Next Article in Journal
One-Step Preparation of Phenyl Boron-Modified Magnetic Mesoporous Silica for Selective Enrichment of cis-Diol-Containing Substances
Next Article in Special Issue
Multi-Target Anti-Alzheimer Activities of Four Prenylated Compounds from Psoralea Fructus
Previous Article in Journal
The Complete Chloroplast Genomes of Two Lancea Species with Comparative Analysis
Previous Article in Special Issue
Wedelolactone Enhances Osteoblastogenesis through ERK- and JNK-mediated BMP2 Expression and Smad/1/5/8 Phosphorylation
Article Menu
Issue 3 (March) cover image

Export Article

Open AccessArticle
Molecules 2018, 23(3), 604; https://doi.org/10.3390/molecules23030604

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

1
Graduate Institute of Pharmacognosy, Taipei Medical University, Taipei 11031, Taiwan
2
Department of Science Education, National Taipei University of Education, Taipei 10671, Taiwan
3
Department of Microbiology and Immunology, University of British Columbia, Vancouver, BC V6T1Z4, Canada
4
Graduate Institute of Medical Sciences, Taipei Medical University, Taipei 11031, Taiwan
5
Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 40402, Taiwan
6
Department of Biotechnology, Asia University, Taichung 41354, Taiwan
7
School of Pharmacy, Taipei Medical University, Taipei 11031, Taiwan
8
Ph.D. Program in Biotechnology Research and Development, College of Pharmacy, Taipei Medical University, Taipei 11031, Taiwan
Those authors contribute equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 6 February 2018 / Revised: 4 March 2018 / Accepted: 5 March 2018 / Published: 7 March 2018
(This article belongs to the Collection Bioactive Compounds)
Full-Text   |   PDF [557 KB, uploaded 7 March 2018]   |  

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 (13), 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 437 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. View Full-Text
Keywords: Cupressaceae; Chamaecyparis formosensis; terpenoids; MMP-2; MMP-9; HT-1080 Cupressaceae; Chamaecyparis formosensis; terpenoids; MMP-2; MMP-9; HT-1080
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
SciFeed

Share & Cite This Article

MDPI and ACS Style

Chang, M.-L.; Mei, H.-C.; Kuo, I.-C.; Hsiao, G.; Kuo, Y.-H.; Lee, C.-K. New Terpenoids from Chamaecyparis formosensis (Cupressaceae) Leaves with Modulatory Activity on Matrix Metalloproteases 2 and 9. Molecules 2018, 23, 604.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top