Anti-MMP-2 Activity and Skin-Penetrating Capability of the Chemical Constituents from Rhodiola rosea.

Based on the significant inhibitory activity toward matrix metalloproteinase-2 and collagenase noticed in preliminary studies, crude extracts of Rhodiola rosea were partitioned and chromatographed sequentially to afford three new compounds, 1,2,3,6-tetra- O -galloyl-4- O - p -hydroxybenzoyl- β -D-glucopyranoside ( 1 ), ( E )-creoside I ( 2 ), and ( R,Z )-2-methylhept-2-ene-1,6-diol ( 3 ), along with twenty-four known compounds ( 4 – 27 ). Their structures were determined by spectroscopic data analyses. All isolated compounds were subjected to bioactivity assays. In these, 1 specifically inhibited matrix metalloproteinase-2 activity with an IC 50 value of 16.3 ± 1.6 µM, while its analogue 1,2,3,6-tetra- O -galloyl- β -D-glucopyranonoside ( 17 ) inhibited matrix metalloproteinase-2 with an IC 50 value of 23.0 ± 4.8 µM. In the collagenase activity assay, the inhibitory effects of 1 and 17 at concentrations of both 20 and 40 µM were more potent than those of the positive control, 1,10-phenanthroline. In order to realize whether 17 could penetrate from the epidermal layer into the basal and dermal layers of the human skin to inhibit the activity of matrix metalloproteinase-2 and collagenase or not, a transdermal penetration test in nude and white mice skins was performed. Penetration percentages of 17 quantified by LC-MS were 27.8 % and 74.8 % in 24 hours, respectively.