Lutein: Difference between revisions
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{{Short description|Yellow organic pigment created by plants}}
{{Use dmy dates|date=April 2021}}
{{Chembox
| Watchedfields = changed
| verifiedrevid = 457657742
| ImageFile = Luteine - Lutein.svg
| ImageSize =
| ImageFile1 = Lutein molecule spacefill.png
| ImageSize1 = 300
| ImageAlt1 = Space-filling model of lutein
| IUPACName = (3''R'',6''R'',3{{prime}}''R'')-β,ε-Carotene-3,3{{prime}}-diol
| SystematicName = (1''R'',4''R'')-4-{(1''E'',3''E'',5''E'',7''E'',9''E'',11''E'',13''E'',15''E'',17''E'')-18-[(4''R'')-4-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl}-3,5,5-trimethylcyclohex-2-en-1-ol
| OtherNames = {{Unbulleted list
| Luteine
| ''trans''-Lutein
| Xanthophyll
}}
|Section1={{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| CASNo = 127-40-2
| EINECS =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 173929
| PubChem = 5281243
Line 25 ⟶ 36:
| UNII = X72A60C9MT
| SMILES = CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H]2C(=C[C@@H](CC2(C)C)O)C)/C)/C
| RTECS =
| MeSHName =
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| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
}}
|Section2={{Chembox Properties
| C=40 | H=56 | O=2
| MolarMass = 568.871 g/mol
| Appearance = Red-orange crystalline solid
| Density =
| MeltingPtC = 190
| MeltingPt_ref =<ref name="ref_b">[http://www.carl-roth.de/jsp/de-de/sdpdf/5671.PDF ''MSDS at Carl Roth (Lutein Rotichrom, German)''.]</ref>
| BoilingPt =
|
| Solubility = Insoluble
| SolubleOther = Soluble
| Solvent = fats
| pKa =
| pKb =
}}
|
|
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-
| FlashPt =
|
| ExploLimits =
| PEL =
}}
}}
'''Lutein''' ({{
Animals obtain lutein by ingesting plants.<ref name="lpi">{{cite web |title=Carotenoids |url=http://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/carotenoids |publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis|access-date=10 August 2017 |date=July 2016}}</ref> In the human [[retina]], lutein is absorbed from blood specifically into the [[macula of retina|macula lutea]],<ref name="prer">{{cite journal |pmc=4698241 |year=2015 |last1=Bernstein |first1=P. S. |title=Lutein, Zeaxanthin, and ''meso''-Zeaxanthin: The Basic and Clinical Science Underlying Carotenoid-based Nutritional Interventions against Ocular Disease |journal=Progress in Retinal and Eye Research |volume=50 |pages=34–66 |last2=Li |first2=B |last3=Vachali |first3=P. P. |last4=Gorusupudi |first4=A |last5=Shyam |first5=R |last6=Henriksen |first6=B. S. |last7=Nolan |first7=J. M. |doi=10.1016/j.preteyeres.2015.10.003 |pmid=26541886}}</ref> although its precise role in the body is unknown.<ref name=lpi/> Lutein is also found in egg yolks and animal fats.
Lutein is [[isomer]]ic with [[zeaxanthin]], differing only in the placement of one double bond. Lutein and zeaxanthin can be interconverted in the body through an intermediate called [[meso-zeaxanthin|''meso''-zeaxanthin]].<ref>{{cite journal |last1=Krinksy |first1=Norman |last2=Landrum |first2=John |last3=Bone |first3=Richard |title=Biological Mechanisms of the Protective Role of Lutein and Zeaxanthin in the Eye |journal=Annual Review of Nutrition |date=2003 |volume=23 |issue=1 |pages=171–201 |doi=10.1146/annurev.nutr.23.011702.073307 |pmid=12626691}}</ref> The principal natural [[stereoisomer]] of lutein is [[Chirality (chemistry)#By configuration: R- and S-|(3''R'',3{{prime}}''R'',6{{prime}}''R'')]]-''beta'',''epsilon''-carotene-3,3{{prime}}-diol. Lutein is a [[lipophilic]] molecule and is generally insoluble in water. The presence of the long [[chromophore]] of conjugated double bonds ([[polyene]] chain) provides the distinctive light-absorbing properties. The polyene chain is susceptible to oxidative degradation by light or heat and is chemically unstable in acids.
