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Structure Database (LMSD)

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Common Name

Piceid

Systematic Name

3,5,4'-Trihydroxystilbene-3-O-β-D-glucopyranoside

Synonyms

Polydatin
3,4,5-Trihydroxystilbene-3-beta-monoglucoside
Resveratrol 3-beta-mono-D-glucoside

LM ID

LMPK13090012

Formula

C₂₀H₂₂O₈

Exact Mass

Calculate m/z

390.13147

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

Polydatin is a stilbene glucoside and a precursor to trans-resveratrol that has been found in V. vinifera and has diverse biological activities.^1,2,3 It scavenges DPPH radicals and inhibits copper-induced lipid peroxidation (IC50s = 198 and 19.1 µM, respectively).¹ Polydatin inhibits the proliferation of, and induces cell cycle arrest at the S phase in, Caco-2 colon cancer cells.² It decreases infarct size, cardiomyocyte fibrosis, and apoptosis in a mouse model of myocardial ischemia-reperfusion injury induced by left anterior descending (LAD) coronary artery occlusion when administered at a dose of 40 mg/kg per day.³

This information has been provided by Cayman Chemical

References

1. De Maria, S., Scognamiglio, I., Lombardi, A., et al. Polydatin, a natural precursor of resveratrol, induces cell cycle arrest and differentiation of human colorectal Caco-2 cell. J. Transl. Med. 11, 264 (2013).

2. Teguo, P.W., Fauconneau, B., Deffieux, G., et al. Isolation, identification, and antioxidant activity of three stilbene glucosides newly extracted from Vitis vinifera cell cultures. J. Nat. Prod. 61(5), 655-677 (1998).

3. Ming, D., Songyan, L., Yawen, C., et al. trans-Polydatin protects the mouse heart against ischemia/reperfusion injury via inhibition of the renin-angiotensin system (RAS) and Rho kinase (ROCK) activity. Food Funct. 8(6), 2309-2321 (2017).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Vitis vinifera (#29760)

Magnoliopsida (#3398)

Isolation, identification, and antioxidant activity of three stilbene glucosides newly extracted from vitis vinifera cell cultures,
J Nat Prod, 1998

Pubmed ID: 9599270

String Representations

InChiKey (Click to copy)

HSTZMXCBWJGKHG-CUYWLFDKSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1=C(O)C=C(/C=C/C2=CC=C(O)C=C2)C=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1