{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,23]],"date-time":"2026-04-23T23:48:48Z","timestamp":1776988128242,"version":"3.51.4"},"reference-count":37,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2012,9,19]],"date-time":"2012-09-19T00:00:00Z","timestamp":1348012800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Phytochemical Analysis"],"published-print":{"date-parts":[[2013,2]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:sec><jats:title>Introduction<\/jats:title><jats:p>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\u20102 (COX\u20102) inhibitory substances in <jats:italic>Plantago major<\/jats:italic> L. targeted in this investigation: \u03b1\u2010linolenic acid (\u03b1\u2010LNA) (18:3 \u03c9\u20103) and the triterpenic acids ursolic acid and oleanolic acid.<\/jats:p><\/jats:sec><jats:sec><jats:title>Objective<\/jats:title><jats:p>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.<\/jats:p><\/jats:sec><jats:sec><jats:title>Method<\/jats:title><jats:p>Extraction parameters were varied to optimise extracts\u02bc COX\u20102\/COX\u20101 inhibitory effect ratios. The crude extracts were purified initially using a solid phase extraction (SPE) clean\u2010up procedure and the target compounds were identified with GC\u2010MS, LC\u2010ESI\u2010MS and LC\u2010ESI\u2010MS<jats:sup>2<\/jats:sup> using GC\u2010FID for quantification.<\/jats:p><\/jats:sec><jats:sec><jats:title>Results<\/jats:title><jats:p>\u03b1\u2010LNA was preferentially extracted in dynamic mode using unmodified carbon dioxide at 40\u00b0C and 172\u2009bar, at a 0.04% (w\/w) yield with a COX\u20102\/COX\u20101 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 (\u03b1\u2010LNA) and a COX\u20102\/COX\u20101\u2010inhibitory effect ratio of 1.1 using 10% (v\/v) ethanol as polar modifier at 75\u00b0C and 483\u2009bar. The Soxhlet extracts had ursolic acid, oleanolic acid and \u03b1LNA yields up to 1.36%, 0.34% and 0.15%, respectively, with a COX\u20102\/COX\u20101 inhibitory effect ratio of 1.2.<\/jats:p><\/jats:sec><jats:sec><jats:title>Conclusion<\/jats:title><jats:p>The target substances can be extracted selectively by bioassay guided optimisation of SFE conditions. Copyright \u00a9 2012 John Wiley &amp; Sons, Ltd.<\/jats:p><\/jats:sec>","DOI":"10.1002\/pca.2398","type":"journal-article","created":{"date-parts":[[2012,9,19]],"date-time":"2012-09-19T02:31:57Z","timestamp":1348021917000},"page":"176-183","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Bioassay\u2010guided Supercritical Fluid Extraction of Cyclooxygenase\u20102 Inhibiting Substances in <i>Plantago major<\/i> L."],"prefix":"10.1002","volume":"24","author":[{"given":"\u00c5.","family":"Stenholm","sequence":"first","affiliation":[{"name":"High Throughput and Analysis, R&amp;D, GE Healthcare  Bj\u00f6rkgatan 30 S\u2010751 84 Uppsala Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"U.","family":"G\u00f6ransson","sequence":"additional","affiliation":[{"name":"Division of Pharmacognosy, Department of Medicinal Chemistry Uppsala University  Biomedical Centre, Box\u2009574 S\u2010751 23 Uppsala Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"L.","family":"Bohlin","sequence":"additional","affiliation":[{"name":"Division of Pharmacognosy, Department of Medicinal Chemistry Uppsala University  Biomedical Centre, Box\u2009574 S\u2010751 23 Uppsala Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,9,19]]},"reference":[{"key":"e_1_2_5_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf00039a023"},{"key":"e_1_2_5_3_1","first-page":"24","article-title":"Supercritical fluid extraction of avocado oil","volume":"27","author":"Botha BM","year":"2004","journal-title":"South African Grower's Assoc Yearb"},{"key":"e_1_2_5_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-59259-256-2"},{"key":"e_1_2_5_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pmr.2005.12.012"},{"key":"e_1_2_5_6_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02542527"},{"key":"e_1_2_5_7_1","doi-asserted-by":"crossref","first-page":"1259","DOI":"10.1021\/jf00053a025","article-title":"Optimization of supercritical fluid conditions for the rapid determination of free fatty acids in soy and cottonseed meals","volume":"43","author":"Fischer M","year":"1995","journal-title":"J