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Mar. Drugs 2014, 12(4), 1911-1923; doi:10.3390/md12041911
Article

Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoei

1,* , 2,3
, 1,4
, 1,5
, 6
 and 7,8
1 Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi Arabia 2 Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi Arabia 3 Suez Canal University Hospital, Suez Canal University, Ismailia 41522, Egypt 4 Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut Branch, Assiut 71524, Egypt 5 Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt 6 Department of Clinical Biochemistry, Faculty of Medicine, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi Arabia 7 Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt 8 Department of Pharmacognosy and Medicinal Chemistry, Faculty of Pharmacy, Taibah University, Al Madinah Al Munawwarah 41477, Kingdom of Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 10 February 2014 / Revised: 12 March 2014 / Accepted: 13 March 2014 / Published: 1 April 2014
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Abstract

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.
Keywords: Theonella swinhoei; glycopeptide; theonellamide G; antifungal activity; cytotoxic activity Theonella swinhoei; glycopeptide; theonellamide G; antifungal activity; cytotoxic activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Youssef, D.T.A.; Shaala, L.A.; Mohamed, G.A.; Badr, J.M.; Bamanie, F.H.; Ibrahim, S.R.M. Theonellamide G, a Potent Antifungal and Cytotoxic Bicyclic Glycopeptide from the Red Sea Marine Sponge Theonella swinhoei. Mar. Drugs 2014, 12, 1911-1923.

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