Profiling of Carotenoids in Tomato Juice by One- and Two-Dimensional NMR

Stefano Tiziani,† Steven J. Schwartz,§ and Yael Vodovotz*§
CR U.K. Institute for Cancer Studies, University of Birmingham, Henry Wellcome Building for Biomolecular NMR Spectroscopy (HWB-NMR), Vincent Drive Edgbaston, Birmingham B152TT, United Kingdom, and Department of Food Science and Technology, Parker Food Science and Technology Building, The Ohio State University, 2015 Fyffe Road, Columbus, Ohio 43210
J. Agric. Food Chem., 2006, 54 (16), pp 6094–6100
DOI: 10.1021/jf061154m
Publication Date (Web): July 7, 2006
Copyright © 2006 American Chemical Society
†

 University of Birmingham.

,
§

 The Ohio State University.

,
*

 Author to whom correspondence should be addressed [telephone (614) 247-7696; fax (614) 292-0218; e-mail vodovotz.1@osu.edu].

Abstract

Epidemiological data have shown a link between dietary intake of tomatoes and tomato products (rich in carotenoids) and a decreased risk of chronic diseases. The carotenoid profile in tomato products depends on tomato variety as well as the thermal conditions used in processing. The final carotenoid profile may affect the bioaccessibility and bioavailability of these biomolecules. Therefore, nondestructive, reliable methods are needed to characterize the structural and stereochemical variation of carotenoids. CDCl3 rapid extraction was used to extract carotenoids from tomato juice as an alternative rapid procedure that minimizes solvents and time consumption prior to NMR analysis. The profile of these biomolecules was characterized by application of high-resolution multidimensional NMR techniques using a cryogenic probe. The combination of homonuclear and heteronuclear two-dimensional NMR techniques served to identify (all-E)-, (5Z)-, (9Z)-, and (13Z)-lycopene isomers and other carotenoids such as (all-E)-β-carotene and (15Z)-phytoene dissolved in the extracted lipid mixture. The use of one-dimensional NMR enabled the rapid identification of lycopene isomers, thereby minimizing further isomerization of (all-E)-lycopene as compared to HPLC data. On the basis of the assignments accomplished, the carotenoid profile of typical tomato juice was successfully determined with minimal purification procedures.

Keywords: 1D and 2D NMR; HPLC; UV−visible; carotenoids; lycopene isomers; lipid mixture

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History

  • Published In Issue August 09, 2006
  • Received for review April 24, 2006. Revised manuscript received June 8, 2006. Accepted June 13, 2006. This material is based upon work supported by the USDA under Award 2001-52102-11333.

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