(±)-Peniorthoesters A and B, Two Pairs of Novel Spiro-Orthoester en-antiomers With an Unusual 1,4,6-Trioxaspi-ro[4.5]decane-7-One Unit From Penicillium minioluteum

(±)-Peniorthoesters A and B (±1 and ±2), two pairs of unprecedented spiro-orthoester enantiomers with a 1,4,6-trioxaspiro[4. 5]decane-7-one unit, were obtained from Penicillium minioluteum. Their structures were determined by spectroscopic methods, X-ray diffraction analyses, and ECD calculations. (...

Descripción completa

Detalles Bibliográficos
Autores principales: Liu, Xiaorui, Chen, Chunmei, Zheng, Yinyu, Zhang, Mi, Tong, Qingyi, Liu, Junjun, Zhou, Qun, Wang, Jianping, Luo, Zengwei, Zhu, Hucheng, Zhang, Yonghui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6292945/
https://www.ncbi.nlm.nih.gov/pubmed/30581815
http://dx.doi.org/10.3389/fchem.2018.00605
_version_ 1783380463808675840
author Liu, Xiaorui
Chen, Chunmei
Zheng, Yinyu
Zhang, Mi
Tong, Qingyi
Liu, Junjun
Zhou, Qun
Wang, Jianping
Luo, Zengwei
Zhu, Hucheng
Zhang, Yonghui
author_facet Liu, Xiaorui
Chen, Chunmei
Zheng, Yinyu
Zhang, Mi
Tong, Qingyi
Liu, Junjun
Zhou, Qun
Wang, Jianping
Luo, Zengwei
Zhu, Hucheng
Zhang, Yonghui
author_sort Liu, Xiaorui
collection PubMed
description (±)-Peniorthoesters A and B (±1 and ±2), two pairs of unprecedented spiro-orthoester enantiomers with a 1,4,6-trioxaspiro[4. 5]decane-7-one unit, were obtained from Penicillium minioluteum. Their structures were determined by spectroscopic methods, X-ray diffraction analyses, and ECD calculations. (±)-Peniorthoesters A and B are the first examples of spiro-orthoester enantiomers, and they represent the first spiro-orthoesters originating from fungi. All compounds showed potential inhibitory activities comparable to dexamethasone against NO production with IC(50) values ranging from 14.2 to 34.5 μM.
format Online
Article
Text
id pubmed-6292945
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Frontiers Media S.A.
record_format MEDLINE/PubMed
spelling pubmed-62929452018-12-21 (±)-Peniorthoesters A and B, Two Pairs of Novel Spiro-Orthoester en-antiomers With an Unusual 1,4,6-Trioxaspi-ro[4.5]decane-7-One Unit From Penicillium minioluteum Liu, Xiaorui Chen, Chunmei Zheng, Yinyu Zhang, Mi Tong, Qingyi Liu, Junjun Zhou, Qun Wang, Jianping Luo, Zengwei Zhu, Hucheng Zhang, Yonghui Front Chem Chemistry (±)-Peniorthoesters A and B (±1 and ±2), two pairs of unprecedented spiro-orthoester enantiomers with a 1,4,6-trioxaspiro[4. 5]decane-7-one unit, were obtained from Penicillium minioluteum. Their structures were determined by spectroscopic methods, X-ray diffraction analyses, and ECD calculations. (±)-Peniorthoesters A and B are the first examples of spiro-orthoester enantiomers, and they represent the first spiro-orthoesters originating from fungi. All compounds showed potential inhibitory activities comparable to dexamethasone against NO production with IC(50) values ranging from 14.2 to 34.5 μM. Frontiers Media S.A. 2018-12-07 /pmc/articles/PMC6292945/ /pubmed/30581815 http://dx.doi.org/10.3389/fchem.2018.00605 Text en Copyright © 2018 Liu, Chen, Zheng, Zhang, Tong, Liu, Zhou, Wang, Luo, Zhu and Zhang. http://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
Liu, Xiaorui
Chen, Chunmei
Zheng, Yinyu
Zhang, Mi
Tong, Qingyi
Liu, Junjun
Zhou, Qun
Wang, Jianping
Luo, Zengwei
Zhu, Hucheng
Zhang, Yonghui
(±)-Peniorthoesters A and B, Two Pairs of Novel Spiro-Orthoester en-antiomers With an Unusual 1,4,6-Trioxaspi-ro[4.5]decane-7-One Unit From Penicillium minioluteum
title (±)-Peniorthoesters A and B, Two Pairs of Novel Spiro-Orthoester en-antiomers With an Unusual 1,4,6-Trioxaspi-ro[4.5]decane-7-One Unit From Penicillium minioluteum
title_full (±)-Peniorthoesters A and B, Two Pairs of Novel Spiro-Orthoester en-antiomers With an Unusual 1,4,6-Trioxaspi-ro[4.5]decane-7-One Unit From Penicillium minioluteum
title_fullStr (±)-Peniorthoesters A and B, Two Pairs of Novel Spiro-Orthoester en-antiomers With an Unusual 1,4,6-Trioxaspi-ro[4.5]decane-7-One Unit From Penicillium minioluteum
title_full_unstemmed (±)-Peniorthoesters A and B, Two Pairs of Novel Spiro-Orthoester en-antiomers With an Unusual 1,4,6-Trioxaspi-ro[4.5]decane-7-One Unit From Penicillium minioluteum
title_short (±)-Peniorthoesters A and B, Two Pairs of Novel Spiro-Orthoester en-antiomers With an Unusual 1,4,6-Trioxaspi-ro[4.5]decane-7-One Unit From Penicillium minioluteum
title_sort (±)-peniorthoesters a and b, two pairs of novel spiro-orthoester en-antiomers with an unusual 1,4,6-trioxaspi-ro[4.5]decane-7-one unit from penicillium minioluteum
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6292945/
https://www.ncbi.nlm.nih.gov/pubmed/30581815
http://dx.doi.org/10.3389/fchem.2018.00605
work_keys_str_mv AT liuxiaorui peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum
AT chenchunmei peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum
AT zhengyinyu peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum
AT zhangmi peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum
AT tongqingyi peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum
AT liujunjun peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum
AT zhouqun peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum
AT wangjianping peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum
AT luozengwei peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum
AT zhuhucheng peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum
AT zhangyonghui peniorthoestersaandbtwopairsofnovelspiroorthoesterenantiomerswithanunusual146trioxaspiro45decane7oneunitfrompenicilliumminioluteum

Ejemplares similares