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Zeaxanthin
View on Wikipedia| Names | |
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| IUPAC name
(3R,3′R)-β,β-Carotene-3,3′-diol
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| Systematic IUPAC name
(1R,1′R)-4,4′-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(3,5,5-trimethylcyclohex-3-en-1-ol) | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.005.125 |
| E number | E161h (colours) |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C40H56O2 | |
| Molar mass | 568.88 g/mol |
| Appearance | orange-red |
| Melting point | 215.5 °C (419.9 °F; 488.6 K) |
| insol. | |
| Related compounds | |
Related compounds
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lutein xanthophyll |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Zeaxanthin is one of the most common carotenoids in nature, and is used in the xanthophyll cycle. Synthesized in plants and some micro-organisms, it is the pigment that gives paprika (made from bell peppers), corn, saffron, goji (wolfberries), and many other plants and microbes their characteristic color.[1][2]
The name (pronounced zee-uh-zan'-thin) is derived from Zea mays (common yellow maize corn, in which zeaxanthin provides the primary yellow pigment), plus xanthos, the Greek word for "yellow" (see xanthophyll).[citation needed]
Xanthophylls such as zeaxanthin are found in highest quantity in the leaves of most green plants, where they act to modulate light energy and perhaps serve as a non-photochemical quenching agent to deal with triplet chlorophyll (an excited form of chlorophyll) which is overproduced at high light levels during photosynthesis.[3] Zeaxanthin in guard cells acts as a blue light photoreceptor which mediates the stomatal opening.[4]
Animals derive zeaxanthin from a plant diet.[2] Zeaxanthin is one of the two primary xanthophyll carotenoids contained within the retina of the eye. Zeaxanthin supplements are typically taken on the supposition of supporting eye health. Although there are no reported side effects from taking zeaxanthin supplements, the actual health effects of zeaxanthin and lutein are not proven,[5][6][7] and, as of 2018, there is no regulatory approval in the European Union or the United States for health claims about products that contain zeaxanthin.
As a food additive, zeaxanthin is a food dye with E number E161h.[citation needed]
Isomers and macular uptake
[edit]Lutein and zeaxanthin have identical chemical formulas and are isomers, but they are not stereoisomers. The only difference between them is in the location of the double bond in one of the end rings. This difference gives lutein three chiral centers whereas zeaxanthin has two. Because of symmetry, the (3R,3′S) and (3S,3′R) stereoisomers of zeaxanthin are identical. Therefore, zeaxanthin has only three stereoisomeric forms. The (3R,3′S) stereoisomer is called meso-zeaxanthin.[citation needed]
The principal natural form of zeaxanthin is (3R,3′R)-zeaxanthin. The macula mainly contains the (3R,3′R)- and meso-zeaxanthin forms, but it also contains much smaller amounts of the third (3S,3′S) form.[8] Evidence exists that a specific zeaxanthin-binding protein recruits circulating zeaxanthin and lutein for uptake within the macula.[9]
Due to the commercial value of carotenoids, their biosynthesis has been studied extensively in both natural products and non-natural (heterologous) systems such as the bacteria Escherichia coli and yeast Saccharomyces cerevisiae. Zeaxanthin biosynthesis proceeds from beta-carotene via the action of a single protein, known as a beta-carotene hydroxylase, that is able to add a hydroxyl group (-OH) to carbon 3 and 3′ of the beta-carotene molecule. Zeaxanthin biosynthesis therefore proceeds from beta-carotene to zeaxanthin (a di-hydroxylated product) via beta-cryptoxanthin (the mono hydroxylated intermediate). Although functionally identical, several distinct beta-carotene hydroxylase proteins are known.[citation needed]
Due to the nature of zeaxanthin, relative to astaxanthin (a carotenoid of significant commercial value) beta-carotene hydroxylase proteins have been studied extensively.[10]
Relationship with diseases of the eye
[edit]Several observational studies have provided preliminary evidence for high dietary intake of foods including lutein and zeaxanthin with lower incidence of age-related macular degeneration (AMD), most notably the Age-Related Eye Disease Study (AREDS2).[11][12] Because foods high in one of these carotenoids tend to be high in the other, research does not separate effects of one from the other.[13][14]
