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The Carotenoid Pigment Zeaxanthin—A Review M.G

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The Carotenoid Pigment Zeaxanthin—A Review M.G The Carotenoid Pigment Zeaxanthin—A Review M.G. Sajilata, R.S. Singhal, and M.Y. Kamat ABSTRACT: Scientific evidence linking several diseases with diet has brought to light the beneficial effects of a number of natural food ingredients. Zeaxanthin is one such natural pigment emphasized for its critical role in the prevention of age-related macular degeneration (AMD), the leading cause of blindness. The review highlights zeaxanthin as a carotenoid pigment with promising nutraceutical implications, and enumerates the important plant and microbial sources for its production, the absorptive pathway of zeaxanthin in human system, and methods to assess its bioavailability besides other relevant aspects. Introduction 2003). Zeaxanthin exhibits no vitamin A activity. Zeaxanthin Carotenoids are pigments naturally occurring in a number of and its close relative lutein (Figure 1 and 2) play a critical role fruits and vegetables. They are synthesized by all photosynthetic in the prevention of age-related macular degeneration (AMD), organisms and many nonphotosynthetic bacteria and fungi. They the leading cause of blindness (Snodderly 1995; Moeller and are liposoluble tetraterpenes originating from the condensation of others 2000). Zeaxanthin is isomeric with lutein; the 2 carotene isoprenyl units, which form a series of conjugated double bonds alcohols differ from each other just by the shift of a single double constituting a chromophoric system (Britton 1995). There are 2 bond so that in zeaxanthin all double bonds are conjugated. main classes of naturally occurring carotenoids: (1) carotenes Zeaxanthin is used as a feed additive and colorant in the food such as β-carotene and α-carotene, which are hydrocarbons, are industry for birds, swine, and fish (Hadden and others 1999). either linear or cyclized at one or both ends of the molecule, The pigment imparts a yellow coloration to the skin and egg yolk and (2) xanthophylls, the oxygenated derivatives of carotenes. of birds, whereas in pigs and fish it is used for skin pigmentation All xanthophylls produced by higher plants, such as violaxanthin, (Nelis and DeLeenheer 1991). antheraxanthin, zeaxanthin, neoxanthin, and lutein, are also syn- thesized by green algae (Eonseon and others 2003). Epidemiolog- ical studies have established an inverse relationship between the Stereoisomers of Zeaxanthin risk of laryngeal, lung, and colon cancers and the consumption of Zeaxanthin has 2 chiral centers and, hence, 22 or 4 stereoiso- foods containing carotenoids (Block and others 1992; Steinmetz meric forms. One chiral center is the number ‘3’ atom in the left and Potter 1993). end ring, while the other chiral center is the number ‘3’ carbon The chemical name of zeaxanthin is (all-E)-1,1-(3,7,12,16- in the right end ring (Garnett and others 1998). One stereoiso- tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl) mer is (3R, 3R)-zeaxanthin; the other is (3S-3S)-zeaxanthin. The bis [2,6,6-trimethylcyclohexene-3-ol]. Synonyms are: 3R, 3rd stereoisomer is (3R, 3S)-zeaxanthin and the 4th (3S-3R)- 3R-β,β-carotene-3,3-diol; all-trans-β-carotene-3,3-diol; zeaxanthin. However, since zeaxanthin is a symmetric molecule, (3R,3R)-dihydroxy-β-carotene; zeaxanthol; and anchovyx- the (3R, 3S)—and (3S, 3R)—stereoisomers are identical. There- anthin. Zeaxanthin, the principal pigment of yellow corn, fore, zeaxanthin has only 3 stereoisomeric forms. The (3R, Zeaxanthin mays L. (from which its name is derived), has a 3S)—or (3S, 3R)—stereoisomer is called meso-zeaxanthin. The molecular formula of C40H56O2 and a molecular weight of principal natural form of zeaxanthin is (3R, 3 R)-zeaxanthin. (3R, 568.88 daltons. Its CAS number is 144-68-3. It is composed of 3R)-zeaxanthin and meso-zeaxanthin are found in the macula of 40 carbon atoms, yellow in color, and naturally found in corn, the retina, with much smaller amounts of (3S, 3S)-zeaxanthin. egg yolks, and some of the orange and yellow vegetables and Meso-zeaxanthin is a rare isomer present in significant quantities fruits such as alfalfa and marigold flowers (Nelis and DeLeenheer in commercially produced chickens and eggs in Mexico where 1991; Handelman and others 1999; Humphries and Khachik it is commonly added to the feed to achieve desirable coloration in these products (Bone and others 2007). MS 20070403 Submitted 5/28/2007, Accepted 8/13/2007. Authors are with Food Engineering and Technology Dept., Inst. of Chemical Technology, Univ. Properties of Zeaxanthin of Mumbai, Matunga, Mumbai-400 019, India. Direct inquiries to author Singhal (E-mail: [email protected]). One gram of zeaxanthin dissolves in about 1.5 L of boiling methanol. The pigment is almost insoluble in petroleum ether