Rhaponticin

Rhaponticin
Names

IUPAC name (2S,3R,4S,5S,6R)-2-[3-Hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]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
CAS Number	155-58-8^Y
ChEMBL	ChEMBL109266^N
ChemSpider	552853^N
EC Number	205-845-0
Jmol interactive 3D	Image
KEGG	C10288^N
PubChem	637213
InChI 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
SMILES 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
Chemical formula	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).
N verify (what is ^YN ?)
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]

References

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.
↑ 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.

Hydroxystilbenes and their glycosides (monomeric forms)

Dihydroxylated

Trihydroxylated

Resveratrol

Tetrahydroxylated

O-methylated

4-Methoxyresveratrol Gnetucleistol D (2-methoxyoxyresveratrol) Gnetucleistol E (3-methoxy-isorhapontigenin) Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene) Pinostilbene (3-methoxyresveratrol) Pterostilbene (3',5'-dimethoxyresveratrol) Rhapontigenin (piceatannol 4'-methyl ether)

Combretastatins	Combretastatin A-1 Combretastatin A-4

carboxylated

Hydrangeic acid

other acylations

3,5-Dihydroxy-4-isopropyl-trans-stilbene

Glycosides

Astringin (Piceatannol 3-O-glucoside)
Isorhapontin (Isorhapontigenin glucoside)
Mulberroside A (Oxyresveratrol diglucoside)

of resveratrol	Piceid (trans-Resveratrol-3-O-glucoside) trans-Resveratrol-3-O-glucuronide Resveratroloside (trans-resveratrol-4'-O-beta-D-glucopyranoside)

of rhapontigenin	Rhapontigenin 3-O-rutinoside 4'-Methoxy-(E)-resveratrol 3-O-rutinoside Rhaponticin (Rhapontigenin glucoside)

Oligomeric forms

oligostilbenoids

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