Cranberry Xyloglucan Structure and Inhibition of Escherichia coli Adhesion to Epithelial Cells

Abstract

Cranberry juice has been recognized as a treatment for urinary tract infections on the basis of scientific reports of proanthocyanidin anti-adhesion activity against Escherichia coli as well as from folklore. Xyloglucan oligosaccharides were detected in cranberry juice and the residue remaining following commercial juice extraction that included pectinase maceration of the pulp. A novel xyloglucan was detected through tandem mass spectrometry analysis of an ion at m/z 1055 that was determined to be a branched, three hexose, four pentose oligosaccharide consistent with an arabino-xyloglucan structure. Two-dimensional nuclear magnetic resonance spectroscopy analysis provided through-bond correlations for the α-L-Araf (1→2) α-D-Xylp (1→6) β-D-Glcp sequence, proving the S-type cranberry xyloglucan structure. Cranberry xyloglucan-rich fractions inhibited the adhesion of E. coli CFT073 and UTI89 strains to T24 human bladder epithelial cells and that of E. coli O157:H7 to HT29 human colonic epithelial cells. SSGG xyloglucan oligosaccharides represent a new cranberry bioactive component with E. coli anti-adhesion activity and high affinity for type 1 fimbriae.

A Human Gut Commensal Ferments Cranberry Carbohydrates To Produce Formate

“…S2). Consistent with previous studies (22,24), the purified oligosaccharides were identified as xyloglucans with degrees of polymerization (DPs) ranging from 6 to 9. MALDI-TOF MS analysis identified sodium adduct ions at 923, 953, 1,055, 1,085, 1,217, 1,247, and 1,379, which were interpreted as xyloglucan compositions of hexose 3 -pentose 3 (H 3 P 3 ), H 4 P 2 , H 3 P 4 , H 4 P 3 , H 4 P 4 , H 5 P 3 , and H 5 P 4 , respectively.…”

“…As the A2 fraction retains a pink color, there are likely small quantities of phenolic compounds that may contribute to the observed growth differential between the A2 fraction and the highly purified xyloglucans. Furthermore, the most abundant oligosaccharides within the A6 fraction are identical to the xyloglucans purified in this study (22). However, XSGGG-Ac and XSGGG-Ac2 structures (i.e., acetylated xyloglucan oligosaccharides) have been identified in the A6 fractions and did not remain in the highly purified xyloglucans.…”

“…Both of these preparations have been previously reported (22). However, the precise distribution of glycans and noncarbohydrate molecules in A2 is not fully characterized.…”

“…The cranberry cell wall does not contain appreciable quantities of monosaccharides (44) and is not expected to influence growth (22). As the A2 fraction retains a pink color, there are likely small quantities of phenolic compounds that may contribute to the observed growth differential between the A2 fraction and the highly purified xyloglucans.…”

Pectic oligosaccharide structure-function relationships: Prebiotics, inhibitors of Escherichia coli O157:H7 adhesion and reduction of Shiga toxin cytotoxicity in HT29 cells

“…The POS and MCP monosaccharide composition was analyzed, following methanolysis (Manderson, et al, 2005), by high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD), using a DX-500 (Dionex, Sunnyvale, CA, USA) system and a CarboPac PA-20 column operated at 0.5 ml/min, as described previously (Hotchkiss, Nunez, Strahan, Chau, White, Marais, et al, 2015). The HPAEC-PAD mobile phase consisted of 14 mM NaOH for 13 min, followed by a 0-120 mM CH3COONa gradient in 100 mM NaOH for 17 min and it was returned to 14 mM NaOH for 40 min prior to the next injection.…”