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Medicinal Chemistry Research

, Volume 28, Issue 5, pp 696–710 | Cite as

First report of antioxidative abeo-oleanenes from red seaweed Gracilaria salicornia as dual inhibitors of starch digestive enzymes

  • Kajal ChakrabortyEmail author
  • Tima Antony
Original Research
  • 31 Downloads

Abstract

Carbolytic enzyme-associated cascades have been considered as potential curative target in attenuating diabetic mellitus pathogenesis. Two oleanene class of triterpenoids characterised as 24(4 → 23), 27(8 → 26), 30(20 → 29)-tris-abeo-olean-(12-oxo)-1,15,22-triene-methyl hept-5-enoate (1) and 24(4 → 23)-abeo-olean-(12-oxo)-3,5-diene-deconoate (2) with potential inhibitory activities against the starch digestive enzymes α-glucosidase and α-amylase, were purified from the organic extract of intertidal red seaweed Gracilaria salicornia (family Gracilariaceae). Structural interpretation of compounds was carried out by detailed spectroscopic analysis, and their antioxidant/anti-diabetic potentials were assessed. Inhibitory potential of abeo-oleanene derivative (2) towards the starch digestive enzymes, α-glucosidase (IC50 0.29 mM) and α-amylase (IC50 0.32 mM) were greater than those displayed by its abeo-oleanene chemotype 1 (IC50 0.34–0.40 mM). The molecular modelling studies were performed to designate the α-amylase and α-glucosidase inhibitory mechanism of oleanene analogues, and the comparison of docking parameters suggested that compound 2 exhibited least binding energy of −10.04 and −9.84 kcal mol−1 towards α-amylase and α-glucosidase respectively, and those results were corroborated with its greater inhibition potential against carbolytic enzymes. These results demonstrated that abeo-oleanene derivative (2) might constitute prospective anti-hyperglycaemic pharmaceutical candidate to moderate the likelihood of type-II diabetes.

Keywords

Gracilaria salicornia Gracilariaceae Abeo-oleanenes Anti-diabetic Starch digestive enzymes Biosynthetic pathway 

Notes

Acknowledgements

The present work was supported by Science and Engineering Research Board (SERB) (grant number SR/S1/OC-96A/2012) of Department of Science and Technology, New Delhi, India. The authors thank the Director, Indian Council of Agricultural Research-Central Marine Fisheries Research Institute (ICAR-CMFRI), and Head, Marine Biotechnology Division, ICAR-CMFRI for guidance and support.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Supplementary material

44_2019_2328_MOESM1_ESM.doc (10.4 mb)
Supplementary Item.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Marine Bioprospecting Section of Marine Biotechnology DivisionCentral Marine Fisheries Research InstituteCochinIndia
  2. 2.Department of ChemistryMangalore UniversityMangaluruIndia

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