Management of cellular metabolism and blood glucose level is significant in diabetes mellitus and oxidative diseases treatment; however, there are several limitations. As a result of the medicinal benefit of steroid-drugs; this study investigated the inhibitory potentials of functionalised steroids on digestive enzymes and oxidative species. Synthesis of the steroids was accomplished by esterification, imination and chromic acid oxidation of the respective steroids. Characterisation of the steroids was achieved by spectroscopic techniques; followed by in-vitro enzyme and oxidative suppression studies. NMR data revealed the presence of a steroid backbone, azomethine, carbonyl, and oxymethine peaks while the vibrational bands of the carboxylic acid, hydroxyl and oxo groups were identified on the FTIR spectra. The enzyme suppression activities of the steroids were influenced by the presence of histidine residue, free acid and hydroxyl groups at C-3 and C-17. However, the antioxidant activities were dependent on the number of histidine residue on the backbone. Steroids  exhibited a potent inhibitory effect on the activities 𝛼-amylase and 𝛼-glucosidase (IC50 ≈ 2667.78 µM) compared to (IC50 ≈ 3485.46 µM) while potent antioxidant activity was exhibited by steroid. The hydrolysis of the 𝛼-1,4-glycosidic bonds of saccharides into glucose molecules by the enzyme was hindered. An implication that the enzyme suppression by the steroids with the α-amino acid is dependent on the strong affinity for the enzyme active site than the substrate. However, the presence of free acid and hydroxyl groups with one histidine residue results in a potent antioxidant activity. Keywords: α-amylase; α-glucosidase; antioxidant activity; enzyme suppression; histidine; steroids.