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3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus

Three isopimarane diterpenes [fladins B (1), C (2), and D (3)] were isolated from the twigs and leaves of Chinese folk medicine, Isodon flavidus. The chemical structures were determined by the analysis of the comprehensive spectroscopic data, and the absolute configuration was confirmed by X-ray cry...

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Autores principales: Li, Wan-Fei, Liang, Zheng-Ming, Zhao, Chen-Liang, Tsang, Nga Yi, Li, Ji-Xin, Liu, Ya-Hua, He, Kang, Pan, Lu-Tai, Rong, Lijun, Zou, Juan, Zhang, Hong-Jie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9143206/
https://www.ncbi.nlm.nih.gov/pubmed/35630575
http://dx.doi.org/10.3390/molecules27103098
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author Li, Wan-Fei
Liang, Zheng-Ming
Zhao, Chen-Liang
Tsang, Nga Yi
Li, Ji-Xin
Liu, Ya-Hua
He, Kang
Pan, Lu-Tai
Rong, Lijun
Zou, Juan
Zhang, Hong-Jie
author_facet Li, Wan-Fei
Liang, Zheng-Ming
Zhao, Chen-Liang
Tsang, Nga Yi
Li, Ji-Xin
Liu, Ya-Hua
He, Kang
Pan, Lu-Tai
Rong, Lijun
Zou, Juan
Zhang, Hong-Jie
author_sort Li, Wan-Fei
collection PubMed
description Three isopimarane diterpenes [fladins B (1), C (2), and D (3)] were isolated from the twigs and leaves of Chinese folk medicine, Isodon flavidus. The chemical structures were determined by the analysis of the comprehensive spectroscopic data, and the absolute configuration was confirmed by X-ray crystallographic analysis. The structures of 1–3 were formed from isopimaranes through the rearrangement of ring A by the bond break at C-3 and C-4 to form a new δ-lactone ring system between C-3 and C-9. This structure type represents the first discovery of a natural isopimarane diterpene with an unusual lactone moiety at C-9 and C-10. In the crystal of 1, molecules are linked to each other by intermolecular O-H···O bonds, forming chains along the b axis. Compounds 1–3 were evaluated for their bioactivities against different diseases. None of these compounds displayed cytotoxic activities against HCT116 and A549 cancer cell lines, antifungal activities against Trichophyton rubrum and T. mentagrophytes, or antiviral activities against HIV entry at 20 µg/mL (62.9–66.7) µM. Compounds 1 and 3 did not show antiviral activities against Ebola entry at 20 µg/mL either; only 2 was found to show an 81% inhibitory effect against Ebola entry activity at 20 µg/mL (66.7 µM). The bioactivity evidence suggested that this type of compound could be a valuable antiviral lead for further structure modification to improve the antiviral potential.
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spelling pubmed-91432062022-05-29 3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus Li, Wan-Fei Liang, Zheng-Ming Zhao, Chen-Liang Tsang, Nga Yi Li, Ji-Xin Liu, Ya-Hua He, Kang Pan, Lu-Tai Rong, Lijun Zou, Juan Zhang, Hong-Jie Molecules Article Three isopimarane diterpenes [fladins B (1), C (2), and D (3)] were isolated from the twigs and leaves of Chinese folk medicine, Isodon flavidus. The chemical structures were determined by the analysis of the comprehensive spectroscopic data, and the absolute configuration was confirmed by X-ray crystallographic analysis. The structures of 1–3 were formed from isopimaranes through the rearrangement of ring A by the bond break at C-3 and C-4 to form a new δ-lactone ring system between C-3 and C-9. This structure type represents the first discovery of a natural isopimarane diterpene with an unusual lactone moiety at C-9 and C-10. In the crystal of 1, molecules are linked to each other by intermolecular O-H···O bonds, forming chains along the b axis. Compounds 1–3 were evaluated for their bioactivities against different diseases. None of these compounds displayed cytotoxic activities against HCT116 and A549 cancer cell lines, antifungal activities against Trichophyton rubrum and T. mentagrophytes, or antiviral activities against HIV entry at 20 µg/mL (62.9–66.7) µM. Compounds 1 and 3 did not show antiviral activities against Ebola entry at 20 µg/mL either; only 2 was found to show an 81% inhibitory effect against Ebola entry activity at 20 µg/mL (66.7 µM). The bioactivity evidence suggested that this type of compound could be a valuable antiviral lead for further structure modification to improve the antiviral potential. MDPI 2022-05-12 /pmc/articles/PMC9143206/ /pubmed/35630575 http://dx.doi.org/10.3390/molecules27103098 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
Li, Wan-Fei
Liang, Zheng-Ming
Zhao, Chen-Liang
Tsang, Nga Yi
Li, Ji-Xin
Liu, Ya-Hua
He, Kang
Pan, Lu-Tai
Rong, Lijun
Zou, Juan
Zhang, Hong-Jie
3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus
title 3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus
title_full 3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus
title_fullStr 3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus
title_full_unstemmed 3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus
title_short 3,4-Seco-Isopimarane Diterpenes from the Twigs and Leaves of Isodon Flavidus
title_sort 3,4-seco-isopimarane diterpenes from the twigs and leaves of isodon flavidus
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9143206/
https://www.ncbi.nlm.nih.gov/pubmed/35630575
http://dx.doi.org/10.3390/molecules27103098
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