Lycopene: Difference between revisions
imported>Marbletan mNo edit summary |
imported>Graywalls →Staining and removal: WP:NOTGUIDE and this is based on WP:HUFFPOCON, so it doesn't need to be here. |
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| ImageSize3 = 300px | | ImageSize3 = 300px | ||
| IUPACName = ψ,ψ-Carotene | | IUPACName = ψ,ψ-Carotene | ||
| SystematicName = (6''E'',8''E'',10''E'',12''E'',14''E'',16''E'',18''E'',20''E'',22''E'',24''E'',26''E'')-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30- | | SystematicName = (6''E'',8''E'',10''E'',12''E'',14''E'',16''E'',18''E'',20''E'',22''E'',24''E'',26''E'')-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecene | ||
| OtherNames = | | OtherNames = | ||
|Section1={{Chembox Identifiers | |Section1={{Chembox Identifiers | ||
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| Density = 0.889 g/cm<sup>3</sup> | | Density = 0.889 g/cm<sup>3</sup> | ||
| MeltingPtC = 177 | | MeltingPtC = 177 | ||
| MeltingPt_ref =<ref>{{cite book | editor= Haynes, William M. | year = 2011 | title = CRC Handbook of Chemistry and Physics | edition = 92nd | publisher = [[CRC Press]] | isbn = 978- | | MeltingPt_ref =<ref>{{cite book | editor= Haynes, William M. | year = 2011 | title = CRC Handbook of Chemistry and Physics | edition = 92nd | publisher = [[CRC Press]] | isbn = 978-1-4398-5511-9|page=3.94| title-link = CRC Handbook of Chemistry and Physics }}</ref> | ||
| BoilingPtC = 660.9 | | BoilingPtC = 660.9 | ||
| BoilingPt_notes = <br> at 760 mmHg<ref name=ec21 /> | | BoilingPt_notes = <br /> at 760 mmHg<ref name=ec21 /> | ||
| Solubility = insoluble | | Solubility = insoluble | ||
| SolubleOther = soluble in [[carbon disulfide|CS<sub>2</sub>]], [[chloroform|CHCl<sub>3</sub>]], [[tetrahydrofuran|THF]], [[diethyl ether|ether]], [[hexane|C<sub>6</sub>H<sub>14</sub>]], [[vegetable oil]]<br> insoluble in [[methanol|CH<sub>3</sub>OH]], [[ethanol|C<sub>2</sub>H<sub>5</sub>OH]]<ref name=ec21>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/lycopene|title=Lycopene|publisher=PubChem, US National Library of Medicine|date=2016|access-date=13 October 2016}}</ref> | | SolubleOther = soluble in [[carbon disulfide|CS<sub>2</sub>]], [[chloroform|CHCl<sub>3</sub>]], [[tetrahydrofuran|THF]], [[diethyl ether|ether]], [[hexane|C<sub>6</sub>H<sub>14</sub>]], [[vegetable oil]]<br /> insoluble in [[methanol|CH<sub>3</sub>OH]], [[ethanol|C<sub>2</sub>H<sub>5</sub>OH]]<ref name=ec21>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/lycopene|title=Lycopene|publisher=PubChem, US National Library of Medicine|date=2016|access-date=13 October 2016}}</ref> | ||
| Solubility1 = 1 g/L (14 °C)<ref name=ec21 /> | | Solubility1 = 1 g/L (14 °C)<ref name=ec21 /> | ||
| Solvent1 = hexane | | Solvent1 = hexane | ||
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}} | }} | ||
'''Lycopene''' is an [[organic compound]] classified as a [[tetraterpene]] and a [[carotene]].<ref name=KO>{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn= | '''Lycopene''' is an [[organic compound]] classified as a [[tetraterpene]] and a [[carotene]].<ref name=KO>{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0-471-23896-1 }}</ref> Lycopene (from the [[Neo-Latin]] ''[[Lycopersicon]]'', the name of a former tomato genus) is a bright red [[carotenoid]] [[hydrocarbon]] found in [[tomato]]es and other red fruits and vegetables. | ||
==Occurrence== | ==Occurrence== | ||
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|volume = 74 | |volume = 74 | ||
|issue = 15 | |issue = 15 | ||
| | |article-number = 155420 | ||
