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

研究成果: 雜誌貢獻文章

摘要

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.
原文英語
文章編號604
期刊Molecules
23
發行號3
DOIs
出版狀態已發佈 - 三月 7 2018

指紋

Chamaecyparis
Cupressaceae
Terpenes
Metalloproteases
leaves
acids
Acids
Fibrosarcoma
metabolites
ultraviolet spectroscopy
gelatins
magnetic resonance spectroscopy
Taiwan
Gelatin
matrices
Metabolites
activity (biology)
Bioactivity
Ultraviolet spectroscopy
cells

Keywords

  • Chamaecyparis formosensis
  • Cupressaceae
  • HT-1080
  • MMP-2
  • MMP-9
  • Terpenoids

ASJC Scopus subject areas

  • Organic Chemistry

引用此文

New terpenoids from Chamaecyparis formosensis (Cupressaceae) leaves with modulatory activity on matrix metalloproteases 2 and 9. / Chang, Meng Lun; Mei, Hui Ching; Kuo, I. Chih; Hsiao, George; Kuo, Yueh Hsiung; Lee, Ching Kuo.

於: Molecules, 卷 23, 編號 3, 604, 07.03.2018.

研究成果: 雜誌貢獻文章

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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.",
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AU - Chang, Meng Lun

AU - Mei, Hui Ching

AU - Kuo, I. Chih

AU - Hsiao, George

AU - Kuo, Yueh Hsiung

AU - Lee, Ching Kuo

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N2 - 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.

AB - 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.

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