Procyanidin B3
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Procyanidin B3
Procyanidin B3 is a B type proanthocyanidin. Procyanidin B3 is a catechin dimer (catechin-(4α→8)-catechin). Natural occurrences It can be found in red wine, in barley, in beer, in peach or in '' Jatropha macrantha'', the Huanarpo Macho. Health effects It has been identified as a hair-growth stimulant. Chemical synthesis Molar equivalents of synthetic (2R,3S,4R or S)- leucocyanidin and (+)-catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans- ,8 and ,6bi- +)-catechins(procyanidins B3, B6) the all-trans- ,8:4,8 and ,8:4,6tri- +)-catechins(procyanidin C2 and isomer). See also * Phenolic content in wine The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include ... References Procyanidin dimers {{Aromatic-stub ...
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B Type Proanthocyanidin
B type proanthocyanidins are a specific type of proanthocyanidin, which are a class of flavanoids. They are oligomers of flavan-3-ols. Dimeric B type proanthocyanidins These molecules have the molecular formula C30H26O12 (molar mass : 578.52 g/mol, exact mass : 578.142426). Molecules with 4→8 bonds The 4-8 bond can be in the alpha or in the beta position. * Procyanidin B1 or epicatechin-(4β→8)-catechin * Procyanidin B2 or (−)-epicatechin-(4β→8)-(−)-epicatechin * Procyanidin B3 or catechin-(4α→8)-catechin * Procyanidin B4 or catechin-(4α→8)-epicatechin Molecules with 4→6 bonds * Procyanidin B5 or epicatechin-(4β→6)-epicatechin * Procyanidin B6 or catechin-(4α→6)-catechin * Procyanidin B8 or catechin-(4α→6)-epicatechin Chemistry B-type procyanidin (catechin dimer) can be converted to A-type procyanidin by radical oxidation. Dimeric proanthocyanidins can also be synthesized with procyanidin-rich grape seed extracts reacted with flavan-3-ol ...
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Catechin
Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids. The name of the catechin chemical family derives from ''catechu'', which is the tannic juice or boiled extract of ''Mimosa catechu'' (''Acacia catechu'' L.f). Chemistry Catechin possesses two benzene rings (called the A- and B-rings) and a dihydropyran heterocycle (the C-ring) with a hydroxyl group on carbon 3. The A-ring is similar to a resorcinol moiety while the B-ring is similar to a catechol moiety. There are two chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configuration and are called ''catechin'' and the other two are in cis configuration and are called ''epicatechin''. The most common catechin isomer is (+)-catechin. The other stereoisomer is (-)-catechin or ''ent''-catechin. The most common epicatechin isomer is (-)-epicatech ...
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Barley
Barley (''Hordeum vulgare''), a member of the grass family, is a major cereal grain grown in temperate climates globally. It was one of the first cultivated grains, particularly in Eurasia as early as 10,000 years ago. Globally 70% of barley production is used as animal fodder, while 30% as a source of fermentable material for beer and certain distilled beverages, and as a component of various foods. It is used in soups and stews, and in barley bread of various cultures. Barley grains are commonly made into malt in a traditional and ancient method of preparation. In 2017, barley was ranked fourth among grains in quantity produced () behind maize, rice and wheat. Etymology The Old English word for barley was ', which traces back to Proto-Indo-European and is cognate to the Latin word ' "flour" (''see corresponding entries''). The direct ancestor of modern English ''barley'' in Old English was the derived adjective ''bærlic'', meaning "of barley". The first citation ...
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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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Peach
The peach (''Prunus persica'') is a deciduous tree first domesticated and cultivated in Zhejiang province of Eastern China. It bears edible juicy fruits with various characteristics, most called peaches and others (the glossy-skinned, non-fuzzy varieties), nectarines. The specific name ''persica'' refers to its widespread cultivation in Persia (modern-day Iran), from where it was transplanted to Europe. It belongs to the genus ''Prunus'', which includes the cherry, apricot, almond, and plum, in the rose family. The peach is classified with the almond in the subgenus '' Amygdalus'', distinguished from the other subgenera by the corrugated seed shell (endocarp). Due to their close relatedness, the kernel of a peach stone tastes remarkably similar to almond, and peach stones are often used to make a cheap version of marzipan, known as persipan. Peaches and nectarines are the same species, though they are regarded commercially as different fruits. The skin of nectarines ...
