Phenyl-0-glucoside

Jung, J.-H., John, G., Yoshida, K. and Shimizu, T. (2004) Self-assembling structures of long-chain phenyl glucoside influenced by the introduction of double bonds. Journal of the American Chemical Society, 124 (36), 10674-10675. 

The use of the enzyme system then known as invertin, which was extracted from beer yeast with water and precipitated from the aqueous solution, was available to Fischer when he began his classical studies of the enzymic hydrolysis of glucosides reported in 1894. The stage was also set by another enzyme known as emulsin, which Fischer purchased from E. Merck, Darmstadt, and which was known to hydrolyze several natural aromatic glucosides such as salicin, coniferin, arbutin, and the synthetic phenyl glucoside. These aryl glucosides were already known to not be cleaved by invertin. 

Edwards VT, Jones BC, Hutson DH. 1986. A comparison of the metabolic fate of phenol, phenyl glucoside and phenyl 6-O-malonyl-glucoside in the rat. Xenobiotica 16 801-807. 

The whole plant of Swertia japonica Makino (Gentianaceae) is an important bitter stomachic in Japan where it is called "senburi". The plant is also claimed to be effective in the treatment of hepatitis (57). Components of this plant such as the bitter secoiridoids (58-63), phenyl glucosides (64), flavonoids (65) and xanthones (66-68) have been intensively studied mainly by Japanese researchers but, to date, there are few reports on the production of these constituents in vitro. Callus culture produced no bitter principles (secoiridoids) (69, 70), xanthones and flavones but coumarin derivatives, scopoletin and its glucoside were detected (71). 

In summary, the metabolic fate of glucoside conjugates In animals Is very dependent on the structure of the aglycone. It appears that the glucosides which are most rapidly absorbed are most likely to be excreted Intact whereas, where Intestinal hydrolysis takes place prior to (or at the same time as) absorption, the elimination products are the same as those of the aglycone. It should be noted that phenol Itself (and possibly other phenols) Is efficiently conjugated In the Intestinal wall (18) and thus phenol liberated from, for example, phenyl glucoside within the Intestine or In the Intestinal cells, need not necessarily appear as free phenol In the systemic circulation. 

To our knowledge there has been no published work on the fate In animals of these malonylated xenobiotic conjugates. Therefore, we have recently carried out a study of the metabolism of phenyl 6-0-malonyl-glucoslde, phenyl glucoside and phenol In rats The... 

Going to the next more complex situation, that of enzymic reactions, it can be shown that the linear combination of ir and a can account for the substituent effects in the hydrolysis of phenyl glucosides by emulsin . Using regression analysis, eq 10-13 are derived to illustrate how one can... 

Phenyl glucoside iV-Arylglucosamine V-Carboethoxyglucosamine Glucose dithioacetal Gulose Derivatives Gulose... 

Evidence for the configuration of carbon atom 1 of some phenyl glucosides has been obtained by the conversion of the jS-glucosides to 1,6-anhydro derivatives (see Chapter IV, Glycosans), and by the stability of the a-anomers to strong alkali (3 ). 

Substituent group (group X) Phenyl glucoside (E,E,) Vanillin 6-X-jS-glucoside<> Volume of group (Biltz)... 

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