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Bioassay-guided Supercritical Fluid Extraction of Cyclooxygenase-2 Inhibiting Substances in Plantago major L.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
2013 (English)In: Phytochemical Analysis, ISSN 0958-0344, E-ISSN 1099-1565, Vol. 24, no 2, 176-183 p.Article in journal (Refereed) Published
Abstract [en]

Introduction - Selective extraction of plant materials is advantageous for obtaining extracts enriched with desired constituents, thereby reducing the need for subsequent chromatography purification. Such compounds include three cyclooxygenase-2 (COX-2) inhibitory substances in Plantago major L. targeted in this investigation: alpha-linolenic acid (alpha-LNA) (18:3 omega-3) and the triterpenic acids ursolic acid and oleanolic acid. Objective - To investigate the scope for tuning the selectivity of supercritical fluid extraction (SFE) using bioassay guidance, and Soxhlet extraction with dichloromethane as solvent as a reference technique, to optimise yields of these substances. Method - Extraction parameters were varied to optimise extracts' COX-2/COX-1 inhibitory effect ratios. The crude extracts were purified initially using a solid phase extraction (SPE) clean-up procedure and the target compounds were identified with GC-MS, LC-ESI-MS and LC-ESI-MS2 using GC-FID for quantification. Results - alpha-LNA was preferentially extracted in dynamic mode using unmodified carbon dioxide at 40 degrees C and 172 bar, at a 0.04% (w/w) yield with a COX-2/COX-1 inhibitory effect ratio of 1.5. Ursolic and oleanolic acids were dynamically extracted at 0.25% and 0.06% yields, respectively, with no traces of (alpha-LNA) and a COX-2/COX-1-inhibitory effect ratio of 1.1 using 10% (v/v) ethanol as polar modifier at 75 degrees C and 483 bar. The Soxhlet extracts had ursolic acid, oleanolic acid and alpha LNA yields up to 1.36%, 0.34% and 0.15%, respectively, with a COX-2/COX-1 inhibitory effect ratio of 1.2. Conclusion - The target substances can be extracted selectively by bioassay guided optimisation of SFE conditions.

Place, publisher, year, edition, pages
2013. Vol. 24, no 2, 176-183 p.
Keyword [en]
In vitro enzyme assay, Soxhlet, supercritical fluid extraction (SFE), cyclooxygenase-2, Plantago major L.
National Category
Medical and Health Sciences
Identifiers
URN: urn:nbn:se:uu:diva-200457DOI: 10.1002/pca.2398ISI: 000318002600012OAI: oai:DiVA.org:uu-200457DiVA: diva2:623756
Available from: 2013-05-28 Created: 2013-05-28 Last updated: 2017-12-06Bibliographically approved

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Göransson, UlfBohlin, Lars

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