|year = 2006 | |year = 2006 | ||
|url = http://pubman.nims.go.jp/pubman/item/escidoc:1587358:2/component/escidoc:1597178/Prb155420.pdf | |url = http://pubman.nims.go.jp/pubman/item/escidoc:1587358:2/component/escidoc:1597178/Prb155420.pdf | ||
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|archive-date = 2020-10-02 | |archive-date = 2020-10-02 | ||
|archive-url = https://web.archive.org/web/20201002235524/http://pubman.nims.go.jp/pubman/item/escidoc:1587358:2/component/escidoc:1597178/Prb155420.pdf | |archive-url = https://web.archive.org/web/20201002235524/http://pubman.nims.go.jp/pubman/item/escidoc:1587358:2/component/escidoc:1597178/Prb155420.pdf | ||
}}</ref> Efficient energy transfer occurs between the encapsulated dye and nanotube—light is absorbed by the dye and without significant loss is transferred to the nanotube. Encapsulation increases chemical and thermal stability of lycopene molecules; it also allows their isolation and individual characterization.<ref> | |||
}}</ref> Efficient energy transfer occurs between the encapsulated dye and nanotube—light is absorbed by the dye and without significant loss is transferred to the nanotube. Encapsulation increases chemical and thermal stability of lycopene molecules; it also allows their isolation and individual characterization.<ref> | |||
{{cite journal | {{cite journal | ||
|author=Saito, Yuika | |author=Saito, Yuika | ||
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===Biosynthesis=== | ===Biosynthesis=== | ||
The unconditioned biosynthesis of lycopene in eukaryotic plants and in prokaryotic cyanobacteria is similar, as are the enzymes involved.<ref name=lpi/> Synthesis begins with [[mevalonic acid]], which is converted into [[dimethylallyl pyrophosphate]]. This is then condensed with three molecules of [[isopentenyl pyrophosphate]] (an isomer of dimethylallyl pyrophosphate), to give the 20-carbon [[geranylgeranyl pyrophosphate]]. Two molecules of this product are then condensed in a tail-to-tail configuration to give the 40-carbon [[phytoene]], the first committed step in carotenoid biosynthesis. Through several desaturation steps, phytoene is converted into lycopene. The two terminal isoprene groups of lycopene can be cyclized to produce beta-carotene, which can then be transformed into a wide variety of xanthophylls.<ref name=lpi/> | The unconditioned biosynthesis of lycopene in eukaryotic plants and in prokaryotic cyanobacteria is similar, as are the enzymes involved.<ref name=lpi/> Synthesis begins with [[mevalonic acid]], which is converted into [[dimethylallyl pyrophosphate]]. This is then condensed with three molecules of [[isopentenyl pyrophosphate]] (an isomer of dimethylallyl pyrophosphate), to give the 20-carbon [[geranylgeranyl pyrophosphate]]. Two molecules of this product are then condensed in a tail-to-tail configuration to give the 40-carbon [[phytoene]], the first committed step in carotenoid biosynthesis. Through several desaturation steps, phytoene is converted into lycopene. The two terminal isoprene groups of lycopene can be cyclized to produce beta-carotene, which can then be transformed into a wide variety of xanthophylls.<ref name=lpi/> | ||
==Diet== | ==Diet== | ||
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|- | |- | ||
| [[Gac]] aril | | [[Gac]] aril | ||
