Toonaolides A-X, limonoids from Toona ciliata : Isolation, structural elucidation, and bioactivity against NLRP3 inflammasome
Copyright © 2020 Elsevier Inc. All rights reserved..
Twenty-four new limonoids, toonaolides A-X (1-24), characterized with an α,β-unsaturated-γ-lactone A-ring were isolated from the twigs of Toona ciliata. Their structures and absolute configurations were elucidated by spectroscopic data, X-ray diffraction crystallography, and quantum chemistry calculations. Most of the isolated compounds (except 9, 18, and 24 which possessed the maleimide ring) featured the rare 21-hydroxybutenolide or 23-hydroxybutenolide moieties. In particular, compound 1 has an unprecedented limonoid architecture with 6/6 cis-fused A/B ring system and 2 has an unusual tetrahydrofuran ring B skeleton, featuring a 7/5/6/5 ring system. The biological evaluation showed that compounds 9, 11, 12, 14, and 18 exhibited significantly anti-NLRP3 inflammasome activity with IC50 values ranging from 3.2 to 9.7 μM. Analysis of IL-1β and caspase-1 expression revealed that compounds 11 and 12 are selective inhibitors of NLRP3 inflammasome, which could ameliorate cell pyroptosis by blocking NLRP3 inflammasome activation.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:105 |
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| Enthalten in: |
Bioorganic chemistry - 105(2020) vom: 01. Dez., Seite 104363 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Shi, Qiang-Qiang [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 16.06.2021 Date Revised 16.06.2021 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.bioorg.2020.104363 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 500 | |a published: Print-Electronic | ||
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| 520 | |a Copyright © 2020 Elsevier Inc. All rights reserved. | ||
| 520 | |a Twenty-four new limonoids, toonaolides A-X (1-24), characterized with an α,β-unsaturated-γ-lactone A-ring were isolated from the twigs of Toona ciliata. Their structures and absolute configurations were elucidated by spectroscopic data, X-ray diffraction crystallography, and quantum chemistry calculations. Most of the isolated compounds (except 9, 18, and 24 which possessed the maleimide ring) featured the rare 21-hydroxybutenolide or 23-hydroxybutenolide moieties. In particular, compound 1 has an unprecedented limonoid architecture with 6/6 cis-fused A/B ring system and 2 has an unusual tetrahydrofuran ring B skeleton, featuring a 7/5/6/5 ring system. The biological evaluation showed that compounds 9, 11, 12, 14, and 18 exhibited significantly anti-NLRP3 inflammasome activity with IC50 values ranging from 3.2 to 9.7 μM. Analysis of IL-1β and caspase-1 expression revealed that compounds 11 and 12 are selective inhibitors of NLRP3 inflammasome, which could ameliorate cell pyroptosis by blocking NLRP3 inflammasome activation | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a Limonoids | |
| 650 | 4 | |a NLRP3 inflammasome | |
| 650 | 4 | |a Quantum chemistry calculations | |
| 650 | 4 | |a Toona ciliate | |
| 650 | 7 | |a Inflammasomes |2 NLM | |
| 650 | 7 | |a Limonins |2 NLM | |
| 650 | 7 | |a NLR Family, Pyrin Domain-Containing 3 Protein |2 NLM | |
| 650 | 7 | |a NLRP3 protein, human |2 NLM | |
| 650 | 7 | |a Plant Extracts |2 NLM | |
| 700 | 1 | |a Zhang, Xing-Jie |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yu |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Qi |e verfasserin |4 aut | |
| 700 | 1 | |a Amin, Muhammad |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Qing |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Xue-Wen |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Xiao-Li |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Rui-Han |e verfasserin |4 aut | |
| 700 | 1 | |a Dai, Xiao-Chang |e verfasserin |4 aut | |
| 700 | 1 | |a Xiao, Wei-Lie |e verfasserin |4 aut | |
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