Lutein is present in plants as fatty-acid
==As a pigment==
This [[xanthophyll]], like its sister compound [[zeaxanthin]], has primarily been used
in food and supplement manufacturing as a
Many songbirds (like [[golden oriole]], [[evening grosbeak]], [[American yellow warbler|yellow warbler]], [[common yellowthroat]] and [[Cissa (genus)|Javan green magpies]], but not [[American goldfinch]] or yellow [[domestic canary|canaries]]<ref>Mary E. Rawles, "The Integumentary System", in A. J. Marshall (ed.), 2012, "Biology and Comparative Physiology of Birds", vol. 1, [https://books.google.com/books?id=QBzgBAAAQBAJ&pg=PA220 p. 220]. {{ISBN|9781483263793}}.</ref>) deposit lutein obtained from the diet into growing tissues to color their feathers.<ref name="pmid12892761">{{cite journal |vauthors=McGraw KJ, Beebee MD, Hill GE, Parker RS |title=Lutein-based plumage coloration in songbirds is a consequence of selective pigment incorporation into feathers |journal=Comparative Biochemistry and Physiology. Part B, Biochemistry & Molecular Biology |volume=135 |issue=4 |pages=689–96 |date=August 2003 |pmid=12892761 |doi=10.1016/S1096-4959(03)00164-7}}</ref><ref>{{cite news |url=https://www.bbc.co.uk/news/resources/idt-sh/sold_for_a_song |title=Sold for a song: The forest birds captured for their tuneful voices |last=Gill |first=Victoria |work=BBC News|access-date=31 December 2017}}</ref>
==Role in human eyes==
Although lutein is concentrated in the [[macula of retina|macula]] – a small area of the [[retina]] responsible for three-color vision – the precise functional role of retinal lutein has not been determined.<ref name=lpi/>
===Macular degeneration===
In 2013, findings of the [[Age-Related Eye Disease Study]] (AREDS2) showed that a [[dietary supplement]] formulation containing lutein reduced progression of [[age-related macular degeneration]] (AMD) by 25 percent.<ref name="AREDS2">{{cite web |url=https://nei.nih.gov/news/pressreleases/050513 |title=NIH study provides clarity on supplements for protection against blinding eye disease |date=5 May 2013 |access-date=10 August 2017 |publisher=US National Eye Institute, National Institutes of Health, Bethesda, MD |archive-date=15 August 2019 |archive-url=https://web.archive.org/web/20190815055737/https://nei.nih.gov/news/pressreleases/050513 |url-status=dead }}</ref><ref name="formula">{{cite web |title=The AREDS Formulation and Age-Related Macular Degeneration |url=https://nei.nih.gov/amd/summary |publisher=US National Eye Institute, National Institutes of Health, Bethesda, MD|access-date=10 August 2017 |date=November 2011}}</ref> However, lutein and zeaxanthin had no overall effect on preventing AMD, but rather "the participants with low dietary intake of lutein and zeaxanthin at the start of the study, but who took an AREDS formulation with lutein and zeaxanthin during the study, were about 25 percent less likely to develop advanced AMD compared with participants with similar dietary intake who did not take lutein and zeaxanthin."<ref name=formula/>
In AREDS2, participants took one of four AREDS formulations: the original AREDS formulation, AREDS formulation with no beta-carotene, AREDS with low zinc, AREDS with no beta-carotene and low zinc. In addition, they took one of four additional supplement or combinations including lutein and zeaxanthin (10 mg and 2 mg), omega-3 fatty acids (1,000 mg), lutein/zeaxanthin and omega-3 fatty acids, or placebo. The study reported that there was no overall additional benefit from adding omega-3 fatty acids or lutein and zeaxanthin to the formulation. However, the study did find benefits in two subgroups of participants: those not given beta-carotene, and those who had little lutein and zeaxanthin in their diets. Removing beta-carotene did not curb the formulation's protective effect against developing advanced AMD, which was important given that high doses of beta-carotene had been linked to higher risk of lung cancers in smokers. It was recommended to replace beta-carotene with lutein and zeaxanthin in future formulations for these reasons.<ref name=AREDS2/>
