Cargando…

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

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Wang, Yanan, Zhang, Min, Zhou, Xue, Xu, Chengbo, Zhu, Chenggen, Yuan, Yuhe, Chen, Naihong, Yang, Yongchun, Guo, Qinglan, Shi, Jiangong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Singapore 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7933327/
https://www.ncbi.nlm.nih.gov/pubmed/32761444
http://dx.doi.org/10.1007/s13659-020-00258-w
_version_ 1783660585501589504
author Wang, Yanan
Zhang, Min
Zhou, Xue
Xu, Chengbo
Zhu, Chenggen
Yuan, Yuhe
Chen, Naihong
Yang, Yongchun
Guo, Qinglan
Shi, Jiangong
author_facet Wang, Yanan
Zhang, Min
Zhou, Xue
Xu, Chengbo
Zhu, Chenggen
Yuan, Yuhe
Chen, Naihong
Yang, Yongchun
Guo, Qinglan
Shi, Jiangong
author_sort Wang, Yanan
collection PubMed
description 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. [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s13659-020-00258-w) contains supplementary material, which is available to authorized users.
format Online
Article
Text
id pubmed-7933327
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher Springer Singapore
record_format MEDLINE/PubMed
spelling pubmed-79333272021-03-19 Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata Wang, Yanan Zhang, Min Zhou, Xue Xu, Chengbo Zhu, Chenggen Yuan, Yuhe Chen, Naihong Yang, Yongchun Guo, Qinglan Shi, Jiangong Nat Prod Bioprospect Original Article 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. [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s13659-020-00258-w) contains supplementary material, which is available to authorized users. Springer Singapore 2020-08-06 /pmc/articles/PMC7933327/ /pubmed/32761444 http://dx.doi.org/10.1007/s13659-020-00258-w Text en © The Author(s) 2020 Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Original Article
Wang, Yanan
Zhang, Min
Zhou, Xue
Xu, Chengbo
Zhu, Chenggen
Yuan, Yuhe
Chen, Naihong
Yang, Yongchun
Guo, Qinglan
Shi, Jiangong
Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata
title Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata
title_full Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata
title_fullStr Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata
title_full_unstemmed Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata
title_short Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata
title_sort insight into medicinal chemistry behind traditional chinese medicines: p-hydroxybenzyl alcohol-derived dimers and trimers from gastrodia elata
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7933327/
https://www.ncbi.nlm.nih.gov/pubmed/32761444
http://dx.doi.org/10.1007/s13659-020-00258-w
work_keys_str_mv AT wangyanan insightintomedicinalchemistrybehindtraditionalchinesemedicinesphydroxybenzylalcoholderiveddimersandtrimersfromgastrodiaelata
AT zhangmin insightintomedicinalchemistrybehindtraditionalchinesemedicinesphydroxybenzylalcoholderiveddimersandtrimersfromgastrodiaelata
AT zhouxue insightintomedicinalchemistrybehindtraditionalchinesemedicinesphydroxybenzylalcoholderiveddimersandtrimersfromgastrodiaelata
AT xuchengbo insightintomedicinalchemistrybehindtraditionalchinesemedicinesphydroxybenzylalcoholderiveddimersandtrimersfromgastrodiaelata
AT zhuchenggen insightintomedicinalchemistrybehindtraditionalchinesemedicinesphydroxybenzylalcoholderiveddimersandtrimersfromgastrodiaelata
AT yuanyuhe insightintomedicinalchemistrybehindtraditionalchinesemedicinesphydroxybenzylalcoholderiveddimersandtrimersfromgastrodiaelata
AT chennaihong insightintomedicinalchemistrybehindtraditionalchinesemedicinesphydroxybenzylalcoholderiveddimersandtrimersfromgastrodiaelata
AT yangyongchun insightintomedicinalchemistrybehindtraditionalchinesemedicinesphydroxybenzylalcoholderiveddimersandtrimersfromgastrodiaelata
AT guoqinglan insightintomedicinalchemistrybehindtraditionalchinesemedicinesphydroxybenzylalcoholderiveddimersandtrimersfromgastrodiaelata
AT shijiangong insightintomedicinalchemistrybehindtraditionalchinesemedicinesphydroxybenzylalcoholderiveddimersandtrimersfromgastrodiaelata