Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus <i>Penicillium cyclopium</i> SD-413

Nine secondary metabolites (<b>1</b>–<b>9</b>), including two new polyketide derivatives 9-dehydroxysargassopenilline A (<b>4</b>) and 1,2-didehydropeaurantiogriseol E (<b>5</b>), along with seven known related secondary metabolites (<b>1</b&g...

Full description

Bibliographic Details
Main Authors: Yan-He Li, Xiao-Ming Li, Xin Li, Sui-Qun Yang, Xiao-Shan Shi, Hong-Lei Li, Bin-Gui Wang
Format: Article
Language:English
Published: MDPI AG 2020-11-01
Series:Marine Drugs
Subjects:
Online Access:https://www.mdpi.com/1660-3397/18/11/553
_version_ 1797548604996452352
author Yan-He Li
Xiao-Ming Li
Xin Li
Sui-Qun Yang
Xiao-Shan Shi
Hong-Lei Li
Bin-Gui Wang
author_facet Yan-He Li
Xiao-Ming Li
Xin Li
Sui-Qun Yang
Xiao-Shan Shi
Hong-Lei Li
Bin-Gui Wang
author_sort Yan-He Li
collection DOAJ
description Nine secondary metabolites (<b>1</b>–<b>9</b>), including two new polyketide derivatives 9-dehydroxysargassopenilline A (<b>4</b>) and 1,2-didehydropeaurantiogriseol E (<b>5</b>), along with seven known related secondary metabolites (<b>1</b>–<b>3</b> and <b>6</b>–<b>9</b>), were isolated and identified from the deep sea-derived fungus <i>Penicillium</i><i>cyclopium</i> SD-413. Their structures were elucidated on the basis of 1D/2D NMR spectroscopic and mass spectrometric analysis and the absolute configurations were determined by the combination of NOESY correlations and time-dependent density functional (TDDFT) ECD calculations. Compounds <b>1</b>–<b>9</b> inhibited some pathogenic bacteria including <i>Escherichia coli</i>, <i>E. ictaluri</i>, <i>Edwardsiella tarda</i>, <i>Micrococcus luteus</i>, <i>Vibrio anguillarum</i>, and <i>V. harveyi</i>, with MIC (minimum inhibitory concentration) values ranging from 4 to 32 μg/mL.
first_indexed 2024-03-10T15:02:01Z
format Article
id doaj.art-464d018d2f1d4877ba008918a77a054c
institution Directory Open Access Journal
issn 1660-3397
language English
last_indexed 2024-03-10T15:02:01Z
publishDate 2020-11-01
publisher MDPI AG
record_format Article
series Marine Drugs
spelling doaj.art-464d018d2f1d4877ba008918a77a054c2023-11-20T20:04:40ZengMDPI AGMarine Drugs1660-33972020-11-01181155310.3390/md18110553Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus <i>Penicillium cyclopium</i> SD-413Yan-He Li0Xiao-Ming Li1Xin Li2Sui-Qun Yang3Xiao-Shan Shi4Hong-Lei Li5Bin-Gui Wang6Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaKey Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaKey Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaKey Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaKey Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaKey Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaKey Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, ChinaNine secondary metabolites (<b>1</b>–<b>9</b>), including two new polyketide derivatives 9-dehydroxysargassopenilline A (<b>4</b>) and 1,2-didehydropeaurantiogriseol E (<b>5</b>), along with seven known related secondary metabolites (<b>1</b>–<b>3</b> and <b>6</b>–<b>9</b>), were isolated and identified from the deep sea-derived fungus <i>Penicillium</i><i>cyclopium</i> SD-413. Their structures were elucidated on the basis of 1D/2D NMR spectroscopic and mass spectrometric analysis and the absolute configurations were determined by the combination of NOESY correlations and time-dependent density functional (TDDFT) ECD calculations. Compounds <b>1</b>–<b>9</b> inhibited some pathogenic bacteria including <i>Escherichia coli</i>, <i>E. ictaluri</i>, <i>Edwardsiella tarda</i>, <i>Micrococcus luteus</i>, <i>Vibrio anguillarum</i>, and <i>V. harveyi</i>, with MIC (minimum inhibitory concentration) values ranging from 4 to 32 μg/mL.https://www.mdpi.com/1660-3397/18/11/553<i>Penicillium cyclopium</i>marine sediment-derived fungusquinazoline alkaloidpolyketide derivativesantibacterial activity
spellingShingle Yan-He Li
Xiao-Ming Li
Xin Li
Sui-Qun Yang
Xiao-Shan Shi
Hong-Lei Li
Bin-Gui Wang
Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus <i>Penicillium cyclopium</i> SD-413
Marine Drugs
<i>Penicillium cyclopium</i>
marine sediment-derived fungus
quinazoline alkaloid
polyketide derivatives
antibacterial activity
title Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus <i>Penicillium cyclopium</i> SD-413
title_full Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus <i>Penicillium cyclopium</i> SD-413
title_fullStr Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus <i>Penicillium cyclopium</i> SD-413
title_full_unstemmed Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus <i>Penicillium cyclopium</i> SD-413
title_short Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus <i>Penicillium cyclopium</i> SD-413
title_sort antibacterial alkaloids and polyketide derivatives from the deep sea derived fungus i penicillium cyclopium i sd 413
topic <i>Penicillium cyclopium</i>
marine sediment-derived fungus
quinazoline alkaloid
polyketide derivatives
antibacterial activity
url https://www.mdpi.com/1660-3397/18/11/553
work_keys_str_mv AT yanheli antibacterialalkaloidsandpolyketidederivativesfromthedeepseaderivedfungusipenicilliumcyclopiumisd413
AT xiaomingli antibacterialalkaloidsandpolyketidederivativesfromthedeepseaderivedfungusipenicilliumcyclopiumisd413
AT xinli antibacterialalkaloidsandpolyketidederivativesfromthedeepseaderivedfungusipenicilliumcyclopiumisd413
AT suiqunyang antibacterialalkaloidsandpolyketidederivativesfromthedeepseaderivedfungusipenicilliumcyclopiumisd413
AT xiaoshanshi antibacterialalkaloidsandpolyketidederivativesfromthedeepseaderivedfungusipenicilliumcyclopiumisd413
AT hongleili antibacterialalkaloidsandpolyketidederivativesfromthedeepseaderivedfungusipenicilliumcyclopiumisd413
AT binguiwang antibacterialalkaloidsandpolyketidederivativesfromthedeepseaderivedfungusipenicilliumcyclopiumisd413