Caffeic acid 4-O-glucoside

Biosci Biotechnol Biochem . 2010;74(9):1920-1924.

Biotransformation of cinnamic acid, p-coumaric acid, caffeic acid, and ferulic acid by plant cell cultures of Eucalyptus perriniana[Pubmed: 20834169]

Biotransformations of phenylpropanoids such as cinnamic acid, p-coumaric acid, caffeic acid, and ferulic acid were investigated with plant-cultured cells of Eucalyptus perriniana. The plant-cultured cells of E. perriniana converted cinnamic acid into cinnamic acid β-D-glucopyranosyl ester, p-coumaric acid, and 4-O-β-D-glucopyranosylcoumaric acid. p-Coumaric acid was converted into 4-O-β-D-glucopyranosylcoumaric acid, p-coumaric acid β-D-glucopyranosyl ester, 4-O-β-D-glucopyranosylcoumaric acid β-D-glucopyranosyl ester, a new compound, caffeic acid, and 3-O-β-D-glucopyranosylcaffeic acid. On the other hand, incubation of caffeic acid with cultured E. perriniana cells gave 3-O-β-D-glucopyranosylcaffeic acid, 3-O-(6-O-β-D-glucopyranosyl)-β-D-glucopyranosylcaffeic acid, a new compound, 3-O-β-D-glucopyranosylcaffeic acid β-D-glucopyranosyl ester, 4-O-β-D-glucopyranosylcaffeic acid, 4-O-β-D-glucopyranosylcaffeic acid β-D-glucopyranosyl ester, ferulic acid, and 4-O-β-D-glucopyranosylferulic acid. 4-O-β-D-Glucopyranosylferulic acid, ferulic acid β-D-glucopyranosyl ester, and 4-O-β-D-glucopyranosylferulic acid β-D-glucopyranosyl ester were isolated from E. perriniana cells treated with ferulic acid.

Food Chem . 2020 Jun 1;314:126181.

Polyphenols and inhibitory effects of crude and purified extracts from tomato varieties on the formation of advanced glycation end products and the activity of angiotensin-converting and acetylcholinesterase enzymes[Pubmed: 31954938]

The study analyzed the inhibitory effects (IC50) of crude and purified extracts from Maliniak, Cerise, Black Prince and Lima tomatoes on the formation of advanced glycation end products (AGEs), the activity of angiotensin-converting (ACE) and acetylcholinesterase (AChE) enzymes. Polyphenol composition (LC-MS) and antioxidant capacity (PCL, FRAP) were measured. The purified extracts of Black Prince tomatoes were the most potent inhibitors of AGEs in BSA-GLU (7.20mg/mL) and BSA-MGO (9.53mg/mL) models. The purified extracts of Cerise and Black Prince tomatoes had the highest ACE (0.50-0.44mg/mL) and AChE (7.93-5.83mg/mL) inhibitory activity. Cerise variety showed the highest polyphenol concentrations in crude (488.93μg/g DM) and purified (8394.99μg/g DM) extracts. The highest PCLACW and FRAP values were found for Cerise purified extracts (71.83 and 87.78μmol Trolox/g DM). Caffeic acid, caffeoyl-glucose, linocaffein, glucosyl-coumarate, vanillic acid, rutin and TPI values were significantly correlated with BSA-MGO, anti-ACE, anti-AChE and PCLACW parameters.

Nat Prod Res . 2015 Feb;29(3):262-267.

A new hemiterpene glycoside from the ripe tomatoes[Pubmed: 25421719]

A new hemiterpene glycoside (1) was isolated from ripe tomatoes (the fruit of Lycopersicon esculentum, Solanaceae) along with eight known compounds. The chemical structure of 1 was determined to be 2-methylbutan-1-ol β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside, based on spectroscopic data as well as chemical evidence. In addition, the radical-scavenging activities of the isolated compounds on the free radical of 1,1-diphenyl-2-picrylhydrazyl were examined. Among the tested compounds, tryptophan, 4-O-β-d-glucopyranosyl caffeic acid and dihydro-p-coumaryl alcohol γ-O-β-d-glucopyranoside demonstrated 42.0%, 50.1% and 76.0% scavenging activities, respectively, at a concentration of 0.5 mM.

J Nat Prod . 2015 Sep 25;78(9):2297-2300.

Active Constituents from Drynaria fortunei Rhizomes on the Attenuation of Aβ(25-35)-Induced Axonal Atrophy[Pubmed: 26299900]

Axonal regeneration might contribute to the restoration of damaged neuronal networks and improvement of memory deficits in a murine Alzheimer's disease (AD) model. A search for axonal regenerative drugs was performed to discover novel therapeutic options for AD. In this study, an aqueous extract of Drynaria fortunei rhizomes reversed Aβ25-35-induced axonal atrophy in cultured cortical neurons of mice. Bioassay-guided fractionation of this extract led to the isolation and identification of compounds 1-5. Among them, (2S)-neoeriocitrin (2) and Caffeic acid 4-O-glucoside (4) showed significant axonal elongation effects on Aβ25-35-induced atrophy.

Molecules . 2008 Mar 27;13(4):729-735.

Three new caffeoyl glycosides from the roots of Picrorhiza scrophulariiflora[Pubmed: 18463574]

From the underground parts of Picrorhiza scrophulariiflora, three new caffeoyl glycosides, scrocaffeside A-C (1-3), together with two caffeic acid derivates, 4-O-beta-D-glucopyranosyl caffeic acid (4) and 4-methoxy caffeic acid (5) and a phenylethanoid glycoside, scroside D (6), were isolated. Their structures were elucidated on the basis of chemical and spectroscopic evidence and comparisons with literature data of related compounds.