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Structure Database (LMSD)

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Common Name

Rhaponticin

Systematic Name

3',5-Dihydroxy-4'-methoxystilbene 3-O-β-D-glucopyranoside

Synonyms

Rhapontin

LM ID

LMPK13090002

Formula

C₂₁H₂₄O₉

Exact Mass

Calculate m/z

420.142035

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Rhapontin is a natural stilbenoid glycoside first isolated from rhubarb rhizomes. It is converted by glucosidases to rhapontigenin , a resveratrol analog with antioxidant and anti-cancer activity.^1,2,3 Rhapontigenin derived enzymatically from rhapontin has also been found to have antibiotic activity as well as inhibit melanin synthesis.^4,5

This information has been provided by Cayman Chemical

References

1. Roberti, M., Pizzirani, D., Simoni, D., et al. Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J. Med. Chem. 46(16), 3546-3554 (2003).

2. Chun, Y.J., Ryu, S.Y., Jeong, T.C., et al. Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin. Drug Metab. Dispos. 29(4), 389-393 (2001).

3. Roupe, K.A., Helms, G.L., Halls, S.C., et al. Preparative enzymatic synthesis and HPLC analysis of rhapontigenin: Applications to metabolism, pharmacokinetics and anti-cancer studies. J. Pharm. Pharm. Sci. 8(3), 374-386 (2005).

4. Kim, J.-K., Kim, N., and Lim, Y.-H. Evaluation of the antibacterial activity of rhapontigenin produced from rhapontin by biotransformation against Propionibacterium acnes. J. Microbiol. Biotechnol. 20(1), 82-87 (2010).

5. Lee, H.-S., Kim, J.-K., Park, K.-T., et al. Rhapontigenin converted from rhapontin purified from Rheum undulatum enhances the inhibition of melanin synthesis. Biosci. Biotechnol. Biochem. 76(12), 2307-2309 (2012).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rheum rhabarbarum (#3621)

Magnoliopsida (#3398)

Rhaponticin from rhubarb rhizomes alleviates liver steatosis and improves blood glucose and lipid profiles in KK/Ay diabetic mice.,
Planta Med, 2009

Pubmed ID: 19235684

String Representations

InChiKey (Click to copy)

GKAJCVFOJGXVIA-DXKBKAGUSA-N

InChi (Click to copy)

InChI=1S/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1

SMILES (Click to copy)

C1=C(O)C=C(/C=C/C2=CC(O)=C(OC)C=C2)C=C1O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CO