Lately, there has been increased interest in the development of phytochemical alternatives for the prevention and treatment of type 2 diabetes, the alternatives that are able to reduce or prevent glucose absorption by inhibiting digestive enzymes. In this context, this study aims to analyze the inhibitory α-amylase and α-glucosidase activities of Artemisia abrotanum and Symphytum officinale polyphenolic compound-rich extracts obtained by membrane technologies (micro- and ultrafiltration). Polyphenols and flavones content, HPLC-MS polyphenolic compounds profiling, antioxidant activity, and cytotoxic potential of these herbs were determined. Major phenolic acid compounds were chlorogenic acid, ellagic acid, caffeic acid, and rosmarinic acid. The flavone content was higher in the case of A. abrotanum extracts, and the major compounds were rutin and umbelliferone. The polyphenolic-rich extract of A. abrotanum had the highest quantities of polyphenols, 977.75 µg/mL, and flavones, 552.85 µg/mL, as well as a pronounced α-amylase inhibitory activity (IC50 1881.21 ± 1.8 mg/mL), a value close to acarbose inhibitory activity (IC50 1110.25 ± 8.82 mg/mL) that was used as the control for both enzymes. The α-glucosidase inhibitory activity was higher for both herb extracts, more pronounced for S. officinale polyphenolic-rich extract (IC50 291.56 ± 2.1 mg/mL), a value higher than that of acarbose (IC50 372.35 ± 3.2 mg/mL). These plants show potential as a complementary therapy for type 2 diabetes management.