- Three subsequent meta-analyses of dietary lutein and zeaxanthin concluded that these carotenoids lower the risk of progression from early stage AMD to late stage AMD.[15][16][17]
- A 2023 (updated) Cochrane review of 26 studies from several countries, however, concluded that dietary supplements containing zeaxanthin and lutein have little to no influence on the progression of AMD.[18] In general, there remains insufficient evidence to assess the effectiveness of dietary or supplemental zeaxanthin or lutein in treatment or prevention of early AMD.[2][13][18]
As for cataracts, two meta-analyses confirm a correlation between high serum concentrations of lutein and zeaxanthin and a decrease in the risk of nuclear cataract, but not cortical or subcapsular cataract. The reports did not separate a zeaxanthin effect from a lutein effect.[19][20] The AREDS2 trial enrolled subjects at risk for progression to advanced age-related macular degeneration. Overall, the group getting lutein (10 mg) and zeaxanthin (2 mg) did not reduce the need for cataract surgery.[21] Any benefit is more likely to be apparent in subpopulations of individuals exposed to high oxidative stress, such as heavy smokers, alcoholics or those with low dietary intake of carotenoid-rich foods.[22]
In 2005, the US Food and Drug Administration rejected a Qualified Health Claims application by Xangold, citing insufficient evidence supporting the use of a lutein- and zeaxanthin-containing supplement in prevention of AMD.[23] Dietary supplement companies in the U.S. are allowed to sell lutein and lutein plus zeaxanthin products using dietary supplement, such as "Helps maintain eye health", as long as the FDA disclaimer statement ("These statements have not been evaluated...") is on the label. In Europe, as recently as 2014, the European Food Safety Authority reviewed and rejected claims that lutein or lutein plus zeaxanthin improved vision.[24]
Natural occurrence
[edit]Zeaxanthin is the pigment that gives paprika, corn, saffron, wolfberries (goji), and many other plants their characteristic colors of red, orange or yellow.[2][18] Spirulina is also a rich source and can serve as a dietary supplement.[25] Zeaxanthin breaks down to form picrocrocin and safranal, which are responsible for the taste and aroma of saffron.[26]
Dark green leaf vegetables, such as kale, spinach, turnip greens, collard greens, romaine lettuce, watercress, Swiss chard and mustard greens are rich in lutein[2][27] but contain little to no zeaxanthin, with the exception of scallions cooked in oil.[28] Orange bell peppers (but not green, red, or yellow) are rich in zeaxanthin.[28]
| Food (100 g) | Lutein trans (μg) | Zeaxanthin trans (μg) |
|---|---|---|
| Spinach, cooked | 12,640 | 0 |
| Spinach, raw | 6,603 | 0 |
| Kale, cooked | 8,884 | 0 |
| Cilantro | 7,703 | 0 |
| Scallions, cooked in oil | 2,488 | |
| Scallions, raw | 782 | 0 |
| Bell pepper, green | 173 | 0 |
| Bell pepper, orange | 208 | 1,665 |
| Bell pepper, red | 0 | 22 |
| Bell pepper, yellow | 139 | 18 |
| Cornmeal, yellow | 1 | 531 |
| Cornmeal, white | 13 | 13 |
| Corn, cooked from frozen | 202 | 202 |
| Tortilla, corn | 276 | 255 |
Safety
[edit]An acceptable daily intake level for zeaxanthin was proposed as 0.75 mg/kg of body weight/day, or 53 mg/day for a 70 kg adult.[29] In humans, an intake of 20 mg/day for up to six months had no adverse effects.[29] As of 2016, neither the U.S. Food and Drug Administration nor the European Food Safety Authority had set a Tolerable Upper Intake Level (UL) for lutein or zeaxanthin.[citation needed]
References
[edit]- ^ Encyclopedia.com. "Carotenoids". Retrieved 6 May 2012.
- ^ a b c d e "Lutein + Zeaxanthin Content of Selected Foods". Linus Pauling Institute, Oregon State University, Corvallis. 2014. Retrieved 20 May 2014.
- ^ Bassi, Roberto; Dall'Osto, Luca (2021). "Dissipation of Light Energy Absorbed in Excess: The Molecular Mechanisms". Annual Review of Plant Biology. 72: 47–76. doi:10.1146/annurev-arplant-071720-015522. PMID 34143647. S2CID 235480018.
- ^ Kochhar, S. L.; Gujral, Sukhbir Kaur (2020). "Transpiration". Plant Physiology: Theory and Applications (2 ed.). Cambridge University Press. pp. 75–99. doi:10.1017/9781108486392.006. ISBN 978-1-108-48639-2.
