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Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum

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Title: Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum
Authors: Hui-Chun Wang, Tzu-Yi Ke, Ya-Chen Ko, Jue-Jun Lin, Jui-Sheng Chang, Yuan-Bin Cheng
Source: Marine Drugs, Vol 19, Iss 10, p 529 (2021)
Publisher Information: MDPI AG, 2021.
Publication Year: 2021
Collection: LCC:Biology (General)
Subject Terms: Penicillium sclerotiorum, azaphilone, anti-inflammatory, Biology (General), QH301-705.5
More Details: To discover the new medical entity from edible marine algae, our continuously natural product investigation focused on endophytes from marine macroalgae Grateloupia sp. Two new azaphilones, 8a-epi-hypocrellone A (1), 8a-epi-eupenicilazaphilone C (2), together with five known azaphilones, hypocrellone A (3), eupenicilazaphilone C (4), ((1E,3E)-3,5-dimethylhepta-1,3-dien-1-yl)-2,4-dihydroxy-3-methylbenzaldehyde (5), sclerotiorin (6), and isochromophilone IV (7) were isolated from the alga-derived fungus Penicillium sclerotiorum. The structures of isolated azaphilones (1–7) were elucidated by spectrometric identification, especially HRESIMS, CD, and NMR data analyses. Concerning bioactivity, cytotoxic, anti-inflammatory, and anti-fibrosis activities of those isolates were evaluated. As a result, compound 1 showed selective toxicity toward neuroblastoma cell line SH-SY5Y among seven cancer and one fibroblast cell lines. 20 μM of compounds 1, 3, and 7 inhibited the TNF-α-induced NFκB phosphorylation but did not change the NFκB activity. Compounds 2 and 6 respectively promoted and inhibited SMAD-mediated transcriptional activities stimulated by TGF-β.
Document Type: article
File Description: electronic resource
Language: English
ISSN: 1660-3397
Relation: https://www.mdpi.com/1660-3397/19/10/529; https://doaj.org/toc/1660-3397
DOI: 10.3390/md19100529
Access URL: https://doaj.org/article/28a55ddd1b6c489983a2485a8d06932e
Accession Number: edsdoj.28a55ddd1b6c489983a2485a8d06932e
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  Data: Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum
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  Data: <searchLink fieldCode="AR" term="%22Hui-Chun+Wang%22">Hui-Chun Wang</searchLink><br /><searchLink fieldCode="AR" term="%22Tzu-Yi+Ke%22">Tzu-Yi Ke</searchLink><br /><searchLink fieldCode="AR" term="%22Ya-Chen+Ko%22">Ya-Chen Ko</searchLink><br /><searchLink fieldCode="AR" term="%22Jue-Jun+Lin%22">Jue-Jun Lin</searchLink><br /><searchLink fieldCode="AR" term="%22Jui-Sheng+Chang%22">Jui-Sheng Chang</searchLink><br /><searchLink fieldCode="AR" term="%22Yuan-Bin+Cheng%22">Yuan-Bin Cheng</searchLink>
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  Data: Marine Drugs, Vol 19, Iss 10, p 529 (2021)
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  Data: <searchLink fieldCode="DE" term="%22Penicillium+sclerotiorum%22">Penicillium sclerotiorum</searchLink><br /><searchLink fieldCode="DE" term="%22azaphilone%22">azaphilone</searchLink><br /><searchLink fieldCode="DE" term="%22anti-inflammatory%22">anti-inflammatory</searchLink><br /><searchLink fieldCode="DE" term="%22Biology+%28General%29%22">Biology (General)</searchLink><br /><searchLink fieldCode="DE" term="%22QH301-705%2E5%22">QH301-705.5</searchLink>
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  Data: To discover the new medical entity from edible marine algae, our continuously natural product investigation focused on endophytes from marine macroalgae Grateloupia sp. Two new azaphilones, 8a-epi-hypocrellone A (1), 8a-epi-eupenicilazaphilone C (2), together with five known azaphilones, hypocrellone A (3), eupenicilazaphilone C (4), ((1E,3E)-3,5-dimethylhepta-1,3-dien-1-yl)-2,4-dihydroxy-3-methylbenzaldehyde (5), sclerotiorin (6), and isochromophilone IV (7) were isolated from the alga-derived fungus Penicillium sclerotiorum. The structures of isolated azaphilones (1–7) were elucidated by spectrometric identification, especially HRESIMS, CD, and NMR data analyses. Concerning bioactivity, cytotoxic, anti-inflammatory, and anti-fibrosis activities of those isolates were evaluated. As a result, compound 1 showed selective toxicity toward neuroblastoma cell line SH-SY5Y among seven cancer and one fibroblast cell lines. 20 μM of compounds 1, 3, and 7 inhibited the TNF-α-induced NFκB phosphorylation but did not change the NFκB activity. Compounds 2 and 6 respectively promoted and inhibited SMAD-mediated transcriptional activities stimulated by TGF-β.
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  Data: https://www.mdpi.com/1660-3397/19/10/529; https://doaj.org/toc/1660-3397
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