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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. L-Phenylalanine serves as the starting material, which is converted to cinnamic acid by the PLP-dependent phenylalanine ammonia lyase. Cinnamic acid is oxidized by cinnamate-4-hydroxylase and loaded onto Coenzyme A (CoA) by 4-coumarate CoA ligase to yield 4-hydroxy-cinnamoyl CoA, the starter unit for PKS extension. This molecule is extended three times with malonyl CoA, cyclized through a Claisen condensation, and aromatized through tautomerization to form naringenin cha ...
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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 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. Xanthoh ..., the corresponding prenylated chalcone Refere ...
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Xanthohumol Biosynthesis V2
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. L-Phenylalanine serves as the starting material, which is converted to cinnamic acid by the PLP-dependent phenylalanine ammonia lyase. Cinnamic acid is oxidized by cinnamate-4-hydroxylase and loaded onto Coenzyme A (CoA) by 4-coumarate CoA ligase to yield 4-hydroxy-cinnamoyl CoA, the starter unit for PKS extension. This molecule is extended three times with malonyl CoA, cyclized through a Claisen condensation, and aromatized through tautomerization to form naringenin cha ...
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Humulus Lupulus
''Humulus lupulus'', the common hop or hops, is a species of flowering plant in the hemp family Cannabinaceae, native to Europe, western Asia and North America. It is a perennial, herbaceous climbing plant which sends up new shoots in early spring and dies back to a cold-hardy rhizome in autumn. It is dioecious (having separate male and female plants). As the female cone-shaped flowers (hops) are used to preserve and flavor beer, the species is widely cultivated by the brewing industry. Description ''Humulus lupulus'' is a perennial herbaceous plant up to tall, living up to 20 years. It has simple leaves with 3–5 deep lobes that can be opposite or alternate. The species is triggered by the longer summer days to flower, usually around July or August. The plant is dioecious, with male and female flowers on separate plants. The fragrant flowers are wind-pollinated. The staminate (male) flowers do not have petals, while the pistillate (female) flowers have petals envelopin ...
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Beer
Beer is one of the oldest and the most widely consumed type of alcoholic drink in the world, and the third most popular drink overall after water and tea. It is produced by the brewing and fermentation of starches, mainly derived from cereal grains—most commonly from malted barley, though wheat, maize (corn), rice, and oats are also used. During the brewing process, fermentation of the starch sugars in the wort produces ethanol and carbonation in the resulting beer.Barth, Roger. ''The Chemistry of Beer: The Science in the Suds'', Wiley 2013: . Most modern beer is brewed with hops, which add bitterness and other flavours and act as a natural preservative and stabilizing agent. Other flavouring agents such as gruit, herbs, or fruits may be included or used instead of hops. In commercial brewing, the natural carbonation effect is often removed during processing and replaced with forced carbonation. Some of humanity's earliest known writings refer to the productio ...
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Natural Product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis (both semisynthesis and total synthesis) and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients. Within the field of organic chemistry, the definition of natural products is usually restricted to organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism. Within the field of medicinal chemistry, the definition is often further restricted to secondary metabolites. Secondary metabolites (or specialized metabo ...
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Prenyltransferase
Prenyltransferases (PTs) are a class of enzymes that transfer allylic prenyl groups to acceptor molecules. Prenyl transferases commonly refer to isoprenyl diphosphate syntheses (IPPSs). Prenyltransferases are a functional category and include several enzyme groups that are evolutionarily independent. Prenyltransferases are commonly divided into two classes, cis (or Z) and trans (or E), depending upon the stereochemistry of the resulting products. Examples of trans-prenyltranferases include dimethylallyltranstransferase, and geranylgeranyl pyrophosphate synthase. Cis-prenyltransferases include dehydrodolichol diphosphate synthase (involved in the production of a precursor to dolichol). Trans- and cis-prenyltransferases are evolutionarily unrelated to each other and there is no sequential and structural similarity. The beta subunit of the farnesyltransferases is responsible for peptide binding. Squalene-hopene cyclase is a bacterial enzyme that catalyzes the cyclization of squalene ...
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Alpha Acid
Alpha acids (α acids) are a class of chemical compounds primarily of importance to the production of beer. They are found in the resin glands of the flowers of the hop plant and are the source of hop bitterness. Alpha acids may be isomerized to form iso-alpha acids by the application of heat in solution. Iso-alpha acids (iso-α-acids) are typically produced in beer from the addition of hops to the boiling wort. The degree of isomerization and the amount of bitter flavor produced by the addition of hops is highly dependent on the length of time the hops are boiled. Longer boil times will result in isomerization of more alpha acids and thus increased bitterness. Common alpha acids include humulone, adhumulone, cohumulone, posthumulone, and prehumulone. The most common iso-α-acids are ''cis''- and ''trans''-isohumulone. Bittering The alpha acid "rating" on hops indicates the amount of alpha acid as a percentage of total weight of the hop. Hops with a higher alpha ...
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Extract
An extract is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures, absolutes or in powder form. The aromatic principles of many spices, nuts, herbs, fruits, etc., and some flowers, are marketed as extracts, among the best known of true extracts being almond, cinnamon, cloves, ginger, lemon, nutmeg, orange, peppermint, pistachio, rose, spearmint, vanilla, violet, rum, and wintergreen. Extraction techniques Most natural essences are obtained by extracting the essential oil from the feedstock, such as blossoms, fruit, and roots, or from intact plants through multiple techniques and methods: * Expression ( juicing, pressing) involves physical extraction material from feedstock, used when the oil is plentiful and easily obtained from materials such as citrus peels, olives, and grapes. * Absorption ( steeping, decoction). Extraction is done by soaking material in ...
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Basic Research
Basic research, also called pure research or fundamental research, is a type of scientific research with the aim of improving scientific theory, theories for better understanding and prediction of natural or other phenomena. In contrast, applied research uses scientific theories to develop technology or techniques which can be used to intervene and ''alter'' natural or other phenomena. Though often driven simply by curiosity,"Curiosity creates cures: The value and impact of basic research
, National Institute of General Medical Sciences, National Institutes of Health.
basic research often fuels the technological innovations of applied science. The two aims are often practiced simultaneously in coordinated research and development. In addition to innovations, b ...
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Flavanone
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 * Eriodictyol * Hesperetin * Hesperidin * Homoeriodictyol * Isosakuranetin * Naringenin * Naringin * Pinocembrin * Poncirin * Sakuranetin * Sakuranin * Sterubin Sterubin (7-methoxy-3',4',5-trihydroxyflavanone) is a bitter-masking flavanone extracted from Yerba Santa (''Eriodictyon californicum'') a plant growing in America. Sterubin is one of the four flavanones identified by Symrise in this plant whic ... * Pinostrobin Metabolism The enzyme chalcone isomerase uses a 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 Exte ...
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Brewing
Brewing is the production of beer by steeping a starch source (commonly cereal grains, the most popular of which is barley) in water and fermenting the resulting sweet liquid with yeast. It may be done in a brewery by a commercial brewer, at home by a homebrewer, or communally. Brewing has taken place since around the 6th millennium BC, and archaeological evidence suggests that emerging civilizations, including ancient Egypt and Mesopotamia, brewed beer. Since the nineteenth century the brewing industry has been part of most western economies. The basic ingredients of beer are water and a fermentable starch source such as malted barley. Most beer is fermented with a brewer's yeast and flavoured with hops. Less widely used starch sources include millet, sorghum and cassava. Secondary sources (adjuncts), such as maize (corn), rice, or sugar, may also be used, sometimes to reduce cost, or to add a feature, such as adding wheat to aid in retaining the foamy head of the beer. ...
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