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Structure Database (LMSD)

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Common Name

Avicularin

Systematic Name

Synonyms

Quercetin 3-alpha-L-arabinofuranoside

LM ID

LMPK12112167

Formula

C₂₀H₁₈O₁₁

Exact Mass

Calculate m/z

434.084915

Status

Curated

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Classification

Biological Context

Avicularin is a flavonoid glycoside that has been found in R. sachalinensis and has diverse biological activities.^1,2,3,4,5 It inhibits fatty acid synthase (FASN) and aldose reductase (IC50s = 6.15 and 19.05 µM for the chicken liver and human enzymes, respectively).^1,2 Avicularin scavenges DPPH and superoxide radicals, as well as inhibits copper-induced oxidation of LDL in cell-free assays (IC50s = 64.3, 6, and 3.8 µM, respectively).³ It inhibits LPS-induced increases in nitric oxide (NO) and prostaglandin E2 (PGE2) production in RAW 264.7 macrophages when used at concentrations ranging from 30 to 300 µM.⁴ Avicularin (100 µg/ml) inhibits the proliferation, migration, and invasion of, as well as induces apoptosis and cell cycle arrest at the G0/G1 phase in, Huh7 hepatocellular carcinoma cells.⁵

This information has been provided by Cayman Chemical

References

1. Wang, Z., Li, F., Quan, Y., et al. Avicularin ameliorates human hepatocellular carcinoma via the regulation of NF‑κB/COX‑2/PPAR‑γ activities. Mol. Med. Rep. 19(6), 5417-5423 (2019).

2. Vo, V.A., Lee, J.-W., Chang, J.-E., et al. Avicularin inhibits lipopolysaccharide-induced inflammatory response by suppressing ERK phosphorylation in RAW 264.7 macrophages. Biomol. Ther. (Seoul) 20(6), 532-537 (2012).

3. Zhang, X., Thuong, P.T., Jin, W., et al. Antioxidant activity of anthraquinones and flavonoids from flower of Reynoutria sachalinensis. Arch. Pharm. Res. 28(1), 22-27 (2005).

4. Naeem, S., Hylands, P., and Barlow, D. Construction of an Indonesian herbal constituents database and its use in Random Forest modelling in a search for inhibitors of aldose reductase. Bioorg. Med. Chem. 20(3), 1251-1258 (2012).

5. Abramson, H.N. The lipogenesis pathway as a cancer target. J. Med. Chem. 54(16), 5615-5638 (2011).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)

BDCDNTVZSILEOY-UXYNSRGZSA-N

InChi (Click to copy)

InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1

SMILES (Click to copy)

C1(O)=CC2OC(C3C=C(O)C(O)=CC=3)=C(O[C@@H]3O[C@@H](CO)[C@H](O)[C@H]3O)C(=O)C=2C(O)=C1