Nine tetraoxygenated xanthones [l,5,8-trihydroxy-3- methoxyxanthone (I), l-hydroxy-3,5,8-trimethoxyxanthone (II), l-hydroxy-3,7,8-trimethoxyxanthone (III), l,8-dihydroxy-3,5-di- methoxyxanthone (IV), l,8-dihydroxy-3,7-dimethoxyxanthone (V), l,3,6,7-tetrahydroxyxanthone-Cr0-D-glucoside (mangiferin, VI), l,3,8-trihydroxy-5-methoxyxanthone (VII), 1,3,5,8-tetrahydroxy- xanthone (VIII), and 1,3,7,8-tetrahydroxyxanthone (IX)] were isolated from the roots and aerial parts of Swertia chirata Buch.-Ham. (Gentianaceae) collected from Nepal and India. The identity of the xanthones was established by direct comparison with reference materials in most cases, preparation of derivatives, and spectral evidence (UV, IR, proton magnetic resonance, and mass spectrometry). Among these xanthones, II was not encountered before in nature and VI was found for the first time in the genus swertia. The biogenetic significance of the co-occurrence of several tetraoxygenated xanthones, of varying oxygenation patterns, in absence of the “standard” 1,3,5- and 1,3,7-trioxygenated xanthones in 5. chirata and in related species is appraised. In addition to the tetraoxygenated xanthones (1-IX), a number of heterosides, triterpenes, and monoterpene alkaloids were isolated from this plant. Preliminary pharmacological screening of the total xanthones of S. chirata indicated that the medicinal properties ascribed to the plant extracts were due to these constituents.