| 2~6 per gram<ref>{{cite journal|last1=Ishida|first1=BK|last2=Turner|first2=C|last3=Chapman|first3=MH|last4=McKeon|first4=TA|title=Fatty acid and carotenoid composition of gac (Momordica cochinchinensis Spreng) fruit|journal=Journal of Agricultural and Food Chemistry|date=28 January 2004|volume=52|issue=2|pages=274–9|doi=10.1021/jf030616i|pmid=14733508|bibcode=2004JAFC...52..274I }}</ref><ref>{{cite web|title=Gac (Momordica cochinchinensis) Analysis report|url=https://www.volkerkleinhenz.com/presentations/Gac-Analysis-Report.pdf|access-date=2018-04-13|archive-date=2018-04-13|archive-url=https://web.archive.org/web/20180413125442/https://www.volkerkleinhenz.com/presentations/Gac-Analysis-Report.pdf | | 2~6 per gram<ref>{{cite journal|last1=Ishida|first1=BK|last2=Turner|first2=C|last3=Chapman|first3=MH|last4=McKeon|first4=TA|title=Fatty acid and carotenoid composition of gac (Momordica cochinchinensis Spreng) fruit|journal=Journal of Agricultural and Food Chemistry|date=28 January 2004|volume=52|issue=2|pages=274–9|doi=10.1021/jf030616i|pmid=14733508|bibcode=2004JAFC...52..274I }}</ref><ref>{{cite web|title=Gac (Momordica cochinchinensis) Analysis report|url=https://www.volkerkleinhenz.com/presentations/Gac-Analysis-Report.pdf|access-date=2018-04-13|archive-date=2018-04-13|archive-url=https://web.archive.org/web/20180413125442/https://www.volkerkleinhenz.com/presentations/Gac-Analysis-Report.pdf}}</ref> | ||
|- | |- | ||
| Raw [[tomato]] | | Raw [[tomato]] | ||
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[[Fruit]]s and [[vegetable]]s that are high in lycopene include [[autumn olive]], [[gac]], tomatoes, [[watermelon]], pink [[grapefruit]], pink [[guava]], [[papaya]], [[seabuckthorn]], [[wolfberry]] ([[goji]], a berry relative of tomato), and [[rosehip]].<ref name=lpi/> [[Ketchup]] is a common dietary source of lycopene.<ref name=lpi/> Although [[gac]] (''Momordica cochinchinensis'' Spreng) has the highest content of lycopene of any known fruit or vegetable (multiple times more than tomatoes),<ref name="tran">{{cite journal|pmc=4779482|year=2015|last1=Tran|first1=X. T.|title=Effects of maturity on physicochemical properties of Gac fruit (Momordica cochinchinensis Spreng.)|journal=Food Science & Nutrition|volume=4|issue=2|pages=305–314|last2=Parks|first2=S. E.|last3=Roach|first3=P. D.|last4=Golding|first4=J. B.|last5=Nguyen|first5=M. H.|doi=10.1002/fsn3.291|pmid=27004120}}</ref><ref name="Ishida2004">{{Cite journal|vauthors=Ishida BK, Turner C, Chapman MH, McKeon TA |title=Fatty acid and carotenoid composition of gac (Momordica cochinchinensis Spreng) fruit |journal=[[Journal of Agricultural and Food Chemistry]] |volume=52 |issue=2 |pages=274–9 |date=January 2004 |pmid=14733508 |doi=10.1021/jf030616i |bibcode=2004JAFC...52..274I }}</ref> tomatoes and tomato-based sauces, juices, and ketchup account for more than 85% of the dietary intake of lycopene for most people.<ref name=lpi/> The lycopene content of tomatoes depends on variety and increases as the fruit ripens.<ref>{{cite journal|pmid=26462607|year=2016|last1=Ilahy|first1=R|title=Fractionate analysis of the phytochemical composition and antioxidant activities in advanced breeding lines of high-lycopene tomatoes|journal=Food Funct|volume=7|issue=1|pages=574–83|last2=Piro|first2=G|last3=Tlili|first3=I|last4=Riahi|first4=A|last5=Sihem|first5=R|last6=Ouerghi|first6=I|last7=Hdider|first7=C|last8=Lenucci|first8=M. S.|doi=10.1039/c5fo00553a}}</ref> | [[Fruit]]s and [[vegetable]]s that are high in lycopene include [[autumn olive]], [[gac]], tomatoes, [[watermelon]], pink [[grapefruit]], pink [[guava]], [[papaya]], [[seabuckthorn]], [[wolfberry]] ([[goji]], a berry relative of tomato), and [[rosehip]].<ref name=lpi/> [[Ketchup]] is a common dietary source of lycopene.