Synthesis and characterisation of steroidal inhibitors of α -amylase,α -glucosidase and oxidative species

Abstract

BACKGROUND:

Management of cellular metabolism and blood glucose levels are significant in the treatment of diabetes mellitus and oxidative diseases. Consequently, steroid and peptide hormone-based drugs such as methylprednisolone and insulin have been the most effective and safe methods of treatment.

OBJECTIVE:

Our study investigated the digestive enzymes and oxidative species inhibitory potentials of seven derived biologically important steroids.

METHODS:

Syntheses of the steroidal inhibitors (SIs) were accomplished by functional group transformations. Characterisation of SIs was achieved by spectroscopic techniques; followed by in-vitro enzyme and oxidative suppression studies.

RESULTS:

NMR data revealed the presence of a steroid backbone, azomethine, carbonyl, and oxymethine peaks while the vibrational bands were further confirmed by the FTIR. The enzyme suppression activities of the SIs were influenced by the presence of histidine residue and free proton groups. However, the antioxidant activities were solely dependent on the free proton groups on the steroid backbone or the number of the histidine side chain. SIs [3, 4, and 6] exhibited a potent inhibitory effect on the enzyme activities compared to SIs [1, 2, 5, and 7], while a potent antioxidant activity was reported by SI [5].

CONCLUSIONS:

Generally, SIs with hydroxyl and α-amino acid functionalities have a strong affinity for the enzyme active site than the substrate; hence, the hydrolysis of the α-1,4-glycosidic bonds of saccharide was hindered. In vivo administration of SIs [3, 4, and 6] should take into cognizance the suppression effect at doses ≤939.49 μg/mL as well as the potential to induce abnormal bacterial fermentation of undigested carbohydrates in the colon at high concentration.