Article · Wikipedia archive · Last revised Jul 1, 2026

Piceid

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, hence its name. It can also be isolated from Japanese knotweed.

Last revised
Jul 1, 2026
Read time
≈ 2 min
Length
392 w
Citations
7
Source
Wikipedia ↗
Piceid
source ↗
Trans-piceid
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.208.708
KEGG
UNII
  • 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
  • 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
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 checkY☒N ?)

Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices.1 It can be found in the bark of the Sitka spruce (Picea sitchensis), hence its name.2 It can also be isolated from Japanese knotweed (Reynoutria japonica).3

Resveratrol can be produced from piceid by the mold Aspergillus oryzae,3 the mold used to make sake and soy sauce, 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

See also

See also

References

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.