Piceid

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Piceid
Piceid.svg
Trans-piceid
Identifiers
CAS number 27208-80-6 YesY
PubChem 5281718
ChemSpider 4445034 N
UNII XM261C37CQ N
ChEMBL CHEMBL142652 N
Jmol-3D images Image 1
Properties
Molecular formula C20H22O8
Molar mass 390.384 g/mol
Appearance white powder
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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 Polygonum cuspidatum,[3] the Japanese knotweed (syn. Fallopia japonica).

Resveratrol can be produced from piceid fermented by Aspergillus oryzae.[3] This latter species produces a piceid-b-D-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 has been used for the prevention of aberrant crypt foci in mice.[6]

See also[edit]

References[edit]

  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.  edit
  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.  edit
  3. ^ 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.  edit
  4. ^ Purification and characterization of piceid-b-D-glucosidase from Aspergillus oryzae. Chunzhi Zhang, Dai Li, Hongshan Yu, Bo Zhang and Fengxie Jin, Process Biochemistry, 2007, 42, pages 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: 219. doi:10.1016/j.jchromb.2007.04.025.  edit
  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.  edit