Chiral separation of isoxanthohumol and 8-prenylnaringenin in beer, hop pellets and hops by HPLC with chiral columns
Chiral separation of isoxanthohumol and 8-prenylnaringenin in beer, hop pellets and hops by HPLC with chiral columns
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使用 HPLC 手性柱手性分离啤酒、啤酒花颗粒和啤酒花中的异黄腐酚和 8-异戊二烯柚皮素
DOI：
10.1002/bmc.4289
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发表时间：
2018
影响因子：
1.8
通讯作者：
Kodama Shuji
中科院分区：
文献类型：
--
作者：
Moriya Hyuga;Tanaka Sohei;Iida Yukari;Kitagawa Satomi;Aizawa Sen-ichi;Taga Atsushi;Terashima Hiroyuki;Yamamoto Atsushi;Kodama Shuji
使用InertSustain苯基色谱柱和含有40%甲醇和12%异丙醇的移动的流动相，通过HPLC分析啤酒、啤酒花和啤酒花颗粒样品中的黄腐酚、异黄腐酚和8-异戊二烯基柚皮素。分别收集通过上述HPLC获得的异黄腐酚和8-异戊二烯基柚皮素的级分。异黄腐酚和8-异戊烯基柚皮素通过HPLC进行对映体分离，分别使用Chiralcel OD-H柱（移动的流动相由己烷-乙醇（90：10，v/v）组成）和Chiralpak AD-RH柱（移动的流动相由甲醇-2-丙醇-水（40：20：40，v/v/v）组成）。发现来自啤酒、啤酒花和啤酒花颗粒样品的异黄腐酚和8-异戊二烯基柚皮素存在于外消旋混合物中。这可以解释为这两种分析物是由非酶促过程产生的。研究了沸腾条件对黄腐酚转化为异黄腐酚的影响。加热溶剂中较高浓度的乙醇导致转化率降低，并且通过添加>50%（v/v）的乙醇来停止转化。异构化受pH（2 - 10）的显著影响，pH 5的沸腾介质对转化率影响最小。因此，在煮沸过程中，黄腐酚在麦芽汁（pH 5 - 5.5）中相对难以转化为异黄腐酚。
Xanthohumol, isoxanthohumol, and 8‐prenylnaringenin 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‐propanol. Fractions of isoxanthohumol and 8‐prenylnaringenin obtained by the above HPLC were separately collected. Isoxanthohumol and 8‐prenylnaringenin were enantioseparated by HPLC using a Chiralcel OD‐H column with a mobile phase composed of hexane–ethanol (90:10,v/v) and a Chiralpak AD‐RH column with a mobile phase composed of methanol–2‐propanol–water (40:20:40,v/v/v), respectively. Isoxanthohumol and 8‐prenylnaringenin 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 >50% (v/v). The isomerization was significantly affected pH (2−10) and the boiling medium at pH 5 was minimum for the conversion. Therefore, it was suggested that xanthohumol was relatively difficult to convert to isoxanthohumol in wort (pH 5−5.5) during boiling.