Deconvolution of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry isotope patterns to determine ratios of A-type to B-type interflavan bonds in cranberry proanthocyanidins

Feliciano, Rodrigo P.; Krueger, Christian G.; Shanmuganayagam, Dhanansayan; Vestling, Martha M.; Reed, Jess D.

doi:10.1016/j.foodchem.2012.05.102

Cited by 53 publications

(55 citation statements)

References 25 publications

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“…Over 90% of procyanidin oligomers (dimer to tetramers) in PPCP were A-type (Supporting Information Table S1). Our results were consistent with a previous study which showed that procyanidins with at least one A-type bond accounted for more than 90% of trimers through undecamers in cranberry press cake [3]. Monomers through tetramers accounted for 45% of total procyanidin, with the rest being high polymers.…”

Section: Procyanidin Composition and Content In Ppcp And Ppapsupporting

confidence: 93%

Profiling the metabolome changes caused by cranberry procyanidins in plasma of female rats using ¹H NMR and UHPLC‐Q‐Orbitrap‐HRMS global metabolomics approaches

Liu

Garrett

Tayyari

et al. 2015

Molecular Nutrition Food Res

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Scope-The objective was to investigate the metabolome changes in female rats gavaged with partially purified cranberry procyanidins (PPCP) using 1 H NMR and UHPLC-Q-Orbitrap-HRMS metabolomics approaches, and to identify the contributing metabolites.Methods and results-Twenty four female Sprague-Dawley rats were randomly separated into two groups and administered PPCP or partially purified apple procyanidins (PPAP) for 3 times using a 250 mg extracts/kg body weight dose. Plasma were collected six hours after the last gavage and analyzed using 1 H NMR and UHPLC-Q-Orbitrap-HRMS. No metabolome difference was observed using 1 H NMR metabolomics approach. However, LC-HRMS metabolomics data show that metabolome in plasma of female rats administered PPCP differed from those gavaged with PPAP. Eleven metabolites were tentatively identified from a total of 36 discriminant metabolic features based on accurate masses and/or product ion spectra. PPCP caused a greater increase of exogenous metabolites including p-hydroxybenzoic acid, phenol, phenol-sulfate, catechol sulphate, 3, 4-dihydroxyphenylvaleric acid, and 4′-O-methyl-(−)-epicatechin-3′-O-betaglucuronide in rat plasma. Furthermore, the plasma level of O-methyl-(−)-epicatechin-Oglucuronide, 4-hydroxy-5-(hydroxyphenyl)-valeric acid-O-sulphate, 5-(hydroxyphenyl)-γ-valerolactone-O-sulphate, 4-hydroxydiphenylamine, and peonidin-3-O-hexose were higher in female rats administered with PPAP.Conclusion-The metabolome changes caused by cranberry procyanidins were revealed using an UHPLC-Q-Orbitrap-HRMS global metabolomics approach. Exogenous and microbial metabolites were the major identified discriminate biomarkers.

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Section: Procyanidin Composition and Content In Ppcp And Ppapsupporting

confidence: 93%

Profiling the metabolome changes caused by cranberry procyanidins in plasma of female rats using ¹H NMR and UHPLC‐Q‐Orbitrap‐HRMS global metabolomics approaches

Liu

Garrett

Tayyari

et al. 2015

Molecular Nutrition Food Res

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“…6 Cranberry PACs are unique in the structure with a higher percentage of A-type bonds, compared with other commonly consumed fruits. In a previous study conducted by Feliciano and colleagues, 36 cranberry PACs with one A-type bond were found most abundant in DP between 2 and 5. PACs with two A-type bonds were most abundant in DP between 6 and 9.…”

Section: Discussionmentioning

confidence: 75%

A randomized, double-blind, placebo-controlled pilot study to assess bacterial anti-adhesive activity in human urine following consumption of a cranberry supplement

et al. 2019

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“…However, like Orbitrap and triple quadrupoles, when using Table 2. Percentage of PAC with at least 1 "A-type" and 2 "A-type" interflavan bonds after applying the MALDI-TOF MS deconvolution method [132] between DP 3 and 8 for cinnamon, cranberry and blueberry PAC fractions extracted with 70% acetone and isolated with Sephadex LH-20 as described previously [19] DP…”

Section: Mass Spectrometrymentioning

confidence: 99%

Methods to determine effects of cranberry proanthocyanidins on extraintestinal infections: Relevance for urinary tract health

Feliciano

Krueger

Reed

2015

Molecular Nutrition Food Res

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Urinary tract infections (UTI) are one of the most frequent extraintestinal infections caused by Escherichia coli (ExPEC). Cranberry juice has been used for decades to alleviate symptoms and prevent recurrent UTI. The putative compounds in cranberries are proanthocyanidins (PAC), specifically PAC with "A-type" bonds. Since PAC are not absorbed, their health benefits in UTI may occur through interactions at the mucosal surface in the gastrointestinal tract. Recent research showed that higher agglutination of ExPEC and reduced bacterial invasion are correlated with higher number of "A-type" bonds and higher degree of polymerization of PAC. An understanding of PAC structure-activity relationship is becoming feasible due to advancements, not only in obtaining purified PAC fractions that allow accurate estimation, but also in high-resolution MS methodologies, specifically, MALDI-TOF MS. A recent MALDI-TOF MS deconvolution method allows quantification of the ratios of "A-type" to "B-type" bonds enabling characteristic fingerprints. Moreover, the generation of fluorescently labeled PAC allows visualization of the interaction between ExPEC and PAC with microscopy. These tools can be used to establish structure-activity relationships between PAC and UTI and give insight on the mechanism of action of these compounds in the gut without being absorbed.

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Deconvolution of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry isotope patterns to determine ratios of A-type to B-type interflavan bonds in cranberry proanthocyanidins

Cited by 53 publications

References 25 publications

Profiling the metabolome changes caused by cranberry procyanidins in plasma of female rats using ¹H NMR and UHPLC‐Q‐Orbitrap‐HRMS global metabolomics approaches

Profiling the metabolome changes caused by cranberry procyanidins in plasma of female rats using ¹H NMR and UHPLC‐Q‐Orbitrap‐HRMS global metabolomics approaches

A randomized, double-blind, placebo-controlled pilot study to assess bacterial anti-adhesive activity in human urine following consumption of a cranberry supplement

Methods to determine effects of cranberry proanthocyanidins on extraintestinal infections: Relevance for urinary tract health

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Deconvolution of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry isotope patterns to determine ratios of A-type to B-type interflavan bonds in cranberry proanthocyanidins

Cited by 53 publications

References 25 publications

Profiling the metabolome changes caused by cranberry procyanidins in plasma of female rats using 1H NMR and UHPLC‐Q‐Orbitrap‐HRMS global metabolomics approaches

Profiling the metabolome changes caused by cranberry procyanidins in plasma of female rats using 1H NMR and UHPLC‐Q‐Orbitrap‐HRMS global metabolomics approaches

A randomized, double-blind, placebo-controlled pilot study to assess bacterial anti-adhesive activity in human urine following consumption of a cranberry supplement

Methods to determine effects of cranberry proanthocyanidins on extraintestinal infections: Relevance for urinary tract health

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Resources

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Profiling the metabolome changes caused by cranberry procyanidins in plasma of female rats using ¹H NMR and UHPLC‐Q‐Orbitrap‐HRMS global metabolomics approaches

Profiling the metabolome changes caused by cranberry procyanidins in plasma of female rats using ¹H NMR and UHPLC‐Q‐Orbitrap‐HRMS global metabolomics approaches