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Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change

Three new diastereomers of polyketides (PKs), raistrickiones A−C (1–3), together with two new analogues, raistrickiones D and E (4 and 5), were isolated from a highly productive strain of Penicillium raistrickii, which was subjected to an experimental thermo-change strategy to tap its potential of p...

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Autores principales: Liu, De-Sheng, Rong, Xian-Guo, Kang, Hui-Hui, Ma, Li-Ying, Hamann, Mark T., Liu, Wei-Zhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6025261/
https://www.ncbi.nlm.nih.gov/pubmed/29912165
http://dx.doi.org/10.3390/md16060213
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author Liu, De-Sheng
Rong, Xian-Guo
Kang, Hui-Hui
Ma, Li-Ying
Hamann, Mark T.
Liu, Wei-Zhong
author_facet Liu, De-Sheng
Rong, Xian-Guo
Kang, Hui-Hui
Ma, Li-Ying
Hamann, Mark T.
Liu, Wei-Zhong
author_sort Liu, De-Sheng
collection PubMed
description Three new diastereomers of polyketides (PKs), raistrickiones A−C (1–3), together with two new analogues, raistrickiones D and E (4 and 5), were isolated from a highly productive strain of Penicillium raistrickii, which was subjected to an experimental thermo-change strategy to tap its potential of producing new secondary metabolites. Metabolites 1 and 2 existed in a diastereomeric mixture in the crystal packing according to the X-ray data, and were laboriously separated by semi-preparative HPLC on a chiral column. The structures of 1–5 were determined on the basis of the detailed analyses of the spectroscopic data (UV, IR, HRESIMS, 1D, and 2D NMR), single-crystal X-ray diffractions, and comparison of the experimental and calculated electronic circular dichroism spectra. Compounds 1–5 represented the first case of 3,5-dihydroxy-4-methylbenzoyl derivatives of natural products. Compounds 1–5 exhibited moderate radical scavenging activities against 1,1-diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl (DPPH).
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spelling pubmed-60252612018-07-09 Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change Liu, De-Sheng Rong, Xian-Guo Kang, Hui-Hui Ma, Li-Ying Hamann, Mark T. Liu, Wei-Zhong Mar Drugs Article Three new diastereomers of polyketides (PKs), raistrickiones A−C (1–3), together with two new analogues, raistrickiones D and E (4 and 5), were isolated from a highly productive strain of Penicillium raistrickii, which was subjected to an experimental thermo-change strategy to tap its potential of producing new secondary metabolites. Metabolites 1 and 2 existed in a diastereomeric mixture in the crystal packing according to the X-ray data, and were laboriously separated by semi-preparative HPLC on a chiral column. The structures of 1–5 were determined on the basis of the detailed analyses of the spectroscopic data (UV, IR, HRESIMS, 1D, and 2D NMR), single-crystal X-ray diffractions, and comparison of the experimental and calculated electronic circular dichroism spectra. Compounds 1–5 represented the first case of 3,5-dihydroxy-4-methylbenzoyl derivatives of natural products. Compounds 1–5 exhibited moderate radical scavenging activities against 1,1-diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl (DPPH). MDPI 2018-06-18 /pmc/articles/PMC6025261/ /pubmed/29912165 http://dx.doi.org/10.3390/md16060213 Text en © 2018 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Liu, De-Sheng
Rong, Xian-Guo
Kang, Hui-Hui
Ma, Li-Ying
Hamann, Mark T.
Liu, Wei-Zhong
Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change
title Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change
title_full Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change
title_fullStr Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change
title_full_unstemmed Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change
title_short Raistrickiones A−E from a Highly Productive Strain of Penicillium raistrickii Generated through Thermo Change
title_sort raistrickiones a−e from a highly productive strain of penicillium raistrickii generated through thermo change
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6025261/
https://www.ncbi.nlm.nih.gov/pubmed/29912165
http://dx.doi.org/10.3390/md16060213
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