Piceid: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 400656814

| ImageSize = 250px

| ImageCaption = Trans-piceid

| IUPACName = 3-Hydroxy-5-[(''E'')-2-(4-hydroxyphenyl)ethen-1-yl]phenyl β-<small>D</small>-glucopyranoside

| SystematicName = (2''S'',3''R'',4''S'',5''S'',6''R'')-2-{3-Hydroxy-5-[(''E'')-2-(4-hydroxyphenyl)ethen-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

| OtherNames = Polydatin<br>Resveratrol 3-β-mono-<small>D</small>-glucoside<br>''cis''-Piceid<br>''trans''-Piceid<br>3,5,4'-Trihydroxystilbene-3-O-β-D-glucopyranoside

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 142652

| PubChem = 5281718

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = XM261C37CQ

| 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

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4445034

| 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

| InChIKey = HSTZMXCBWJGKHG-CUYWLFDKBI

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = HSTZMXCBWJGKHG-CUYWLFDKSA-N

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 8198

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C10275

}}

|Section2={{Chembox Properties

| C=20 | H=22 | O=8

| Appearance = White powder

| MeltingPt_notes =

| BoilingPt_notes =

|Section7={{Chembox Hazards

| NFPA-S =

| HPhrases =

| PPhrases =

| GHS_ref =

| AutoignitionPt =

| PEL =

}}

'''Piceid''' is a [[stilbenoid]] [[glucoside]] and is a major [[resveratrol]] derivative in grape juices.<ref>{{Cite journal | last1 = Romero-Pérez | first1 = A. I. | last2 = Ibern-Gómez | first2 = M. | last3 = Lamuela-Raventós | first3 = R. M. | last4 = De La Torre-Boronat | first4 = M. C. | title = Piceid, the Major Resveratrol Derivative in Grape Juices | doi = 10.1021/jf981024g | journal = Journal of Agricultural and Food Chemistry | volume = 47 | issue = 4 | pages = 1533–1536 | year = 1999 | pmid = 10564012}}</ref> It can be found in the bark of ''[[Picea sitchensis]]''.<ref>{{Cite journal | last1 = Aritomi | first1 = M. | last2 = Donnelly | first2 = D. M. X. | doi = 10.1016/S0031-9422(00)88881-0 | title = Stilbene glucosides in the bark of ''Picea sitchensis'' | journal = Phytochemistry | volume = 15 | issue = 12 | pages = 2006 | year = 1976 }}</ref> It can also be isolated from ''[[Reynoutria japonica]]'' ([[Synonym (taxonomy)|syn.]] ''Fallopia japonica''),<ref name=Wang>{{Cite journal

| last1 = Wang | first1 = H.

| last2 = Liu | first2 = L.

| last3 = Guo | first3 = Y. -X.

| last4 = Dong | first4 = Y. -S.

| last5 = Zhang | first5 = D. -J.

| last6 = Xiu | first6 = Z. -L.

| doi = 10.1007/s00253-007-0874-3

| title = Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae

| journal = Applied Microbiology and Biotechnology

| volume = 75

| issue = 4

| pages = 763–768

| year = 2007

| pmid = 17333175

}}</ref> the Japanese knotweed (syn. ''Polygonum cuspidatum'').

[[Resveratrol]] can be produced from piceid via the mold ''[[Aspergillus oryzae]]''.<ref name=Wang/> as the fungus produces a potent [[beta-glucosidase]].<ref>{{cite journal | doi = 10.1016/j.procbio.2006.07.019| title = Purification and characterization of piceid-β-d-glucosidase from Aspergillus oryzae| journal = Process Biochemistry| volume = 42| pages = 83–88| year = 2007| last1 = Zhang| first1 = Chunzhi| last2 = Li| first2 = Dai| last3 = Yu| first3 = Hongshan| last4 = Zhang| first4 = Bo| last5 = Jin| first5 = Fengxie}}</ref>

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

[[Trans-Resveratrol-3-O-glucuronide|''trans''-Resveratrol-3-''O''-glucuronide]] is one of the two metabolites of ''trans''-piceid in rat.<ref>{{Cite journal | last1 = Zhou | first1 = M. | last2 = Chen | first2 = X. | last3 = Zhong | first3 = D. | title = Simultaneous determination of trans-resveratrol-3-O-glucoside and its two metabolites in rat plasma using liquid chromatography with ultraviolet detection | doi = 10.1016/j.jchromb.2007.04.025 | journal = Journal of Chromatography B | volume = 854 | issue = 1–2 | pages = 219–223 | year = 2007 | pmid = 17500049}}</ref>

Resveratrol glucoside from transgenic alfalfa prevents [[aberrant crypt foci]] in mice.<ref>R{{Cite journal | last1 = Kineman | first1 = B. D. | last2 = Brummer | first2 = E. C. | last3 = Paiva | first3 = N. L. | last4 = Birt | first4 = D. F. | title = Resveratrol from Transgenic Alfalfa for Prevention of Aberrant Crypt Foci in Mice | doi = 10.1080/01635580903407213 | journal = Nutrition and Cancer | volume = 62 | issue = 3 | pages = 351–361 | year = 2010 | pmid = 20358473}}</ref>

== See also ==

* [[Resveratroloside]] (3,5,4'-trihydroxystilbene-4'-O-β-D-glucopyranoside)

== References ==

{{Reflist}}

{{stilbenes}}

[[Category:Resveratrol glycosides]]