Cargando…
Bioactive Monoterpenes and Polyketides from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722
There has been a tremendous increase in the rate of new terpenoids from marine-derived fungi being discovered, while new monoterpenes were rarely isolated from marine-derived fungi in the past two decades. Three new monoterpenes, diaporterpenes A–C (1–3), and one new α-pyrones, diaporpyrone A (6), a...
Autores principales: | , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9504586/ https://www.ncbi.nlm.nih.gov/pubmed/36135742 http://dx.doi.org/10.3390/md20090553 |
_version_ | 1784796254252826624 |
---|---|
author | Zhai, Guifa Chen, Senhua Shen, Hongjie Guo, Heng Jiang, Minghua Liu, Lan |
author_facet | Zhai, Guifa Chen, Senhua Shen, Hongjie Guo, Heng Jiang, Minghua Liu, Lan |
author_sort | Zhai, Guifa |
collection | PubMed |
description | There has been a tremendous increase in the rate of new terpenoids from marine-derived fungi being discovered, while new monoterpenes were rarely isolated from marine-derived fungi in the past two decades. Three new monoterpenes, diaporterpenes A–C (1–3), and one new α-pyrones, diaporpyrone A (6), along with nine known polyketides 4, 5, and 7–13 were isolated from the ascidian-derived fungus Diaporthe sp. SYSU-MS4722. Their planar structures were elucidated based on extensive spectroscopic analyses (1D and 2D NMR and HR-ESIMS). The absolute configurations of 1 and 3 were identified by an X-ray crystallographic diffraction experiment using Cu-Ka radiation, and those of compound 2 were assigned by calculating NMR chemical shifts and ECD spectra. It afforded an example of natural epimers with different physical properties, especially crystallization, due to the difference in intermolecular hydrogen bonding. Compounds 9, 10, and 13 showed moderate total antioxidant capacity (0.82 of 9; 0.70 of 10; 0.48 of 13) with Trolox (total antioxidant capacity: 1.0) as a positive control, and compounds 5 and 7 showed anti-inflammatory activity with IC(50) values of 35.4 and 40.8 µM, respectively (positive control indomethacin: IC(50) = 35.8 µM). |
format | Online Article Text |
id | pubmed-9504586 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-95045862022-09-24 Bioactive Monoterpenes and Polyketides from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722 Zhai, Guifa Chen, Senhua Shen, Hongjie Guo, Heng Jiang, Minghua Liu, Lan Mar Drugs Article There has been a tremendous increase in the rate of new terpenoids from marine-derived fungi being discovered, while new monoterpenes were rarely isolated from marine-derived fungi in the past two decades. Three new monoterpenes, diaporterpenes A–C (1–3), and one new α-pyrones, diaporpyrone A (6), along with nine known polyketides 4, 5, and 7–13 were isolated from the ascidian-derived fungus Diaporthe sp. SYSU-MS4722. Their planar structures were elucidated based on extensive spectroscopic analyses (1D and 2D NMR and HR-ESIMS). The absolute configurations of 1 and 3 were identified by an X-ray crystallographic diffraction experiment using Cu-Ka radiation, and those of compound 2 were assigned by calculating NMR chemical shifts and ECD spectra. It afforded an example of natural epimers with different physical properties, especially crystallization, due to the difference in intermolecular hydrogen bonding. Compounds 9, 10, and 13 showed moderate total antioxidant capacity (0.82 of 9; 0.70 of 10; 0.48 of 13) with Trolox (total antioxidant capacity: 1.0) as a positive control, and compounds 5 and 7 showed anti-inflammatory activity with IC(50) values of 35.4 and 40.8 µM, respectively (positive control indomethacin: IC(50) = 35.8 µM). MDPI 2022-08-29 /pmc/articles/PMC9504586/ /pubmed/36135742 http://dx.doi.org/10.3390/md20090553 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Zhai, Guifa Chen, Senhua Shen, Hongjie Guo, Heng Jiang, Minghua Liu, Lan Bioactive Monoterpenes and Polyketides from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722 |
title | Bioactive Monoterpenes and Polyketides from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722 |
title_full | Bioactive Monoterpenes and Polyketides from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722 |
title_fullStr | Bioactive Monoterpenes and Polyketides from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722 |
title_full_unstemmed | Bioactive Monoterpenes and Polyketides from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722 |
title_short | Bioactive Monoterpenes and Polyketides from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722 |
title_sort | bioactive monoterpenes and polyketides from the ascidian-derived fungus diaporthe sp. sysu-ms4722 |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9504586/ https://www.ncbi.nlm.nih.gov/pubmed/36135742 http://dx.doi.org/10.3390/md20090553 |
work_keys_str_mv | AT zhaiguifa bioactivemonoterpenesandpolyketidesfromtheascidianderivedfungusdiaporthespsysums4722 AT chensenhua bioactivemonoterpenesandpolyketidesfromtheascidianderivedfungusdiaporthespsysums4722 AT shenhongjie bioactivemonoterpenesandpolyketidesfromtheascidianderivedfungusdiaporthespsysums4722 AT guoheng bioactivemonoterpenesandpolyketidesfromtheascidianderivedfungusdiaporthespsysums4722 AT jiangminghua bioactivemonoterpenesandpolyketidesfromtheascidianderivedfungusdiaporthespsysums4722 AT liulan bioactivemonoterpenesandpolyketidesfromtheascidianderivedfungusdiaporthespsysums4722 |