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Piceid

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Piceid
Names
Trans-piceid
IUPAC name 3-Hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]phenyl β-D-glucopyranoside
Systematic IUPAC name (2S,3R,4S,5S,6R)-2-{3-Hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Other names Polydatin Resveratrol 3-β-mono-D-glucoside cis-Piceid trans-Piceid 3,5,4'-Trihydroxystilbene-3-O-β-D-glucopyranoside
Identifiers
CAS Number	27208-80-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8198^Y
ChEMBL	ChEMBL142652^N
ChemSpider	4445034^N
ECHA InfoCard	100.208.708
KEGG	C10275^Y
PubChem CID	5281718
UNII	XM261C37CQ^N
CompTox Dashboard (EPA)	DTXSID001030555 DTXSID20897454, DTXSID001030555
InChI InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1^N Key: HSTZMXCBWJGKHG-CUYWLFDKSA-N^N InChI=1/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1 Key: HSTZMXCBWJGKHG-CUYWLFDKBI
SMILES OC1=CC(/C=C/C3=CC=C(O)C=C3)=CC(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)=C1
Properties
Chemical formula	C₂₀H₂₂O₈
Molar mass	390.388 g·mol⁻¹
Appearance	White powder
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

Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices.^[1] It can be found in the bark of Picea sitchensis.^[2] It can also be isolated from Reynoutria japonica (syn. Fallopia japonica),^[3] the Japanese knotweed (syn. Polygonum cuspidatum).

Resveratrol can be produced from piceid via the mold Aspergillus oryzae.^[3] as the fungus produces a potent beta-glucosidase.^[4]

trans-Piceid is the glucoside formed with trans-resveratrol, while cis-piceid is formed with cis-resveratrol.

trans-Resveratrol-3-O-glucuronide is one of the two metabolites of trans-piceid in rat.^[5]

Resveratrol glucoside from transgenic alfalfa prevents aberrant crypt foci in mice.^[6]

References[edit]

^ Romero-Pérez, A. I.; Ibern-Gómez, M.; Lamuela-Raventós, R. M.; De La Torre-Boronat, M. C. (1999). "Piceid, the Major Resveratrol Derivative in Grape Juices". Journal of Agricultural and Food Chemistry. 47 (4): 1533–1536. doi:10.1021/jf981024g. PMID 10564012.

^ Aritomi, M.; Donnelly, D. M. X. (1976). "Stilbene glucosides in the bark of Picea sitchensis". Phytochemistry. 15 (12): 2006. doi:10.1016/S0031-9422(00)88881-0.

^ ^a ^b Wang, H.; Liu, L.; Guo, Y. -X.; Dong, Y. -S.; Zhang, D. -J.; Xiu, Z. -L. (2007). "Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae". Applied Microbiology and Biotechnology. 75 (4): 763–768. doi:10.1007/s00253-007-0874-3. PMID 17333175.

^ Zhang, Chunzhi; Li, Dai; Yu, Hongshan; Zhang, Bo; Jin, Fengxie (2007). "Purification and characterization of piceid-β-d-glucosidase from Aspergillus oryzae". Process Biochemistry. 42: 83–88. doi:10.1016/j.procbio.2006.07.019.

^ 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 (1–2): 219–223. doi:10.1016/j.jchromb.2007.04.025. PMID 17500049.

^ RKineman, B. D.; Brummer, E. C.; Paiva, N. L.; Birt, D. F. (2010). "Resveratrol from Transgenic Alfalfa for Prevention of Aberrant Crypt Foci in Mice". Nutrition and Cancer. 62 (3): 351–361. doi:10.1080/01635580903407213. PMID 20358473.