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Bioassay-guided purification of α-glucosidase inhibitor fatty acids from Padina tetrastromatica

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Abstract

Anti-diabetic potential of a brown alga, Padina tetrastromatica, using bioassay-guided purification approach yielded the most active α-glucosidase inhibitor agents as fatty acids. Initially, α-glucosidase inhibition of the MeOH and 80% MeOH extracts were evaluated via a colorimetric assay. The liquid–liquid fractionation of 80% MeOH extract, as the most potent α-glucosidase inhibitor, resulted in four fractions: n-hexane, ethyl acetate, n-butanol and water. The hexane and ethyl acetate fractions were selected for further study with IC50 values of 38.0 ± 0.3 µg mL−1 and 53.7 ± 2.6 µg mL−1, respectively. α-Glucosidase inhibition of the sub-fractions from the hexane fraction using flash column chromatography gave F18-21 as the most potent enzyme inhibitor. After further purification of F18-21 by semi preparative HPLC, the mentioned fraction and two purified compounds, 8-octadecenoic acid (8) and all-cis-5,8,11,14-eicosatetraenoic acid (10) were identified by GC–MS analysis, resulting fatty acids 1-12. In addition, 1D and 2D NMR evaluations were performed for characterisation of 8-octadecenoic acid. Furthermore, three fatty acids, all-cis-8,11,14,17-eicosatetraenoic acid (6), cis-9,12-octadecadienoic acid (7), and all-cis-5,8,11,14,17-eicosapentaenoic acid (11), were isolated from the ethyl acetate fraction and identified by HPLC and GC–MS, respectively. Finally, α-glucosidase inhibition percent of the purified fatty acids were evaluated in two concentrations in microplates, showing their great potential for further investigation as anti-diabetic agents, in comparison with acarbose as the positive control. Furthermore, molecular docking analysis and MD simulation were used to investigate the structure activity of the purified compounds.

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All data generated or analyzed during this study can be obtained from the authors upon reasonable request.

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Acknowledgements

ARJ is thankful to Alexander von Humboldt foundation for a research stay support at the department of pharmacognosy of Kiel University.

Funding

The authors wish to acknowledge the financial supports of Shiraz University of Medical Sciences (grant number: 18830). This study was part of the Ph.D. thesis of Niloofar Moheimanian.

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Authors and Affiliations

  1. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

    Niloofar Moheimanian, Hossein Mirkhani, Najmeh Edraki, Alireza Poustforoosh, Najmeh Khalighian & Amir Reza Jassbi

  2. Department of Pharmacology, School of Medicine, Shiraz University of Medical Sciences, Shiraz, Iran

    Hossein Mirkhani

  3. Persian Gulf Marine Biotechnology Research Center, The Persian Gulf Biomedical Sciences Research Institute, Bushehr University of Medical Sciences, Bushehr, 75147, Iran

    Safieh Momeni

  4. Pharmazeutisches Institut, Abteilung Pharmazeutische Biologie, Christian-Albrechts-Universität zu Kiel, Gutenbergstraße 76, 24118, Kiel, Germany

    Christian Zidorn

  5. Department of Natural Resources Research, Agriculture and Natural Resources Research and Education Center, Agricultural Research, Education and Extension Organization (AREEO), Bandar Abbas, Iran

    Jelveh Sohrabipour

Authors
  1. Niloofar Moheimanian
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  2. Hossein Mirkhani
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  9. Amir Reza Jassbi
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Contributions

Author contribution Nioofar Moheimanian: Conceptualization, Methodology, Investigation, Formal analysis, Writing-original draft preparation. Hossein Mirkhani Supervision, Conceptualization, Writing-review & editing. Najmeh Edraki Methodology, Conceptualization, Writing—review & editing. Alireza Poustforoosh Molecular docking analysis, Conceptualization, Writing-review & editing. Safieh Momeni Collecting the algae, Writing-review & editing. Najmeh Khalighian Collaborating in HPLC analysis, Writing-review & editing. Christian Zidorn NMR analysis, Conceptualization, Writing-review & editing. Jelveh Sohrabipour Identification of the algae, Writing-review & editing. Amir Reza Jassbi Supervision, Methodology, Conceptualization, Resources, Writing-review & editing.

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Correspondence to Amir Reza Jassbi.

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Competing interests

Amir Reza Jassbi is founder and scientific leader of the startup company: "Aryana Phytochemistry of Tirazis".

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Moheimanian, N., Mirkhani, H., Edraki, N. et al. Bioassay-guided purification of α-glucosidase inhibitor fatty acids from Padina tetrastromatica. J Appl Phycol 36, 359–370 (2024). https://doi.org/10.1007/s10811-023-03125-6

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