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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

Hyuga Moriya, Sohei Tanaka, Yukari Iida, Satomi Kitagawa, Sen-Ichi Aizawa, Atsushi Taga, Hiroyuki Terashima, Atsushi Yamamoto, Shuji Kodama

Biomed Chromatogr. 2018 Oct;32(10):e4289.

PMID: 29768665

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP521482	Isoxanthohumol		521-48-2	Price

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