Rhapontin, 土大黄苷

3,3',5-Trihydroxy-4'-methoxystilbene 3-O-b-D-glucoside

3,3',5-Trihydroxy-4'-methoxystilbene 3-O-β-D-glucoside (TMS) is a coumarin derivative that has been shown to have anthelmintic properties. This compound prevents the release of acetylcholine from the synapse by binding to the nicotinic acetylcholine receptor in worms and other invertebrates. It has also been shown to be a potent inhibitor of DNA polymerase in vitro. TMS binds to the enzyme's active site and inhibits its activity. The drug also interacts with human serum proteins, which may cause adverse effects such as proteinuria or hematuria. The drug is metabolized by glucuronidation, sulfation, and oxidation. Chromatographic analysis and an analytical method have been developed for quantification of TMS in biological fluids. TMS is a natural product that can be found in rhaponticum plants.

Title: Rhapontin

CAS Registry Number: 155-58-8

CAS Name: (E)-3-Hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl b-D-glucopyranoside

Additional Names: 4'-methoxy-3,3',5-stilbenetriol 3-glucoside; rhaponticin; ponticin

Molecular Formula: C21H24O9

Molecular Weight: 420.41

Percent Composition: C 59.99%, H 5.75%, O 34.25%

Literature References: From root of Rheum rhaponticum L., Polygonaceae: Hesse, J. Prakt. Chem. 77, 321 (1908); Schürhoff, Plettner, Arch. Pharm. 275, 281 (1937). On hydrolysis yields rhapontigenin and glucose: Kawamura, J. Pharm. Soc. Jpn. 58, 405 (1938), C.A. 32, 66554 (1938). Constitution of rhapontigenin: Takaoka, Proc. Imp. Acad. Tokyo 16, 408 (1940), C.A. 35, 13992 (1941).

Properties: Crystals, dec 236-237°. [a]D32 -59.5° (acetone). Exhibits bright blue fluorescence. Sol in dil alcohol, hot acetone, hot water; slightly sol in ether, alc, acetone, cold water; practically insol in benzene, petr ether, chloroform.

Optical Rotation: [a]D32 -59.5° (acetone)