- ^ Age-Related Eye Disease Study 2 Research Group (2013). "Lutein + zeaxanthin and omega-3 fatty acids for age-related macular degeneration: The Age-Related Eye Disease Study 2 (AREDS2) randomized clinical trial". JAMA. 309 (19): 2005–15. doi:10.1001/jama.2013.4997. PMID 23644932.
{{cite journal}}: CS1 maint: numeric names: authors list (link) - ^ Pinazo-Durán, M. D.; Gómez-Ulla, F; Arias, L; et al. (2014). "Do Nutritional Supplements Have a Role in Age Macular Degeneration Prevention?". Journal of Ophthalmology. 2014: 1–15. doi:10.1155/2014/901686. PMC 3941929. PMID 24672708.
- ^ Koo, E; Neuringer, M; Sangiovanni, J. P. (2014). "Macular xanthophylls, lipoprotein-related genes, and age-related macular degeneration". American Journal of Clinical Nutrition. 100 (Supplement 1): 336S – 346S. doi:10.3945/ajcn.113.071563. PMC 4144106. PMID 24829491.
- ^ Nolan, J. M.; Meagher, K; Kashani, S; Beatty, S (2013). "What is meso-zeaxanthin, and where does it come from?". Eye. 27 (8): 899–905. doi:10.1038/eye.2013.98. PMC 3740325. PMID 23703634.
- ^ Li, B; Vachali, P; Bernstein, P. S. (2010). "Human ocular carotenoid-binding proteins". Photochemical & Photobiological Sciences. 9 (11): 1418–25. Bibcode:2010PhPhS...9.1418L. doi:10.1039/c0pp00126k. PMC 3938892. PMID 20820671.
- ^ Scaife, Mark A.; Ma, Cynthia A.; Ninlayarn, Thanyanun; et al. (22 May 2012). "Comparative Analysis of β-Carotene Hydroxylase Genes for Astaxanthin Biosynthesis". Journal of Natural Products. 75 (6): 1117–24. doi:10.1021/np300136t. PMID 22616944.
- ^ "NIH study provides clarity on supplements for protection against blinding eye disease". US National Eye Institute, National Institutes of Health, Bethesda, MD. 5 May 2013. Archived from the original on 15 August 2019. Retrieved 10 August 2017.
- ^ Bernstein, P. S.; Li, B; Vachali, P. P.; et al. (2015). "Lutein, Zeaxanthin, and meso-Zeaxanthin: The Basic and Clinical Science Underlying Carotenoid-based Nutritional Interventions against Ocular Disease". Progress in Retinal and Eye Research. 50: 34–66. doi:10.1016/j.preteyeres.2015.10.003. PMC 4698241. PMID 26541886.
- ^ a b Krishnadev N, Meleth AD, Chew EY (May 2010). "Nutritional supplements for age-related macular degeneration". Current Opinion in Ophthalmology. 21 (3): 184–9. doi:10.1097/ICU.0b013e32833866ee. PMC 2909501. PMID 20216418.
- ^ SanGiovanni JP, Chew EY, Clemons TE, et al. (September 2007). "The relationship of dietary carotenoid and vitamin A, E, and C intake with age-related macular degeneration in a case-control study: AREDS Report No. 22". Archives of Ophthalmology. 125 (9): 1225–1232. doi:10.1001/archopht.125.9.1225. PMID 17846363.
- ^ Liu R, Wang T, Zhang B, et al. (2014). "Lutein and zeaxanthin supplementation and association with visual function in age-related macular degeneration". Invest. Ophthalmol. Vis. Sci. 56 (1): 252–8. doi:10.1167/iovs.14-15553. PMID 25515572.
- ^ Wang X, Jiang C, Zhang Y, et al. (2014). "Role of lutein supplementation in the management of age-related macular degeneration: meta-analysis of randomized controlled trials". Ophthalmic Res. 52 (4): 198–205. doi:10.1159/000363327. PMID 25358528. S2CID 5055854.
- ^ Ma L, Dou HL, Wu YQ, et al. (2012). "Lutein and zeaxanthin intake and the risk of age-related macular degeneration: a systematic review and meta-analysis". Br. J. Nutr. 107 (3): 350–9. doi:10.1017/S0007114511004260. PMID 21899805.
