Names | |
---|---|
IUPAC name (2S,4S,5S)-2-[[(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol | |
Other names (2R,3S)-Catechin-7-O-β-D-glucopyranoside Catechin 7-O-β-glucopyranoside (+)-Catechin 7-O-β-glucoside (+)-Catechin 7-O-beta-D-glucopyranoside Catechin 7-glucoside C7G CA-G | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
| |
| |
Properties | |
C21H24O11 | |
Molar mass | 452.412 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Catechin-7-O-glucoside is a flavan-3-ol glycoside formed from catechin.
Catechin-7-O-glucoside can be isolated from the hemolymph of the European pine sawfly ( Neodiprion sertifer ). [1] It also occurs in relatively large quantities in cowpea (Vigna unguiculata) as the dominant flavan-3-ol monomer, and actually accounts for up to 70% of cowpea proanthocyanidins (tannins). [2]
It can also be produced by biotransformation of (+)-catechin by cultured cells of Eucalyptus perriniana . [3]
Catechin-7-O-glucoside can be found in paeoniae radix, the crude drug made from the roots of Chinese peony ( Paeonia lactiflora ), [4] in red knotweed ( Bistorta macrophylla , also known as Polygonum macrophyllum), [5] in the stem barks of the Nepali hog plum ( Choerospondias axillaris ), [6] in the Korean plum yew ( Cephalotaxus koreana ) [7] and in Huanarpo Macho ( Jatropha macrantha ). [8] (−)-Catechin 7-O-β-D-glucopyranoside is found in the bark of Rhaphiolepis umbellata . [9]
It is found in buckwheat groats, [10] in the red bean (the seed of Vigna umbellata , formerly known as Phaseolus calcaratus), [11] in barley ( Hordeum vulgare L.) and malt. [12] (−)-Catechin 7-O'-β-D-glucopyranoside is found in rhubarb. [9]
This compound has an antioxidant activity leading to a cytoprotective effect. [11] [13]
Flavan-3-ols are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They play a part in plant defense and are present in the majority of plants.
The cowpea is an annual herbaceous legume from the genus Vigna. Its tolerance for sandy soil and low rainfall have made it an important crop in the semiarid regions across Africa and Asia. It requires very few inputs, as the plant's root nodules are able to fix atmospheric nitrogen, making it a valuable crop for resource-poor farmers and well-suited to intercropping with other crops. The whole plant is used as forage for animals, with its use as cattle feed likely responsible for its name.
Vigna is a genus of plants in the legume family, Fabaceae, with a pantropical distribution. It includes some well-known cultivated species, including many types of beans. Some are former members of the genus Phaseolus. According to Hortus Third, Vigna differs from Phaseolus in biochemistry and pollen structure, and in details of the style and stipules.
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.
Vigna umbellata, previously Phaseolus calcaratus, is a warm-season annual vine legume with yellow flowers and small edible beans. It is commonly called ricebean or rice bean. To date, it is little known, little researched and little exploited. It is regarded as a minor food and fodder crop and is often grown as intercrop or mixed crop with maize, sorghum or cowpea, as well as a sole crop in the uplands, on a very limited area. Like the other Asiatic Vigna species, ricebean is a fairly short-lived warm-season annual. Grown mainly as a dried pulse, it is also important as a fodder, a green manure and a vegetable. Ricebean is most widely grown as an intercrop, particularly of maize, throughout Indo-China and extending into southern China, India, Nepal and Bangladesh. In the past it was widely grown as lowland crop on residual soil water after the harvest of long-season rice, but it has been displaced to a great extent where shorter duration rice varieties are grown. Ricebean grows well on a range of soils. It establishes rapidly and has the potential to produce large amounts of nutritious animal fodder and high quality grain.
Rhaphiolepis umbellata is a species of flowering plant in the family Rosaceae, native to Korea, Japan and Taiwan. Growing to 1.5 m (5 ft) tall and wide, it is an evergreen shrub with glossy oval leaves, and scented white flowers, sometimes tinged with pink, in early summer.
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.
Prodelphinidin is a name for the polymeric tannins composed of gallocatechin. It yields delphinidin during depolymerisation under oxidative conditions.
Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols. It is extracted from plants such as Siberian larch and milk thistle.
Phellamurin, a flavonoid, is the 7-O-β-D-glucopyranoside, 8-C-prenyl derivative of the flavan-on-ol Aromadendrin, and may be seen as the 7-O-glucoside of noricaritin. Being a flavanonol, it has two stereocenters on the C-ring, so four stereoisomers of phellamurin are possible.
Procyanidin C2 is a B type proanthocyanidin trimer, a type of condensed tannin.
Afzelechin is a flavan-3-ol, a type of flavonoid. It can be found in Bergenia ligulata. It exists as at least 2 major epimers.
Lindera aggregata is a plant species belonging to the genus Lindera.
Procyanidin C1 (PCC1) is a B type proanthocyanidin. It is an epicatechin trimer found in grape, unripe apples, and cinnamon.
Condensed tannins are polymers formed by the condensation of flavans. They do not contain sugar residues.
B type proanthocyanidins are a specific type of proanthocyanidin, which are a class of flavanoids. They are oligomers of flavan-3-ols.
Malvidin glucoside-ethyl-catechin is a flavanol-anthocyanin adduct. Flavanol-anthocyanin adducts are formed during wine ageing through reactions between anthocyanins and tannins present in grape, with yeast metabolites such as acetaldehyde. Acetaldehyde-induced reactions yield ethyl-linked species such as malvidin glucoside-ethyl-catechin.
Neodiprion sertifer, the European pine sawfly or red pine sawfly, is a sawfly species in the genus Neodiprion. Although native to Europe, it was accidentally introduced to North America in 1925.
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 5-O-glucoside is a flavanol glucoside. It can be found in rhubarb and in the bark of Rhaphiolepis umbellata. It can also be formed from (+)-catechin by plant-cultured cells of Eucalyptus perriniana.