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Piceid

Trans-piceid
Names
IUPAC name 3-Hydroxy-5-phenyl β-D-glucopyranoside
Systematic IUPAC name (2S,3R,4S,5S,6R)-2-{3-Hydroxy-5-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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8198
ChEMBL	ChEMBL142652
ChemSpider	4445034
ECHA InfoCard	100.208.708
KEGG	C10275
PubChem CID	5281718
UNII	XM261C37CQ
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/s1Key: HSTZMXCBWJGKHG-CUYWLFDKSA-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/s1Key: HSTZMXCBWJGKHG-CUYWLFDKBI
SMILES OC1=CC(/C=C/C3=CC=C(O)C=C3)=CC(O2(O)(O)(O)(CO)O2)=C1
Properties
Chemical formula	C20H22O8
Molar mass	390.388 g·mol
Appearance	White powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. It can be found in the bark of the Sitka spruce (Picea sitchensis), hence its name. It can also be isolated from Japanese knotweed (Reynoutria japonica).

Resveratrol can be produced from piceid by the mold Aspergillus oryzae, the mold used to make sake and soy sauce, as the fungus produces a potent beta-glucosidase.

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.

Resveratrol glucoside from transgenic alfalfa prevents aberrant crypt foci in mice.

See also

• Resveratroloside (3,5,4'-trihydroxystilbene-4'-O-β-D-glucopyranoside)

References

1. 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.
2. 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.
3. ^ 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.
4. 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.
5. 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.
6. 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.

• Resveratrol glycosides