Cargando…

Polyoxygenated cyathane diterpenoids from the mushroom Cyathus africanus, and their neurotrophic and anti-neuroinflammatory activities

In a previous study, we reported ten new polyoxygenated cyathane diterpenoids, neocyathins A–J, and their anti-neuroinflammatory effects from the liquid culture of the medicinal Basidiomycete Cyathus africanus. In the present study, eight new highly polyoxygenated cyathane diterpenoids, named neocya...

Descripción completa

Detalles Bibliográficos
Autores principales: Wei, Jing, Guo, Wan-Hui, Cao, Chen-Yu, Kou, Rong-Wei, Xu, Yuan-Zhen, Górecki, Marcin, Di Bari, Lorenzo, Pescitelli, Gennaro, Gao, Jin-Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5794895/
https://www.ncbi.nlm.nih.gov/pubmed/29391558
http://dx.doi.org/10.1038/s41598-018-20472-4
_version_ 1783297189544460288
author Wei, Jing
Guo, Wan-Hui
Cao, Chen-Yu
Kou, Rong-Wei
Xu, Yuan-Zhen
Górecki, Marcin
Di Bari, Lorenzo
Pescitelli, Gennaro
Gao, Jin-Ming
author_facet Wei, Jing
Guo, Wan-Hui
Cao, Chen-Yu
Kou, Rong-Wei
Xu, Yuan-Zhen
Górecki, Marcin
Di Bari, Lorenzo
Pescitelli, Gennaro
Gao, Jin-Ming
author_sort Wei, Jing
collection PubMed
description In a previous study, we reported ten new polyoxygenated cyathane diterpenoids, neocyathins A–J, and their anti-neuroinflammatory effects from the liquid culture of the medicinal Basidiomycete Cyathus africanus. In the present study, eight new highly polyoxygenated cyathane diterpenoids, named neocyathins K–R (1–8), were isolated from the solid culture of C. africanus cultivated on cooked rice, together with three known congeners (9–11). The structures and the absolute configurations of the new compounds were elucidated through comprehensive NMR and HRESIMS spectroscopic data, electronic circular dichroism (ECD) data, and chemical conversion. Compounds 1 and 2 represent the first reported naturally occurring compounds with 4,9-seco-cyathane carbon skeleton incorporating an unprecedented medium-sized 9/7 fused ring system, while the 3,4-seco-cyathane derivative (3) was isolated from Cyathus species for the first time. All compounds were evaluated for their neurotrophic and anti-neuroinflammatory activity. All the isolates at 1–25 μM displayed differential nerve growth factor (NGF)-induced neurite outgrowth-promoting activity in PC-12 cells, while one of the compounds, allocyathin B(2) (11), inhibited NO production in lipopolysaccharide (LPS)-stimulated microglia BV-2 cells. In addition, molecular docking studies showed that compound 11 generated interactions with the inducible nitric oxide synthase (iNOS) protein.
format Online
Article
Text
id pubmed-5794895
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-57948952018-02-12 Polyoxygenated cyathane diterpenoids from the mushroom Cyathus africanus, and their neurotrophic and anti-neuroinflammatory activities Wei, Jing Guo, Wan-Hui Cao, Chen-Yu Kou, Rong-Wei Xu, Yuan-Zhen Górecki, Marcin Di Bari, Lorenzo Pescitelli, Gennaro Gao, Jin-Ming Sci Rep Article In a previous study, we reported ten new polyoxygenated cyathane diterpenoids, neocyathins A–J, and their anti-neuroinflammatory effects from the liquid culture of the medicinal Basidiomycete Cyathus africanus. In the present study, eight new highly polyoxygenated cyathane diterpenoids, named neocyathins K–R (1–8), were isolated from the solid culture of C. africanus cultivated on cooked rice, together with three known congeners (9–11). The structures and the absolute configurations of the new compounds were elucidated through comprehensive NMR and HRESIMS spectroscopic