trans-Resveratrol-3-O-glucuronide

*trans*-Resveratrol-3-O-glucuronide
Names

IUPAC name (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]oxane-2-carboxylic acid
Identifiers
CAS Registry Number	387372-17-0
ChemSpider	4437760
InChI InChI=1S/C20H20O9/c21-12-5-3-10(4-6-12)1-2-11-7-13(22)9-14(8-11)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h1-9,15-18,20-25H,(H,26,27)/b2-1+/t15-,16-,17+,18-,20+/m0/s1 Key: QWSAYEBSTMCFKY-OTPOQTMVSA-N InChI=1/C20H20O9/c21-12-5-3-10(4-6-12)1-2-11-7-13(22)9-14(8-11)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h1-9,15-18,20-25H,(H,26,27)/b2-1+/t15-,16-,17+,18-,20+/m0/s1 Key: QWSAYEBSTMCFKY-OTPOQTMVBZ
Jmol-3D images	Image
PubChem	5273285
SMILES O=C(O)[C@H]3O[C@@H](Oc2cc(O)cc(\C=C\c1ccc(O)cc1)c2)[C@H](O)[C@@H](O)[C@@H]3O
Properties
Molecular formula	C₂₀H₂₀O₉
Molar mass	404.37 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

trans-Resveratrol-3-O-glucuronide is a metabolite of resveratrol^[1] and trans-resveratrol-3-O-glucoside (piceid).^[2]^[3]

References

↑ Urpi-Sarda, M.; Zamora-Ros, R.; Lamuela-Raventos, R.; Cherubini, A.; Jauregui, O.; De La Torre, R.; Covas, M. I.; Estruch, R.; Jaeger, W.; Andres-Lacueva, C. (2006). "HPLC-Tandem Mass Spectrometric Method to Characterize Resveratrol Metabolism in Humans". Clinical Chemistry 53 (2): 292–299. doi:10.1373/clinchem.2006.071936. PMID 17170057.
↑ Zhou, M.; Chen, X.; Zhong, D. (2007). "Simultaneous determination of trans-resveratrol-3-O-glucoside and its two metabolites in rat plasma using liquid chromatography with ultraviolet detection". Journal of Chromatography B 854: 219. doi:10.1016/j.jchromb.2007.04.025.
↑ Mikulski, D.; Molski, M. (2010). "Quantitative structure–antioxidant activity relationship of trans-resveratrol oligomers, trans-4,4′-dihydroxystilbene dimer, trans-resveratrol-3-O-glucuronide, glucosides: Trans-piceid, cis-piceid, trans-astringin and trans-resveratrol-4′-O-β-D-glucopyranoside". European Journal of Medicinal Chemistry 45 (6): 2366–2380. doi:10.1016/j.ejmech.2010.02.016. PMID 20199826.

Hydroxystilbenes and their glycosides (monomeric forms)

Dihydroxylated

Trihydroxylated

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

other acylations

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