LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Astringin

Systematic Name

Synonyms

LM ID

LMPK13090007

Formula

C₂₀H₂₂O₉

Exact Mass

Calculate m/z

406.126385

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Astringin is a phenolic stilbene glucoside that has been found in V. vinifera and has antioxidant and antineoplastic activities.^1,2 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals (IC50 = 30.2 μM) in a cell-free assay and inhibits cupric ion-induced lipid peroxidation of human LDL (IC50 = 3 μM).¹ Astringin (10 µg/ml) inhibits development of preneoplastic lesions induced by 7,12-dimethylbenz(a)anthracene (DMBA) in mouse mammary gland organ cultures by 68.8%.²

This information has been provided by Cayman Chemical

References

1. Tegeo, 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), 655-657 (1998).

2. Waffo-Téguo, P., Hawthorne, M.E., Cuendet, M., et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr. Cancer 40(2), 173-179 (2001).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Picea sitchensis (#3332)

Pinopsida (#58019)

Astringin and isorhapontin distribution in Sitka spruce trees,
Phytochemistry, 1991

DOI: 10.1016/0031-9422(91)83610-W

String Representations

InChiKey (Click to copy)

PERPNFLGJXUDDW-CUYWLFDKSA-N

InChi (Click to copy)

InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1

SMILES (Click to copy)

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