* 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.<ref>{{cite journal |vauthors=Liu R, Wang T, Zhang B, Qin L, Wu C, Li Q, Ma L |display-authors=3 |title=Lutein and zeaxanthin supplementation and association with visual function in age-related macular degeneration |journal=Invest. Ophthalmol. Vis. Sci. |volume=56 |issue=1 |pages=252–8 |year=2014 |pmid=25515572 |doi=10.1167/iovs.14-15553}}</ref><ref>{{cite journal |vauthors=Wang X, Jiang C, Zhang Y, Gong Y, Chen X, Zhang M |display-authors=3 |title=Role of lutein supplementation in the management of age-related macular degeneration: meta-analysis of randomized controlled trials |journal=Ophthalmic Res. |volume=52 |issue=4 |pages=198–205 |year=2014 |pmid=25358528 |doi=10.1159/000363327 |s2cid=5055854}}</ref><ref>{{cite journal |vauthors=Ma L, Dou HL, Wu YQ, Huang YM, Huang YB, Xu XR, Zou ZY, Lin XM |display-authors=3 |title=Lutein and zeaxanthin intake and the risk of age-related macular degeneration: a systematic review and meta-analysis |journal=Br. J. Nutr. |volume=107 |issue=3 |pages=350–9 |year=2012 |pmid=21899805 |doi=10.1017/S0007114511004260 |doi-access=free}}</ref>
* An updated 2023 [[Cochrane (organisation)|Cochrane]] review of 26 studies from several countries, however, concluded that [[dietary supplement]]s containing zeaxanthin and lutein alone have little effect when compared to placebo on the progression of AMD.<ref name=":0">{{Cite journal |last1=Evans |first1=Jennifer R. |last2=Lawrenson |first2=John G. |date=2023-09-13 |title=Antioxidant vitamin and mineral supplements for slowing the progression of age-related macular degeneration |journal=The Cochrane Database of Systematic Reviews |volume=2023 |issue=9 |pages=CD000254 |doi=10.1002/14651858.CD000254.pub5 |issn=1469-493X |pmc=10498493 |pmid=37702300 |pmc-embargo-date=September 13, 2024 }}</ref> In general, there remains insufficient evidence to assess the effectiveness of dietary or supplemental zeaxanthin or lutein in treatment or prevention of early AMD.<ref name="LPI">{{cite web |url=http://lpi.oregonstate.edu/infocenter/phytochemicals/carotenoids/index.html#sources |title=Lutein + Zeaxanthin Content of Selected Foods |publisher=Linus Pauling Institute, Oregon State University, Corvallis |date=2014|access-date=20 May 2014}}</ref><ref name=":0" />
===Cataract research===
There is preliminary epidemiological evidence that increasing lutein and zeaxanthin intake lowers the risk of [[cataract]] development.<ref name=lpi/><ref name="PMID17846363" /><ref name=PM18332316>{{cite journal |title=Associations between age-related nuclear cataract and lutein and zeaxanthin in the diet and serum in the Carotenoids in the Age-Related Eye Disease Study, an Ancillary Study of the Women's Health Initiative |pmid=18332316 |doi=10.1001/archopht.126.3.354 |volume=126 |issue=3 |pmc=2562026 |journal=Arch Ophthalmol |pages=354–64 |vauthors=Moeller SM, Voland R, Tinker L, Blodi BA, Klein ML, Gehrs KM, Johnson EJ, Snodderly DM, Wallace RB, Chappell RJ, Parekh N, Ritenbaugh C, Mares JA |year=2008}}</ref> Consumption of more than 2.4 mg of lutein/zeaxanthin daily from foods and supplements was significantly correlated with reduced incidence of nuclear lens opacities, as revealed from data collected during a 13- to 15-year period in one study.<ref>{{cite journal |pmid=20590393 |year=2010 |last1=Barker Fm |first1=2nd |title=Dietary supplementation: effects on visual performance and occurrence of AMD and cataracts. |volume=26 |issue=8 |pages=2011–23 |doi=10.1185/03007995.2010.494549 |journal=Current Medical Research and Opinion |s2cid=206965363}}</ref>
Two meta-analyses confirm a correlation between high diet content or high serum concentrations of lutein and zeaxanthin and a decrease in the risk of cataract.<ref>{{cite journal |vauthors=Liu XH, Yu RB, Liu R, Hao ZX, Han CC, Zhu ZH, Ma L |title=Association between lutein and zeaxanthin status and the risk of cataract: a meta-analysis |journal=Nutrients |volume=6 |issue=1 |pages=452–65 |year=2014 |pmid=24451312 |pmc=3916871 |doi=10.3390/nu6010452|doi-access=free }}</ref><ref>{{cite journal |vauthors=Ma L, Hao ZX, Liu RR, Yu RB, Shi Q, Pan JP |title=A dose-response meta-analysis of dietary lutein and zeaxanthin intake in relation to risk of age-related cataract |journal=Graefes Arch. Clin. Exp. Ophthalmol. |volume=252 |issue=1 |pages=63–70 |year=2014 |pmid=24150707 |doi=10.1007/s00417-013-2492-3 |s2cid=13634941}}</ref> There is only one published clinical intervention trial testing for an effect of lutein and zeaxanthin supplementation on cataracts. 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) were NOT less likely to progress to needing cataract surgery. The authors speculated that there may be a cataract prevention benefit for people with low dietary intake of lutein and zeaxanthin, but recommended more research.<ref>{{cite journal |vauthors=Chew EY, SanGiovanni JP, Ferris FL, Wong WT, Agron E, Clemons TE, Sperduto R, Danis R, Chandra SR, Blodi BA, Domalpally A, Elman MJ, Antoszyk AN, Ruby AJ, Orth D, Bressler SB, Fish GE, Hubbard GB, Klein ML, Friberg TR, Rosenfeld PJ, Toth CA, Bernstein P |title=Lutein/zeaxanthin for the treatment of age-related cataract: AREDS2 randomized trial report no. 4 |journal=JAMA Ophthalmol |volume=131 |issue=7 |pages=843–50 |year=2013 |pmid=23645227 |doi=10.1001/jamaophthalmol.2013.4412 |pmc=6774801 |doi-access=free}}</ref>
