New Cytotoxic Cyclic Peptide from the Marine Sponge-Associated Nocardiopsis sp. UR67
Alyaa Hatem Ibrahim,
Eman Zekry Attia,
Dina Hajjar,
Mohamed A. Anany,
Samar Yehia Desoukey,
Mostafa Ahmed Fouad,
Mohamed Salah Kamel,
Harald Wajant,
Tobias A. M. Gulder,
Usama Ramadan Abdelmohsen
Affiliations
Alyaa Hatem Ibrahim
Department of Pharmacognosy, Faculty of Pharmacy, Sohag University, 82524 Sohag, Egypt
Eman Zekry Attia
Department of Pharmacognosy, Faculty of Pharmacy, Minia University, 61519 Minia, Egypt
Dina Hajjar
Department of Biochemistry, Faculty of Science, Center for Science and Medical Research, University of Jeddah, 80203 Jeddah, Saudi Arabia
Mohamed A. Anany
Division of Molecular Internal Medicine, Department of Internal Medicine II, University Hospital Würzburg, Röntenring 11, 97070 Würzburg, Germany
Samar Yehia Desoukey
Department of Pharmacognosy, Faculty of Pharmacy, Minia University, 61519 Minia, Egypt
Mostafa Ahmed Fouad
Department of Pharmacognosy, Faculty of Pharmacy, Minia University, 61519 Minia, Egypt
Mohamed Salah Kamel
Department of Pharmacognosy, Faculty of Pharmacy, Deraya University, Universities Zone, 61111 New Minia City, Egypt
Harald Wajant
Division of Molecular Internal Medicine, Department of Internal Medicine II, University Hospital Würzburg, Röntenring 11, 97070 Würzburg, Germany
Tobias A. M. Gulder
Biosystems Chemistry, Department of Chemistry and Center for Integrated Protein Science Munich (CIPSM), Technical University of Munich, Lichtenbergstraβe 4, 85748 Garching, Germany
Usama Ramadan Abdelmohsen
Department of Pharmacognosy, Faculty of Pharmacy, Minia University, 61519 Minia, Egypt
A new cyclic hexapeptide, nocardiotide A (1), together with three known compounds—tryptophan (2), kynurenic acid (3), and 4-amino-3-methoxy benzoic acid (4)—were isolated and identified from the broth culture of Nocardiopsis sp. UR67 strain associated with the marine sponge Callyspongia sp. from the Red Sea. The structure elucidation of the isolated compounds were determined based on detailed spectroscopic data including 1D and 2D nuclear magnetic resonance (NMR) experimental analyses in combination with high resolution electrospray ionization mass spectrometry (HR-ESI-MS), while the absolute stereochemistry of all amino acids components of nocardiotide A (1) was deduced using Marfey’s method. Additionally, ten known metabolites were dereplicated using HR-ESI-MS analysis. Nocardiotide A (1) displayed significant cytotoxic effects towards the murine CT26 colon carcinoma, human HeLa cervix carcinoma, and human MM.1S multiple myeloma cell lines. The results obtained revealed sponge-associated Nocardiopsis as a substantial source of lead natural products with pronounced pharmacological activities.
