Discovery of bioactive polycyclic polyprenylated acylphloroglucinols with adamantine/homoadamantane skeletons from Hypericum wilsonii
Copyright © 2023 Elsevier Ltd. All rights reserved..
In this work, nine previous undescribed polycyclic polyprenylated acylphloroglucinols with adamantine/homoadamantane skeletons, cumilcinols A-I (1-9), along with six known analogues, were isolated and identified from the stems, leaves and flowers of Hypericum wilsonii. Their structures were determined by HRESIMS, NMR spectroscopic analysis, single-crystal X-ray crystallography as well as electronic circular dichroism calculations and comparisons. Compound 2 formed a unique furan ring bearing a rare acetal functionality. In bioassays, hyperacmosin G (13) could significantly inhibit the production of NO in LPS-stimulated RAW264.7 cell (IC50 = 4.350 ± 1.146 μM), and increased expression of related transcription factors at the gene level, inhibit the nuclear translocation of NF-κBp65, and reduce the protein expression of COX-2. Additionally, compound 5 showed significant inhibitory activity on Con A-induced T-lymphocyte proliferation (IC50 = 4.803 ± 3.149 μM), and treatment of 5 could reduce the increased ratio of CD4 and CD8 subpopulations induced by Con A in vitro. Those results indicated 13 possesses potential anti-inflammatory activity, and 5 exhibits a certain degree of immunosuppressive activity.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:218 |
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| Enthalten in: |
Phytochemistry - 218(2024) vom: 25. Jan., Seite 113953 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Tao, Bo [VerfasserIn] |
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| Links: |
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| Themen: |
Anti-inflammatory activities |
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| Anmerkungen: |
Date Completed 15.01.2024 Date Revised 15.01.2024 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.phytochem.2023.113953 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a In this work, nine previous undescribed polycyclic polyprenylated acylphloroglucinols with adamantine/homoadamantane skeletons, cumilcinols A-I (1-9), along with six known analogues, were isolated and identified from the stems, leaves and flowers of Hypericum wilsonii. Their structures were determined by HRESIMS, NMR spectroscopic analysis, single-crystal X-ray crystallography as well as electronic circular dichroism calculations and comparisons. Compound 2 formed a unique furan ring bearing a rare acetal functionality. In bioassays, hyperacmosin G (13) could significantly inhibit the production of NO in LPS-stimulated RAW264.7 cell (IC50 = 4.350 ± 1.146 μM), and increased expression of related transcription factors at the gene level, inhibit the nuclear translocation of NF-κBp65, and reduce the protein expression of COX-2. Additionally, compound 5 showed significant inhibitory activity on Con A-induced T-lymphocyte proliferation (IC50 = 4.803 ± 3.149 μM), and treatment of 5 could reduce the increased ratio of CD4 and CD8 subpopulations induced by Con A in vitro. Those results indicated 13 possesses potential anti-inflammatory activity, and 5 exhibits a certain degree of immunosuppressive activity | ||
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| 650 | 4 | |a Immunosuppressive activity | |
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| 700 | 1 | |a Shi, Zhengyi |e verfasserin |4 aut | |
| 700 | 1 | |a Duan, Yulin |e verfasserin |4 aut | |
| 700 | 1 | |a Guo, Yi |e verfasserin |4 aut | |
| 700 | 1 | |a Huang, Xinye |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Jie |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yeting |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Ming |e verfasserin |4 aut | |
| 700 | 1 | |a Song, Fei |e verfasserin |4 aut | |
| 700 | 1 | |a Lan, Xueqi |e verfasserin |4 aut | |
| 700 | 1 | |a Sun, Weiguang |e verfasserin |4 aut | |
| 700 | 1 | |a Gu, Lianghu |e verfasserin |4 aut | |
| 700 | 1 | |a Qi, Changxing |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yonghui |e verfasserin |4 aut | |
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