title: Cinnamomulactone, a new butyrolactone from the twigs of Cinnamomum cassia and its inhibitory activity of matrix metalloproteinases.
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 (3JHH) 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.
authors.affiliation: College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk, 38541, Republic of Korea.
authors.forename: Geum Jin
authors.initials: GJ
authors.lastname: Kim
authors.affiliation: Department of Pharmacology, School of Medicine, Kyungpook National University, Daegu, 41944, Republic of Korea.
authors.forename: Jong Yeong
authors.initials: JY
authors.lastname: Lee
authors.affiliation: Duksung IDC, Duksung Women's University, Seoul, 01369, Republic of Korea.
authors.forename: Hyun Gyu
authors.initials: HG
authors.lastname: Choi
authors.affiliation: College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk, 38541, Republic of Korea.
authors.forename: So Young
authors.initials: SY
authors.lastname: Kim
authors.affiliation: College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk, 38541, Republic of Korea.
authors.forename: Eonmi
authors.initials: E
authors.lastname: Kim
authors.affiliation: Duksung IDC, Duksung Women's University, Seoul, 01369, Republic of Korea.
authors.forename: Sang Hee
authors.initials: SH
authors.lastname: Shim
authors.affiliation: College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk, 38541, Republic of Korea.
authors.forename: Joo-Won
authors.initials: JW
authors.lastname: Nam
authors.affiliation: Department of Pharmacology, School of Medicine, Kyungpook National University, Daegu, 41944, Republic of Korea. shkim72@knu.ac.kr.
authors.forename: Sang-Hyun
authors.initials: SH
authors.lastname: Kim
authors.affiliation: College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk, 38541, Republic of Korea. h5choi@yu.ac.kr.
authors.forename: Hyukjae
authors.identifier: http://orcid.org/0000-0002-7707-4767
authors.initials: H
authors.lastname: Choi
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D001172:Arthritis, Rheumatoid / Q000201:enzymology; D002470:Cell Survival / Q000187:drug effects; D027424:Cinnamomum / Q000737:chemistry*; D003907:Dexamethasone / Q000494:pharmacology; D005347:Fibroblasts / Q000187:drug effects; D006801:Humans; D053583:Interleukin-1beta / Q000096:biosynthesis / Q000235:genetics; D020781:Matrix Metalloproteinase 1 / Q000096:biosynthesis / Q000235:genetics; D019278:Matrix Metalloproteinase 3 / Q000096:biosynthesis / Q000235:genetics; D061965:Matrix Metalloproteinase Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D018547:Plant Stems / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D014409:Tumor Necrosis Factor-alpha / Q000494:pharmacology
chemical_list: D053583:Interleukin-1beta; D061965:Matrix Metalloproteinase Inhibitors; D010936:Plant Extracts; D014409:Tumor Necrosis Factor-alpha; C000616636:cinnamomulactone; D003907:Dexamethasone; D019278:Matrix Metalloproteinase 3; D020781:Matrix Metalloproteinase 1; D015107:4-Butyrolactone
keywords: Butyrolactone; Cinnamomum cassia; Matrix metalloproteinases; Rheumatoid arthritis