- ^ a b c Evans, Jennifer R.; Lawrenson, John G. (2023-09-13). "Antioxidant vitamin and mineral supplements for slowing the progression of age-related macular degeneration". The Cochrane Database of Systematic Reviews. 2023 (9) CD000254. doi:10.1002/14651858.CD000254.pub5. ISSN 1469-493X. PMC 10498493. PMID 37702300.
- ^ Liu XH, Yu RB, Liu R, et al. (2014). "Association between lutein and zeaxanthin status and the risk of cataract: a meta-analysis". Nutrients. 6 (1): 452–65. doi:10.3390/nu6010452. PMC 3916871. PMID 24451312.
- ^ Ma L, Hao ZX, Liu RR, et al. (2014). "A dose-response meta-analysis of dietary lutein and zeaxanthin intake in relation to risk of age-related cataract". Graefes Arch. Clin. Exp. Ophthalmol. 252 (1): 63–70. doi:10.1007/s00417-013-2492-3. PMID 24150707. S2CID 13634941.
- ^ Chew EY, SanGiovanni JP, Ferris FL, et al. (2013). "Lutein/zeaxanthin for the treatment of age-related cataract: AREDS2 randomized trial report no. 4". JAMA Ophthalmol. 131 (7): 843–50. doi:10.1001/jamaophthalmol.2013.4412. PMC 6774801. PMID 23645227.
- ^ Fernandez MM, Afshari NA (January 2008). "Nutrition and the prevention of cataracts". Current Opinion in Ophthalmology. 19 (1): 66–70. doi:10.1097/ICU.0b013e3282f2d7b6. PMID 18090901. S2CID 25735519.
- ^ "Letter of Denial - Xangold Lutein Esters, Lutein, or Zeaxanthin and Reduced Risk of Age-related Macular Degeneration or Cataract Formation (Docket No. 2004Q-0180". US FDA, Qualified Health Claims. 19 December 2005. Archived from the original on May 21, 2014.
- ^ "Scientific Opinion on the substantiation of a health claim related to a combination of lutein and zeaxanthin and improved vision under bright light conditions pursuant to Article 13(5) of Regulation (EC) No 1924/2006". EFSA Journal. 12 (7): 3753. 2014. doi:10.2903/j.efsa.2014.3753. ISSN 1831-4732.
- ^ Yu, B.; Wang, J.; Suter, P. M.; et al. (2012). "Spirulina is an effective dietary source of zeaxanthin to humans". British Journal of Nutrition. 108 (4): 611–619. doi:10.1017/S0007114511005885. PMID 22313576.
- ^ Frusciante, Sarah; Diretto, Gianfranco; Bruno, Mark; et al. (2014-08-19). "Novel carotenoid cleavage dioxygenase catalyzes the first dedicated step in saffron crocin biosynthesis". Proceedings of the National Academy of Sciences. 111 (33): 12246–12251. Bibcode:2014PNAS..11112246F. doi:10.1073/pnas.1404629111. ISSN 0027-8424. PMC 4143034. PMID 25097262.
- ^ "Foods highest in lutein-zeaxanthin per 100 grams". Conde Nast for the USDA National Nutrient Database, release SR-21. 2014. Retrieved 23 December 2015.
- ^ a b c Alisa Perry; Helen Rasmussen; Elizabeth J. Johnson (Feb 2009). "Xanthophyll (lutein, zeaxanthin) content in fruits, vegetables and corn and egg products". Journal of Food Composition and Analysis. 22 (1): 9–15. doi:10.1016/j.jfca.2008.07.006. Retrieved 4 February 2024.
- ^ a b Edwards JA (2016). "Zeaxanthin: Review of Toxicological Data and Acceptable Daily Intake". Journal of Ophthalmology. 2016: 1–15. doi:10.1155/2016/3690140. PMC 4738691. PMID 26885380.
• In their evaluation of the safety of synthetic zeaxanthin as a Novel Food, the EFSA NDA Scientific Panel [37] applied a 200-fold safety factor to this NOAEL to define an ADI of 0.75 mg/kg bw/day, or 53 mg/day for a 70 kg adult.
• Formulated zeaxanthin was not mutagenic or clastogenic in a series of in vitro and in vivo tests for genotoxicity.
• Information from human intervention studies also supports that an intake higher than 2 mg/day is safe, and an intake level of 20 mg/day for up to 6 months was without adverse effect.
