Identification of 3-methoxyzeaxanthin as a novel age-related carotenoid metabolite in the human macula

Invest Ophthalmol Vis Sci. 2007 Apr;48(4):1435-40. doi: 10.1167/iovs.06-1046.

Abstract

Purpose: The xanthophyll carotenoids lutein and zeaxanthin, along with their major metabolites, meso-zeaxanthin, and 3'-oxolutein, are highly concentrated in the human macula. In addition to these two metabolites, there are still others that have not yet been identified. A highly sensitive HPLC-mass spectral method was used to identify and quantify a new xanthophyll metabolite that increases with age.

Methods: Maculae (4-mm diameter) from donor eyes free of ocular disease were procured from the local eye bank. The carotenoid extracts from each tissue sample were analyzed by HPLC coupled with an in-line single quadrupole mass spectrometer in a positive ion atmospheric pressure chemical ionization mode. The elution profile, visible absorption spectra and mass spectra were compared to synthetic standards to identify the ocular carotenoids and their metabolites.

Results: Along with 3'-oxolutein and meso-zeaxanthin, a relatively nonpolar zeaxanthin derivative was identified, with m/z 582.5 and spectral properties similar to those of dietary zeaxanthin. This compound was identified as 3-methoxyzeaxanthin (3-MZ) based on elution profile, absorption spectra, and mass spectra in comparison to a synthetic standard. 3-MZ increased with age (P < 0.001) and was not detectable in peripheral retina or in nonretinal tissues.

Conclusions: Identification of 3-MZ in the macula of aged donors indicates that O-methylation of carotenoids is a potential biomarker for aging and age-related ocular disorders.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adult
  • Aged
  • Aging / physiology*
  • Chromatography, High Pressure Liquid
  • Eye Proteins / analysis*
  • Eye Proteins / chemical synthesis
  • Eye Proteins / chemistry
  • Humans
  • Lutein / analysis
  • Macula Lutea / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Tissue Donors
  • Xanthophylls / analysis*
  • Xanthophylls / chemical synthesis
  • Xanthophylls / chemistry
  • Zeaxanthins

Substances

  • 3-methoxyzeaxanthin
  • Eye Proteins
  • Xanthophylls
  • Zeaxanthins
  • meso-zeaxanthin
  • Lutein