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Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus Phomopsis sp. xz-18

Eight new cytochalasins 1–8 and ten known analogs 9–18 were isolated from the endophytic fungus Phomopsis sp. xz-18. The planar structures of the cytochalasins were determined by HR-ESI-MS and NMR analysis. Compounds 1, 2, 9 and 10 were 5/6/6/7/5-fused pentacyclic cytochalasins; compounds 3 and 4 ha...

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Autores principales: Huang, Guichon, Lin, Weiwen, Li, Hanpeng, Tang, Qian, Hu, Zhiyu, Huang, Huiying, Deng, Xianming, Xu, Qingyan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587572/
https://www.ncbi.nlm.nih.gov/pubmed/34770914
http://dx.doi.org/10.3390/molecules26216505
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author Huang, Guichon
Lin, Weiwen
Li, Hanpeng
Tang, Qian
Hu, Zhiyu
Huang, Huiying
Deng, Xianming
Xu, Qingyan
author_facet Huang, Guichon
Lin, Weiwen
Li, Hanpeng
Tang, Qian
Hu, Zhiyu
Huang, Huiying
Deng, Xianming
Xu, Qingyan
author_sort Huang, Guichon
collection PubMed
description Eight new cytochalasins 1–8 and ten known analogs 9–18 were isolated from the endophytic fungus Phomopsis sp. xz-18. The planar structures of the cytochalasins were determined by HR-ESI-MS and NMR analysis. Compounds 1, 2, 9 and 10 were 5/6/6/7/5-fused pentacyclic cytochalasins; compounds 3 and 4 had conjugated diene structures in the macrocycle; and compound 6 had a β,γ-unsaturated ketone. The absolute configuration of 6 was confirmed for the first time by the octant rule. The acid-free purification process proved that the pentacyclic system was a natural biosynthetic product and not an acid-mediated intramolecular cyclized artifact. The new compounds did not exhibit activities against human cancer cell lines in cytotoxicity bioassays or antipathogenic fungal activity, but compounds 1, 3 and 4 showed moderate antibacterial activity in disk diffusion assays.
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spelling pubmed-85875722021-11-13 Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus Phomopsis sp. xz-18 Huang, Guichon Lin, Weiwen Li, Hanpeng Tang, Qian Hu, Zhiyu Huang, Huiying Deng, Xianming Xu, Qingyan Molecules Article Eight new cytochalasins 1–8 and ten known analogs 9–18 were isolated from the endophytic fungus Phomopsis sp. xz-18. The planar structures of the cytochalasins were determined by HR-ESI-MS and NMR analysis. Compounds 1, 2, 9 and 10 were 5/6/6/7/5-fused pentacyclic cytochalasins; compounds 3 and 4 had conjugated diene structures in the macrocycle; and compound 6 had a β,γ-unsaturated ketone. The absolute configuration of 6 was confirmed for the first time by the octant rule. The acid-free purification process proved that the pentacyclic system was a natural biosynthetic product and not an acid-mediated intramolecular cyclized artifact. The new compounds did not exhibit activities against human cancer cell lines in cytotoxicity bioassays or antipathogenic fungal activity, but compounds 1, 3 and 4 showed moderate antibacterial activity in disk diffusion assays. MDPI 2021-10-28 /pmc/articles/PMC8587572/ /pubmed/34770914 http://dx.doi.org/10.3390/molecules26216505 Text en © 2021 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
Huang, Guichon
Lin, Weiwen
Li, Hanpeng
Tang, Qian
Hu, Zhiyu
Huang, Huiying
Deng, Xianming
Xu, Qingyan
Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus Phomopsis sp. xz-18
title Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus Phomopsis sp. xz-18
title_full Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus Phomopsis sp. xz-18
title_fullStr Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus Phomopsis sp. xz-18
title_full_unstemmed Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus Phomopsis sp. xz-18
title_short Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus Phomopsis sp. xz-18
title_sort pentacyclic cytochalasins and their derivatives from the endophytic fungus phomopsis sp. xz-18
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587572/
https://www.ncbi.nlm.nih.gov/pubmed/34770914
http://dx.doi.org/10.3390/molecules26216505
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