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Rubesanolides F and G: Two Novel Lactone-Type Norditerpenoids from Isodon rubescens

A phytochemical investigation of the leaves of the medicinal plant Isodon rubescens led to the isolation of the two new degraded abietane lactone diterpenoids rubesanolides F (1) and G (2). Their structures were elucidated based on the analyses of the HRESIMS and 1D/2D NMR spectral data, and their a...

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Autores principales: He, Kang, Zou, Juan, Wang, Yu-Xue, Zhao, Chen-Liang, Ye, Jiang-Hai, Zhang, Jing-Jie, Pan, Lu-Tai, Zhang, Hong-Jie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8270274/
https://www.ncbi.nlm.nih.gov/pubmed/34202760
http://dx.doi.org/10.3390/molecules26133865
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author He, Kang
Zou, Juan
Wang, Yu-Xue
Zhao, Chen-Liang
Ye, Jiang-Hai
Zhang, Jing-Jie
Pan, Lu-Tai
Zhang, Hong-Jie
author_facet He, Kang
Zou, Juan
Wang, Yu-Xue
Zhao, Chen-Liang
Ye, Jiang-Hai
Zhang, Jing-Jie
Pan, Lu-Tai
Zhang, Hong-Jie
author_sort He, Kang
collection PubMed
description A phytochemical investigation of the leaves of the medicinal plant Isodon rubescens led to the isolation of the two new degraded abietane lactone diterpenoids rubesanolides F (1) and G (2). Their structures were elucidated based on the analyses of the HRESIMS and 1D/2D NMR spectral data, and their absolute configurations were determined by ECD spectrum calculations and X-ray single crystal diffraction methods. Compounds 1 and 2, with a unique γ-lactone subgroup between C-8 and C-20, were found to form a carbonyl carbon at C-13 by removal of the isopropyl group in an abietane diterpene skeleton. Rubesanolide G (2) is a rare case of abietane that possesses a cis-fused configuration between rings B and C. The two isolates were evaluated for their biological activities against two cancer cell lines (A549 and HL60), three fungal strains (Candida alba, Aspergillus niger and Rhizopus nigricans) and three bacterial strains (Escherichia coli, Staphylococcus aureus and Bacillus subtilis).
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spelling pubmed-82702742021-07-10 Rubesanolides F and G: Two Novel Lactone-Type Norditerpenoids from Isodon rubescens He, Kang Zou, Juan Wang, Yu-Xue Zhao, Chen-Liang Ye, Jiang-Hai Zhang, Jing-Jie Pan, Lu-Tai Zhang, Hong-Jie Molecules Article A phytochemical investigation of the leaves of the medicinal plant Isodon rubescens led to the isolation of the two new degraded abietane lactone diterpenoids rubesanolides F (1) and G (2). Their structures were elucidated based on the analyses of the HRESIMS and 1D/2D NMR spectral data, and their absolute configurations were determined by ECD spectrum calculations and X-ray single crystal diffraction methods. Compounds 1 and 2, with a unique γ-lactone subgroup between C-8 and C-20, were found to form a carbonyl carbon at C-13 by removal of the isopropyl group in an abietane diterpene skeleton. Rubesanolide G (2) is a rare case of abietane that possesses a cis-fused configuration between rings B and C. The two isolates were evaluated for their biological activities against two cancer cell lines (A549 and HL60), three fungal strains (Candida alba, Aspergillus niger and Rhizopus nigricans) and three bacterial strains (Escherichia coli, Staphylococcus aureus and Bacillus subtilis). MDPI 2021-06-24 /pmc/articles/PMC8270274/ /pubmed/34202760 http://dx.doi.org/10.3390/molecules26133865 Text en © 2021 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
He, Kang
Zou, Juan
Wang, Yu-Xue
Zhao, Chen-Liang
Ye, Jiang-Hai
Zhang, Jing-Jie
Pan, Lu-Tai
Zhang, Hong-Jie
Rubesanolides F and G: Two Novel Lactone-Type Norditerpenoids from Isodon rubescens
title Rubesanolides F and G: Two Novel Lactone-Type Norditerpenoids from Isodon rubescens
title_full Rubesanolides F and G: Two Novel Lactone-Type Norditerpenoids from Isodon rubescens
title_fullStr Rubesanolides F and G: Two Novel Lactone-Type Norditerpenoids from Isodon rubescens
title_full_unstemmed Rubesanolides F and G: Two Novel Lactone-Type Norditerpenoids from Isodon rubescens
title_short Rubesanolides F and G: Two Novel Lactone-Type Norditerpenoids from Isodon rubescens
title_sort rubesanolides f and g: two novel lactone-type norditerpenoids from isodon rubescens
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8270274/
https://www.ncbi.nlm.nih.gov/pubmed/34202760
http://dx.doi.org/10.3390/molecules26133865
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