Leaves of Ixora undulata Roxb. were investigated phytochemically for the first time for its alkaloidal content, which resulted in the isolation of a novel unusual thiazepine alkaloid glycoside identified as 7-[(β-D-glucopyranosyl)oxy]-6-hydroxy-2-methoxy-4,5-dihydro-1,3-thiazepine and trivially named as Rubiothiazepine. Its structure was determined on the basis of 1D and 2D NMR ( 1 H-, 13 C-NMR, 1 H-1 H COSY, 1 H-13 C HETCOR, 1 H-13 C HMBC, 1 H-15 N HMBC and DIFNOE), high resolution ESI-CID-MS/MS, UV and IR spectroscopy. The isolated compound showed cytotoxic activity against EL 4 (Murine Leukemia) with IC 50 >100 µg/mL, and also showed cytotoxic and HIV-1 activity against MT-4 and HIV-1IIIB with CC 50 >100 µg/mL and EC 50 >100 µg/mL, respectively.