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Planta Med 2016; 82(08): 698-704
DOI: 10.1055/s-0042-101033
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

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

Tzong-Huei Lee
1   Institute of Fisheries Science, National Taiwan University, Taipei, Taiwan
,
Chieh-Chih Hsu
2   Graduate Institute of Pharmacognosy, Taipei Medical University, Taipei, Taiwan
,
George Hsiao
3   Graduate Institute of Medical Science and Department of Pharmacology, College of Medicine, Taipei Medical University, Taipei, Taiwan
,
Jia-You Fang
4   Research Center for Industry of Human Ecology, Chang Gung University of Science and Technology, Kweishan, Taoyuan, Taiwan
5   Pharmaceutics Laboratory, Graduate Institute of Natural Products, Chang Gung University, Kweishan, Taoyuan, Taiwan
,
Wei-Min Liu
6   Department of Obstetrics and Gynecology, Taipei Medical University Hospital, Taipei, Taiwan
,
Ching-Kuo Lee
2   Graduate Institute of Pharmacognosy, Taipei Medical University, Taipei, Taiwan
7   School of Pharmacy, Taipei Medical University, Taipei, Taiwan
› Author Affiliations
Further Information

Publication History

received 16 October 2015
revised 30 November 2015

accepted 28 December 2015

Publication Date:
22 March 2016 (online)

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Abstract

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 IC50 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 IC50 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.

Key words

Rhodiola rosea - Crassulaceae - matrix metalloproteinase - collagenase - 1,2,3,6-tetra-O-galloyl-4-O-p-hydroxybenzoyl-β-D-glucopyranoside - (E)-creoside I - (Z)-2-methyl-2-hepten-1,6-diol

Supporting Information

 

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