Glucoside conjugates

Phenanthrene Zraw-l -dihydrodiol, phenanrhrene Zraw-3,4-dihydrodioI, phenanchrene Zraw-9,10-dihydrodiol, glucoside conjugate of 1-phenanthrol, 3-,4-, and 9-hydroxyphenanchrene, 2,2, -diphenic acid. 

Fluoranchene /raw-2,3-dihydrodiol, 8- 9-hydroxyfluoranthene /raw-2,3-dihydrodiols, glucoside conjugates... 

Birt, D.F., Hendrich, S., and Wang, W. 2001. Dietary agents in cancer prevention Flavonoids and isoflavonoids. Pharmacol. Ther. 90.157-177. Coward, L., Baines, N.C., Setchell, K.D.R., and Barnes, S. 1993. Genistein, daidzein, and their P-glucoside conjugates Antitumor isoflavones in soybean foods from American and Asian diets. 

Frear, D.S., E.R. Mansager, and H.R. Swanson (1981). N-glucoside conjugates Major metribuzin detoxification products in tomato. Presented to the North Central Weed Control Conference in Des Moines, Iowa. Miles Ag. Div. Report Number 80304.2... 

Figure 4.3 Chemical structures of Isoflavone glycosides. In soy foods, Isoflavones form 7-0-P-glucosIde conjugates. A Is the simple glucoside commonly found In soy milk, B Is the 6"-0-malonyl-7-0-p-glucoslde from the soybean, and C Is the 6"-0-acetyl-7-O-p-glucoside, a product of toasting of soy flour. D is the 7-0-P-glucuronide that is the principal conjugate in the blood.

The ability of insect sulfotransferases to catalyze the sulfation of plant and insect steroids may simply reflect the broad substrate specificity of the enzymes. On the other hand, it may be indicative of a more important physiological function of the enzymes. Sulfate esters of cholesterol, campesterol and e-sitosterol have been identified in the meconium of tobacco hornworm (M. sexta) pupae ( ), and these steroids are known precursors of a-and e-ecdysone and other molting hormones in this species ( ). Further, there is evidence that houseflies (M. domestica) and diapausing pupae of M. sexta convert 22,25 bisdeoxyecdysone, a-ecdysone and 20-hydroxyecdysone into sulfate and glucoside conjugates ( ). 

Phase I Reaction Class of Xenobiotic Metabolite Susceptible to Glucoside Conjugation... 

Malonate hemi-ester glucose conjugates of xenobiotics are one of the most common forms of complex glucoside conjugate produced In plants. They are formed by the action of malonyl CoA transferase on glucose conjugates In the presence of malonyl CoA as Indicated In Equation 14. At least 9 pesticides have been Isolated from 7... 

D The final synthetic product Is a protected glucoside conjugate 2. G - The final product lo the free 6-D-glucoslde conjugate. 

Crown ethers have been used as phase transfer catalysts In the formation of 0-glucosldes (, ). A number of xenobiotic glucoside conjugates were also prepared under FTC conditions (30-70Z yield) from tetra-0-benzyl- -D-glucopyranosyl bromide, aglycone and trlethylbenzylammonlum chloride In a two-phase... 

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. 

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