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).
 Trans-piceid
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| Names | |
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| IUPAC name
3-Hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]phenyl β-D-glucopyranoside
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| 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)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.208.708 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
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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]
See also
edit- Resveratroloside (3,5,4'-trihydroxystilbene-4'-O-β-D-glucopyranoside)
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.