Cargando…

Identification of Photocatalytic Alkaloids from Coptidis Rhizome by an Offline HPLC/CC/SCD Approach

Natural products continue to be a valuable source of active metabolites; however, researchers of natural products are mostly focused on the biological effects, and their chemical utility has been less explored. Furthermore, low throughput is a bottleneck for classical natural product research. In th...

Descripción completa

Detalles Bibliográficos
Autores principales: Qin, Shu-Qin, Ma, Jun, Wang, Qi-Qi, Xu, Wei, Ye, Wen-Cai, Jiang, Ren-Wang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9570981/
https://www.ncbi.nlm.nih.gov/pubmed/36234715
http://dx.doi.org/10.3390/molecules27196179
_version_ 1784810248216772608
author Qin, Shu-Qin
Ma, Jun
Wang, Qi-Qi
Xu, Wei
Ye, Wen-Cai
Jiang, Ren-Wang
author_facet Qin, Shu-Qin
Ma, Jun
Wang, Qi-Qi
Xu, Wei
Ye, Wen-Cai
Jiang, Ren-Wang
author_sort Qin, Shu-Qin
collection PubMed
description Natural products continue to be a valuable source of active metabolites; however, researchers of natural products are mostly focused on the biological effects, and their chemical utility has been less explored. Furthermore, low throughput is a bottleneck for classical natural product research. In this work, a new offline HPLC/CC/SCD (high performance liquid chromatography followed by co-crystallization and single crystal diffraction) workflow was developed that greatly expedites the discovery of active compounds from crude natural product extracts. The photoactive total alkaloids of the herbal medicine Coptidis rhizome were firstly separated by HPLC, and the individual peaks were collected. A suitable coformer was screened by adding it to the individual peak solution and observing the precipitation, which was then redissolved and used for co-crystallization. Seven new co-crystals were obtained, and all the single crystals were subjected to X-ray diffraction analysis. The molecular structures of seven alkaloids from milligrams of crude extract were resolved within three days. NDS greatly decreases the required crystallization amounts of alkaloids to the nanoscale and enables rapid stoichiometric inclusion of all the major alkaloids with full occupancy, typically without disorder, affording well-refined structures. It is noteworthy that anomalous scattering by the coformer sulfur atoms enables reliable assignment of absolute configuration of stereogenic centers. Moreover, the identified alkaloids were firstly found to be photocatalysts for the green synthesis of benzimidazoles. This study demonstrates a new and green phytochemical workflow that can greatly accelerate natural product discovery from complex samples.
format Online
Article
Text
id pubmed-9570981
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-95709812022-10-17 Identification of Photocatalytic Alkaloids from Coptidis Rhizome by an Offline HPLC/CC/SCD Approach Qin, Shu-Qin Ma, Jun Wang, Qi-Qi Xu, Wei Ye, Wen-Cai Jiang, Ren-Wang Molecules Article Natural products continue to be a valuable source of active metabolites; however, researchers of natural products are mostly focused on the biological effects, and their chemical utility has been less explored. Furthermore, low throughput is a bottleneck for classical natural product research. In this work, a new offline HPLC/CC/SCD (high performance liquid chromatography followed by co-crystallization and single crystal diffraction) workflow was developed that greatly expedites the discovery of active compounds from crude natural product extracts. The photoactive total alkaloids of the herbal medicine Coptidis rhizome were firstly separated by HPLC, and the individual peaks were collected. A suitable coformer was screened by adding it to the individual peak solution and observing the precipitation, which was then redissolved and used for co-crystallization. Seven new co-crystals were obtained, and all the single crystals were subjected to X-ray diffraction analysis. The molecular structures of seven alkaloids from milligrams of crude extract were resolved within three days. NDS greatly decreases the required crystallization amounts of alkaloids to the nanoscale and enables rapid stoichiometric inclusion of all the major alkaloids with full occupancy, typically without disorder, affording well-refined structures. It is noteworthy that anomalous scattering by the coformer sulfur atoms enables reliable assignment of absolute configuration of stereogenic centers. Moreover, the identified alkaloids were firstly found to be photocatalysts for the green synthesis of benzimidazoles. This study demonstrates a new and green phytochemical workflow that can greatly accelerate natural product discovery from complex samples. MDPI 2022-09-21 /pmc/articles/PMC9570981/ /pubmed/36234715 http://dx.doi.org/10.3390/molecules27196179 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Qin, Shu-Qin
Ma, Jun
Wang, Qi-Qi
Xu, Wei
Ye, Wen-Cai
Jiang, Ren-Wang
Identification of Photocatalytic Alkaloids from Coptidis Rhizome by an Offline HPLC/CC/SCD Approach
title Identification of Photocatalytic Alkaloids from Coptidis Rhizome by an Offline HPLC/CC/SCD Approach
title_full Identification of Photocatalytic Alkaloids from Coptidis Rhizome by an Offline HPLC/CC/SCD Approach
title_fullStr Identification of Photocatalytic Alkaloids from Coptidis Rhizome by an Offline HPLC/CC/SCD Approach
title_full_unstemmed Identification of Photocatalytic Alkaloids from Coptidis Rhizome by an Offline HPLC/CC/SCD Approach
title_short Identification of Photocatalytic Alkaloids from Coptidis Rhizome by an Offline HPLC/CC/SCD Approach
title_sort identification of photocatalytic alkaloids from coptidis rhizome by an offline hplc/cc/scd approach
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9570981/
https://www.ncbi.nlm.nih.gov/pubmed/36234715
http://dx.doi.org/10.3390/molecules27196179
work_keys_str_mv AT qinshuqin identificationofphotocatalyticalkaloidsfromcoptidisrhizomebyanofflinehplcccscdapproach
AT majun identificationofphotocatalyticalkaloidsfromcoptidisrhizomebyanofflinehplcccscdapproach
AT wangqiqi identificationofphotocatalyticalkaloidsfromcoptidisrhizomebyanofflinehplcccscdapproach
AT xuwei identificationofphotocatalyticalkaloidsfromcoptidisrhizomebyanofflinehplcccscdapproach
AT yewencai identificationofphotocatalyticalkaloidsfromcoptidisrhizomebyanofflinehplcccscdapproach
AT jiangrenwang identificationofphotocatalyticalkaloidsfromcoptidisrhizomebyanofflinehplcccscdapproach