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Jatropha Macrantha
''Jatropha macrantha'', also called the ''huanarpo macho'', is a medium size shrubby tree species in the genus ''Jatropha'' with orange red flowers. It is indigenous to Peru. It is as popular in Peru as Muira Puama is in Brazil. Catechin, catechin-7-O-β-glucopyranoside and procyanidin B3 Procyanidin B3 is a B type proanthocyanidin. Procyanidin B3 is a catechin dimer (catechin-(4α→8)-catechin). Natural occurrences It can be found in red wine, in barley, in beer, in peach or in '' Jatropha macrantha'', the Huanarpo Macho. H ... can be found in Huanarpo Macho.Catechin derivatives in Jatropha macrantha stems: Characterisation and LC/ESI/MS/MS quali-quantitative analysis. Benavides A, Montoro P, Bassarello C, Piacente S and Pizza C, Journal of Pharmaceutical and Biomedical Analysis, 2006, Vol. 40, No. 3, pages 639-647, References External links rainforest-database.com macrantha Flora of Peru Plants described in 1865 {{Euphorbiaceae-stub ...
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Hair-growth Stimulant
The growth of human hair occurs everywhere on the body except for the soles of the feet, the inside of the mouth, the lips, the backs of the ears, the palms of the hands, some external genital areas, the navel, scar tissue, and, apart from eyelashes, the eyelids. Hair is a stratified squamous keratinized epithelium made of multi-layered flat cells whose rope-like filaments provide structure and strength to the hair shaft. The protein called keratin makes up hair and stimulates hair growth. Hair follows a specific growth cycle with three distinct and concurrent phases: anagen, catagen, and telogen. Each phase has specific characteristics that determine the length of the hair. The body has different types of hair, including vellus hair and androgenic hair, each with its own type of cellular construction. This varied construction gives the hair unique characteristics, serving specific purposes, mainly warmth (redundant in modern humans) and physical protection. Most humans devel ...
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Leucocyanidin
Leucocyanidin is a colorless chemical compound that is a member of the class of natural products known as leucoanthocyanidins. Chemistry (+)-Leucocyanidin can be synthesized from (+)-dihydroquercetin by reduction with sodium borohydride. Molar equivalents of synthetic (2R,3S,4R or S)-leucocyanidin and (+)-catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-''trans''- ,8 and ,6bi- +)-catechins( procyanidins B3, B6) the all-''trans''- ,8:4,8 and ,8:4,6tri- +)-catechins(procyanidin C2 and isomer). Metabolism Leucocyanidin oxygenase uses leucocyanidin, 2-oxoglutarate, and O2 to produce ''cis''-dihydroquercetin, ''trans''-dihydroquercetin (taxifolin), succinate, CO2, and H2O. Leucoanthocyanidin reductase (LAR or leucocyanidin reductase LCR) uses (2''R'',3''S'')-catechin, NADP+, and H2O to produce 2,3-''trans''-3,4-cis-leucocyanidin, NADPH, and H+. Its gene expression has been studied in developing grape berries and grapevine leaves ...
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Procyanidin B6
Procyanidin B6 is a B type proanthocyanidin. Procyanidin B6 is a catechin-(4α→6)-catechin dimer. It can be found in grape seeds and in beer.


Chemical synthesis

Molar equivalents of synthetic (2R,3S,4R or S)- and (+)- condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans- ,8 and ,6bi- +)-catechins(
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Procyanidin C2
Procyanidin C2 is a B type proanthocyanidin trimer, a type of condensed tannin. Natural occurrences Procyanidin C2 is found in grape seeds (''Vitis vinifera'') and wine, in barley (''Hordeum vulgare''), malt and beer, in '' Betula spp.'', in '' Pinus radiata'', in '' Potentilla viscosa'', in '' Salix caprea'' or in '' Cryptomeria japonica''. The contents in barley grain of trimeric proanthocyanidins, including procyanidin C2, range from 53 to 151 μg catechin equivalents/g. Possible health uses Proanthocyanidin oligomers, extracted from grape seeds, have been used for the experimental treatment of androgenic alopecia. When applied topically, they promote hair growth ''in vitro'', and induce anagen ''in vivo''. Procyanidin C2 is the subtype of extract most effective. Experiments showed that both procyanidin C2 and Pycnogenol (French maritime pine bark extract) increase TNF-α secretion in a concentration- and time-dependent manner. These results demonstrate that procyanidi ...
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Phenolic Content In Wine
The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids. Origin of the phenolic compounds The natural phenols are not evenly distributed within the fruit. Phenolic acids are largely present in the pulp, anthocyanins and stilbenoids in the skin, and other phenols (catechins, proanthocyanidins and flavonols) i ...
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