Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus <i>Cladosporium sphaerospermum</i> EIODSF 008

Seven new unstable tetramic acid derivatives, cladosporiumins I-O (<b>1</b>&#8315;<b>7</b>), together with the known analogue cladodionen (<b>8</b>) were isolated from the extract of the deep-sea-derived fungus <i>Cladosporium sphaerospermum</i> EI...

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Main Authors: Xiao Liang, Zhong-Hui Huang, Xuan Ma, Shu-Hua Qi
Format: Article
Language:English
Published: MDPI AG 2018-11-01
Series:Marine Drugs
Subjects:
Online Access:https://www.mdpi.com/1660-3397/16/11/448
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author Xiao Liang
Zhong-Hui Huang
Xuan Ma
Shu-Hua Qi
author_facet Xiao Liang
Zhong-Hui Huang
Xuan Ma
Shu-Hua Qi
author_sort Xiao Liang
collection DOAJ
description Seven new unstable tetramic acid derivatives, cladosporiumins I-O (<b>1</b>&#8315;<b>7</b>), together with the known analogue cladodionen (<b>8</b>) were isolated from the extract of the deep-sea-derived fungus <i>Cladosporium sphaerospermum</i> EIODSF 008. Their structures were elucidated by spectroscopic analysis, quantum chemical calculations and ECD spectra. Compound <b>4</b> was a Mg complex of tetramic acid derivative. In acidic solvent, <b>4</b> could change to <b>1</b> and <b>6</b>, and <b>7</b> could change to <b>5</b>. In addition, <b>1</b>, <b>5</b> and <b>8</b> existed as two exchangeable isomers, respectively. The structures of cladosporiumins E-H were reassigned as their Na complexes. The antibacterial and cytotoxic activities of <b>1</b>&#8315;<b>8</b> were also evaluated. However, because of their instability, all of the isolated compounds did not show significant antibacterial activity as the preliminary EtOAc extracts of the fungal strain.
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spelling doaj.art-6a7e1fdf6dbd4713af3b50cccc30c2e62022-12-22T02:55:19ZengMDPI AGMarine Drugs1660-33972018-11-01161144810.3390/md16110448md16110448Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus <i>Cladosporium sphaerospermum</i> EIODSF 008Xiao Liang0Zhong-Hui Huang1Xuan Ma2Shu-Hua Qi3CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, Guangdong, ChinaCAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, Guangdong, ChinaCAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, Guangdong, ChinaCAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, Guangdong, ChinaSeven new unstable tetramic acid derivatives, cladosporiumins I-O (<b>1</b>&#8315;<b>7</b>), together with the known analogue cladodionen (<b>8</b>) were isolated from the extract of the deep-sea-derived fungus <i>Cladosporium sphaerospermum</i> EIODSF 008. Their structures were elucidated by spectroscopic analysis, quantum chemical calculations and ECD spectra. Compound <b>4</b> was a Mg complex of tetramic acid derivative. In acidic solvent, <b>4</b> could change to <b>1</b> and <b>6</b>, and <b>7</b> could change to <b>5</b>. In addition, <b>1</b>, <b>5</b> and <b>8</b> existed as two exchangeable isomers, respectively. The structures of cladosporiumins E-H were reassigned as their Na complexes. The antibacterial and cytotoxic activities of <b>1</b>&#8315;<b>8</b> were also evaluated. However, because of their instability, all of the isolated compounds did not show significant antibacterial activity as the preliminary EtOAc extracts of the fungal strain.https://www.mdpi.com/1660-3397/16/11/448deep-sea-derived fungus<i>Cladosporium sphaerospermum</i>tetramic acidcladosporiumins I-O
spellingShingle Xiao Liang
Zhong-Hui Huang
Xuan Ma
Shu-Hua Qi
Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus <i>Cladosporium sphaerospermum</i> EIODSF 008
Marine Drugs
deep-sea-derived fungus
<i>Cladosporium sphaerospermum</i>
tetramic acid
cladosporiumins I-O
title Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus <i>Cladosporium sphaerospermum</i> EIODSF 008
title_full Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus <i>Cladosporium sphaerospermum</i> EIODSF 008
title_fullStr Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus <i>Cladosporium sphaerospermum</i> EIODSF 008
title_full_unstemmed Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus <i>Cladosporium sphaerospermum</i> EIODSF 008
title_short Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus <i>Cladosporium sphaerospermum</i> EIODSF 008
title_sort unstable tetramic acid derivatives from the deep sea derived fungus i cladosporium sphaerospermum i eiodsf 008
topic deep-sea-derived fungus
<i>Cladosporium sphaerospermum</i>
tetramic acid
cladosporiumins I-O
url https://www.mdpi.com/1660-3397/16/11/448
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AT zhonghuihuang unstabletetramicacidderivativesfromthedeepseaderivedfungusicladosporiumsphaerospermumieiodsf008
AT xuanma unstabletetramicacidderivativesfromthedeepseaderivedfungusicladosporiumsphaerospermumieiodsf008
AT shuhuaqi unstabletetramicacidderivativesfromthedeepseaderivedfungusicladosporiumsphaerospermumieiodsf008