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10.3390/molecules23030604
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Article

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

by
Meng-Lun Chang
1,†,
Hui-Ching Mei
2,†,
I-Chih Kuo
3,
George Hsiao
4,
Yueh-Hsiung Kuo
5,6,* and
Ching-Kuo Lee
1,7,8,*
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
*
Authors to whom correspondence should be addressed.
†
Those authors contribute equally to this work.
Molecules 2018, 23(3), 604; https://doi.org/10.3390/molecules23030604
Submission received: 6 February 2018 / Revised: 4 March 2018 / Accepted: 5 March 2018 / Published: 7 March 2018
(This article belongs to the Collection Bioactive Compounds)
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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.
Keywords: Cupressaceae; Chamaecyparis formosensis; terpenoids; MMP-2; MMP-9; HT-1080 Cupressaceae; Chamaecyparis formosensis; terpenoids; MMP-2; MMP-9; HT-1080
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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. https://doi.org/10.3390/molecules23030604

AMA 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(3):604. https://doi.org/10.3390/molecules23030604

Chicago/Turabian Style

Chang, Meng-Lun, Hui-Ching Mei, I-Chih Kuo, George Hsiao, Yueh-Hsiung Kuo, and Ching-Kuo Lee. 2018. "New Terpenoids from Chamaecyparis formosensis (Cupressaceae) Leaves with Modulatory Activity on Matrix Metalloproteases 2 and 9" Molecules 23, no. 3: 604. https://doi.org/10.3390/molecules23030604

APA Style

Chang, M.-L., Mei, H.-C., Kuo, I.-C., Hsiao, G., Kuo, Y.-H., & Lee, C.-K. (2018). New Terpenoids from Chamaecyparis formosensis (Cupressaceae) Leaves with Modulatory Activity on Matrix Metalloproteases 2 and 9. Molecules, 23(3), 604. https://doi.org/10.3390/molecules23030604

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