(+)-Syringaresinol

Inhibition of Helicobacter pylori motility by (+)-Syringaresinol from unripe Japanese apricot.[Pubmed:16394533]

Biol Pharm Bull. 2006 Jan;29(1):172-3.

A methanol extract from unripe Japanese apricot showed inhibitory activity of Helicobacter pylori motility. Inhibitory compound 1 was isolated and identified as (+)-Syringaresinol (1) by spectoroscopic means. (+)-Syringaresinol (1) inhibited >90% of the H. pylori motility at a concentration of 500 microg/ml and the IC50 value was 50 microg/ml.

Isolation and identification of compounds responsible for antioxidant capacity of Euryale ferox seeds.[Pubmed:21280632]

J Agric Food Chem. 2011 Feb 23;59(4):1199-204.

Euryale ferox seed is consumed medicinally or for food in China. The present study revealed it to contain significant antioxidant activity, which may be associated with its medical applications as a proteinuria inhibitor of diabetic nephropathy. This study resulted in the identification of 3 new sesquineolignans, named euryalins A-C (1-3), and 16 known compounds, which were all first isolated from this plant apart from 5,7,4-trihydroxy-flavanone. The antioxidant potential of the partial isolates was evaluated using the DPPH radical scavenging assay and mesangial cellular assay. Compounds 2, rel-(2alpha,3beta)-7-O-methylcedrusin (4), syringylglycerol-8-O-4-(sinapyl alcohol) ether (5), and (+)-Syringaresinol (7) were found to be most active on DPPH assay, whereas compounds 2, 4, 7, (1R,2R,5R,6S)-2-(3,4-dimethoxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3. 3.0]octane, and buddlenol E could significantly inhibit high glucose-stimulated reactive oxygen species production in mesangial cells. The results suggested that E. ferox seed could be considered as an excellent source of natural antioxidants and is useful in the prevention of diabetic nephropathy.

Enantioselective induction of SIRT1 gene by syringaresinol from Panax ginseng berry and Acanthopanax senticosus Harms stem.[Pubmed:25479772]

Bioorg Med Chem Lett. 2015 Jan 15;25(2):307-9.

Syringaresinol exists either exclusively as one enantiomer or enantiomeric mixtures in plant foods. We found that (+)-Syringaresinol, but not (-)-syringaresinol, upregulates silent information regulator two ortholog 1 (SIRT1) gene expression, and thus, Panax ginseng berry with predominantly high contents of (+)-Syringaresinol exhibits higher activity in inducing SIRT1 gene expression than Acanthopanax senticosus Harms stem with almost equal proportion of the two enantiomers. These findings highlight the importance of the absolute configuration of syringaresinol for the biological activity.

Lignans and other constituents of the fruits of Euterpe oleracea (Acai) with antioxidant and cytoprotective activities.[Pubmed:18656934]

J Agric Food Chem. 2008 Sep 10;56(17):7759-64.

Using a hydroxyl radical scavenging assay, bioactivity-guided fractionation of a methanol-soluble extract of the fruits of Euterpe oleracea (acai) led to the isolation of 22 compounds of previously known structure. Altogether, 14 of these isolates were found to be active in an in vitro hydroxyl radical scavenging assay and seven of these isolates in a 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Dihydroconiferyl alcohol, (+)-lariciresinol, (+)-pinoresinol, (+)-Syringaresinol, and protocatechuic acid methyl ester exhibited cytoprotective activity in cultured MCF-7 cells stressed by H2O2. Lignans have not been previously reported as constituents of this species and were found to be representative of the aryltetrahydronaphthalene, dihydrobenzofuran, furofuran, 8-O-4'-neolignan, and tetrahydrofuran structural types.