<ref name=lpi/> Although [[gac]] (''Momordica cochinchinensis'' Spreng) has the highest content of lycopene of any known fruit or vegetable (multiple times more than tomatoes),<ref name="tran">{{cite journal|pmc=4779482|year=2015|last1=Tran|first1=X. T.|title=Effects of maturity on physicochemical properties of Gac fruit (Momordica cochinchinensis Spreng.)|journal=Food Science & Nutrition|volume=4|issue=2|pages=305–314|last2=Parks|first2=S. E.|last3=Roach|first3=P. D.|last4=Golding|first4=J. B.|last5=Nguyen|first5=M. H.|doi=10.1002/fsn3.291|pmid=27004120}}</ref><ref name="Ishida2004">{{Cite journal|vauthors=Ishida BK, Turner C, Chapman MH, McKeon TA |title=Fatty acid and carotenoid composition of gac (Momordica cochinchinensis Spreng) fruit |journal=[[Journal of Agricultural and Food Chemistry]] |volume=52 |issue=2 |pages=274–9 |date=January 2004 |pmid=14733508 |doi=10.1021/jf030616i |bibcode=2004JAFC...52..274I }}</ref> tomatoes and tomato-based sauces, juices, and ketchup account for more than 85% of the dietary intake of lycopene for most people.<ref name=lpi/> The lycopene content of tomatoes depends on variety and increases as the fruit ripens.<ref>{{cite journal|pmid=26462607|year=2016|last1=Ilahy|first1=R|title=Fractionate analysis of the phytochemical composition and antioxidant activities in advanced breeding lines of high-lycopene tomatoes|journal=Food Funct|volume=7|issue=1|pages=574–83|last2=Piro|first2=G|last3=Tlili|first3=I|last4=Riahi|first4=A|last5=Sihem|first5=R|last6=Ouerghi|first6=I|last7=Hdider|first7=C|last8=Lenucci|first8=M. S.|doi=10.1039/c5fo00553a}}</ref> | ||
Unlike other fruits and vegetables, where nutritional content such as [[vitamin C]] is diminished upon cooking, [[food processing|processing]] of tomatoes increases the concentration of [[Bioavailability|bioavailable]] lycopene.<ref name=lpi/><ref>{{cite journal|url=http://scielo.isciii.es/scielo.php?script=sci_arttext&pid=S0212-16112012000500025&lng=en&nrm=iso&tlng=en|journal=Hospital Nutrition (Madrid)|volume=27|issue=5|year=2012|pages=1542–6|vauthors=Perdomo F, Cabrera Fránquiz F, Cabrera J, Serra-Majem L |title=Influence of cooking procedure on the bioavailability of lycopene in tomatoes|pmid=23478703|doi=10.3305/nh.2012.27.5.5908}}</ref> Lycopene in tomato paste is up to four times more bioavailable than in fresh tomatoes.<ref>{{Cite journal | doi = 10.1002/jsfa.6546| pmid = 24375495| title = Home processing of tomatoes (Solanum lycopersicum): Effects onin vitrobioaccessibility of total lycopene, phenolics, flavonoids, and antioxidant capacity| journal = Journal of the Science of Food and Agriculture| volume = 94| issue = 11| pages = 2225–33| year = 2014| last1 = Kamiloglu | first1 = S. | last2 = Demirci | first2 = M. | last3 = Selen | first3 = S. | last4 = Toydemir | first4 = G. | last5 = Boyacioglu | first5 = D. | last6 = Capanoglu | first6 = E. | bibcode = 2014JSFA...94.2225K}}</ref> Processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain a higher concentration of bioavailable lycopene compared to raw tomatoes.<ref name=lpi/><ref>{{cite book|last1=Yamaguchi|first1=Masayoshi|title=Carotenoids : Properties, Effects and Diseases|date=2010|publisher=Nova Science Publishers|location=New York|isbn= | Unlike other fruits and vegetables, where nutritional content such as [[vitamin C]] is diminished upon cooking, [[food processing|processing]] of tomatoes increases the concentration of [[Bioavailability|bioavailable]] lycopene.