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

doi:10.1007/s13659-020-00258-w

Natural Products and Bioprospecting ›› 2021, Vol. 11 ›› Issue (1): 31-50.DOI: 10.1007/s13659-020-00258-w

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

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 Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

Received:2020-06-22 Revised:2020-07-09 Online:2021-03-11 Published:2021-02-24
Contact: Jiangong Shi, Qinglan Guo
Supported by:
Financial support from the National Natural Sciences Foundation of China (NNSFC; Grant Nos. 81730093, 81630094, and 81502942), CAMS Innovation Fund for Medical Science of China (2017-I2M-3-010 and 2016-I2M-1-004), and the Drug Innovation Major Project (2018ZX09711001-001, China) is acknowledged is acknowledged.

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

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 Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

通讯作者: Jiangong Shi, Qinglan Guo
基金资助:
Financial support from the National Natural Sciences Foundation of China (NNSFC; Grant Nos. 81730093, 81630094, and 81502942), CAMS Innovation Fund for Medical Science of China (2017-I2M-3-010 and 2016-I2M-1-004), and the Drug Innovation Major Project (2018ZX09711001-001, China) is acknowledged is acknowledged.

Abstract

Abstract: 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.

Key words: Orchidaceae, Gastrodia elata, p-Hydroxybenzyl alcohol dimer, p-Hydroxybenzyl alcohol trimer, Gastrodibenzins, Gastrotribenzins, Medicinal chemistry behind Chinese medicines

摘要： 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.

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

Yanan Wang, Min Zhang, Xue Zhou, Chengbo Xu, Chenggen Zhu, Yuhe Yuan, Naihong Chen, Yongchun Yang, Qinglan Guo, Jiangong Shi. Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata[J]. Natural Products and Bioprospecting, 2021, 11(1): 31-50.

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

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

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