Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from <i>Penicillium sclerotiorum cib-411</i> and Their Anti-Inflammatory Activity
Penazaphilones J–L (<b>1</b>–<b>3</b>), three new hydrophilic azaphilone pigments, as well as six known compounds, were discovered from the filamentous fungus <i>Penicillium sclerotiorum</i> cib-411. Compounds <b>1</b>–<b>3</b> were structu...
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| Format: | Article |
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MDPI AG
2023-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/7/3146 |
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| author | Xia Zhang Yeye Hu Tao Yang Xueqing Qian Weicheng Hu Guoyou Li |
| author_facet | Xia Zhang Yeye Hu Tao Yang Xueqing Qian Weicheng Hu Guoyou Li |
| author_sort | Xia Zhang |
| collection | DOAJ |
| description | Penazaphilones J–L (<b>1</b>–<b>3</b>), three new hydrophilic azaphilone pigments, as well as six known compounds, were discovered from the filamentous fungus <i>Penicillium sclerotiorum</i> cib-411. Compounds <b>1</b>–<b>3</b> were structurally elucidated by the detailed interpretation of their 1D and 2D NMR spectroscopic data. Compound <b>1</b> is an unprecedented hybrid of an azaphilone and a glycerophosphate choline. Compounds <b>2</b> and <b>3</b> each contain an intact amino acid moiety. The bioassay showed that compound <b>3</b> exhibited significant anti-inflammatory activity. Concretely, compound <b>3</b> significantly suppressed the NO production, the expression levels of COX-2, IL-6, IL-1β, and iNOS mRNA in LPS-stimulated RAW264.7 cells. Moreover, treatment of compound <b>3</b> prevented the translocation of NF-κB through inhibiting the phosphorylation of PI3K, PDK1, Akt, and GSK-3β. Thus, the inhibition of compound <b>3</b> against LPS-induced inflammation should rely on its inactivation on NF-κB. |
| first_indexed | 2024-03-11T05:29:26Z |
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| id | doaj.art-245382c4010744d88e1925317ab2db4d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T05:29:26Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-245382c4010744d88e1925317ab2db4d2023-11-17T17:14:14ZengMDPI AGMolecules1420-30492023-03-01287314610.3390/molecules28073146Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from <i>Penicillium sclerotiorum cib-411</i> and Their Anti-Inflammatory ActivityXia Zhang0Yeye Hu1Tao Yang2Xueqing Qian3Weicheng Hu4Guoyou Li5Key Laboratory of Environmental and Applied Microbiology, Environmental Microbiology Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, ChinaInstitute of Translational Medicine, School of Medicine, Yangzhou University, Yangzhou 225009, ChinaKey Laboratory of Environmental and Applied Microbiology, Environmental Microbiology Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, ChinaKey Laboratory of Environmental and Applied Microbiology, Environmental Microbiology Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, ChinaInstitute of Translational Medicine, School of Medicine, Yangzhou University, Yangzhou 225009, ChinaKey Laboratory of Environmental and Applied Microbiology, Environmental Microbiology Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, ChinaPenazaphilones J–L (<b>1</b>–<b>3</b>), three new hydrophilic azaphilone pigments, as well as six known compounds, were discovered from the filamentous fungus <i>Penicillium sclerotiorum</i> cib-411. Compounds <b>1</b>–<b>3</b> were structurally elucidated by the detailed interpretation of their 1D and 2D NMR spectroscopic data. Compound <b>1</b> is an unprecedented hybrid of an azaphilone and a glycerophosphate choline. Compounds <b>2</b> and <b>3</b> each contain an intact amino acid moiety. The bioassay showed that compound <b>3</b> exhibited significant anti-inflammatory activity. Concretely, compound <b>3</b> significantly suppressed the NO production, the expression levels of COX-2, IL-6, IL-1β, and iNOS mRNA in LPS-stimulated RAW264.7 cells. Moreover, treatment of compound <b>3</b> prevented the translocation of NF-κB through inhibiting the phosphorylation of PI3K, PDK1, Akt, and GSK-3β. Thus, the inhibition of compound <b>3</b> against LPS-induced inflammation should rely on its inactivation on NF-κB.https://www.mdpi.com/1420-3049/28/7/3146<i>Penicillium sclerotiorum</i>azaphiloneanti-inflammationfungal pigmentNF-κB signaling pathway |
| spellingShingle | Xia Zhang Yeye Hu Tao Yang Xueqing Qian Weicheng Hu Guoyou Li Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from <i>Penicillium sclerotiorum cib-411</i> and Their Anti-Inflammatory Activity Molecules <i>Penicillium sclerotiorum</i> azaphilone anti-inflammation fungal pigment NF-κB signaling pathway |
| title | Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from <i>Penicillium sclerotiorum cib-411</i> and Their Anti-Inflammatory Activity |
| title_full | Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from <i>Penicillium sclerotiorum cib-411</i> and Their Anti-Inflammatory Activity |
| title_fullStr | Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from <i>Penicillium sclerotiorum cib-411</i> and Their Anti-Inflammatory Activity |
| title_full_unstemmed | Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from <i>Penicillium sclerotiorum cib-411</i> and Their Anti-Inflammatory Activity |
| title_short | Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from <i>Penicillium sclerotiorum cib-411</i> and Their Anti-Inflammatory Activity |
| title_sort | penazaphilones j l three new hydrophilic azaphilone pigments from i penicillium sclerotiorum cib 411 i and their anti inflammatory activity |
| topic | <i>Penicillium sclerotiorum</i> azaphilone anti-inflammation fungal pigment NF-κB signaling pathway |
| url | https://www.mdpi.com/1420-3049/28/7/3146 |
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