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Acorane sesquiterpenes from the deep-sea derived Penicillium bilaiae fungus with anti-neuroinflammatory effects

Acorane-type sesquiterpenes comprise a unique class of natural products with a range of pharmaceutical effects. Genome sequencing and gene annotation, along with qRT-PCR detection, demonstrate that the deep-sea derived Penicillium bilaiae F-28 fungus shows potential to produce acorane sesquiterpenes...

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Autores principales: Zhang, Wenfang, Meng, Qingyu, Wu, Jingshuai, Cheng, Wei, Liu, Dong, Huang, Jian, Fan, Aili, Xu, Jing, Lin, Wenhan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9727179/
https://www.ncbi.nlm.nih.gov/pubmed/36505743
http://dx.doi.org/10.3389/fchem.2022.1036212
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author Zhang, Wenfang
Meng, Qingyu
Wu, Jingshuai
Cheng, Wei
Liu, Dong
Huang, Jian
Fan, Aili
Xu, Jing
Lin, Wenhan
author_facet Zhang, Wenfang
Meng, Qingyu
Wu, Jingshuai
Cheng, Wei
Liu, Dong
Huang, Jian
Fan, Aili
Xu, Jing
Lin, Wenhan
author_sort Zhang, Wenfang
collection PubMed
description Acorane-type sesquiterpenes comprise a unique class of natural products with a range of pharmaceutical effects. Genome sequencing and gene annotation, along with qRT-PCR detection, demonstrate that the deep-sea derived Penicillium bilaiae F-28 fungus shows potential to produce acorane sesquiterpenes. Chromatographic manipulation resulted in the isolation of 20 acorane sesquiterpenes from the large-scale fermented fungal strain. Their structures were established by the interpretation of spectroscopic data, together with X-ray diffraction, chemical conversion, and ECD data for configurational assignments. A total of 18 new sesquiterpenes, namely, bilaiaeacorenols A–R (1–18), were identified. Bilaiaeacorenols A and B represent structurally unique tricyclic acoranes. Compound 18 exhibited efficient reduction against NO production in LPS-induced BV-2 macrophages in a dose-dependent manner, and it abolished LPS-induced NF-κB in the nucleus of BV-2 microglial cells. In addition, marked reductions of iNOS and COX-2 in protein and mRNA levels were observed. This study extends the chemical diversity of acorane-type sesquiterpenoids and suggests that compound 18 is a promising lead for anti-neuroinflammation.
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spelling pubmed-97271792022-12-08 Acorane sesquiterpenes from the deep-sea derived Penicillium bilaiae fungus with anti-neuroinflammatory effects Zhang, Wenfang Meng, Qingyu Wu, Jingshuai Cheng, Wei Liu, Dong Huang, Jian Fan, Aili Xu, Jing Lin, Wenhan Front Chem Chemistry Acorane-type sesquiterpenes comprise a unique class of natural products with a range of pharmaceutical effects. Genome sequencing and gene annotation, along with qRT-PCR detection, demonstrate that the deep-sea derived Penicillium bilaiae F-28 fungus shows potential to produce acorane sesquiterpenes. Chromatographic manipulation resulted in the isolation of 20 acorane sesquiterpenes from the large-scale fermented fungal strain. Their structures were established by the interpretation of spectroscopic data, together with X-ray diffraction, chemical conversion, and ECD data for configurational assignments. A total of 18 new sesquiterpenes, namely, bilaiaeacorenols A–R (1–18), were identified. Bilaiaeacorenols A and B represent structurally unique tricyclic acoranes. Compound 18 exhibited efficient reduction against NO production in LPS-induced BV-2 macrophages in a dose-dependent manner, and it abolished LPS-induced NF-κB in the nucleus of BV-2 microglial cells. In addition, marked reductions of iNOS and COX-2 in protein and mRNA levels were observed. This study extends the chemical diversity of acorane-type sesquiterpenoids and suggests that compound 18 is a promising lead for anti-neuroinflammation. Frontiers Media S.A. 2022-11-23 /pmc/articles/PMC9727179/ /pubmed/36505743 http://dx.doi.org/10.3389/fchem.2022.1036212 Text en Copyright © 2022 Zhang, Meng, Wu, Cheng, Liu, Huang, Fan, Xu and Lin. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Zhang, Wenfang
Meng, Qingyu
Wu, Jingshuai
Cheng, Wei
Liu, Dong
Huang, Jian
Fan, Aili
Xu, Jing
Lin, Wenhan
Acorane sesquiterpenes from the deep-sea derived Penicillium bilaiae fungus with anti-neuroinflammatory effects
title Acorane sesquiterpenes from the deep-sea derived Penicillium bilaiae fungus with anti-neuroinflammatory effects
title_full Acorane sesquiterpenes from the deep-sea derived Penicillium bilaiae fungus with anti-neuroinflammatory effects
title_fullStr Acorane sesquiterpenes from the deep-sea derived Penicillium bilaiae fungus with anti-neuroinflammatory effects
title_full_unstemmed Acorane sesquiterpenes from the deep-sea derived Penicillium bilaiae fungus with anti-neuroinflammatory effects
title_short Acorane sesquiterpenes from the deep-sea derived Penicillium bilaiae fungus with anti-neuroinflammatory effects
title_sort acorane sesquiterpenes from the deep-sea derived penicillium bilaiae fungus with anti-neuroinflammatory effects
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9727179/
https://www.ncbi.nlm.nih.gov/pubmed/36505743
http://dx.doi.org/10.3389/fchem.2022.1036212
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