Rhaponticin

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Rhaponticin

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=
PubChem	637213
	ChEMBL	CHEMBL109266^N
Jmol-3D images	Image 1
SMILES COC1=C(C=C(C=C1)C=CC2=CC(=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O
Properties
Molecular formula	C₂₁H₂₄O₉
Molar mass	420,39 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Rhaponticin is a stilbene glucoside compound. Its aglycone metabolite 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

↑ 1.0 1.1 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.

Stilbenoids and their glycosides

Aglycones

Dihydroxylated

Trihydroxylated

Resveratrol

Tetrahydroxylated

O-methylated

4-Methoxyresveratrol Gnetucleistol D (2-methoxyoxyresveratrol) Gnetucleistol E (3-methoxy-isorhapontigenin) Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene) Pterostilbene Rhapontigenin (3,3',5-trihydroxy-4'-methoxystilbene)

Combretastatins:	Combretastatin A-1 Combretastatin A-4

carboxylated

Hydrangeic acid

other acetylations

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

Glycosides

Astringin (Piceatannol 3-O-glucoside)
Foeniculoside I, II, III and IV
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

Ampelopsin C, E and H
Amurensin A, B, G and H
Balanocarpol
Carasinol B
Dibalanocarpol
Diptoindonesin C
Diptoindonesin F
Flexuosol A
Gnetin H
Hemsleyanol D
Isohopeaphenol
Kobophenol A
Laetevirenol A, B, C, D and E
Malibatol A and B
Suffruticosol A and B
Vaticanol C
Viniferal
E-ω-viniferin
Z-ω-viniferin

Tetramers:

Laetevirenol F and G

of resveratrol

Dimers	Amurensin A and H Ampelopsin A B D and F δ-viniferin ε-viniferin Leachinol F Pallidol Parthenocissin A Quadrangularin A Restrytisol A B and C

Trimers	α-viniferin Amurensin C D and G Malaysianol A Miyabenol C Resviniferin A and B trans-diptoindonesin B

Tetramers	Amurensin E F and K Gnetuhainin R (isorhapontigenin tetramer) Hopeaphenol Vaticanol B Vitisin A B and C β-viniferin (cyclic resveratrol tetramer)

Pentamers	Amurensin E and F

Higher polymers	γ-viniferin

Oligomeric forms
glycosides or conjugates

Diptoindonesin A
Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
Laevifoside (O-glucoside of ampelopsin A)

Synthetic

Stilbenoid drugs

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