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The phytochemical investigation of the twig and root extracts of Erythrina subumbrans (Hassk.) Merr. (Fabaceae) resulted in the isolation and identification of a new pterocarpan, erythrinocarpan (1), along with 27 known compounds (2–28). All isolated compounds were evaluated for their antidiabetic, antimicrobial, and anti-inflammatory properties. Compounds 3, 8, 9, and 22 had α-glucosidase inhibitory activity with IC50 values of 13.4 ± 0.05, 24.5 ± 0.13, 29.0 ± 0.05, and 12.8 ± 0.14 μM, respectively, while compound 2 inhibited α-amylase activity with an IC50 value of 67.6 ± 1.12 μM. Compounds 22 and 24 inhibited glycation activity with the IC50 values of 36.9 ± 0.62 and 40.5 ± 0.37 μM, respectively. From cell-based assays, compound 27 showed the highest ability to induce glucose consumption (IC50 29.1 ± 0.86 μM) and glucose uptake (2.8-fold), and to inhibit nitric oxide (NO) production (IC50 52.5 ± 0.56 μM) without cell toxicity. Furthermore, compound 9 showed antimicrobial activities against Gram-positive bacteria and fungi with MIC values ranging from 2–4 μg/mL.