ABSTRACT
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,3ß-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.
Subject(s)
Chamaecyparis/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Leaves/chemistry , Terpenes/chemistry , Terpenes/pharmacology , Cell Line , Enzyme Activation , Gene Expression Regulation/drug effects , Humans , Magnetic Resonance Spectroscopy , Matrix Metalloproteinase 2/genetics , Matrix Metalloproteinase 2/metabolism , Matrix Metalloproteinase 9/genetics , Matrix Metalloproteinase 9/metabolism , Molecular Structure , Plant Extracts/isolation & purification , Terpenes/isolation & purificationABSTRACT
Two new abietane type diterpenoids, namely seco-helioscopinolide (1) and 3b,7b-dihydroxy-ent-abieta-8,13-diene-12,16-olide (2) were isolated from the aerial parts of Euphorbia formosana Hayata together with helioscopinolide A (3), helioscopinolide B (4), helioscopinolide C (5) and ent-(5b,8a,9b,10a,12a)-12-hydroxyatis-16-ene-3,14-dione (6). The structures of compounds 1-6 were elucidated by analyzing their spectroscopic data and comparison with the literature. Further biological tests by gelatin zymographic analysis revealed that 3-5 significantly up-regulated the expressions and activation of MMP-2 and -9 in human fibrosarcoma cell line HT1080.
