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Mangostanaxanthones III and IV: advanced glycation end-product inhibitors from the pericarp of Garcinia mangostana

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Abstract

Advanced glycation end-products (AGEs) are associated with a non-enzymatic reaction between the amino group of a protein and the carbonyl group of a sugar during hyperglycemia. The precipitation of AGEs in different tissues leads to many complications, such as endothelial dysfunction, cardiovascular complications, atherosclerosis, retinopathy, neuropathy, and Alzheimer’s disease. Garcinia mangostana L. (Clusiaceae) (GM) was selected owing to the ability of its polar and non-polar fractions to inhibit AGE formation. For the first time, the bioguided fractionation of its pericarp MeOH extract (GMT) gave rise to two new xanthones, namely, mangostanaxanthones III (1) and IV (3), in addition to six known compounds, β-mangostin (2), garcinone E (4), rubraxanthone (5), α-mangostin (6), garcinone C (7), and 9-hydroxycalabaxanthone (8), from the non-polar faction. Their structures were verified by various spectroscopic methods, including 1D and 2D NMR studies and high-resolution MS data. All of the isolated xanthones significantly inhibited both sugar (ribose) and dicarbonyl compound (methylglyoxal)-induced protein glycation in a dose-dependent manner. This is explained by the ability of the isolated xanthones to inhibit protein oxidation, as indicated by the decreases in dityrosine and N′-formylkynurenine formation.

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Acknowledgments

This project was funded by the National Plan for Science, Technology and Innovation (MAARIFAH), King Abdulaziz City for Science and Technology, the Kingdom of Saudi Arabia, Award Number 12-BIO3087-03. The authors also acknowledge with thanks the Science and Technology Unit, King Abdulaziz University, for the technical support.

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Authors and Affiliations

  1. Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Hossam M. Abdallah, Gamal A. Mohamed & Ali M. El-Halawany

  2. Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Cairo, 11562, Egypt

    Hossam M. Abdallah & Ali M. El-Halawany

  3. Department of Pharmacology, Faculty of Pharmacy, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Hany M. El-Bassossy

  4. Department of Pharmacology, Faculty of Pharmacy, Zagazig University, Zagazig, 44519, Egypt

    Hany M. El-Bassossy

  5. Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut Branch, Assiut, 71524, Egypt

    Gamal A. Mohamed

  6. Department of Medicine, Faculty of Medicine, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Khalid Z. Alshali

  7. Department of Clinical Biochemistry, Faculty of Medicine, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Zainy M. Banjar

Authors
  1. Hossam M. Abdallah
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  2. Hany M. El-Bassossy
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  3. Gamal A. Mohamed
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  4. Ali M. El-Halawany
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  5. Khalid Z. Alshali
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Correspondence to Hossam M. Abdallah.

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Abdallah, H.M., El-Bassossy, H.M., Mohamed, G.A. et al. Mangostanaxanthones III and IV: advanced glycation end-product inhibitors from the pericarp of Garcinia mangostana . J Nat Med 71, 216–226 (2017). https://doi.org/10.1007/s11418-016-1051-8

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  • DOI: https://doi.org/10.1007/s11418-016-1051-8

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