Phosphodiesterase and Thymidine Phosphorylase-Inhibiting Salirepin Derivatives from Symplocos racemosa

Abstract

A re-investigation of the chemical constituents of the stem bark of Symplocos racemosa Roxb. led to the isolation of four new glycosides, symplocomoside (1), symponoside (2), symplososide (3) and symploveroside (4). Benzoylsalireposide (5) and salireposide (6) were re-isolated from this plant. The structures of the new compounds were determined by 1D and 2D-homonuclear and heteronuclear NMR spectroscopy, chemical evidence, and by comparison with the published data of the closely related compounds. The glycosides 1 - 4 displayed in vitro inhibitory activity against phosphodiesterase I with IC₅₀ values of 122 ± 0.017, 698 ± 0.06, 722 ± 0.03, 909 ± 0.09 μM, respectively. The compounds 1 - 6 also showed in vitro inhibitory activity against thymidine phosphorylase with IC₅₀ values of 189.96 ± 1.02, 195.56 ± 2.36, 207.61 ± 1.06, 488.89 ± 4.10, 427.20 ± 5.36, 354.2 ± 5.69 μM, respectively while 1 was also found to be a urease inhibitor with an IC₅₀ value of 54.13 ± 0.71 μM.

Key words

Symplocos racemosa - Symplocaceae - salirepin derivatives - phosphodiesterase I - thymidine phosphorylase - urease

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