Andrastin-type meroterpenoids, α-pyrone polyketides, and sesquicarane derivatives from Penicillium sp., a fungus isolated from Pinus koraiensis seed

Han, Shouye; Ma, Huabin; Wu, Yumeng; Wang, Chunying; Li, Yuanli; Li, Qin; Cheng, Zhongbin

doi:10.1016/j.phytochem.2024.114202

Phytochemistry

2024

DOI: 10.1016/j.phytochem.2024.114202

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Andrastin-type meroterpenoids, α-pyrone polyketides, and sesquicarane derivatives from Penicillium sp., a fungus isolated from Pinus koraiensis seed

Shouye Han,

Huabin Ma,

Yumeng Wu

et al.

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Herqupenoid A, an Unparalleled Sesquiterpene-Quinone Hybrid Featuring a Multicyclic Caged 2,7-Dioxatetracyclo[5.4.0.0^4,11.0^5,9]Hendecane Fragment from Penicillium herquei

Jin,

Zhao,

Wang

et al. 2024

Org. Lett.

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Herqupenoid A (1), a sesquiterpene-quinone hybrid with an unparalleled 5/5/6/5-fused ring skeleton based on a multicyclic caged 2,7dioxatetracyclo[5.4.0.0 4,11 .0 5,9 ]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 IC 50 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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Herqupenoid A, an Unparalleled Sesquiterpene-Quinone Hybrid Featuring a Multicyclic Caged 2,7-Dioxatetracyclo[5.4.0.0^4,11.0^5,9]Hendecane Fragment from Penicillium herquei

Jin,

Zhao,

Wang

et al. 2024

Org. Lett.

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Andrastin-type meroterpenoids, α-pyrone polyketides, and sesquicarane derivatives from Penicillium sp., a fungus isolated from Pinus koraiensis seed

Cited by 1 publication

References 39 publications

Herqupenoid A, an Unparalleled Sesquiterpene-Quinone Hybrid Featuring a Multicyclic Caged 2,7-Dioxatetracyclo[5.4.0.0^4,11.0^5,9]Hendecane Fragment from Penicillium herquei

Herqupenoid A, an Unparalleled Sesquiterpene-Quinone Hybrid Featuring a Multicyclic Caged 2,7-Dioxatetracyclo[5.4.0.0^4,11.0^5,9]Hendecane Fragment from Penicillium herquei

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Andrastin-type meroterpenoids, α-pyrone polyketides, and sesquicarane derivatives from Penicillium sp., a fungus isolated from Pinus koraiensis seed

Cited by 1 publication

References 39 publications

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, an Unparalleled Sesquiterpene-Quinone Hybrid Featuring a Multicyclic Caged 2,7-Dioxatetracyclo[5.4.0.04,11.05,9]Hendecane Fragment from Penicillium herquei

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Herqupenoid A, an Unparalleled Sesquiterpene-Quinone Hybrid Featuring a Multicyclic Caged 2,7-Dioxatetracyclo[5.4.0.0^4,11.0^5,9]Hendecane Fragment from Penicillium herquei

Herqupenoid A, an Unparalleled Sesquiterpene-Quinone Hybrid Featuring a Multicyclic Caged 2,7-Dioxatetracyclo[5.4.0.0^4,11.0^5,9]Hendecane Fragment from Penicillium herquei