Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoei
In our search for bioactive metabolites from marine organisms, we have investigated the polar fraction of the organic extract of the Red Sea sponge Theonella swinhoei. Successive chromatographic separations and final HPLC purification of the potent antifungal fraction afforded a new bicyclic glycope...
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doaj-dc8b5d685391428cb6cdd62e0ba51b872020-11-24T22:25:32ZengMDPI AGMarine Drugs1660-33972014-04-011241911192310.3390/md12041911md12041911Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoeiDiaa T. A. Youssef0Lamiaa A. Shaala1Gamal A. Mohamed2Jihan M. Badr3Faida H. Bamanie4Sabrin R. M. Ibrahim5Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi ArabiaNatural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi ArabiaDepartment of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi ArabiaDepartment of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi ArabiaDepartment of Clinical Biochemistry, Faculty of Medicine, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, EgyptIn our search for bioactive metabolites from marine organisms, we have investigated the polar fraction of the organic extract of the Red Sea sponge Theonella swinhoei. Successive chromatographic separations and final HPLC purification of the potent antifungal fraction afforded a new bicyclic glycopeptide, theonellamide G (1). The structure of the peptide was determined using extensive 1D and 2D NMR and high-resolution mass spectral determinations. The absolute configuration of theonellamide G was determined by chemical degradation and 2D NMR spectroscopy. Theonellamide G showed potent antifungal activity towards wild and amphotericin B-resistant strains of Candida albicans with IC50 of 4.49 and 2.0 μM, respectively. Additionally, it displayed cytotoxic activity against the human colon adenocarcinoma cell line (HCT-16) with IC50 of 6.0 μM. These findings provide further insight into the chemical diversity and biological activities of this class of compounds.http://www.mdpi.com/1660-3397/12/4/1911Theonella swinhoeiglycopeptidetheonellamide Gantifungal activitycytotoxic activity |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Diaa T. A. Youssef Lamiaa A. Shaala Gamal A. Mohamed Jihan M. Badr Faida H. Bamanie Sabrin R. M. Ibrahim |
spellingShingle |
Diaa T. A. Youssef Lamiaa A. Shaala Gamal A. Mohamed Jihan M. Badr Faida H. Bamanie Sabrin R. M. Ibrahim Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoei Marine Drugs Theonella swinhoei glycopeptide theonellamide G antifungal activity cytotoxic activity |
author_facet |
Diaa T. A. Youssef Lamiaa A. Shaala Gamal A. Mohamed Jihan M. Badr Faida H. Bamanie Sabrin R. M. Ibrahim |
author_sort |
Diaa T. A. Youssef |
title |
Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoei |
title_short |
Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoei |
title_full |
Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoei |
title_fullStr |
Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoei |
title_full_unstemmed |
Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoei |
title_sort |
theonellamide g, a potent antifungal and cytotoxic bicyclic glycopeptide from the red sea marine sponge theonella swinhoei |
publisher |
MDPI AG |
series |
Marine Drugs |
issn |
1660-3397 |
publishDate |
2014-04-01 |
description |
In our search for bioactive metabolites from marine organisms, we have investigated the polar fraction of the organic extract of the Red Sea sponge Theonella swinhoei. Successive chromatographic separations and final HPLC purification of the potent antifungal fraction afforded a new bicyclic glycopeptide, theonellamide G (1). The structure of the peptide was determined using extensive 1D and 2D NMR and high-resolution mass spectral determinations. The absolute configuration of theonellamide G was determined by chemical degradation and 2D NMR spectroscopy. Theonellamide G showed potent antifungal activity towards wild and amphotericin B-resistant strains of Candida albicans with IC50 of 4.49 and 2.0 μM, respectively. Additionally, it displayed cytotoxic activity against the human colon adenocarcinoma cell line (HCT-16) with IC50 of 6.0 μM. These findings provide further insight into the chemical diversity and biological activities of this class of compounds. |
topic |
Theonella swinhoei glycopeptide theonellamide G antifungal activity cytotoxic activity |
url |
http://www.mdpi.com/1660-3397/12/4/1911 |
work_keys_str_mv |
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