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

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, hypocrellon...

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Autores principales: Wang, Hui-Chun, Ke, Tzu-Yi, Ko, Ya-Chen, Lin, Jue-Jun, Chang, Jui-Sheng, Cheng, Yuan-Bin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8537458/
https://www.ncbi.nlm.nih.gov/pubmed/34677428
http://dx.doi.org/10.3390/md19100529
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author Wang, Hui-Chun
Ke, Tzu-Yi
Ko, Ya-Chen
Lin, Jue-Jun
Chang, Jui-Sheng
Cheng, Yuan-Bin
author_facet Wang, Hui-Chun
Ke, Tzu-Yi
Ko, Ya-Chen
Lin, Jue-Jun
Chang, Jui-Sheng
Cheng, Yuan-Bin
author_sort Wang, Hui-Chun
collection PubMed
description 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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spelling pubmed-85374582021-10-24 Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum Wang, Hui-Chun Ke, Tzu-Yi Ko, Ya-Chen Lin, Jue-Jun Chang, Jui-Sheng Cheng, Yuan-Bin Mar Drugs Article 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. MDPI 2021-09-22 /pmc/articles/PMC8537458/ /pubmed/34677428 http://dx.doi.org/10.3390/md19100529 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wang, Hui-Chun
Ke, Tzu-Yi
Ko, Ya-Chen
Lin, Jue-Jun
Chang, Jui-Sheng
Cheng, Yuan-Bin
Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum
title Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum
title_full Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum
title_fullStr Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum
title_full_unstemmed Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum
title_short Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum
title_sort anti-inflammatory azaphilones from the edible alga-derived fungus penicillium sclerotiorum
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8537458/
https://www.ncbi.nlm.nih.gov/pubmed/34677428
http://dx.doi.org/10.3390/md19100529
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