TitleXanthohumol and related prenylflavonoids from hops and beer: to your good health!
Publication TypeJournal Article
Year of Publication2004
AuthorsStevens JF, Page JE
JournalPhytochemistry
Volume65
Issue10
Pagination1317-30
Date Published2004 May
ISSN0031-9422
KeywordsAnticarcinogenic Agents, Beer, Flavonoids, Humans, Humulus, Isoflavones, Phytoestrogens, Phytotherapy, Plant Preparations, Propiophenones
Abstract

Xanthohumol (3'-[3,3-dimethyl allyl]-2',4',4-trihydroxy-6'-methoxychalcone) is the principal prenylated flavonoid of the female inflorescences of the hop plant ('hops'), an ingredient of beer. Human exposure to xanthohumol and related prenylflavonoids, such as 8-prenylnaringenin and isoxanthohumol, is primarily through beer consumption. Xanthohumol has been characterized a 'broad-spectrum' cancer chemopreventive agent in in vitro studies, while 8-prenylnaringenin enjoys fame as the most potent phytoestrogen known to date. These biological activities suggest that prenylflavonoids from hops have potential for application in cancer prevention programs and in prevention or treatment of (post-)menopausal 'hot flashes' and osteoporosis. Xanthohumol and 8-prenylnaringenin are metabolized into many flavonoid derivatives with modified 3,3-dimethyl allyl (prenyl) moieties. Xanthohumol is formed in lupulin glands by a specialized branch of flavonoid biosynthesis that involves prenylation and O-methylation of the polyketide intermediate chalconaringenin. Although a lupulin gland-specific chalcone synthase is known, the aromatic prenyltransferase and O-methyltransferase participating in xanthohumol have not been identified. The prenylflavonoid pathway is a possible target for breeding or biotechnological modification of hops with the aim of increasing xanthohumol levels for beer brewing and 8-prenylnaringenin levels for pharmaceutical production.

DOI10.1016/j.phytochem.2004.04.025
Alternate JournalPhytochemistry
PubMed ID15231405