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Isoxanthohumol
Isoxanthohumol is a prenylflavonoid, and it is a phytoestrogen. It is abbreviated as IX or IXN. 8-Prenylnaringenin can be produced from isoxanthohumol by flora in the human intestine, and by fungi in cell cultures. This prenylflavonoid is found in hops and beer. It has limited estrogenic activity. At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue. Derivatives of isoxanthohumol are: 7,4′-Di-O-methylisoxanthohumol; 7-O-methylisoxanthohumol; 7-O-n-pentylisoxanthohumol; 7,4′-di-O-n-pentyl-8-isoxanthohumol; 7,4′-Di-O-allylisoxanthohumol; 7,4′-Di-O-acetylisoxanthohumol; and 7,4′-Di-O-palmitoylisoxanthohumol. See also * Xanthohumol, the corresponding prenylated chalcone References

Flavanones O-methylated natural phenols Prenylflavonoids Humulus {{aromatic-stub ...
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Xanthohumol
Xanthohumol is a natural product found in the female inflorescences of ''Humulus lupulus'', also known as hops. This compound is also found in beer and belongs to a class of compounds that contribute to the bitterness and flavor of hops. Xanthohumol is a prenylated chalconoid, biosynthesized by a type III polyketide synthase (PKS) and subsequent modifying enzymes. Biosynthesis Xanthohumol is a prenylated chalconoid derived from a plant type III PKS, and is synthesized in the glandular trichromes of hop cones. Phenylalanine, L-Phenylalanine serves as the starting material, which is converted to cinnamic acid by the PLP-dependent Phenylalanine ammonia-lyase, phenylalanine ammonia lyase. Cinnamic acid is oxidized by Trans-cinnamate 4-monooxygenase, cinnamate-4-hydroxylase and loaded onto coenzyme A (CoA) by 4-Coumarate-CoA ligase, 4-coumarate CoA ligase to yield Coumaroyl-CoA, 4-hydroxy-cinnamoyl CoA, the starter unit for PKS extension. This molecule is extended three times with Mal ...
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Prenylflavonoid
Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition of hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid. Monoprenyl isoflavone epoxidase is a key enzyme in fungal ''Botrytis cinerea'' metabolism of prenylated flavonoids. Many prenylflavonoids appear to have anticancer activity in vitro. Prenylchalcones, prenylflavones, prenylflavonols and prenylflavanones are classes of prenylflavonoids. Examples 6-Prenylnaringenin, 6-geranylnaringenin, 8-prenylnaringenin and isoxanthohumol can be found in hops and beer. Of the prenylflavonoids, 8-prenylnaringenin is the most potent phytoe ...
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Hops
Hops are the flowers (also called seed cones or strobiles) of the hop plant ''Humulus lupulus'', a member of the Cannabaceae family of flowering plants. They are used primarily as a bittering, flavouring, and stability agent in beer, to which, in addition to bitterness, they impart floral, fruity, or citrus flavours and aromas. Hops are also used for various purposes in other beverages and herbal medicine. The hops plants have separate female and male plants, and only female plants are used for commercial production. The hop plant is a vigorous climbing herbaceous perennial, usually trained to grow up strings in a field called a hopfield, hop garden (in the South of England), or hop yard (in the West Country and United States) when grown commercially. Many different varieties of hops are grown by farmers around the world, with different types used for particular styles of beer. The first documented use of hops in beer is from the 9th century, though Hildegard of Bingen, 300 y ...
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Beer
Beer is an alcoholic beverage produced by the brewing and fermentation of starches from cereal grain—most commonly malted barley, although wheat, maize (corn), rice, and oats are also used. The grain is mashed to convert starch in the grain to sugars, which dissolve in water to form wort. Fermentation of the wort by yeast produces ethanol and carbonation in the beer. Beer is one of the oldest and most widely consumed alcoholic drinks in the world, and one of the most popular of all drinks. Most modern beer is brewed with hops, which add bitterness and other flavours and act as a natural preservative and stabilising agent. Other flavouring agents, such as gruit, herbs, or fruits, may be included or used instead of hops. In commercial brewing, natural carbonation is often replaced with forced carbonation. Beer is distributed in bottles and cans, and is commonly available on draught in pubs and bars. The brewing industry is a global business, consisting of several ...
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Flavanones
The flavanones, a type of flavonoids, are various aromatic, colorless ketones derived from flavone that often occur in plants as glycosides. List of flavanones * Blumeatin * Butin (molecule), Butin * Dichamanetin * Eriodictyol * Hesperetin * Hesperidin * Homoeriodictyol * Isosakuranetin * Naringenin * Naringin * Pinocembrin * Poncirin * Sakuranetin * Sakuranin * Sterubin * Pinostrobin Metabolism The enzyme chalcone isomerase uses a chalconoid, chalcone-like compound to produce a flavanone. Flavanone 4-reductase is an enzyme that uses (2''S'')-flavan-4-ol and NADP+ to produce (2''S'')-flavanone, NADPH, and H+. Synthesis Numerous methods exist for the enantioselective chemical and biochemical synthesis of flavanones and related compounds. References External links

* {{Flavanone Flavanones, ...
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Prenylflavonoids
Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition of hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid. Monoprenyl isoflavone epoxidase is a key enzyme in fungal ''Botrytis cinerea'' metabolism of prenylated flavonoids. Many prenylflavonoids appear to have anticancer activity in vitro. Prenylchalcones, prenylflavones, prenylflavonols and prenylflavanones are classes of prenylflavonoids. Examples 6-Prenylnaringenin, 6-geranylnaringenin, 8-prenylnaringenin and isoxanthohumol can be found in hops and beer. Of the prenylflavonoids, 8-prenylnaringenin is the most potent phytoes ...
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