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Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus
Three new diketopiperazine alkaloids, including two oxepine-containing diketopiperazines, chrysopiperazines A and B (1 and 2), and one quinazoline-containing diketopiperazine, chrysopiperazine C (5), together with three known analogues (3, 4, and 6), were isolated from the gorgonian-derived Penicill...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6562614/ https://www.ncbi.nlm.nih.gov/pubmed/31035506 http://dx.doi.org/10.3390/md17050250 |
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author | Xu, Wei-Feng Mao, Ning Xue, Xiao-Jia Qi, Yue-Xuan Wei, Mei-Yan Wang, Chang-Yun Shao, Chang-Lun |
author_facet | Xu, Wei-Feng Mao, Ning Xue, Xiao-Jia Qi, Yue-Xuan Wei, Mei-Yan Wang, Chang-Yun Shao, Chang-Lun |
author_sort | Xu, Wei-Feng |
collection | PubMed |
description | Three new diketopiperazine alkaloids, including two oxepine-containing diketopiperazines, chrysopiperazines A and B (1 and 2), and one quinazoline-containing diketopiperazine, chrysopiperazine C (5), together with three known analogues (3, 4, and 6), were isolated from the gorgonian-derived Penicillium chrysogenum fungus. The relative and absolute configurations of C-3 and C-15 in 1 and 2, C-3 and C-14 in 5 were established by NOE modified Marfey’s analysis and electronic circular dichroism (ECD) calculations. Particularly, the absolute configurations of C-19 in 1 and 3, which was very challenging to be identified due to the flexible conformation in a short aliphatic chain, were successfully determined by the vibrational circular dichroism (VCD) method, supplying with a reliable and optional method to define the absolute configurations. Additionally, this is the first report on oxepine-containing diketopiperazines from the genus Penicillium. |
format | Online Article Text |
id | pubmed-6562614 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-65626142019-06-17 Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus Xu, Wei-Feng Mao, Ning Xue, Xiao-Jia Qi, Yue-Xuan Wei, Mei-Yan Wang, Chang-Yun Shao, Chang-Lun Mar Drugs Article Three new diketopiperazine alkaloids, including two oxepine-containing diketopiperazines, chrysopiperazines A and B (1 and 2), and one quinazoline-containing diketopiperazine, chrysopiperazine C (5), together with three known analogues (3, 4, and 6), were isolated from the gorgonian-derived Penicillium chrysogenum fungus. The relative and absolute configurations of C-3 and C-15 in 1 and 2, C-3 and C-14 in 5 were established by NOE modified Marfey’s analysis and electronic circular dichroism (ECD) calculations. Particularly, the absolute configurations of C-19 in 1 and 3, which was very challenging to be identified due to the flexible conformation in a short aliphatic chain, were successfully determined by the vibrational circular dichroism (VCD) method, supplying with a reliable and optional method to define the absolute configurations. Additionally, this is the first report on oxepine-containing diketopiperazines from the genus Penicillium. MDPI 2019-04-26 /pmc/articles/PMC6562614/ /pubmed/31035506 http://dx.doi.org/10.3390/md17050250 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 Xu, Wei-Feng Mao, Ning Xue, Xiao-Jia Qi, Yue-Xuan Wei, Mei-Yan Wang, Chang-Yun Shao, Chang-Lun Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus |
title | Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus |
title_full | Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus |
title_fullStr | Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus |
title_full_unstemmed | Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus |
title_short | Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus |
title_sort | structures and absolute configurations of diketopiperazine alkaloids chrysopiperazines a–c from the gorgonian-derived penicillium chrysogenum fungus |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6562614/ https://www.ncbi.nlm.nih.gov/pubmed/31035506 http://dx.doi.org/10.3390/md17050250 |
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