Rutinose, 芦丁二糖

Rutinose is a naturally occurring polyphenol found in many plants, including the leaves and bark of rue plants. It is a glycoside derivative that has been shown to inhibit human colorectal adenocarcinoma cells (HL-60) by binding to DNA and inhibiting RNA synthesis. Rutinose also has been shown to have anti-inflammatory effects and has been used in the treatment of metabolic disorders such as diabetes mellitus. Rutinose is a bioactive compound with antioxidant properties that may be related to its ability to bind metal ions, including calcium ions at physiological pH levels. Rutinose also has been shown to have a signal peptide sequence that targets it for secretion into the blood stream, where it may act on brain functions.

Title: Rutinose

CAS Registry Number: 90-74-4

CAS Name: 6-O-(6-Deoxy-a-L-mannopyranosyl)-D-glucose

Additional Names: 6-O-a-L-rhamnosyl-D-glucose

Molecular Formula: C12H22O10

Molecular Weight: 326.30

Percent Composition: C 44.17%, H 6.80%, O 49.03%

Literature References: A disaccharide present in glycosides. Prepn from rutin by enzymatic hydrolysis using rhamnodiastase: Charaux, Compt. Rend. 178, 1312 (1924); Bull. Soc. Chim. Biol. 6, 634 (1924); Zemplén, Gerecs, Ber. 68B, 1320 (1935). Synthesis: eidem, Ber. 67B, 2049 (1934); 68B, 1318 (1935). Structure: Gorin, Perlin, Can. J. Chem. 37, 1930 (1959).

Properties: Very hygroscopic powder from alcohol and ether turning into a syrup on exposure to air. The freshly pptd material loses about 6% of its wt at 100°. The dried rutinose softens around 140°, dec 189-192°. [a]D20 +3.2° ® +0.8° (c = 4 in water). [a]D20 -10° (95% alc). Very sol in water. Sol in alc. Hydrolysis with dil HCl yields 1 mol L-rhamnose and 1 mol D-glucose.

Optical Rotation: [a]D20 +3.2° ® +0.8° (c = 4 in water); [a]D20 -10° (95% alc)

Derivative Type: Heptaacetylrutinose

Properties: mp 169-170°. [a]D20 -27.7° (chloroform).

Melting point: mp 169-170°

Optical Rotation: [a]D20 -27.7° (chloroform)