Search resultsXanthohumol and related prenylflavonoids from hops and beer: To your good health!
Title
Xanthohumol and related prenylflavonoids from hops and beer: To your good health!
Publication type
Journal Article
Year of Publication
2004
Authors
Journal
Phytochemistry
Volume
65
Issue
10
Pagination
1317 - 1330
Date published
2004
ISBN
00319422 (ISSN)
Keywords
8 prenylnaringenin, 8-Prenylnaringenin, Anticarcinogenic Agents, antineoplastic agent, antioxidant, antioxidant activity, beer, biotechnological production, breast augmentation, Breast enhancement, breeding, brewing, cancer, Cancer chemoprevention, chalcone synthase, chemical modification, chemical structure, chemoprophylaxis, dietary intake, dimethylallyltransferase, drug activity, drug manufacture, drug synthesis, estrogen activity, flavonoid, Flavonoids, health care, Hops, hot flush, human, Humans, humulon, Humulus, Humulus lupulus, Humulus lupulus extract, IC 50, inflorescence, Isoflavones, isoxanthohumol, menopausal syndrome, menopause, metabolic activation, methylation, methyltransferase, nonhuman, norxanthohumol, osteoporosis, phytoestrogen, Phytoestrogens, Phytotherapy, Plant Preparations, polyketide, prenylation, Prenylflavonoids, Propiophenones, review, transferase, unclassified drug, xanthohumol
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.