Identification of Plasma and Urinary Metabolites and Catabolites

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Identification of Plasma and Urinary Metabolites and Catabolites Derived from Orange Juice (Poly)phenols: Analysis by High Performance Liquid Chromatography-High Resolution-Mass Spectrometry Gema Pereira-Caro, Iziar A Ludwig, Thelma Polyviou, Dalia Malkova, Ada Garcia, Jose-Manuel Moreno Rojas, and Alan Crozier J. Agric. Food Chem., Just Accepted Manuscript • DOI: 10.1021/acs.jafc.6b02088 • Publication Date (Web): 24 Jun 2016 Downloaded from http://pubs.acs.org on July 4, 2016

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Journal of Agricultural and Food Chemistry

Identification of Plasma and Urinary Metabolites and Catabolites Derived from Orange Juice (Poly)phenols: Analysis by High Performance Liquid Chromatography-High Resolution-Mass Spectrometry

Gema Pereira-Caro§, Iziar A. Ludwig$, Thelma Polyviou¶, Dalia Malkova¶ , Ada García¶, José Manuel Moreno-Rojas§, and Alan Crozier#*

§Postharvest

Technology and Agrifood Industry Area, Andalusian Institute of Agricultural

and Fishery Research and Training (IFAPA) Alameda del Obispo, Córdoba. Spain. $Department ¶

of Food Technology, Universitat de Lleida, Lleida, Spain

School of Medicine, Dentistry and Nursing, College of Medical, Veterinary and Life Science,

School of Medicine, University of Glasgow, Glasgow, UK #Department

of Nutrition, University of California, Davis, California, USA

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Journal of Agricultural and Food Chemistry

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ABSTRACT: Orange juice is a rich source of (poly)phenols, in particular the flavanones

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hesperetin-7-O-rutinoside and naringenin-7-O-rutinoside. Following the acute consumption

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of 500 mL of orange juice containing 398 µmol of (poly)phenols by 12 volunteers, 0-24 h

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plasma and urine samples were analysed by targeted high-performance liquid

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chromatography-high resolution-mass spectrometry in order to identify flavanone

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metabolites and phenolic acid and aromatic catabolites. A total of 19 flavanone metabolites

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which comprised di-O-glucuronide, O-glucuronide, O-glucuronyl-sulfate, and sulfate

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derivatives of hesperetin, naringenin and eriodictyol, and 65 microbial-derived phenolic

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catabolites, such as phenylpropanoid, phenylpropionic, phenylacetic, benzoic and

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hydroxycarboxylic acids and benzenetriol and benzoylglycine derivatives, including free

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phenolics and phase II sulfate, glucuronide and methyl metabolites, were identified or

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partially identified in plasma and/or urine samples. The data obtained provide a detailed

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evaluation of the fate of orange juice (poly)phenols as they pass through the gastrointestinal

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tract, and are absorbed into circulatory systems prior to renal excretion. Potential pathways

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for these conversions are proposed.

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KEYWORDS: orange juice, flavanones, HPLC-HR-MS identification, urinary and plasma

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metabolites; phenolic catabolites, bioavailability, humans

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Journal of Agricultural and Food Chemistry

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INTRODUCTION

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Human intervention trials have provided evidence for the protective effects against chronic

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diseases of a fruit and vegetable (poly)phenol-rich diet.1,2 Fruit juices represent a further

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option for consumers to increase their intake of (poly)phenols. In particular, orange juice (OJ)

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is of interest due to its widespread consumption and high flavanone content, predominantly in

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the form of hesperetin-7-O-rutinoside and naringenin-7-O-rutinoside3. Epidemiological

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prospective studies have shown consistent associations between the intake of flavanone-

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containing citrus fruit and prevention of various types of cancer,4,5,6 and regular consumption

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of OJ has been linked to improved vascular function.7

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Among the factors necessary to elucidate the mode of action underlying the potential

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protective effects of flavanones in humans, is an understanding of the absorption, disposition,

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metabolism and excretion (aka bioavailability) of flavanones in vivo. Following ingestion, OJ

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flavanones were, until recently, considered to be poorly bioavailable with only relatively small

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amounts of the ingested dose entering the systemic circulation, not as the parent compounds

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but as phase II metabolites, mainly glucuronide and sulfate derivatives, with studies reporting

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peak plasma concentration ranging from 63 to 1500 nM8,9 and urinary recoveries