C 2008 Institute of Food Technologists Vol. 7, 2008—COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY 29 CRFSFS: Comprehensive Reviews in Food Science and Food Safety Figure 1 --- Structure of zeaxanthin. Figure 2 --- Structure of lutein. Table 1 --- Ultraviolet and visible absorption data of zea- xanthin (Davies 1976; Britton 1995). Carotenoid Solvent λ max nma % III/IIb Zeaxanthin Acetone (430) 452 479 Chloroform (433) 462 493 Ethanol (428) 450 478 26 Petroleum ether (424) 449 476 25 aParentheses indicate a shoulder. bRatio of the height of the longest-wavelength absorption peak, designated III, and that of the middle absorption peak, designated II, taking the minimum between the 2 peaks as baseline multiplied by 100 (hni.ilsi.org/publications). Figure 3 --- Resonance Raman spectra of zeaxanthin (ZX) extracted from bacteria and dissolved in methanol and of Flavobacterium multivorum culture broth (CB, plotted on right Y axis (Bhosale and others 2003). and hexane. Its solubility in ether, chloroform, carbon disulphide, and pyridine is somewhat greater. Zeaxanthin dissolves in con- centrated sulfuric acid with a fairly stable deep blue coloration. On treating a solution of the pigment in chloroform with anti- mony trichloride, a blue coloration is produced (Euler and others 1930). Zeaxanthin is a polyene-like molecule, which contains 9 alter- nating conjugated carbon double and single bonds. The carbon backbone is terminated at each end by an ionone ring to which a hydroxyl group is attached. When excited with monochro- Figure 4 --- Calculation of % III/II as indication of spectral matic laser light, it exhibits characteristic wavelength shifts of fine structure (% III/II × 100) (www.hni.ilsi.org). inelastically back-scattered light caused by vibrational modes in its chemical structure. Two characteristic carotenoid peaks shown in Figure 3 originate from rocking motions of the carbon– carbon single bond stretch vibrations (1159 cm−1) and from the carbon–carbon double bond stretch vibrations (1525 cm−1) of the molecule backbone (Bhosale and others 2003). spectrum of zeaxanthin, a derivative of β-carotene, resembles The conjugated double-bond system constitutes the light- that of β-carotene. The ultraviolet and visible absorption data absorbing chromophore that gives carotenoids their attractive of zeaxanthin are shown in Table 1 with calculation of % III/II color and provides the visible absorption spectrum that serves as a as indication of spectral fine structure (% III/II × 100) illustrated basis for their identification and quantification. Cis-isomerization in Figure 4. Figure 5 shows the absorption spectra of isomers of of a chromophore’s double bond causes a slight loss in color, zeaxanthin. small hypsochromic shift, and hypochromic effect, accompanied Carotenoid molecules are strong Raman scatterers. Hence, by the appearance of a cis peak in or near the ultraviolet region. nondestructive resonance Raman spectroscopy could be an ex- All-trans isomers absorb strongly in the visible region between tremely valuable method for the rapid quantitative assessment 400 and 500 nm while cis-isomers exhibit absorption in the near- of carotenoids. There are reports of the detection of resonance UV region, around 320 nm (Rodriguez-Amaya 2001). The visible Raman scattering of laser radiation of the carotenoid pigments 30 COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY—Vol. 7, 2008 The carotenoid pigment zeaxanthin... from intact plant samples and fruit juices (Gill and others ferent natural carotenoids (Figure 6). In Flavobacterium R1529, 1970). nicotine blocks zeaxanthin biosynthesis by specifically inhibiting the cyclization reaction (McDermott and others 1974). Lycopene and rubixanthin replace zeaxanthin as the main carotenoid. In Biosynthetic Pathway and Genetic Manipulation the absence of nicotine, lycopene is converted to β-carotene un- of the Pathway for Zeaxanthin Production der anaerobic conditions and into zeaxanthin in the presence of A paramount function of xanthophylls in all photosynthetic or- oxygen. ganisms, including cyanobacteria, is to provide protection against The biosynthesis of IPP and DMAPP from acetyl-CoA via photooxidation. It is proposed that zeaxanthin protects the mem- melavonate has been studied using animal cells and yeasts brane directly against lipid peroxidation by reactive radicals that (Bochar and others 1999). Three acetate units afford the 5 carbon have been created as toxic byproducts during photosynthetic re- atoms of IPP from loss of 1 acetate carboxylic group as CO2. actions. Another mechanism suggests specific xanthophylls to be DMAPP is obtained from IPP by an isomerase. A mevalonate- involved in the de-excitation of singlet chlorophyll (1Chl) that ac- independent 2nd pathway for the biosynthesis of IPP and cumulates in the light-harvesting
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