Diabetes mellitus (DM), characterized by abnormal carbohydrate, lipid, and protein metabolism, is a metabolic disorder caused by a shortage of insulin secretion or decreased sensitivity of target cells to insulin. In addition to changes in lifestyle, a low-calorie diet is recommended to reduce the development of DM. Steviol glycosides (SGs), as natural sweeteners, have gained attention as sucrose alternatives because of their advantages of high sweetness and being low calorie. Most SGs with multiple bioactivities are beneficial to regulate physiological functions. Though SGs have been widely applied in food industry, there is little data on their glucosylated derivatives that are glucosylated steviol glycosides (GSGs). In this review, we have discussed the metabolic fate of GSGs in contrast to SGs, and the molecular mechanisms of glycoside metabolites against diabetes-related metabolic disorders are also summarized. SGs are generally extracted from the Stevia leaf, while GSGs are mainly manufactured using enzymes that transfer glucose units from a starch source to SGs. Results from this study suggest that SGs and GSGs share same bioactive metabolites, steviol and steviol glucuronide (SVG), which exhibit anti-hyperglycemic effects by activating glucose-induced insulin secretion to enhance pancreatic β-cell function. In addition, steviol and SVG have been found to ameliorate the inflammatory response, lipid imbalance, myocardial fibrosis and renal functions to modulate diabetes-related metabolic disorders. Therefore, both SGs and GSGs may be used as potential sucrose alternatives and/or pharmacological alternatives for preventing and treating metabolic disorders.