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Rhaponticin

From Wikipedia, the free encyclopedia
Rhaponticin
Chemical structure of 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 InfoCard100.005.315Edit this at Wikidata
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 mass420,39 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Rhaponticin is astilbenoidglucoside compound. Itsaglycone is calledrhapontigenin. It can be found inrhubarbrhizomes.[1]

It has beneficial effects ondiabetic mice,[1] andin vitro results suggest it may be relevant toAlzheimer's disease with an action onbeta amyloid.[2] It is aphytoestrogen and hasestrogenic activity.[3][4]

References

[edit]
  1. ^abChen, 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.Bibcode:2009PlMed..75..472C.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.
Hydroxystilbenes and theirglycosides (monomeric forms)
Dihydroxylated
Trihydroxylated
Tetrahydroxylated
O-methylated
Combretastatins
carboxylated
other acylations
Glycosides
of resveratrol
of rhapontigenin
Oligomeric forms
Phytoestrogens
Flavanones
Flavones
Prenylflavonoids
Isoflavones
Isoflavanes
Dihydrochalcones
Isoflavenes
Coumestans
Lignans
Flavonolignans
Flavonols
Others
Mycoestrogens
Derivatives
Synthetic
Metalloestrogens
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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