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Cinnamomulactone, a new butyrolactone from the twigs of Cinnamomum cassia and its inhibitory activity of matrix metalloproteinases

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Abstract

Cinnamomum cassia (Lauraceae) has long been used as one of the most frequently used traditional oriental medicines for the treatment of gastritis, diabetes, blood circulation disturbance and inflammatory diseases. Cinnamomulactone (1), a new butyrolactone was isolated from the twigs of C. cassia together with nine known compounds, coumarin (2), trans-cinnamic acid (3), cinnamaldehyde (4), 2-hydroxycinnamaldehyde (5), 2-methoxycinnamaldehyde (6), 2-hydroxy-cinnamyl alcohol (7), benzoic acid (8), (+)-syringaresinol (9) and phenethyl (E)-3-[4-methoxyphenyl]-2-propenoate (10). The planar structure of 1 was elucidated on the basis of spectroscopic data analysis and its configurations were determined by coupling constant (3 J HH) analysis and a comparison with specific rotation data of related compounds on the literatures. The structures of known compounds were confirmed by the comparison of their spectroscopic data to the reported values. Compound 10 was isolated for the first time from this plant. Compounds 1, 2, 4, and 9 showed inhibitory activity against matrix metalloproteinases (MMPs) gene expression. Among them, compound 1 has been revealed to suppress the gene expression of MMP-3 and interleukin (IL)-1β as well as MMP-1 in tumor necrosis factor (TNF)-α stimulated rheumatoid arthritis synovial fibroblasts.

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Acknowledgements

This work was supported by the 2015 Yeungnam University Research Grant.

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    Authors and Affiliations

    1. College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk, 38541, Republic of Korea

      Geum Jin Kim, So Young Kim, Eonmi Kim, Joo-Won Nam & Hyukjae Choi

    2. Department of Pharmacology, School of Medicine, Kyungpook National University, Daegu, 41944, Republic of Korea

      Jong Yeong Lee & Sang-Hyun Kim

    3. Duksung IDC, Duksung Women’s University, Seoul, 01369, Republic of Korea

      Hyun Gyu Choi & Sang Hee Shim

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    1. Geum Jin Kim
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    2. Jong Yeong Lee
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    Correspondence to Sang-Hyun Kim or Hyukjae Choi.

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    Geum Jin Kim and Jong Yeong Lee have contributed equally to this work.

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    Kim, G.J., Lee, J.Y., Choi, H.G. et al. Cinnamomulactone, a new butyrolactone from the twigs of Cinnamomum cassia and its inhibitory activity of matrix metalloproteinases. Arch. Pharm. Res. 40, 304–310 (2017). https://doi.org/10.1007/s12272-016-0877-7

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