==In diet==
Lutein is a natural part of a human diet found in orange-yellow fruits and flowers, and in leafy vegetables. According to the NHANES 2013-2014 survey, adults in the United States consume on average 1.7 mg/day of lutein and zeaxanthin combined.<ref name="WWEIA">[https://www.ars.usda.gov/ARSUserFiles/80400530/pdf/1314/Table_1_NIN_GEN_13.pdf NHANES 2013-2014 survey results, reported as What We Eat In America]</ref> No [[recommended dietary allowance]] currently exists for lutein. Some positive health effects have been seen at dietary intake levels of 6–10 mg/day.<ref name="Seddon1994">{{cite journal |vauthors=Seddon JM, Ajani UA, Sperduto RD |title=Dietary carotenoids, vitamins A, C, and E, and advanced age-related macular degeneration. Eye Disease Case-Control Study Group |journal=JAMA |volume=272 |issue=18 |pages=1413–20 |date=November 1994 |pmid=7933422 |doi=10.1001/jama.272.18.1413}}</ref> The only definitive side effect of excess lutein consumption is bronzing of the skin ([[carotenodermia]]).{{citation needed|date=August 2017}}
As a [[food additive]], lutein has the [[E number]] E161b (
[[INS number
]] 161b) and is extracted from the petals of
African marigold (
''[[Tagetes
Some foods
{| class="wikitable"
|-
! Product
! Lutein
|-
| [[Tropaeolum|nasturtium]] (yellow flowers, lutein levels only)
| 45,000<ref name="nasturtium"/>
|-
| [[Calendula officinalis|pot marigold]] (yellow and orange flowers, lutein levels only)
| 29,800
|-
| [[kale]] (raw)
| 39,550
|-
| [[kale]] (cooked)
|
|-
| [[dandelion]] leaves (raw)
| 13,610
|-
| [[Tropaeolum|nasturtium]] (leaves, lutein levels only)
| 13,600<ref name="nasturtium"/>
|-
| [[turnip]] [[leaf vegetables|greens]] (raw)
|
|-
| [[spinach]] (raw)
|
|-
| [[spinach]] (cooked)
|
|-
| [[
|
|-
| [[turnip]] [[leaf vegetables|greens]] (cooked)
| 8,440
|-
| [[collard
|
|-
| [[
|
|-
| garden [[peas]]
(raw)
|
|-
| [[romaine lettuce]]
|
|-
| [[zucchini]]
(courgettes)
|
|-
| [[
|
|-
| [[
|
|-
| [[
|
|-
| [[broccoli]], cooked
|
|-
| [[
| 687
|-
| [[maize]]/corn
| 642
|-
| [[egg (food)|egg]] (hard boiled)
| 353
|-
| [[
| 271
|-
| [[carrot]] (raw)
| 256
|-
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| 122
|}
===Safety===
In humans, the Observed Safe Level (OSL) for lutein, based on a non-government organization evaluation, is 20 mg/day.<ref name="pmid16814439">{{cite journal |vauthors=Shao A, Hathcock JN |title=Risk assessment for the carotenoids lutein and lycopene |journal=Regulatory Toxicology and Pharmacology |volume=45 |issue=3 |pages=289–98 |year=2006 |pmid=16814439 |doi=10.1016/j.yrtph.2006.05.007 |quote=<small>The OSL risk assessment method indicates that the evidence of safety is strong at intakes up to '''20mg/d for lutein''', and 75 mg/d for lycopene, and these levels are identified as the respective OSLs. Although much higher levels have been tested without adverse effects and may be safe, the data for intakes above these levels are not sufficient for a confident conclusion of long-term safety.</small>}}</ref> Although much higher levels have been tested without adverse effects and may also be safe, the data for intakes above the OSL are not sufficient for a confident conclusion of long-term safety.<ref name=lpi/><ref name="pmid16814439"/> Neither the U.S. Food and Drug Administration nor the [[European Food Safety Authority]] considers lutein an essential nutrient or has acted to set a tolerable upper intake level.<ref name=lpi/>
==Commercial value==
The lutein market is segmented into pharmaceutical,
==See also==
*[[Carotenoid]]s
*[[List of phytochemicals in food]]
==References==
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==External links==
{{Carotenoids}}
{{Authority control}}
[[Category:Carotenoids]]
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[[Category:Dietary antioxidants]]
[[Category:Food colorings]]
[[Category:
[[Category:Cyclohexenes]]
[[Category:E-number additives]]
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