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.

Original languageEnglish
Pages (from-to)698-704
JournalPlanta Medica
Volume82
Issue number8
DOIs
Publication statusPublished - May 1 2016

Fingerprint

Rhodiola
Matrix Metalloproteinase 2
Matrix Metalloproteinases
Skin
Collagenases
Inhibitory Concentration 50
Assays
Bioactivity
Complex Mixtures
Nude Mice

Keywords

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

ASJC Scopus subject areas

  • Drug Discovery
  • Pharmacology
  • Pharmaceutical Science
  • Analytical Chemistry
  • Organic Chemistry
  • Molecular Medicine
  • Complementary and alternative medicine

Cite this

Anti-MMP-2 Activity and Skin-Penetrating Capability of the Chemical Constituents from Rhodiola rosea. / Lee, Tzong-Huei; Hsu, Chieh Chih; Hsiao, George; Fang, Jia You; Liu, Wei Min; Lee, Ching Kuo.

In: Planta Medica, Vol. 82, No. 8, 01.05.2016, p. 698-704.

Research output: Contribution to journalArticle

@article{603cf29a09ce4476a64bd6497658cde8,
title = "Anti-MMP-2 Activity and Skin-Penetrating Capability of the Chemical Constituents from Rhodiola rosea",
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.",
keywords = "(E)-creoside I, (Z)-2-methyl-2-hepten-1,6-diol, 1,2,3,6-tetra-O-galloyl-4-O-p-hydroxybenzoyl-β-D-glucopyranoside, collagenase, Crassulaceae, matrix metalloproteinase, Rhodiola rosea",
author = "Tzong-Huei Lee and Hsu, {Chieh Chih} and George Hsiao and Fang, {Jia You} and Liu, {Wei Min} and Lee, {Ching Kuo}",
year = "2016",
month = "5",
day = "1",
doi = "10.1055/s-0042-101033",
language = "English",
volume = "82",
pages = "698--704",
journal = "Planta Medica",
issn = "0032-0943",
publisher = "Georg Thieme Verlag",
number = "8",

}

TY - JOUR

T1 - Anti-MMP-2 Activity and Skin-Penetrating Capability of the Chemical Constituents from Rhodiola rosea

AU - Lee, Tzong-Huei

AU - Hsu, Chieh Chih

AU - Hsiao, George

AU - Fang, Jia You

AU - Liu, Wei Min

AU - Lee, Ching Kuo

PY - 2016/5/1

Y1 - 2016/5/1

N2 - 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.

AB - 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.

KW - (E)-creoside I

KW - (Z)-2-methyl-2-hepten-1,6-diol

KW - 1,2,3,6-tetra-O-galloyl-4-O-p-hydroxybenzoyl-β-D-glucopyranoside

KW - collagenase

KW - Crassulaceae

KW - matrix metalloproteinase

KW - Rhodiola rosea

UR - http://www.scopus.com/inward/record.url?scp=84961644850&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84961644850&partnerID=8YFLogxK

U2 - 10.1055/s-0042-101033

DO - 10.1055/s-0042-101033

M3 - Article

C2 - 27002396

AN - SCOPUS:84961644850

VL - 82

SP - 698

EP - 704

JO - Planta Medica

JF - Planta Medica

SN - 0032-0943

IS - 8

ER -