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New Butenolides and Cyclopentenones from Saline Soil-Derived Fungus Aspergillus Sclerotiorum

Three new γ-hydroxyl butenolides (1–3), a pair of new enantiomeric spiro-butenolides (4a and 4b), a pair of enantiomeric cyclopentenones (5a new and 5b new natural), and six known compounds (6–11), were isolated from Aspergillus sclerotiorum. Their structures were established by spectroscopic data a...

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Autores principales: Ma, Li-Ying, Zhang, Huai-Bin, Kang, Hui-Hui, Zhong, Mei-Jia, Liu, De-Sheng, Ren, Hong, Liu, Wei-Zhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680918/
https://www.ncbi.nlm.nih.gov/pubmed/31330867
http://dx.doi.org/10.3390/molecules24142642
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author Ma, Li-Ying
Zhang, Huai-Bin
Kang, Hui-Hui
Zhong, Mei-Jia
Liu, De-Sheng
Ren, Hong
Liu, Wei-Zhong
author_facet Ma, Li-Ying
Zhang, Huai-Bin
Kang, Hui-Hui
Zhong, Mei-Jia
Liu, De-Sheng
Ren, Hong
Liu, Wei-Zhong
author_sort Ma, Li-Ying
collection PubMed
description Three new γ-hydroxyl butenolides (1–3), a pair of new enantiomeric spiro-butenolides (4a and 4b), a pair of enantiomeric cyclopentenones (5a new and 5b new natural), and six known compounds (6–11), were isolated from Aspergillus sclerotiorum. Their structures were established by spectroscopic data and electronic circular dichroism (ECD) spectra. Two pairs of enantiomers [(+)/(–)-6c and (+)/(–)-6d] obtained from the reaction of 6 with acetyl chloride (AcCl) confirmed that 6 was a mixture of two pairs of enantiomers. In addition, the X-ray data confirmed that 7 was also a racemate. The new metabolites (1−5) were evaluated for their inhibitory activity against cancer and non-cancer cell lines. As a result, compound 1 exhibited moderate cytotoxicity to HL60 and A549 with IC(50) values of 6.5 and 8.9 µM, respectively, and weak potency to HL-7702 with IC(50) values of 17.6 µM. Furthermore, compounds 1−9 were screened for their antimicrobial activity using the micro-broth dilution method. MIC values of 200 μg/mL were obtained for compounds 2 and 3 towards Staphylococcus aureus and Escherichia coli, while compound 8 exhibited a MIC of 50 μ/mL towards Candida albicans.
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spelling pubmed-66809182019-08-09 New Butenolides and Cyclopentenones from Saline Soil-Derived Fungus Aspergillus Sclerotiorum Ma, Li-Ying Zhang, Huai-Bin Kang, Hui-Hui Zhong, Mei-Jia Liu, De-Sheng Ren, Hong Liu, Wei-Zhong Molecules Article Three new γ-hydroxyl butenolides (1–3), a pair of new enantiomeric spiro-butenolides (4a and 4b), a pair of enantiomeric cyclopentenones (5a new and 5b new natural), and six known compounds (6–11), were isolated from Aspergillus sclerotiorum. Their structures were established by spectroscopic data and electronic circular dichroism (ECD) spectra. Two pairs of enantiomers [(+)/(–)-6c and (+)/(–)-6d] obtained from the reaction of 6 with acetyl chloride (AcCl) confirmed that 6 was a mixture of two pairs of enantiomers. In addition, the X-ray data confirmed that 7 was also a racemate. The new metabolites (1−5) were evaluated for their inhibitory activity against cancer and non-cancer cell lines. As a result, compound 1 exhibited moderate cytotoxicity to HL60 and A549 with IC(50) values of 6.5 and 8.9 µM, respectively, and weak potency to HL-7702 with IC(50) values of 17.6 µM. Furthermore, compounds 1−9 were screened for their antimicrobial activity using the micro-broth dilution method. MIC values of 200 μg/mL were obtained for compounds 2 and 3 towards Staphylococcus aureus and Escherichia coli, while compound 8 exhibited a MIC of 50 μ/mL towards Candida albicans. MDPI 2019-07-21 /pmc/articles/PMC6680918/ /pubmed/31330867 http://dx.doi.org/10.3390/molecules24142642 Text en © 2019 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
Ma, Li-Ying
Zhang, Huai-Bin
Kang, Hui-Hui
Zhong, Mei-Jia
Liu, De-Sheng
Ren, Hong
Liu, Wei-Zhong
New Butenolides and Cyclopentenones from Saline Soil-Derived Fungus Aspergillus Sclerotiorum
title New Butenolides and Cyclopentenones from Saline Soil-Derived Fungus Aspergillus Sclerotiorum
title_full New Butenolides and Cyclopentenones from Saline Soil-Derived Fungus Aspergillus Sclerotiorum
title_fullStr New Butenolides and Cyclopentenones from Saline Soil-Derived Fungus Aspergillus Sclerotiorum
title_full_unstemmed New Butenolides and Cyclopentenones from Saline Soil-Derived Fungus Aspergillus Sclerotiorum
title_short New Butenolides and Cyclopentenones from Saline Soil-Derived Fungus Aspergillus Sclerotiorum
title_sort new butenolides and cyclopentenones from saline soil-derived fungus aspergillus sclerotiorum
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680918/
https://www.ncbi.nlm.nih.gov/pubmed/31330867
http://dx.doi.org/10.3390/molecules24142642
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