{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,6]],"date-time":"2026-03-06T21:30:40Z","timestamp":1772832640221,"version":"3.50.1"},"reference-count":37,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2018,6,11]],"date-time":"2018-06-11T00:00:00Z","timestamp":1528675200000},"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":["Biomedical Chromatography"],"published-print":{"date-parts":[[2018,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Xanthohumol, isoxanthohumol, and 8\u2010prenylnaringenin in beer, hop and hop pellet samples were analyzed by HPLC using an InertSustain phenyl column and the mobile phase containing 40% methanol and 12% 2\u2010propanol. Fractions of isoxanthohumol and 8\u2010prenylnaringenin obtained by the above HPLC were separately collected. Isoxanthohumol and 8\u2010prenylnaringenin were enantioseparated by HPLC using a Chiralcel OD\u2010H column with a mobile phase composed of hexane\u2013ethanol (90:10, <jats:italic>v<\/jats:italic>\/v) and a Chiralpak AD\u2010RH column with a mobile phase composed of methanol\u20132\u2010propanol\u2013water (40:20:40, <jats:italic>v<\/jats:italic>\/v\/v), respectively. Isoxanthohumol and 8\u2010prenylnaringenin from beer, hop and hop pellet samples were found to be present in a racemic mixture. This can be explained by the fact that the two analytes were produced by a nonenzymatic process. The effects of boiling conditions on the conversion of xanthohumol into isoxanthohumol were also studied. A higher concentration of ethanol in heating solvent resulted in a decrease in the conversion ratio and the conversion was stopped by addition of ethanol at &gt;50% (<jats:italic>v<\/jats:italic>\/v). The isomerization was significantly affected pH (2\u221210) and the boiling medium at pH\u20095 was minimum for the conversion. Therefore, it was suggested that xanthohumol was relatively difficult to convert to isoxanthohumol in wort (pH 5\u22125.5) during boiling.<\/jats:p>","DOI":"10.1002\/bmc.4289","type":"journal-article","created":{"date-parts":[[2018,5,16]],"date-time":"2018-05-16T15:17:00Z","timestamp":1526483820000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Chiral separation of isoxanthohumol and 8\u2010prenylnaringenin in beer, hop pellets and hops by HPLC with chiral columns"],"prefix":"10.1002","volume":"32","author":[{"given":"Hyuga","family":"Moriya","sequence":"first","affiliation":[{"name":"School of Science Tokai University  Hiratsuka Kanagawa Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sohei","family":"Tanaka","sequence":"additional","affiliation":[{"name":"School of Science Tokai University  Hiratsuka Kanagawa Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yukari","family":"Iida","sequence":"additional","affiliation":[{"name":"School of Science Tokai University  Hiratsuka Kanagawa Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Satomi","family":"Kitagawa","sequence":"additional","affiliation":[{"name":"School of Science Tokai University  Hiratsuka Kanagawa Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8222-9842","authenticated-orcid":false,"given":"Sen\u2010ichi","family":"Aizawa","sequence":"additional","affiliation":[{"name":"Graduate School of Science and Engineering University of Toyama  Toyama Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Atsushi","family":"Taga","sequence":"additional","affiliation":[{"name":"School of Pharmacy Kinki University  Higashi\u2013Osaka Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroyuki","family":"Terashima","sequence":"additional","affiliation":[{"name":"GL Sciences Inc., Shinjuku\u2010ku  Tokyo Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Atsushi","family":"Yamamoto","sequence":"additional","affiliation":[{"name":"Department of Biological Chemistry, College of Bioscience and Biotechnology Chubu University  Kasugai\u2010shi Aichi Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2883-0340","authenticated-orcid":false,"given":"Shuji","family":"Kodama","sequence":"additional","affiliation":[{"name":"School of Science Tokai University  Hiratsuka Kanagawa Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,6,11]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/j.2050-0416.1965.tb02078.x"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12161-010-9186-9"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbrc.2004.10.032"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsbmb.2004.03.118"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1111\/jdv.12204"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1080\/0265203021000014789"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0278-6915(01)00081-3"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.talanta.2010.09.041"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.6b03933"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejca.2005.04.012"},{"key":"e_1_2_6_12_1","first-page":"959","article-title":"Cancer chemopreventive activity of xanthohumol, a natural product derived from hop","volume":"1","author":"Gerhauser C.","year":"2002","journal-title":"Molecular Cancer Therapeutics"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1124\/dmd.105.008250"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2013.04.032"},{"key":"e_1_2_6_15_1","first-page":"185","article-title":"Enantioseparation of 8\u2010prenylnaringenin, a phytoestrogen, by hydroxyl\u2010\u03b3\u2010cyclodextrin\u2010modified micellar electrokinetic chromatography","volume":"31","author":"Kodama S.","year":"2008","journal-title":"Annual Report of Toyama Institute of Health"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf0710478"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/bmc.3177"},{"key":"e_1_2_6_18_1","first-page":"182","article-title":"Stereospecific quantitation of 6\u2010prenylnaringenin in commercially available H. lupulus\u2010containing natural health products and dietary supplements","volume":"10","author":"Martinez S. 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