Synthesis and Antimicrobial and Antituberculosis Activity of the First Conjugates of the Diterpenoid Isosteviol and D-Arabinofuranose.

Previously unknown conjugates of the diterpenoid isosteviol <bold>1</bold> and 1-O-methyl-2,3-di-O-acetyl-β-Darabinofuranoside in which the terpenoid and carbohydrate molecules were linked through polymethylene spacers of various lengths were synthesized. Isosteviol <bold>1</bold> and its conjugate <bold>10</bold> exhibited high bacteriostatic activity selectively against Staphylococcus aureus ATCC 209p. Conjugates <bold>9</bold>-<bold>11</bold> inhibited growth of Mycobacterium tuberculosis H37Rv at the level of the antituberculosis drug pyrazinamide. Removal of the acetyl protection from conjugate <bold>9</bold> increased the antituberculosis activity by eight times. [ABSTRACT FROM AUTHOR]