Herqupenoid A, an Unparalleled Sesquiterpene-Quinone Hybrid Featuring a Multicyclic Caged 2,7-Dioxatetracyclo[5.4.0.04,11.05,9]Hendecane Fragment from Penicillium herquei
Herqupenoid A (1), a sesquiterpene-quinone hybrid with an unparalleled 5/5/6/5-fused ring skeleton based on a multicyclic caged 2,7-dioxatetracyclo[5.4.0.04,11.05,9]hendecane fragment, was isolated from fungus Penicillium herquei. Its structure was assigned by extensive spectroscopic analyses, DP4...
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Veröffentlicht in: | Organic letters 2024-11, Vol.26 (47), p.10146-10151 |
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Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Herqupenoid A (1), a sesquiterpene-quinone hybrid with an unparalleled 5/5/6/5-fused ring skeleton based on a multicyclic caged 2,7-dioxatetracyclo[5.4.0.04,11.05,9]hendecane fragment, was isolated from fungus Penicillium herquei. Its structure was assigned by extensive spectroscopic analyses, DP4+ computational method, and single-crystal X-ray diffraction. Further pharmacology research has established that compound 1 exhibited significant anti-inflammatory activity via inhibiting NF-κB-NLRP3 axis with an IC50 value of 2.63 μM, which was stronger than the positive control dexamethasone. A putative biosynthetic pathway involving the key hemiacetal and aldol condensation reactions for 1 was also discussed. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.4c03867 |