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 <b&g...

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Autores principales:	Guichon Huang, Weiwen Lin, Hanpeng Li, Qian Tang, Zhiyu Hu, Huiying Huang, Xianming Deng, Qingyan Xu
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	cytochalasins pentacyclic system octant rule antibacterial activity Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/c42dc5aaf08448b287a887722217fa0d
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spelling	oai:doaj.org-article:c42dc5aaf08448b287a887722217fa0d2021-11-11T18:30:13ZPentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-1810.3390/molecules262165051420-3049https://doaj.org/article/c42dc5aaf08448b287a887722217fa0d2021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6505https://doaj.org/toc/1420-3049Eight new cytochalasins <b>1</b>–<b>8</b> and ten known analogs <b>9</b>–<b>18</b> 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 <b>1</b>, <b>2</b>, <b>9</b> and <b>10</b> were 5/6/6/7/5-fused pentacyclic cytochalasins; compounds <b>3</b> and <b>4</b> had conjugated diene structures in the macrocycle; and compound <b>6</b> 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 <b>1</b>, <b>3</b> and <b>4</b> showed moderate antibacterial activity in disk diffusion assays.Guichon HuangWeiwen LinHanpeng LiQian TangZhiyu HuHuiying HuangXianming DengQingyan XuMDPI AGarticlecytochalasinspentacyclic systemoctant ruleantibacterial activityOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6505, p 6505 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	cytochalasins pentacyclic system octant rule antibacterial activity Organic chemistry QD241-441
spellingShingle	cytochalasins pentacyclic system octant rule antibacterial activity Organic chemistry QD241-441 Guichon Huang Weiwen Lin Hanpeng Li Qian Tang Zhiyu Hu Huiying Huang Xianming Deng Qingyan Xu Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18
description	Eight new cytochalasins <b>1</b>–<b>8</b> and ten known analogs <b>9</b>–<b>18</b> 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 <b>1</b>, <b>2</b>, <b>9</b> and <b>10</b> were 5/6/6/7/5-fused pentacyclic cytochalasins; compounds <b>3</b> and <b>4</b> had conjugated diene structures in the macrocycle; and compound <b>6</b> 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 <b>1</b>, <b>3</b> and <b>4</b> showed moderate antibacterial activity in disk diffusion assays.
format	article
author	Guichon Huang Weiwen Lin Hanpeng Li Qian Tang Zhiyu Hu Huiying Huang Xianming Deng Qingyan Xu
author_facet	Guichon Huang Weiwen Lin Hanpeng Li Qian Tang Zhiyu Hu Huiying Huang Xianming Deng Qingyan Xu
author_sort	Guichon Huang
title	Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18
title_short	Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18
title_full	Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18
title_fullStr	Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18
title_full_unstemmed	Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18
title_sort	pentacyclic cytochalasins and their derivatives from the endophytic fungus <i>phomopsis</i> sp. xz-18
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/c42dc5aaf08448b287a887722217fa0d
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Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18

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