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Naturally bioactive compounds from Hemimycale aff arabica: antimicrobial, antiglycation, cytotoxicity, and molecular docking studies

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Abstract

Two naturally new cyclic urea and amide derivatives, [1,3]-diazepan-2-one (1) and (S)-1,4-diaza-cyclododecane-2,3-dion (2), were isolated from the organic extract of the sponge Hemimycale aff arabica collected from the Red Sea. This was together with 4-acetamido-2,6-dibromo-4-hydroxy-1,1-dimethoxycyclohexa-2,5-diene (3), 2,4-bis(1-methyl-1-phenylethyl)-phenol (4), β-sitosterol (5), bis-[2-ethyl]-hexyl-phthylester, triglyceride fatty acid ester, and linoleic acid. The chemical structures of compounds 1 and 2 were determined based on 1D and 2D Nuclear Magnetic Resonance (NMR) and HR-ESIMS. Compounds 1 and 2 revealed high potency as antiglycated agents. The molecular docking study of compounds 1 and 2 using α-glucosidase, α-amylase, dipeptidyl peptidase-IV, and glycogen synthase kinase was performed to check their efficiency as hypoglycemic agents. Both the sponge extract and compound 1 showed no cytotoxicity vs. the RPE-1 as a model of normal cell line.

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Acknowledgements

The authors are deeply thankful to Prof. H. Laatsch, Institute of Organic and Biomolecular Chemistry, Göttingen, for his support and lab facilities. We thank Dr. H. Frauendorf and Dr. M. John for the mass and NMR spectra. The authors would like to acknowledge Ms. F. Lissy for antimicrobial activity tests. We are thankful to Dr. Mohamed Abd-Elghany (Hurghada, Red Sea, Egypt) for the collection and morphological taxonomy of the studied marine sponge. M. Shaaban thanks the German Academic Exchange Service (DAAD) for a short-term grant.

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Authors and Affiliations

  1. Institute of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstrasse 2, D-37077, Göttingen, Germany

    Mohamed Shaaban

  2. Chemistry of Natural Compounds Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, El-Behoos st. 33, Dokki-Cairo, 12622, Egypt

    Mohamed Shaaban, Amal Zaki Hassan & Ahmed B. Abdelwahab

  3. Biology Unit, Central Laboratory for Pharmaceutical and Drug Industries Research Division, Chemistry of Medicinal Plants Department, National Research Centre, Dokki, Giza, 12622, Egypt

    Maha M. Soltan

  4. Lorraine University, L2CM, 1 Boulevard Arago, 57070, Lorraine, France

    Ahmed B. Abdelwahab

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  1. Mohamed Shaaban
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  2. Amal Zaki Hassan
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Correspondence to Mohamed Shaaban.

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Shaaban, M., Hassan, A.Z., Soltan, M.M. et al. Naturally bioactive compounds from Hemimycale aff arabica: antimicrobial, antiglycation, cytotoxicity, and molecular docking studies. Med Chem Res 27, 2079–2088 (2018). https://doi.org/10.1007/s00044-018-2217-6

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