New terpenoids from Chamaecyparis formosensis (Cupressaceae) leaves with modulatory activity on matrix metalloproteases 2 and 9

Meng Lun Chang, Hui Ching Mei, I. Chih Kuo, George Hsiao, Yueh Hsiung Kuo, Ching Kuo Lee

Research output: Contribution to journalArticlepeer-review

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,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.

Original languageEnglish
Article number604
JournalMolecules
Volume23
Issue number3
DOIs
Publication statusPublished - Mar 7 2018

Keywords

  • Chamaecyparis formosensis
  • Cupressaceae
  • HT-1080
  • MMP-2
  • MMP-9
  • Terpenoids
  • Cell Line
  • Magnetic Resonance Spectroscopy
  • Humans
  • Terpenes/chemistry
  • Matrix Metalloproteinase 2/genetics
  • Chamaecyparis/chemistry
  • Plant Leaves/chemistry
  • Matrix Metalloproteinase 9/genetics
  • Molecular Structure
  • Enzyme Activation
  • Plant Extracts/chemistry
  • Gene Expression Regulation/drug effects

ASJC Scopus subject areas

  • Organic Chemistry

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