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Volume 28
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10.3390/molecules28073146
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Article

Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from Penicillium sclerotiorum cib-411 and Their Anti-Inflammatory Activity

by
Xia Zhang
1,†,
Yeye Hu
2,†,
Tao Yang
1,†,
Xueqing Qian
1,
Weicheng Hu
2,* and
Guoyou Li
1,*
1
Key Laboratory of Environmental and Applied Microbiology, Environmental Microbiology Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China
2
Institute of Translational Medicine, School of Medicine, Yangzhou University, Yangzhou 225009, China
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Molecules 2023, 28(7), 3146; https://doi.org/10.3390/molecules28073146
Submission received: 8 February 2023 / Revised: 27 March 2023 / Accepted: 29 March 2023 / Published: 31 March 2023
(This article belongs to the Section Natural Products Chemistry)
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Abstract

Penazaphilones J–L (1–3), three new hydrophilic azaphilone pigments, as well as six known compounds, were discovered from the filamentous fungus Penicillium sclerotiorum cib-411. Compounds 1–3 were structurally elucidated by the detailed interpretation of their 1D and 2D NMR spectroscopic data. Compound 1 is an unprecedented hybrid of an azaphilone and a glycerophosphate choline. Compounds 2 and 3 each contain an intact amino acid moiety. The bioassay showed that compound 3 exhibited significant anti-inflammatory activity. Concretely, compound 3 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 3 prevented the translocation of NF-κB through inhibiting the phosphorylation of PI3K, PDK1, Akt, and GSK-3β. Thus, the inhibition of compound 3 against LPS-induced inflammation should rely on its inactivation on NF-κB.
Keywords: Penicillium sclerotiorum; azaphilone; anti-inflammation; fungal pigment; NF-κB signaling pathway Penicillium sclerotiorum; azaphilone; anti-inflammation; fungal pigment; NF-κB signaling pathway

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MDPI and ACS Style

Zhang, X.; Hu, Y.; Yang, T.; Qian, X.; Hu, W.; Li, G. Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from Penicillium sclerotiorum cib-411 and Their Anti-Inflammatory Activity. Molecules 2023, 28, 3146. https://doi.org/10.3390/molecules28073146

AMA Style

Zhang X, Hu Y, Yang T, Qian X, Hu W, Li G. Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from Penicillium sclerotiorum cib-411 and Their Anti-Inflammatory Activity. Molecules. 2023; 28(7):3146. https://doi.org/10.3390/molecules28073146

Chicago/Turabian Style

Zhang, Xia, Yeye Hu, Tao Yang, Xueqing Qian, Weicheng Hu, and Guoyou Li. 2023. "Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from Penicillium sclerotiorum cib-411 and Their Anti-Inflammatory Activity" Molecules 28, no. 7: 3146. https://doi.org/10.3390/molecules28073146

APA Style

Zhang, X., Hu, Y., Yang, T., Qian, X., Hu, W., & Li, G. (2023). Penazaphilones J–L, Three New Hydrophilic Azaphilone Pigments from Penicillium sclerotiorum cib-411 and Their Anti-Inflammatory Activity. Molecules, 28(7), 3146. https://doi.org/10.3390/molecules28073146

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