A new matrix metalloproteinase-9 inhibitor 3,4-dihydroxycinnamic acid (caffeic acid) from methanol extract of Euonymus alatus: isolation and structure determination.
In a previous paper [Cha, B.Y., Park, C.J., Lee, D.G., Lee, Y.C., Kim, D.W., Kim, J.D., Seo, W.G., Moon, S.K., Kim, C.H., 2003. Inhibitory effect of methanol extract from Euonymus alatus on matrix metalloproteinase-9, J. Ethnopharm. 85, 163-167], methanol extracts prepared from stems of Euonymus alatus showed a strong inhibitory effect of matrix metalloproteinase (MMP)-9 activity, which is known to be involved in tumor cell invasion and metastasis, in a concentration-dependent manner on zymography. Assay guided fractionation led to the isolation of a caffeic acid (CA) as the compound responsible for the anti-MMP-9 activity. CA was finally obtained by reversed-phase HPLC, and its structure was elucidated by fast atom bombardment mass spectrometry and tandem mass spectrometry. The purified CA inhibited MMP-9 activity with the IC50 of 10-20 nM.
Park
Won-Hwan
WH
Department of Biochemistry, Molecular Biology and Diagnostics, Dongguk University, College of Oriental Medicine, Sukjang-Dong 707, Kyungju City, Kyungju, Kyungbuk 780-714, Republic of Korea.
Kim
Seog-Ha
SH
Kim
Cheorl-Ho
CH
D002109:Caffeic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006528:Carcinoma, Hepatocellular / Q000188:drug therapy / Q000201:enzymology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029756:Euonymus / Q000737:chemistry*; D006801:Humans; D008113:Liver Neoplasms / Q000188:drug therapy / Q000201:enzymology; D061965:Matrix Metalloproteinase Inhibitors; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment / Q000379:methods
D002109:Caffeic Acids; D004791:Enzyme Inhibitors; D061965:Matrix Metalloproteinase Inhibitors; D010936:Plant Extracts; C040048:caffeic acid