data, electronic circular dichroism (ECD) data, and chemical conversion. Compounds 1 and 2 represent the first reported naturally occurring compounds with 4,9-seco-cyathane carbon skeleton incorporating an unprecedented medium-sized 9/7 fused ring system, while the 3,4-seco-cyathane derivative (3) was isolated from Cyathus species for the first time. All compounds were evaluated for their neurotrophic and anti-neuroinflammatory activity. All the isolates at 1–25 μM displayed differential nerve growth factor (NGF)-induced neurite outgrowth-promoting activity in PC-12 cells, while one of the compounds, allocyathin B(2) (11), inhibited NO production in lipopolysaccharide (LPS)-stimulated microglia BV-2 cells. In addition, molecular docking studies showed that compound 11 generated interactions with the inducible nitric oxide synthase (iNOS) protein. Nature Publishing Group UK 2018-02-01 /pmc/articles/PMC5794895/ /pubmed/29391558 http://dx.doi.org/10.1038/s41598-018-20472-4 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Wei, Jing
Guo, Wan-Hui
Cao, Chen-Yu
Kou, Rong-Wei
Xu, Yuan-Zhen
Górecki, Marcin
Di Bari, Lorenzo
Pescitelli, Gennaro
Gao, Jin-Ming
Polyoxygenated cyathane diterpenoids from the mushroom Cyathus africanus, and their neurotrophic and anti-neuroinflammatory activities
title Polyoxygenated cyathane diterpenoids from the mushroom Cyathus africanus, and their neurotrophic and anti-neuroinflammatory activities
title_full Polyoxygenated cyathane diterpenoids from the mushroom Cyathus africanus, and their neurotrophic and anti-neuroinflammatory activities
title_fullStr Polyoxygenated cyathane diterpenoids from the mushroom Cyathus africanus, and their neurotrophic and anti-neuroinflammatory activities
title_full_unstemmed Polyoxygenated cyathane diterpenoids from the mushroom Cyathus africanus, and their neurotrophic and anti-neuroinflammatory activities
title_short Polyoxygenated cyathane diterpenoids from the mushroom Cyathus africanus, and their neurotrophic and anti-neuroinflammatory activities
title_sort polyoxygenated cyathane diterpenoids from the mushroom cyathus africanus, and their neurotrophic and anti-neuroinflammatory activities
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5794895/
https://www.ncbi.nlm.nih.gov/pubmed/29391558
http://dx.doi.org/10.1038/s41598-018-20472-4
work_keys_str_mv AT weijing polyoxygenatedcyathanediterpenoidsfromthemushroomcyathusafricanusandtheirneurotrophicandantineuroinflammatoryactivities
AT guowanhui polyoxygenatedcyathanediterpenoidsfromthemushroomcyathusafricanusandtheirneurotrophicandantineuroinflammatoryactivities
AT caochenyu polyoxygenatedcyathanediterpenoidsfromthemushroomcyathusafricanusandtheirneurotrophicandantineuroinflammatoryactivities
AT kourongwei polyoxygenatedcyathanediterpenoidsfromthemushroomcyathusafricanusandtheirneurotrophicandantineuroinflammatoryactivities
AT xuyuanzhen polyoxygenatedcyathanediterpenoidsfromthemushroomcyathusafricanusandtheirneurotrophicandantineuroinflammatoryactivities
AT goreckimarcin polyoxygenatedcyathanediterpenoidsfromthemushroomcyathusafricanusandtheirneurotrophicandantineuroinflammatoryactivities
AT dibarilorenzo polyoxygenatedcyathanediterpenoidsfromthemushroomcyathusafricanusandtheirneurotrophicandantineuroinflammatoryactivities
AT pescitelligennaro polyoxygenatedcyathanediterpenoidsfromthemushroomcyathusafricanusandtheirneurotrophicandantineuroinflammatoryactivities
AT gaojinming polyoxygenatedcyathanediterpenoidsfromthemushroomcyathusafricanusandtheirneurotrophicandantineuroinflammatoryactivities