Phlorizin, 根皮苷

Potent, competitive SGLT inhibitor (IC50 values are 400 and 65 nM for SGLT1 and SLGT2 respectively). Induces renal glycosuria and blocks intestinal glucose absorption in vivo. Orally active.

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 SGLT2.2,3 It competitively inhibits the initial rate of α-methyl-D-glucopyranoside (α-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.

Phloridzin analytical standard provided with w/w absolute assay, to be used for quantitative titration.

Phlorizin, also known as phlorizoside or phlorrhizen, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Phlorizin exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Within the cell, phlorizin is primarily located in the cytoplasm. Phlorizin can be biosynthesized from phloretin. Phlorizin is a bitter tasting compound that can be found in a number of food items such as moth bean, chinese broccoli, celeriac, and japanese persimmon. This makes phlorizin a potential biomarker for the consumption of these food products.

Phlorizin is an aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 2' via a glycosidic linkage. It has a role as a plant metabolite and an antioxidant. It is an aryl beta-D-glucoside, a member of dihydrochalcones and a monosaccharide derivative. It derives from a phloretin.

Title: Phloridzin

CAS Registry Number: 60-81-1

CAS Name: 1-[2-(b-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone

Additional Names: phlorhizin; phlorizin; phlorrhizen; phloretin-2¢-b-glucoside; 4,6-dihydroxy-2-(b-D-glucosido)-b-(p-hydroxyphenyl)propiophenone

Molecular Formula: C21H24O10

Molecular Weight: 436.41

Percent Composition: C 57.80%, H 5.54%, O 36.66%

Literature References: 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: A. H. Williams in Comparative Phytochemistry, T. Swain, Ed. (Academic Press, New York, 1966) pp 297-307. Isoln from root bark: De Koninck, Ann. 15, 75, 258 (1835); Stass, Ann. 30, 192 (1839); Bridel, Kramer, Bull. Soc. Chim. Biol. 15, 544 (1933). Hydrolysis by dil mineral acids yields phloretin and glucose. Procedure for acid hydrolysis: Wessely, Sturm, Monatsh. Chem. 53-54, 557 (1929); Müller, Robertson, J. Chem. Soc. 1933, 1170. The energy of activation required for the hydrolysis is much less than for other glucosides and approaches that for g-fructosides (sucrose, raffinose). Is hydrolyzed by saccharase at pH 4.45, by enzymes of Aspergillus niger and other enzymes found in invertebrates: Kobert, Pfluegers Arch. Gesamte Physiol. Menschen Tiere 99, 116 (1903); Moelwyn-Hughes, J. Gen. Physiol. 13, 807 (1930); cf. Trans. Faraday Soc. 25, 81 (1929). Synthesis: Zemplen, Bognár, Ber. 75B, 1040 (1942); cf. ibid. 645 and 76B, 386 (1943).

Derivative Type: Dihydrate

Properties: Long needles from water, mp 110°. Sweet, with bitter aftertaste. [a]D25 -52° (0.16 g in 5 ml of 96% alcohol). One gram dissolves in about one liter of water at 22°, in 64 ml at 60°, in 22 ml at 70°. Freely sol in boiling water; in about 4 parts alcohol, in methanol, amyl alcohol, acetone, ethyl acetate, pyridine, aniline, quinoline and other organic bases; in aq alkaline solns and in glacial acetic acid. Practically insol in ether, chloroform, benzene.

Melting point: mp 110°

Optical Rotation: [a]D25 -52° (0.16 g in 5 ml of 96% alcohol)

Use: Experimentally to produce glycosuria in animals.