Rhaponticin
Chemical structure of rhaponticin
Names
IUPAC name
3-Hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethen-1-yl]phenyl β-D-glucopyranoside
Systematic IUPAC name
(2S,3R,4S,5S,6R)-2-{3-Hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethen-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
3',5-Dihydroxy-4'-methoxystilbene 3-O-beta-D-glucopyranoside
Ponticin
Rhapontin
Rhapontigenin glucoside
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.315
EC Number
  • 205-845-0
KEGG
UNII
  • 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 ☒N
    Key: GKAJCVFOJGXVIA-DXKBKAGUSA-N ☒N
  • InChI=1/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
    Key: GKAJCVFOJGXVIA-DXKBKAGUBB
  • COc1ccc(cc1O)/C=C/c2cc(cc(c2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
Properties
C21H24O9
Molar mass 420,39 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Rhaponticin is a stilbenoid glucoside compound. Its aglycone is called rhapontigenin. It can be found in rhubarb rhizomes.[1]

It has beneficial effects on diabetic mice,[1] and in vitro results suggest it may be relevant to Alzheimer's disease with an action on beta amyloid.[2] It is a phytoestrogen and has estrogenic activity.[3][4]

References

  1. 1 2 Chen, Jinlong; Ma, Mengmeng; Lu, Yanwei; Wang, Lisheng; Wu, Chutse; Duan, Haifeng (2009). "Rhaponticin from Rhubarb Rhizomes Alleviates Liver Steatosis and Improves Blood Glucose and Lipid Profiles in KK/Ay Diabetic Mice". Planta Medica. 75 (5): 472–7. doi:10.1055/s-0029-1185304. PMID 19235684.
  2. ↑ Misiti, F; Sampaolese, B; Mezzogori, D; Orsini, F; Pezzotti, M; Giardina, B; Clementi, M (2006). "Protective effect of rhubarb derivatives on amyloid beta (1–42) peptide-induced apoptosis in IMR-32 cells: A case of nutrigenomic". Brain Research Bulletin. 71 (1–3): 29–36. doi:10.1016/j.brainresbull.2006.07.012. PMID 17113925. S2CID 31748806.
  3. ↑ Nirali Prakashan (2009). Pharmacognosy. Nirali Prakashan. pp. 8–. ISBN 978-81-963961-5-2.
  4. ↑ Andrea R. Genazzani; Basil C. Tarlatzis (1 December 2015). Frontiers in Gynecological Endocrinology: Volume 3: Ovarian Function and Reproduction - From Needs to Possibilities. Springer. pp. 178–. ISBN 978-3-319-23865-4.


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