Zeaxanthin
View on GrokipediaChemistry
Molecular Structure and Properties
Zeaxanthin is a xanthophyll carotenoid characterized by the molecular formula C₄₀H₅₆O₂ and the systematic IUPAC name (3R,3'R)-β,β-carotene-3,3'-diol.[1] Its structure consists of a linear polyene chain with 11 conjugated double bonds flanked by two β-ionone rings, each bearing a hydroxyl group at the 3 and 3' positions, respectively, which imparts its oxygenated nature as a diol.[2] This configuration distinguishes it from non-hydroxylated carotenoids like β-carotene, enhancing its polarity while maintaining lipophilicity. Zeaxanthin is a structural isomer of lutein, differing primarily in the ring double-bond positions.[1] Physically, zeaxanthin manifests as an orange-red crystalline powder that is highly lipophilic, exhibiting good solubility in fats, oils, chloroform, and ethanol but negligible solubility in water due to its non-polar hydrocarbon backbone and limited hydrophilic hydroxyl groups.[1] Its melting point is approximately 215 °C, at which it decomposes without boiling.[7] In terms of optical properties, zeaxanthin displays characteristic UV-Vis absorption maxima at 450 nm and 478 nm in ethanol, corresponding to its extended conjugated system that enables light absorption in the blue-violet range.[8] In plants, zeaxanthin is biosynthesized within plastids through the carotenoid pathway, starting from the acyclic precursor lycopene. Lycopene undergoes stereospecific cyclization catalyzed by lycopene β-cyclase (LCYB) to form β-carotene, which features two β-ionone rings. Subsequent hydroxylation at the 3 and 3' positions of β-carotene is mediated by β-carotene 3-hydroxylase (BCH), a non-heme diiron enzyme (also known as HYD in algae and bacteria), often proceeding via the mono-hydroxylated intermediate β-cryptoxanthin to yield the final diol structure.[9] This enzymatic pathway is tightly regulated and localized in chloroplasts and chromoplasts, contributing to zeaxanthin's role in pigment accumulation. Industrial production of zeaxanthin relies on chemical synthesis, typically employing a C15 + C10 + C15 coupling strategy using β-ionone or citral as starting materials. β-Ionone, a key C13 building block derived from citral via aldol condensation with acetone followed by cyclization, is extended through Wittig olefination or Horner-Wadsworth-Emmons reactions to construct the central polyene chain, with subsequent introduction of hydroxyl groups and stereoselective adjustments to achieve the (3R,3'R) configuration.[10] For structural identification, zeaxanthin exhibits a molecular ion peak at m/z 568 [M]⁺ in electron impact mass spectrometry, confirming its molecular weight, while ¹H NMR spectroscopy reveals characteristic signals including olefinic protons in the 6.0–6.7 ppm range for the conjugated double bonds, methyl singlets at 1.0–1.5 ppm, and hydroxyl protons around 4.0–5.0 ppm in CDCl₃.[11]Isomers and Synthesis
Zeaxanthin possesses two chiral centers at the C3 and C3' positions of its β-ionone rings, resulting in three stereoisomers: (3R,3'R)-zeaxanthin, which is the predominant all-trans form in nature; meso-zeaxanthin ((3R,3'S)-zeaxanthin); and (3S,3'S)-zeaxanthin. The (3R,3'R) and (3S,3'S) forms are enantiomers exhibiting optical activity, whereas meso-zeaxanthin is meso due to its plane of symmetry and lacks optical rotation.[12][13] These isomers differ in key properties relevant to their biological roles. Meso-zeaxanthin demonstrates greater accumulation in the central macular region compared to (3R,3'R)-zeaxanthin, contributing to its prominence in ocular tissues. Additionally, meso-zeaxanthin exhibits distinct antioxidant capabilities, including superior quenching of singlet oxygen relative to (3R,3'R)-zeaxanthin under certain conditions, though both provide effective protection against lipid peroxidation when interacting with glutathione S-transferase P1.[14][15][16] Chemical synthesis of zeaxanthin primarily employs a double Wittig olefination as the key step, condensing a symmetrical C10 dialdehyde (such as pseudoionone-derived) with two equivalents of the C15 Wittig salt prepared from β-ionone, followed by hydrolysis and purification to yield the all-trans (3R,3'R) isomer with purity exceeding 98%. This route, developed through advancements in organophosphorus chemistry, enables scalable production of stereospecific zeaxanthin. For sustainable alternatives, microbial fermentation utilizes metabolically engineered organisms, including yeasts like Yarrowia lipolytica and algae such as Chlamydomonas reinhardtii, where pathway modifications—such as overexpression of β-carotene hydroxylase genes—achieve titers up to 81.5 mg/L and purities suitable for nutraceutical applications, reducing reliance on plant extraction. More recent engineering in other yeasts, such as Saccharomyces cerevisiae, has reported titers exceeding 800 mg/L in fed-batch processes as of 2023.[17][18][19][20][21] Zeaxanthin was first isolated from corn in 1929 by Paul Karrer and colleagues, marking a milestone in carotenoid chemistry. Synthetic production advanced significantly in the post-1950s period, coinciding with the broader application of Wittig reactions to complex polyene structures, enabling efficient total synthesis and stereocontrol by the 1970s.[22][23]Biological Role
