheng-Gen Zhu, Jiangong Shi |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
p-Hydroxybenzyl alcohol dimer
Electrospray ionization Gastrotribenzins Alcohol Plant Science Toxicology 01 natural sciences Biochemistry Medicinal chemistry Aldehyde Analytical Chemistry 03 medical and health sciences chemistry.chemical_compound Gastrodin Orchidaceae 030304 developmental biology Pharmacology chemistry.chemical_classification 0303 health sciences Gastrodibenzins Ethanol biology 010405 organic chemistry Organic Chemistry Botany p-Hydroxybenzyl alcohol trimer biology.organism_classification Gastrodia elata 0104 chemical sciences Rhizome chemistry QK1-989 Medicinal chemistry behind Chinese medicines Original Article Methanol Food Science |
| Zdroj: | Natural Products and Bioprospecting Natural Products and Bioprospecting, Vol 11, Iss 1, Pp 31-50 (2020) |
| ISSN: | 2192-2209 2192-2195 |
| Popis: | From an aqueous extract of “tian ma” (the steamed and dried rhizomes of Gastrodia elata), ten new compounds gastrodibenzins 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 analysis. Meanwhile, 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 alcohol. Methylation 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, respectively. using ultra-performance liquid chromatography high-resolution electrospray ionization mass spectrometry (UPLC-HRESIMS) analysis of the refluxed solutions of p-hydroxybenzyl alcohol and the refluxed extracts of the fresh G. elata 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 time. In 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 G. elata rhizomes, demonstrating insights into medicinal chemistry behind application protocols of traditional Chinese medicines. Graphic Abstract |
| Databáze: | OpenAIRE |
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