Chemistry and biology of hop flavonoids

The flavonoids of hops include flavonol glycosides, condensed tannins, and prenylflavonoids. The first two flavonoid classes are located intracellularly, while the prenylflavonoids are secreted along with bitter acids and essential oils by the lupulin glands of the inflorescences. The chemistry and biological activities of prenylflavonoids isolated from the lupulin fraction are reviewed. An LC-MS method was developed for quantitation of these phenolics in hops, hop-derived products, and beer. The fate of xanthohumol and related prenylflavonoids during the brewing process was investigated by LC-MS. The partial carryover of the prenylflavonoids from hops into beer was attributed mainly to incomplete extraction and adsorption to insoluble proteins and yeast. Moreover, the prenylchalcone-type flavonoids were largely converted into isomeric prenylflavanones during wort boiling. The biological activities of some of the prenylflavonoids isolated were examined using in vitro techniques. Some of the prenylflavonoi...

[1]  F. B. Power,et al.  CXXXV.—The constituents of hops , 1913 .

[2]  H. Hübner,et al.  Zur Konstitution des Xanthohumols , 1960 .

[3]  Konstitution und Synthese des Tetrahydro‐xanthohumols , 1963 .

[4]  P. Bhandari IDENTIFICATION OF FLAVONOIDS IN HOPS (HUMULUS LUPULUS LINNE) BY THIN-LAYER CHROMATOGRAPHY. , 1964, Journal of chromatography.

[5]  T. Mabry,et al.  Reagents and Procedures for the Ultraviolet Spectral Analysis of Flavonoids , 1970 .

[6]  T. Tomimori,et al.  [Studies on the constituents of Sophora species. IV. Constituents of the root of Sophora angustifolia Sieb. et Zucc]. , 1970, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.

[7]  J. Kuhnau The flavonoids. A class of semi-essential food components: their role in human nutrition. , 1976 .

[8]  J. P. Brown,et al.  A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds. , 1980, Mutation research.

[9]  I. Mcmurrough High-performance liquid chromatography of flavonoids in barley and hops , 1981 .

[10]  J. Schulz,et al.  Desmethylxanthohumol: Isolierung aus Hopfen und Cyclisierung zu Flavanonen , 1988 .

[11]  Satoru Watanabe,et al.  Chalcones from Humulus lupulus , 1989 .

[12]  K. R. Markham,et al.  Malonylated flavone 5-O-glucosides in the barren sprouts of Equisetum arvense , 1990 .

[13]  M. Takayama,et al.  Mass Spectrometry of Prenylated Flavonoids , 1992 .

[14]  R J Miksicek,et al.  Commonly occurring plant flavonoids have estrogenic activity. , 1993, Molecular pharmacology.

[15]  R. Verpoorte,et al.  Formation of aromatic intermediates in the biosynthesis of bitter acids in Humulus lupulus , 1995 .

[16]  M. Deinzer,et al.  HPLC-ion spray-tandem mass spectrometry of flavonol glycosides in hops , 1996 .

[17]  D. Barron,et al.  Isoprenylated flavonoids—a survey , 1996 .

[18]  Xanthohumols, diacylglycerol acyltransferase inhibitors, from Humulus lupulus. , 1997, Phytochemistry.

[19]  H. Tobe,et al.  Bone resorption inhibitors from hop extract. , 1997, Bioscience, biotechnology, and biochemistry.

[20]  J. F. Stevens,et al.  Prenylflavonoids from Humulus lupulus , 1997 .