Matrix metalloproteinase-1 inhibitor from the stem bark of Styrax japonica S. et Z.
A bioassay-guided fractionation of the ethyl acetate soluble fraction from the stem bark of Styrax japonica S. et Z. (Styracaceae) yielded two new lignan compounds, styraxjaponoside A (1) and styraxjaponoside B (2), along with three known compounds, matairesinoside (3), egonol glucoside (4), and dihydrodehydrodiconiferyl alcohol 9'-O-glucoside (5). The structures of compounds 1-5 were determined by spectroscopic method, as well as 1D- and 2D-NMR (HSQC, 1H-1H COSY, and HMBC) spectroscopy. Among them, compound 2 exhibited potent inhibitory activity against matrix metalloproteinase (MMP)-1, and prevented the UV-induced changes in the MMP-1 expression. In addition, compounds 3 and 5 were isolated from this plant for the first time.
Kim
Mi-Ran
MR
Research Center for Proteineous Materials, Chosun University, Gwangju, Korea.
Moon
Hyung-In
HI
Chung
Jin Ho
JH
Moon
Young Hee
YH
Hahm
Kyung-Soo
KS
Woo
Eun-Rhan
ER
D015153:Blotting, Western; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects / Q000528:radiation effects; D002478:Cells, Cultured; D002855:Chromatography, Thin Layer; D004354:Drug Screening Assays, Antitumor; D005347:Fibroblasts / Q000187:drug effects; D006801:Humans; D006868:Hydrolysis; D017705:Lignans / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D061965:Matrix Metalloproteinase Inhibitors; D024301:Plant Bark / Q000737:chemistry; D011347:Procollagen / Q000737:chemistry; D011480:Protease Inhibitors / Q000737:chemistry* / Q000302:isolation & purification; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet; D032362:Styrax / Q000737:chemistry*; D014466:Ultraviolet Rays
D017705:Lignans; D061965:Matrix Metalloproteinase Inhibitors; D011347:Procollagen; D011480:Protease Inhibitors; C499866:styraxjaponoside A; C499868:styraxjaponoside B