Phlorizin

Phlonzm is obtained from the root bark of apple pear cherry and plum trees It has the molecular formula C21H24O10 and yields a compound A and D glucose on hydrolysis in the pres ence of emulsin When phlorizin is treated with excess methyl iodide in the presence of potassium carbonate and then subjected to acid catalyzed hydrolysis a compound B is obtained Deduce the structure of phlorizin from this information... 

Phlorizin, the glucoside of the dihydrochalcone phloretin, is a constituent of the tissues of the apple tree. Its distribution and bio-... 

Phloretin inhibits FATP-mediated traversing of fatty acids across lipid bilayers. Phloretin is the aglycon of phlorizin and has been used to terminate the uptake of LCFAs and VLCFAs in timed in vitro uptake assays with cultured cells or in ex vivo uptake assays with isolated primary cells. 

DAY A, CANADA F J, DIAZ J C, KROON P A, MCLAUCHLAN R, FAULDS C B, PLUMB G W, MORGAN M R A and WILLIAMSON G (2000) Dietary flavonoid and isoflavone glycosides are hydrolyzed by the lactase site of lactase phlorizin hydrolase. FEES Lett 468, 166-70. 

Potential enzymes involved in anthocyanin metabolism — The lactase phlorizin hydrolase (LPH EC 3.2.1.108) present only in the small intestine on the outside of the brush border membrane and the cytosolic P-glucosidase (CBG EC 3.2.1.1) found in many tissues, particularly in liver, can catalyze the deglycosylation (or hydrolysis) of polyphenols. LPH may play a major role in polyphenol metabolism... 

The hypothesis of Gray and Bonner (31, 32) that 3-acetyl-6-methoxybenzaldehyde, which is found in the leaves of Encelia farinosa and in the soil beneath these plants, is responsible for the suppression of other plant species has not been substantiated by Muller (33, 34). The same is true for the presumed role of trans-cinnamic acid in "soil sickness associated with guayule (Parthenium argentatum), for the amygdalin of peach roots, and for the phlorizin of apple roots or its breakdown products (35), which were thought to be associated with the "soil sickness" of orchards. 

Chlorogenic acid 2. Genistic acid 2. 0-Pinene 2. Phlorizin... 

Completely negative results on the formation of liver glycogen were obtained when the sodium salts of caproic or caprylic acid61 60 were fed, as well as after the administration of the ethyl esters of caproic, caprylic, capric, myristic or oleic acids or methyl laurate.81 Caproic acid was found to be ineffective as a D-glucose-former in the phlorizinized dog.89... 

There is no indisputable proof that fat can be directly oxidized in the muscles. Gemmill207 was unable to demonstrate any decrease in the fat present in the working muscle of the normal or phlorizinized rat. He believed that when fat is used by muscle, it is used indirectly. 

Phlorizin (74) Polyphenolic Dapagliflozin Antidiabetic Sodium glucose Phase III Bristol-Myers 602-607... 

Rossetti L, Smith D, Shuhnan GI, Papachristou D, DeFronzo RA. (1987) Correction of hyperglycemia with phlorizin normalizes tissue sensitivity to insulin in diabetic rats. J Clin Invest 79 1510-1515. 

Oulianova N, Falk S, Berteloot A. (2001) Two-step mechanism of phlorizin binding to the SGLTl protein in the kidney. JMembr Biol 179 223-242. White JR. (2010) Apple trees to sodinm glucose co-transporter inhibitors A review of SGLT2 inhibition. Clinical Diabetes 28 5-10. 

Ehrenkranz JRL, Lewis NG Kahn CR, Roth J. (2004) Phlorizin A review. Diabetes Metab Res Rev 21 31-38. 

Many allelochemicals are decomposed in soil, either abiotically (37) or by microorganisms (95-100). Obviously, the attainment of active concentrations of allelochemicals in soil depends on the relative rates of addition and inactivation. It is important to understand also that microbial decomposition of allelochemicals does not necessarily result in a decrease in allelopathic activity. In fact, the reverse may be true. Hydrojuglone is oxidized in soil to juglone, a quinone that is inhibitory to some species at a 10 ° M concentration (101). Isoflavonoids produced by red clover are decomposed to even more toxic phenolic compounds (95) and to repeat, amygdalin from peach roots is changed to hydrogen cyanide and benzaldehyde which cause the peach replant problem (88), and phlorizin from apple roots is decomposed to several phenolic compounds that appear to be responsible for the apple replant problem (100). 

Figure 1. Representative polarographic traces that depict inhibition by energy transfer inhibitors and allelochemicals of ADP-stimulated electron transport in isolated spinach thylakoids and circumvention of the inhibition by an uncoupler (FCCP, 2 pM). Trace A chlorotributyltin (TBT, 1 pM) trace B phlorizin (400 pM) trace C DCCD (20 pM) trace D quercetin (200 pM) trace E naringenin (1 mM). Water served as electron donor and methyl viologen as electron acceptor. Rates of oxygen utilization, that resulted from the autooxidation of methyl viologen, expressed as pmol 0 consumed/mg Chi h, are indicated parenthet ically.

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