Occurrence in Nature
Zeaxanthin is a xanthophyll carotenoid widely distributed in photosynthetic organisms, where it serves as an accessory pigment in photosynthesis, absorbing blue-green light (450–500 nm) to facilitate energy transfer to chlorophyll while contributing to photoprotection against excess light energy. In plants, it is particularly abundant in certain species and tissues, such as corn (Zea mays), where concentrations in sweet corn kernels can exceed 2 mg/100 g fresh weight in biofortified varieties, and orange bell peppers (Capsicum annuum), with levels ranging from 2.6 to 25 mg/100 g fresh weight depending on the cultivar. Goji berries (Lycium barbarum) are another notable source, containing up to 2 mg/g dry weight primarily as zeaxanthin dipalmitate, while marigold flowers (Tagetes erecta) exhibit exceptionally high levels, reaching 10–20 mg/g dry weight in petals of select cultivars. These concentrations highlight zeaxanthin's role in pigmentation and its accumulation in reproductive and protective plant structures.[24][25][26][27] In animals, zeaxanthin is not synthesized de novo but accumulates through dietary uptake from plant sources, often depositing in tissues for coloration and structural purposes. It contributes to the vibrant hues in bird feathers, such as the pink pigmentation in flamingos (Phoenicopterus spp.), where it is metabolized alongside other carotenoids like astaxanthin from algal diets, and in canaries (Serinus canaria), where supplemental zeaxanthin enhances yellow-to-orange feather colors via direct deposition and metabolic conversion. Similarly, zeaxanthin is found in fish skin, particularly in species like rainbow trout (Oncorhynchus mykiss), aiding in pigmentation, and in egg yolks of poultry, where concentrations of 6–10 μg/g arise from feed-derived uptake, imparting the characteristic yellow tint. This bioaccumulation underscores zeaxanthin's ecological role in animal signaling and camouflage without endogenous production.[28][18][29] Microorganisms also produce zeaxanthin, primarily for photoprotection in light-exposed environments. In algae, species like Chlorella zofingiensis accumulate zeaxanthin as part of the xanthophyll cycle to dissipate excess energy and prevent oxidative damage, though Haematococcus pluvialis is better known for astaxanthin, with zeaxanthin serving as a biosynthetic precursor. Bacteria such as Flavobacterium spp. are prolific producers, yielding up to 190 mg/L in cultures, where zeaxanthin shields against UV radiation and supports membrane stability. These microbial sources demonstrate zeaxanthin's conserved function across prokaryotes and simple eukaryotes in harsh, illuminated habitats.[30][31][32] Biosynthetic pathways for zeaxanthin vary significantly across taxa, reflecting evolutionary adaptations. In plants and microorganisms, it is synthesized from β-carotene through hydroxylation by β-carotene hydroxylase enzymes within the terpenoid pathway, enabling active production for photosynthetic needs. In contrast, animals lack these enzymes and rely solely on dietary absorption and selective deposition into tissues like feathers and skin, without the capacity for de novo synthesis. This distinction highlights zeaxanthin's role as a dietary-dependent pigment in higher organisms versus an endogenously produced protectant in photosynthetic lineages.[33][34][35]Function in Human Physiology
