Castalagin
Encyclopedia
Castalagin is a ellagitannin
, a type of hydrolyzable tannin, found in oak
and chestnut
wood and in the stem barks of Anogeissus leiocarpus
and Terminalia avicennoides.
Castalagin is the (33beta)-isomer of vescalagin. During aging of alcohols in oak barrels, vescalagin can be extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions. Vescalagin is one of the most abundant ellagitannins extracted from oak wood using white wine.
In 2003, scientists at Institut Européen de Chimie et Biologie in Pessac, France found that when the oak tannin vescalagin interacts with a phenol in wine a flavono-ellagitannin known as acutissimin A
is created. In separate studies this polyphenol
has been shown to be 250 times more effective than the pharmaceutical drug Etoposide
in stopping the growth of cancerous tumors.
and casuarictin
formations). After conversion of casuarictin
to pedunculagin, the pyranose ring of the glucose
opens and the family of compounds including casuariin, casuarinin, castalagin, and castlin, stachyurin, vescalagin and vescalin forms.
Castalagin thus forms from a pentagalloyl-glucose structure. Castalagin and vescalagin (1,2,3,5-nonahydroxytriphenoyl-4,6-hexahydroxydiphenoyl-glucoses) can be further polymerized in their corresponding dimers roburin A
and roburin D, and 33-carboxy-33-deoxyvescalagin.
Ellagitannin
The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-Pentagalloyl glucose...
, a type of hydrolyzable tannin, found in oak
Oak
An oak is a tree or shrub in the genus Quercus , of which about 600 species exist. "Oak" may also appear in the names of species in related genera, notably Lithocarpus...
and chestnut
Chestnut
Chestnut , some species called chinkapin or chinquapin, is a genus of eight or nine species of deciduous trees and shrubs in the beech family Fagaceae, native to temperate regions of the Northern Hemisphere. The name also refers to the edible nuts they produce.-Species:The chestnut belongs to the...
wood and in the stem barks of Anogeissus leiocarpus
Anogeissus leiocarpus
Anogeissus leiocarpa is a tall evergreen tree native to savannas of Tropical Africa. It is the sole West African species of the genus Anogeissus, a genus otherwise distributed from tropical central and east Africa through tropical Southeast Asia. A...
and Terminalia avicennoides.
Castalagin is the (33beta)-isomer of vescalagin. During aging of alcohols in oak barrels, vescalagin can be extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions. Vescalagin is one of the most abundant ellagitannins extracted from oak wood using white wine.
In 2003, scientists at Institut Européen de Chimie et Biologie in Pessac, France found that when the oak tannin vescalagin interacts with a phenol in wine a flavono-ellagitannin known as acutissimin A
Acutissimin A
Acutissimin A is a flavono-ellagitannin, a type of tannin formed from the linking of a flavonoid with an ellagitannin.In 2003, scientists at Institut Européen de Chimie et Biologie in Pessac, France found that when the oak tannin vescalagin interacts with phenols in wine acutissimin A is created...
is created. In separate studies this polyphenol
Polyphenol
Polyphenols are a structural class of natural, synthetic, and semisynthetic organic chemicals characterized by the presence of large multiples of phenol structural units...
has been shown to be 250 times more effective than the pharmaceutical drug Etoposide
Etoposide
Etoposide phosphate is an anti-cancer agent. It is known in the laboratory as a topoisomerase poison. Etoposide is often incorrectly referred to as a topoisomerase inhibitor in order to avoid using the term "poison" in a clinical setting...
in stopping the growth of cancerous tumors.
Chemistry
In some plants including oak and chestnut, the ellagitannins are formed from 1,2,3,4,6-pentagalloyl-glucose and further elaborated via oxidative dehydrogenation (tellimagrandin IITellimagrandin II
Tellimagrandin II is the first of the ellagitannins formed from 1,2,3,4,6-pentagalloyl-glucose. It can be found in Geum japonicum and Syzygium aromaticum . The compound shows anti-herpesvirus properties....
and casuarictin
Casuarictin
Casuarictin is an ellagitannin, a type of hydrolysable tannin. It can be found in Casuarina and Stachyurus species.The molecule is formed from tellimagrandin II, itself formed from pentagalloyl glucose via oxidation. Casuarictin is transformed into pedunculagin via loss of a gallate group, and...
formations). After conversion of casuarictin
Casuarictin
Casuarictin is an ellagitannin, a type of hydrolysable tannin. It can be found in Casuarina and Stachyurus species.The molecule is formed from tellimagrandin II, itself formed from pentagalloyl glucose via oxidation. Casuarictin is transformed into pedunculagin via loss of a gallate group, and...
to pedunculagin, the pyranose ring of the glucose
Glucose
Glucose is a simple sugar and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate...
opens and the family of compounds including casuariin, casuarinin, castalagin, and castlin, stachyurin, vescalagin and vescalin forms.
Castalagin thus forms from a pentagalloyl-glucose structure. Castalagin and vescalagin (1,2,3,5-nonahydroxytriphenoyl-4,6-hexahydroxydiphenoyl-glucoses) can be further polymerized in their corresponding dimers roburin A
Roburin A
Roburin A is a tannin found in oak wood or oak cork .It is a dimeric compound, composed of two vescalagin subunits probably linked through an ether bond between the diphenoyl group of one subunit and the triphenoyl moiety of the other one....
and roburin D, and 33-carboxy-33-deoxyvescalagin.