New Terpenoids from Chamaecyparis formosensis (Cupressaceae) Leaves with Modulatory Activity on Matrix Metalloproteases 2 and 9.

Chamaecyparis formosensis is Taiwan's most representative tree, and has high economic value. To date, only a few active chemical constituents have been reported for C. formosensis . In this study, 37 secondary metabolites, including three new compounds ( 1 - 3 ), were extracted from the leaves of C. formosensis . The compounds isolated from the ethyl acetate layer were used at different concentrations to treat HT-1080 human fibrosarcoma cells and to evaluate their effects on matrix metalloprotease 2 (MMP-2) and 9 (MMP-9) expression. Based on extensive analysis of data from high-resolution mass spectrometry (HR-MS) as well as nuclear magnetic resonance (NMR), infrared (IR), and ultraviolet (UV) spectroscopy, the new compounds were identified as 11,12-dihydroxyisodaucenoic acid ( 1 ), 12-hydroxyisodaucenoic acid ( 2 ), and 1-oxo-2α,3β-dihydroxytotarol ( 3 ). Known compounds 4 - 37 were identified by comparing their spectroscopic data with data reported in the literature. Biological activity tests by gelatin zymographic analysis revealed that seven compounds, including new compound 2 , have no cytotoxic effect on HT-1080 cells and were found to increase MMP-2 or MMP-9 expression by 1.25- to 1.59-fold at lower concentrations of 10-50 µM. These naturally derived regulatory compounds could potentially serve as a novel pharmaceutical basis for medical purposes.