Chemical Properties
Light Yellow Powder
Uses
induces experimental glucosuria, antifeedant
Uses
It is a dihydrochalcone occurring in all parts of the apple tree except the mature fruit. Once thought to occur in pear, plum, cherry trees and other Rosaceae
Uses
Sodium-glucose cotransporter 1 (SGLT1) is a high affinity, low capacity transporter abundant in the small intestine, with some expression in the kidney as well. SGLT2 is a low affinity, high capacity transporter in the kidney that accounts for approximately 90% of glucose reabsorption into the blood stream. Selective inhibition of SGLT2 is a potential strategy for reducing plasma glucose levels as a treatment for diabetes. Phlorizin is a natural product, first isolated from the bark of apple trees, that reduces plasma glucose levels by blocking renal and intestinal glucose absorption through inhibition of SGLT1 and SGLT2. It competitively inhibits the initial rate of a-methyl-D-glucopyranoside (a-MDG) uptake in human COS-1 cells expressing hSGLT1 and hSGLT2 with IC50 values of 400 and 65 nM, respectively. In HEK293T cells expressing human SGLT1 and SGLT2, phlorizin exhibits Ki values of 140 and 11 nM, respectively, at 37°C.
Definition
ChEBI: An aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 2' via a glycosidic linkage.
Synthesis
The precursors for the synthesis of Phlorizin are malonyl-coenzyme A (Malonyl-CoA) and p-coumaroyl-coenzyme A (p-coumaroyl-CoA).
Firstly, p-coumaroyl-CoA generates 4-hydroxydihydrocinnamoyl-CoA through NADPH pathway; then, malonyl-CoA and 4-hydroci
in vivo
Prior to Phlorizin treatment, the blood glucose level in SDT fatty rats is 370±49 mg/dL. Six hours after dosing, the blood glucose level in the Phlorizin treated group decreases to an almost normal level (139±32 mg/dL). Phlorizin-treated SDT fatty rats are heavier than vehicle-treated SDT fatty rats after 12 weeks. Phlorizin treatment significantly decreases glucose excretion and delays insulin decreases. Creatinine clearance decreases significantly with Phlorizin treatment. 23 weeks of Phlorizin treatment prevents the decrease of nerve fibers (23.6±3.2 fibers/mm). Retinal abnormalities are completely prevented with Phlorizin[4].
Purification Methods
-D-glucoside] [60-81-1] M 472.5, m 110o, [] 20 -62o (c 3.2, EtOH). Phlorizin crystallises as the dihydrate from water and causes glycosuria. [Brazy & Dennis Am J Physiol 234 1279 1978, Zemplen & Bognár Chem Ber 17B 1040 1943, Beilstein 17/7 V 177.]
Figure 1. the p technological process of the phlorizin extraction;