Freischmidt, A. and Juergenliemk, G. and Kraus, B. and Okpanyi, S. N. and Mueller, J. and Kelber, O. and Weiser, D. and Heilmann, J. (2012) Contribution of flavonoids and catechol to the reduction of ICAM-1 expression in endothelial cells by a standardised Willow bark extract. PHYTOMEDICINE, 19 (3-4). pp. 245-252. ISSN 0944-7113,
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Introduction: A quantified aqueous Willow bark extract (STW 33-1) was tested concerning its inhibitory activity on TNF-alpha induced ICAM-1 expression in human microvascular endothelial cells (HMEC-1) and further fractionated to isolate the active compounds. Results: At 50 mu g/ml the extract, which had been prepared from Salix purpurea L, decreased ICAM-1 expression to 40% compared to control cells without showing cytotoxic effects. Further liquid-liquid partition revealed an ethyl acetate phase with potent reduction of ICAM-1 expression to 40% at 8 mu g/ml. This fraction was comprehensively characterised by the isolation of flavanone aglyca and their corresponding glycosides, chalcone glycosides, salicin derivatives, cyclohexane-1,2-diol glycosides, catechol and trans-p-coumaric acid. All compounds were investigated for their activity on TNF-alpha induced ICAM-1 expression. The flavonoid and chalcone glycosides were not active up to 50 mu M, whereas catechol and eriodictyol at the same concentration showed a significant reduction of ICAM-1 expression to 50% of control. Interestingly, other isolated flavanone aglyca like taxifolin, dihydrokaempferol and naringenin showed only weak or moderate inhibitory activity. Eriodictyol was a minor compound in the extract, whereas the catechol content in the extract (without excipients) reached 2.3%, determined by HPLC. One of the isolated cyclohexan-1,2-diol glucosides, 6'-O-4-hydroxybenzoyl-grandidentin, is a new natural compound. Conclusion: As catechol is quantitatively important in Willow bark extracts it can be concluded from the in vitro data that not only flavonoids and salicin derivatives, but also catechol can probably contribute to the anti-inflammatory activity of Willow bark extracts. (C) 2011 Elsevier GmbH. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | NECROSIS-FACTOR-ALPHA; LIQUID-CHROMATOGRAPHY; ADHESION MOLECULES; PHENOLIC-COMPOUNDS; C-13 NMR; ELECTROPHORESIS; SALICYLATES; ENANTIOMERS; INHIBITION; SEPARATION; Salix purpurea; Salicaceae; Willow bark extract; ICAM-1; Catechol; Flavonoids |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 19 May 2020 09:08 |
| Last Modified: | 19 May 2020 09:08 |
| URI: | https://pred.uni-regensburg.de/id/eprint/19227 |
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