Penijanacoranes A—F, Acorane‐Type Sesquiterpenes from a Deep Sea‐Derived Fungus <i>Penicillium janthinellum</i><scp>SH0301</scp>

Comprehensive Summary Six new acorane‐type sesquiterpenes, named penijanacoranes A—F ( 1 — 6 ), as well as one known eudesmane sesquiterpenoid 1 α ,6 β ,11‐eudesm‐triol ( 7 ) have been isolated from a deep‐sea‐derived fungus Penicillium janthinellum SH0301. Their structures and absolute configurations were established by the comprehensive spectroscopic analysis, TDDFT‐ECD calculations, and X‐ray diffraction. Penijanacorane A ( 1 ) was identified as a rare acorane‐type sesquiterpene lactone featuring a novel 6/5/6 tricyclic system, while penijanacoranes E and F ( 5 and 6 ) represented undescribed examples of nor‐acorane sesquiterpenes at C‐1. Penijanacorane C ( 3 ) exhibited significant inhibitory activity against LPS‐induced NO production in Raw264.7 macrophages with an IC 50 value of 6.23 μM, which was more potent than that of positive control dexamethasone (IC 50 = 11.49 μM). This study expanded the chemical diversity of acorane‐type sesquiterpenoids and revealed that compound 3 was a potential molecule for anti‐inflammatory agents.

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Publication Details

Journal
Chinese Journal of Chemistry
Published
2024-10-17
DOI
https://doi.org/10.1002/cjoc.202400836
Citations
2
Primary Topic
Microbial Natural Products and Biosynthesis
Type
article
Field-Weighted Citation Impact
0.90

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article

Penijanacoranes A—F, Acorane‐Type Sesquiterpenes from a Deep Sea‐Derived Fungus Penicillium janthinellumSH0301

Yu‐Cheng Gu, Zhuang Han, Chang‐Lun Shao, Chang‐Yun Wang et al.
2 citations
Chinese Journal of Chemistry
Microbial Natural Products and Biosynthesis
0.90
article

Penijanacoranes A—F, Acorane‐Type Sesquiterpenes from a Deep Sea‐Derived Fungus Penicillium janthinellumSH0301

Yu‐Cheng Gu, Zhuang Han, Chang‐Lun Shao, Chang‐Yun Wang, Ling Lv, Xin Li, Zhiqing Liu, Lujia Yang
article en
2 citations

Abstract

Comprehensive Summary Six new acorane‐type sesquiterpenes, named penijanacoranes A—F ( 1 — 6 ), as well as one known eudesmane sesquiterpenoid 1 α ,6 β ,11‐eudesm‐triol ( 7 ) have been isolated from a deep‐sea‐derived fungus Penicillium janthinellum SH0301. Their structures and absolute configurations were established by the comprehensive spectroscopic analysis, TDDFT‐ECD calculations, and X‐ray diffraction. Penijanacorane A ( 1 ) was identified as a rare acorane‐type sesquiterpene lactone featuring a novel 6/5/6 tricyclic system, while penijanacoranes E and F ( 5 and 6 ) represented undescribed examples of nor‐acorane sesquiterpenes at C‐1. Penijanacorane C ( 3 ) exhibited significant inhibitory activity against LPS‐induced NO production in Raw264.7 macrophages with an IC 50 value of 6.23 μM, which was more potent than that of positive control dexamethasone (IC 50 = 11.49 μM). This study expanded the chemical diversity of acorane‐type sesquiterpenoids and revealed that compound 3 was a potential molecule for anti‐inflammatory agents.

Chinese Journal of ChemistryVol. 43(3)
Chinese Academy of Sciences (CN), Syngenta (United Kingdom) (GB), Qingdao National Laboratory for Marine Science and Technology (CN), Institute of Deep-Sea Science and Engineering (CN), Ocean University of China (CN)
Fundamental Research Funds for the Central Universities
Life below water
Openalex Percentile: Top 23%
Microbial Natural Products and Biosynthesis
0.90
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