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Procyanidin C1
Procyanidin C1 (PCC1) is a B type proanthocyanidin. It is an epicatechin trimer found in grape (''Vitis vinifera''), unripe apples, and cinnamon. Natural occurrence and function Procyanidin C1 can be isolated from grape seed extract. Chemical synthesis The stereoselective synthesis of seven benzylated proanthocyanidin trimers (epicatechin-(4β-8)-epicatechin-(4β-8)-epicatechin trimer (procyanidin C1), catechin-(4α-8)-catechin-(4α-8)-catechin trimer (procyanidin C2), epicatechin-(4β-8)-epicatechin-(4β-8)-catechin trimer and epicatechin-(4β-8)-catechin-(4α-8)-epicatechin trimer derivatives) can be achieved with TMSOTf-catalyzed condensation reaction, in excellent yields. The structure of benzylated procyanidin C2 was confirmed by comparing the 1H NMR spectra of protected procyanidin C2 that was synthesized by two different condensation approaches. Finally, deprotection of (+)-catechin and (-)-epicatechin trimers derivatives gives four natural procyanidin trimers in good ...
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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 proanthocyanidin, A-type procyanidin by radical oxidation. Dimeric proanthocyanidins can also be synthesized with procyanidin-rich grape seed extracts re ...
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Epicatechin
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 (− ...
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Vitis Vinifera
''Vitis vinifera'', the common grape vine, is a species of flowering plant, native to the Mediterranean Basin, Mediterranean region, Central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern Iran. , there were between List of grape varieties, 5,000 and 10,000 varieties of ''Vitis vinifera'' grapes though only a few are of commercial significance for wine and table grape production. The wild grape is often classified as ''Vitis vinifera'' ''sylvestris'' (in some classifications considered ''Vitis sylvestris''), with ''Vitis vinifera'' ''vinifera'' restricted to cultivated forms. Domesticated vines have hermaphrodite#Plants, hermaphrodite flowers, but ''sylvestris'' is plant sexuality, dioecious (male and female flowers on separate plants) and pollination is required for fruit to develop. Grapes can be eaten fresh or dried to produce raisins, Sultana (grape)#Raisins, sultanas, and Zante currant, currants. Grape leaves are used ...
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Cinnamon
Cinnamon is a spice obtained from the inner bark of several tree species from the genus ''Cinnamomum''. Cinnamon is used mainly as an aromatic condiment and flavouring additive in a wide variety of cuisines, sweet and savoury dishes, biscuits, breakfast cereals, Snack, snack foods, bagels, teas, hot chocolate and traditional foods. The aroma and flavour of cinnamon derive from its essential oil and principal component, cinnamaldehyde, as well as numerous other constituents, including eugenol. Cinnamon is the name for several species of trees and the commercial spice products that some of them produce. All are members of the genus ''Cinnamomum'' in the family Lauraceae. Only a few ''Cinnamomum'' species are grown commercially for spice. ''Cinnamomum verum'' (alternatively ''C. zeylanicum''), known as "Ceylon cinnamon" after its origins in Sri Lanka (formerly Ceylon), is considered to be "true cinnamon", but most cinnamon in international commerce is derived from four other speci ...
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Procyanidin C2
Procyanidin C2 is a B type proanthocyanidin trimer (chemistry), 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 Management of hair loss, 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 Tumor necrosis factor alpha, TNF-α secretion in a concentration- an ...
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Trimethylsilyl Trifluoromethanesulfonate
Trimethylsilyl trifluoromethanesulfonate (TMSOTf) is an organosilicon compound with the formula . It is a colorless moisture-sensitive liquid. It is the trifluoromethanesulfonate derivative of trimethylsilyl. It is mainly used to activate ketones and aldehydes in organic synthesis. Reactions TMSOTf is quite sensitive toward hydrolysis: : It is far more electrophilic than trimethylsilyl chloride. Related to its tendency to hydrolyze, TMSOTf is effective for silylation of alcohols: : A common use of is for the preparation of silyl enol ethers. One example involves the synthesis of the silyl enol ether of camphor: : It was also used in Takahashi Taxol total synthesis and in chemical glycosylation reactions. Trimethylsilyl trifluoromethanesulfonate has a variety of other specialized uses. It has been used to install tert-alkyl groups on phosphine (R = alkyl): :PH3 + R3C–OAc + Me3SiOTf → R3C)2PH2Tf Deprotection of Boc-protected amines can be achieved using ...