Agric Food Chem"},{"key":"e_1_2_5_8_1","first-page":"1","article-title":"Application of supercritical fluids","volume":"35","author":"Fukushima Y","year":"2000","journal-title":"R&D Rev Toyota CRDL"},{"key":"e_1_2_5_9_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.162.3849.67"},{"key":"e_1_2_5_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/0021-9673(95)00877-2"},{"key":"e_1_2_5_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/pca.743"},{"key":"e_1_2_5_12_1","doi-asserted-by":"crossref","first-page":"272","DOI":"10.1201\/9781420006834","volume-title":"Hansen Solubility Parameters, A User's Handbook","author":"Hansen CM","year":"2007"},{"key":"e_1_2_5_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2009.12.019"},{"key":"e_1_2_5_14_1","first-page":"104","volume-title":"The Solubility of Nonelectrolytes","author":"Hildebrand J","year":"1950"},{"key":"e_1_2_5_15_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2005-864130"},{"key":"e_1_2_5_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/ie00093a014"},{"key":"e_1_2_5_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0023-6438(95)91398-X"},{"key":"e_1_2_5_18_1","doi-asserted-by":"publisher","DOI":"10.3989\/gya.2002.v53.i1.286"},{"key":"e_1_2_5_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(01)95740-1"},{"key":"e_1_2_5_20_1","unstructured":"K\u2010Tek Corporation.2011.Dielectric Constants Chart.http:\/\/www.asiinstr.com\/technical\/Dielectric%20Constants.htm(accessed February 2011)."},{"key":"e_1_2_5_21_1","first-page":"438","article-title":"Isolation of functional fatty acids in cosolvent induced SFE process","volume":"10","author":"Lee SB","year":"1999","journal-title":"J Korean Ind Eng Chem"},{"key":"e_1_2_5_22_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1745-7254.2005.00150.x"},{"key":"e_1_2_5_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2275(20)38553-9"},{"key":"e_1_2_5_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/0165-9936(96)88035-6"},{"key":"e_1_2_5_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/np970343j"},{"key":"e_1_2_5_26_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules14072573"},{"key":"e_1_2_5_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/np980088i"},{"key":"e_1_2_5_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/np000620d"},{"key":"e_1_2_5_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jbbm.2006.09.012"},{"key":"e_1_2_5_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-8741(00)00212-9"},{"key":"e_1_2_5_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/cjce.5450640225"},{"key":"e_1_2_5_32_1","doi-asserted-by":"publisher","DOI":"10.1365\/s10337-009-1439-7"},{"key":"e_1_2_5_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(01)01592-8"},{"key":"e_1_2_5_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-4347(99)00161-9"},{"key":"e_1_2_5_35_1","first-page":"196","volume-title":"Properties of Polymers","author":"Van Krevelen DW","year":"1990"},{"key":"e_1_2_5_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/bbpc.19961000816"},{"key":"e_1_2_5_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2006.05.027"},{"key":"e_1_2_5_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0165-9936(04)00524-2"}],"container-title":["Phytochemical Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fpca.2398","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fpca.2398","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/pca.2398","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,21]],"date-time":"2025-10-21T12:35:17Z","timestamp":1761050117000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/pca.2398"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,9,19]]},"references-count":37,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2013,2]]}},"alternative-id":["10.1002\/pca.2398"],"URL":"https:\/\/doi.org\/10.1002\/pca.2398","archive":["Portico"],"relation":{},"ISSN":["0958-0344","1099-1565"],"issn-type":[{"value":"0958-0344","type":"print"},{"value":"1099-1565","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,9,19]]},"assertion":[{"value":"2012-06-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2012-07-28","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2012-09-19","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}