Cargando…

Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens

(±)-Decumicorine A (1) and (±)-epi-decumicorine A (2), two pairs of enantiomeric isoquinoline alkaloids featuring a novel phenylpropanoid-conjugated protoberberine skeleton, were isolated and purified from the rhizomes of Corydalis decumbens. The separation of (±)-1 and (±)-2 was achieved by chiral...

Descripción completa

Detalles Bibliográficos
Autores principales: Lu, Jing-Guang, Wang, Yingwei, Yang, Ming-Rong, Wang, Cai-Yun, Meng, Jieru, Liu, Jiazheng, Yang, Zifeng, Wu, Kongsong, Bai, Li-Ping, Zhu, Guo-Yuan, Jiang, Zhi-Hong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Pharmaceutical Society of Korea 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9484358/
https://www.ncbi.nlm.nih.gov/pubmed/36121609
http://dx.doi.org/10.1007/s12272-022-01401-6
_version_ 1784791865209389056
author Lu, Jing-Guang
Wang, Yingwei
Yang, Ming-Rong
Wang, Cai-Yun
Meng, Jieru
Liu, Jiazheng
Yang, Zifeng
Wu, Kongsong
Bai, Li-Ping
Zhu, Guo-Yuan
Jiang, Zhi-Hong
author_facet Lu, Jing-Guang
Wang, Yingwei
Yang, Ming-Rong
Wang, Cai-Yun
Meng, Jieru
Liu, Jiazheng
Yang, Zifeng
Wu, Kongsong
Bai, Li-Ping
Zhu, Guo-Yuan
Jiang, Zhi-Hong
author_sort Lu, Jing-Guang
collection PubMed
description (±)-Decumicorine A (1) and (±)-epi-decumicorine A (2), two pairs of enantiomeric isoquinoline alkaloids featuring a novel phenylpropanoid-conjugated protoberberine skeleton, were isolated and purified from the rhizomes of Corydalis decumbens. The separation of (±)-1 and (±)-2 was achieved by chiral HPLC to produce four optically pure enantiomers. The structures and absolute configurations of compounds (−)-1, (+)-1, (−)-2, and (+)-2 were elucidated by spectroscopic analysis, ECD calculations, and X-ray crystallographic analyses. The two racemates were generated from a Diels-Alder [4 + 2] cycloaddition between jatrorrhizine and ferulic acid in the proposed biosynthetic pathways, which were fully verified by a biomimetic synthesis. Moreover, compound (+)-1 exhibited an antiviral entry effect on SARS-CoV-2 pseudovirus by blocking spike binding to the ACE2 receptor on HEK-293T-ACE2(h) host cells. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s12272-022-01401-6.
format Online
Article
Text
id pubmed-9484358
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher Pharmaceutical Society of Korea
record_format MEDLINE/PubMed
spelling pubmed-94843582022-09-19 Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens Lu, Jing-Guang Wang, Yingwei Yang, Ming-Rong Wang, Cai-Yun Meng, Jieru Liu, Jiazheng Yang, Zifeng Wu, Kongsong Bai, Li-Ping Zhu, Guo-Yuan Jiang, Zhi-Hong Arch Pharm Res Research Article (±)-Decumicorine A (1) and (±)-epi-decumicorine A (2), two pairs of enantiomeric isoquinoline alkaloids featuring a novel phenylpropanoid-conjugated protoberberine skeleton, were isolated and purified from the rhizomes of Corydalis decumbens. The separation of (±)-1 and (±)-2 was achieved by chiral HPLC to produce four optically pure enantiomers. The structures and absolute configurations of compounds (−)-1, (+)-1, (−)-2, and (+)-2 were elucidated by spectroscopic analysis, ECD calculations, and X-ray crystallographic analyses. The two racemates were generated from a Diels-Alder [4 + 2] cycloaddition between jatrorrhizine and ferulic acid in the proposed biosynthetic pathways, which were fully verified by a biomimetic synthesis. Moreover, compound (+)-1 exhibited an antiviral entry effect on SARS-CoV-2 pseudovirus by blocking spike binding to the ACE2 receptor on HEK-293T-ACE2(h) host cells. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s12272-022-01401-6. Pharmaceutical Society of Korea 2022-09-19 2022 /pmc/articles/PMC9484358/ /pubmed/36121609 http://dx.doi.org/10.1007/s12272-022-01401-6 Text en © The Pharmaceutical Society of Korea 2022, Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.
spellingShingle Research Article
Lu, Jing-Guang
Wang, Yingwei
Yang, Ming-Rong
Wang, Cai-Yun
Meng, Jieru
Liu, Jiazheng
Yang, Zifeng
Wu, Kongsong
Bai, Li-Ping
Zhu, Guo-Yuan
Jiang, Zhi-Hong
Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens
title Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens
title_full Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens
title_fullStr Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens
title_full_unstemmed Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens
title_short Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens
title_sort structures, biomimetic synthesis, and anti-sars-cov-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of corydalis decumbens
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9484358/
https://www.ncbi.nlm.nih.gov/pubmed/36121609
http://dx.doi.org/10.1007/s12272-022-01401-6
work_keys_str_mv AT lujingguang structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens
AT wangyingwei structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens
AT yangmingrong structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens
AT wangcaiyun structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens
AT mengjieru structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens
AT liujiazheng structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens
AT yangzifeng structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens
AT wukongsong structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens
AT bailiping structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens
AT zhuguoyuan structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens
AT jiangzhihong structuresbiomimeticsynthesisandantisarscov2activityoftwopairsofenantiomericphenylpropanoidconjugatedprotoberberinealkaloidsfromtherhizomesofcorydalisdecumbens