Abstract

Bioassay guided isolation of the methanolic extract of marine macro brown alga Dictyopteris hoytii afforded one new metabolite (ethyl methyl 2-bromobenzene 1,4-dioate, 1), one new natural metabolite (diethyl-2-bromobenzene 1,4-dioate, 2) along with six known metabolites (3–8) reported for the first time from this source. The structure elucidation of all these compounds was achieved by extensive spectroscopic techniques including 1D (1H and 13C) and 2D (NOESY, COSY, HMBC and HSQC) NMR and mass spectrometry and comparison of the spectral data of known compounds with those reported in literature. The in vitro α-glucosidase inhibition studies confirmed compound 7 to be the most active against α-glucosidase enzyme with IC50 value of 30.5 ± 0.41 μM. Compounds 2 and 3 demonstrated good inhibition with IC50 values of 234.2 ± 4.18 and 289.4 ± 4.91 μM, respectively, while compounds 1, 5, and 6 showed moderate to low inhibition. Furthermore, the molecular docking studies of the active compounds were performed to examine their mode of inhibition in the binding site of the α-glucosidase enzyme.

Highlights

  • According to World Health Organization (WHO) estimates, about 90% of the world’s diabetic people have type 2, and from 2012 to 2014 about 1.5 million peoples died from complications of this disease [1]

  • The infrared (IR) absorption bands at υmax 1739, 1725, 1602 and 1433 cm−1 indicated the presence of methyl and ethyl esters and aromatic functionalities in the molecule

  • Correlations of Me-10 (δ 1.43) with C-7/C-9 and Me-12 (δ 1.40) with C-8/C-11 indicated the presence of diethyl ester groups which were further confirmed through HMBC correlations among H-3 to C2, C-4, C-1, and

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Summary

Introduction

According to World Health Organization (WHO) estimates, about 90% of the world’s diabetic people have type 2, and from 2012 to 2014 about 1.5 million peoples died from complications of this disease [1]. Type 2 diabetes mellitus (T2DM) patients still suffer hyperglycemia and serious complications in spite of having clinically approved anti-diabetic drugs. Diabetic disorders can be controlled by reducing the absorption of glucose level via inhibiting α-glucosidase enzyme [2]. Prevention of α-glucosidase enzyme activity suppresses the enhancement of sugar level in the blood after carbohydrate-rich diet intake [3]. The clinically used α-glucosidase inhibitors (AGIs), such as acarbose, voglibose and miglitol, successfully decrease the post-prandial glucose levels in T2DM patients [4].

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