Cargando…
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...
Autores principales: | , , , , , , , , |
---|---|
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 |
_version_ | 1784844952833884160 |
---|---|
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. |
format | Online Article Text |
id | pubmed-9727179 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT zhangwenfang acoranesesquiterpenesfromthedeepseaderivedpenicilliumbilaiaefunguswithantineuroinflammatoryeffects AT mengqingyu acoranesesquiterpenesfromthedeepseaderivedpenicilliumbilaiaefunguswithantineuroinflammatoryeffects AT wujingshuai acoranesesquiterpenesfromthedeepseaderivedpenicilliumbilaiaefunguswithantineuroinflammatoryeffects AT chengwei acoranesesquiterpenesfromthedeepseaderivedpenicilliumbilaiaefunguswithantineuroinflammatoryeffects AT liudong acoranesesquiterpenesfromthedeepseaderivedpenicilliumbilaiaefunguswithantineuroinflammatoryeffects AT huangjian acoranesesquiterpenesfromthedeepseaderivedpenicilliumbilaiaefunguswithantineuroinflammatoryeffects AT fanaili acoranesesquiterpenesfromthedeepseaderivedpenicilliumbilaiaefunguswithantineuroinflammatoryeffects AT xujing acoranesesquiterpenesfromthedeepseaderivedpenicilliumbilaiaefunguswithantineuroinflammatoryeffects AT linwenhan acoranesesquiterpenesfromthedeepseaderivedpenicilliumbilaiaefunguswithantineuroinflammatoryeffects |