Zeaxanthin absorption occurs primarily in the small intestine, where it is incorporated into mixed micelles along with dietary fats after hydrolysis of its esters by pancreatic enzymes such as carboxyl ester lipase.[2] These micelles facilitate passive diffusion or transporter-mediated uptake into enterocytes via scavenger receptors like SR-BI and CD36.[36] Inside enterocytes, zeaxanthin is esterified or remains free and packaged into chylomicrons, which enter the lymphatic system and deliver it to the liver.[37] From the liver, zeaxanthin is redistributed to peripheral tissues, including the retina, bound to lipoproteins such as LDL and HDL, with bioavailability enhanced by concurrent dietary fat intake.[38] Humans cannot synthesize zeaxanthin endogenously due to the absence of necessary biosynthetic enzymes, making dietary intake essential for its presence in the body.[39] Zeaxanthin esters from food are efficiently hydrolyzed in the intestinal lumen prior to absorption, ensuring high bioaccessibility of the free form.[40] Once absorbed, zeaxanthin exhibits a plasma half-life of approximately 38 days, allowing for accumulation in target tissues over time.[41] In the retina, zeaxanthin shows selective uptake and accumulation in the macula lutea, where it contributes significantly to macular pigment optical density (MPOD) alongside lutein and the isomer meso-zeaxanthin.[36] This localization enables zeaxanthin to protect photoreceptors by absorbing high-energy blue light and quenching reactive oxygen species through non-photochemical quenching, dissipating excess energy as harmless heat without generating further oxidants.[36] Zeaxanthin exhibits synergistic interactions with lutein in retinal tissues, where the two carotenoids form stable complexes within cell membranes, enhancing membrane rigidity and amplifying overall antioxidant protection.[42] This partnership optimizes the structural and functional integrity of photoreceptor membranes under oxidative stress.[36]Health Effects
Benefits for Eye Health
Zeaxanthin, often studied alongside lutein, has been linked to a reduced risk of age-related macular degeneration (AMD) through its accumulation in the macula, where it contributes to the macular pigment optical density (MPOD). In the Age-Related Eye Disease Study 2 (AREDS2), supplementation with 10 mg lutein and 2 mg zeaxanthin replaced beta-carotene in the original AREDS formula, resulting in an 18% lower risk of progression to late AMD over 10 years compared to beta-carotene, particularly benefiting those at high risk without increasing lung cancer incidence.[43] Follow-up analyses through 2024 have confirmed these sustained MPOD benefits, with high-intake cohorts showing 10-20% risk reductions in AMD progression.[44] This protective effect is attributed to zeaxanthin's ability to filter harmful blue light, thereby mitigating photooxidative damage to retinal cells.[45] Higher dietary intake of zeaxanthin, exceeding 2 mg per day, is inversely associated with cataract risk, with meta-analyses indicating 15-25% reductions through its antioxidant properties. A 2023 meta-analysis of observational studies found that the highest versus lowest consumption of lutein and zeaxanthin was linked to a 19% decrease in age-related cataract incidence.[46] Dose-response analyses further support this, showing approximately a 3% risk reduction in nuclear cataracts for every 300 μg daily increment in intake, equating to notable protection at levels above 2 mg.[47] Zeaxanthin's antioxidant effects help preserve lens proteins by neutralizing free radicals and reducing oxidative stress, which otherwise leads to protein aggregation and lens opacification.[48] Zeaxanthin also offers protection against other ocular conditions, including light-induced retinal damage. Experimental models confirm zeaxanthin's role in preventing light-induced photoreceptor cell death by elevating retinal levels and quenching reactive oxygen species.[49] In pediatric populations, zeaxanthin supports visual development, with supplementation improving dynamic visual performance and macular pigment levels in children.[50] Randomized clinical trials have shown that lutein/zeaxanthin supplementation at 10-20 mg daily enhances visual function in 6-12 months. For instance, a double-blind study found that 10 mg lutein plus 2 mg zeaxanthin over 6 months significantly improved contrast sensitivity and glare recovery time in healthy adults.[51] Similar trials report gains in chromatic contrast and photostress recovery.Potential Benefits Beyond Vision