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Senolytic
A senolytic (from the words ''senescence'' and ''-lytic'', "destroying") is among a class of small molecules under basic research to determine if they can selectively induce death of senescent cells and improve health in humans. A goal of this research is to discover or develop agents to delay, prevent, alleviate, or reverse age-related diseases. Removal of senescent cells with senolytics has been proposed as a method of enhancing immunity during aging. A related concept is "senostatic", which means to suppress senescence. Research Possible senolytic agents are under preliminary research, including some which are in early-stage human trials. The majority of candidate senolytic compounds are repurposed anti-cancer molecules, such as the chemotherapeutic drug dasatinib and the experimental small molecule navitoclax. Soluble urokinase plasminogen activator surface receptor have been found to be highly expressed on senescent cells, leading researchers to use chimeric antigen ...
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Chemotherapy
Chemotherapy (often abbreviated chemo, sometimes CTX and CTx) is the type of cancer treatment that uses one or more anti-cancer drugs (list of chemotherapeutic agents, chemotherapeutic agents or alkylating agents) in a standard chemotherapy regimen, regimen. Chemotherapy may be given with a cure, curative intent (which almost always involves combinations of drugs), or it may aim only to prolong life or to Palliative care, reduce symptoms (Palliative care, palliative chemotherapy). Chemotherapy is one of the major categories of the medical discipline specifically devoted to pharmacotherapy for cancer, which is called ''oncology#Specialties, medical oncology''. The term ''chemotherapy'' now means the non-specific use of intracellular poisons to inhibit mitosis (cell division) or to induce DNA damage (naturally occurring), DNA damage (so that DNA repair can augment chemotherapy). This meaning excludes the more-selective agents that block extracellular signals (signal transduction) ...
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Prostate Cancer
Prostate cancer is the neoplasm, uncontrolled growth of cells in the prostate, a gland in the male reproductive system below the bladder. Abnormal growth of the prostate tissue is usually detected through Screening (medicine), screening tests, typically blood tests that check for prostate-specific antigen (PSA) levels. Those with high levels of PSA in their blood are at increased risk for developing prostate cancer. Diagnosis requires a prostate biopsy, biopsy of the prostate. If cancer is present, the pathologist assigns a Gleason score; a higher score represents a more dangerous tumor. Medical imaging is performed to look for cancer that has spread outside the prostate. Based on the Gleason score, PSA levels, and imaging results, a cancer case is assigned a cancer staging, stage 1 to 4. A higher stage signifies a more advanced, more dangerous disease. Most prostate tumors remain small and cause no health problems. These are managed with active surveillance of prostate cancer, ...
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Phenolic Content In Wine
Phenolic compounds— natural phenol and polyphenols—occur naturally in wine. These 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 grape. Phenolic acids are largely present in the pulp, anthocyanins and stilbenoids in the skin, and other phenols ( catechins, proanthocyanidins and flavonols) in the skin a ...
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Procyanidins
Procyanidins are members of the proanthocyanidin (or condensed tannins) class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions. See the box below entitled "Types of procyanidins" for links to articles on the various types. Distribution in plants Procyanidins, including the lesser bioactive / bioavailable polymers (4 or more catechines), represent a group of condensed flavan-3-ols that can be found in many plants, most notably apples, maritime pine bark, cinnamon, aronia fruit, cocoa beans, grape seed, grape skin, and red wines of ''Vitis vinifera'' (the common grape). However, bilberry, cranberry, black currant, green tea, black tea, and other plants also contain these flavonoids.USDA, August 2004USDA Database for the Proanthocyanidin Content of Selected Foods PDF summary accessed from main USDA pag Page accessed July 31, 2015 Procyanidins can also be isolated fr ...
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