Emerging research indicates that zeaxanthin may offer protective effects in various non-ocular health domains, primarily through its antioxidant and anti-inflammatory properties. These benefits are supported by clinical trials, epidemiological studies, and animal models, often examining zeaxanthin in combination with lutein due to their similar bioavailability and synergistic actions. In cognitive health, supplementation with zeaxanthin has shown promise for improving memory and processing speed in older adults. A randomized, double-blind, placebo-controlled trial involving 90 adults aged 40–75 with self-reported mild cognitive complaints found that daily intake of 2 mg zeaxanthin combined with 10 mg lutein for 6 months led to significant improvements in visual episodic memory (p = 0.005) and visual learning (p = 0.001) compared to placebo, with no notable effects on executive function or mood. These outcomes are attributed to zeaxanthin's ability to reduce brain oxidative stress, particularly in regions like the hippocampus, by neutralizing reactive oxygen species. Epidemiological evidence further links higher serum levels of zeaxanthin to better overall brain health and reduced cognitive decline in aging populations.[52] For skin protection, zeaxanthin exhibits photoprotective effects against ultraviolet (UV) radiation, potentially mitigating photoaging and erythema. In a 2025 study using BALB/c mice exposed to UVB radiation, oral zeaxanthin from Lycium barbarum reduced skin damage by downregulating matrix metalloproteinases and preserving collagen integrity by 35%, while activating the Nrf2 pathway to enhance antioxidant defenses. Human studies support these findings; for instance, supplementation with 2 mg zeaxanthin and 10 mg lutein daily increased the skin's minimal erythemal dose, delaying UV-induced redness and oxidative damage in clinical assessments. A 2024 review of oral photoprotection strategies highlighted that carotenoid mixtures including zeaxanthin slowed UVB-induced erythema development by 2–3 days and lowered expression of inflammatory enzymes like MMP-1 and MMP-9 in participants.[53][54][55] Regarding cardiovascular health, zeaxanthin helps lower LDL oxidation, a key factor in atherosclerosis. A 2024 clinical trial demonstrated that supplementation with zeaxanthin, lutein, and meso-zeaxanthin significantly decreased serum oxidized LDL levels, alongside reductions in inflammatory markers like IL-1β and TNF-α, suggesting systemic anti-atherogenic effects.[56] Epidemiological links also connect higher zeaxanthin intake to reduced cancer risk, particularly for breast and prostate cancers. In a 2025 population-based case-control study in Iran involving 600 breast cancer cases and 600 controls, higher dietary lutein/zeaxanthin intake (>2.51 mg/day) was associated with a 55% lower risk of breast cancer (adjusted OR = 0.45, 95% CI: 0.29–0.70, p < 0.001) compared to lower intake. For prostate cancer, an umbrella meta-analysis of 19 studies indicated that elevated carotenoid levels, including zeaxanthin, significantly decreased risk (pooled effect showing protective association). These benefits likely stem from zeaxanthin's inhibition of oxidative DNA damage and tumor promotion.[57][58] Other potential roles include support for bone health and modulation of inflammation. Cross-sectional analyses from 2023 showed that higher blood zeaxanthin concentrations were positively associated with femoral neck bone strength indices (e.g., cortical strength index, buckling ratio) in older adults, suggesting a protective effect against osteoporosis. In animal models of inflammation, such as acetic acid-induced ulcerative colitis in rats, zeaxanthin reduced pro-inflammatory cytokines (TNF-α, IL-6, IL-1β) and inhibited the NF-κB pathway, alleviating colonic damage and oxidative stress. These findings highlight zeaxanthin's broader neuroprotective and anti-inflammatory potential in preclinical settings.[59][60]Sources and Intake
Dietary Sources
Zeaxanthin is primarily obtained from plant-based foods and animal products derived from animals fed carotenoid-rich diets, with corn, orange peppers, egg yolks, and goji berries among the richest sources. Corn contains approximately 0.2–1.0 mg of zeaxanthin per 100 g, depending on the variety and preparation, making it a staple contributor in many diets.[61][4] Orange bell peppers provide 0.6–1.7 mg per 100 g fresh weight, with higher concentrations in certain cultivars.[61] Egg yolks offer 0.2–0.5 mg of zeaxanthin per yolk (typically from a 17 g yolk), enhanced by the hens' feed.[4] Dried goji berries stand out with 25–152 mg per 100 g, primarily as zeaxanthin dipalmitate.[62]| Food Source | Zeaxanthin Content (mg/100 g or per serving) | Notes |
|---|---|---|
| Corn (cooked, yellow sweet) | 0.2–1.0 mg/100 g | Varies by variety; major source in processed corn products.[4] |
| Orange bell pepper (raw) | 0.6–1.7 mg/100 g | Highest in orange varieties; green peppers contain negligible amounts.[61] |
| Egg yolk (cooked) | 0.2–0.5 mg per yolk (~1.2–2.9 mg/100 g yolk) | Bioavailability improved due to fat content.[4] |
| Goji berries (dried) | 25–152 mg/100 g | Predominantly zeaxanthin esters; common in Asian cuisine.[62] |