<ref name=lpi/><ref>{{cite journal|url=http://scielo.isciii.es/scielo.php?script=sci_arttext&pid=S0212-16112012000500025&lng=en&nrm=iso&tlng=en|journal=Hospital Nutrition (Madrid)|volume=27|issue=5|year=2012|pages=1542–6|vauthors=Perdomo F, Cabrera Fránquiz F, Cabrera J, Serra-Majem L |title=Influence of cooking procedure on the bioavailability of lycopene in tomatoes|pmid=23478703|doi=10.3305/nh.2012.27.5.5908}}</ref> Lycopene in tomato paste is up to four times more bioavailable than in fresh tomatoes.<ref>{{Cite journal | doi = 10.1002/jsfa.6546| pmid = 24375495| title = Home processing of tomatoes (Solanum lycopersicum): Effects onin vitrobioaccessibility of total lycopene, phenolics, flavonoids, and antioxidant capacity| journal = Journal of the Science of Food and Agriculture| volume = 94| issue = 11| pages = 2225–33| year = 2014| last1 = Kamiloglu | first1 = S. | last2 = Demirci | first2 = M. | last3 = Selen | first3 = S. | last4 = Toydemir | first4 = G. | last5 = Boyacioglu | first5 = D. | last6 = Capanoglu | first6 = E. | bibcode = 2014JSFA...94.2225K}}</ref> Processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain a higher concentration of bioavailable lycopene compared to raw tomatoes.<ref name=lpi/><ref>{{cite book|last1=Yamaguchi|first1=Masayoshi|title=Carotenoids: Properties, Effects and Diseases|date=2010|publisher=Nova Science Publishers|location=New York|isbn=978-1-61209-713-8|page=125}}</ref> | ||
Cooking and crushing tomatoes (as in the [[canning]] process) and serving in oil-rich dishes (such as [[spaghetti]] sauce or [[pizza]]) greatly increases assimilation from the digestive tract into the bloodstream. Lycopene is fat-soluble, so the oil is said to help absorption. Gac has high lycopene content derived mainly from its [[seed coat]]s.<ref>{{Cite journal | Cooking and crushing tomatoes (as in the [[canning]] process) and serving in oil-rich dishes (such as [[spaghetti]] sauce or [[pizza]]) greatly increases assimilation from the digestive tract into the bloodstream. Lycopene is fat-soluble, so the oil is said to help absorption. Gac has high lycopene content derived mainly from its [[seed coat]]s.<ref>{{Cite journal | ||
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| bibcode = 2008PChem..69.1997A | | bibcode = 2008PChem..69.1997A | ||
}}</ref> Some foods that do not appear red also contain lycopene, e.g., baked beans.<ref name=lpi/> | }}</ref> Some foods that do not appear red also contain lycopene, e.g., baked beans.<ref name=lpi/> | ||
When lycopene is used as a food additive (E160d), it is usually obtained from tomatoes.<ref name=lpi/><ref>{{cite journal |last1=Li |first1=Lei |last2=Liu |first2=Zhen |last3=Jiang |first3=Hong |last4=Mao |first4=Xiangzhao |title=Biotechnological production of lycopene by microorganisms |journal=Appl. Microbiol. Biotechnol. |date=2020 |volume=104 |issue=24 |pages=10307–10324 |doi=10.1007/s00253-020-10967-4 |pmid=33097966 |s2cid=225058089 | When lycopene is used as a food additive (E160d), it is usually obtained from tomatoes.<ref name=lpi/><ref>{{cite journal |last1=Li |first1=Lei |last2=Liu |first2=Zhen |last3=Jiang |first3=Hong |last4=Mao |first4=Xiangzhao |title=Biotechnological production of lycopene by microorganisms |journal=Appl. Microbiol. Biotechnol. |date=2020 |volume=104 |issue=24 |pages=10307–10324 |doi=10.1007/s00253-020-10967-4 |pmid=33097966 |s2cid=225058089 }}</ref> | ||
===Adverse effects=== | ===Adverse effects=== | ||
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| archive-date = 23 September 2017 | | archive-date = 23 September 2017 | ||
| archive-url = https://web.archive.org/web/20170923043049/http://www.mayoclinic.org/drugs-supplements/lycopene/background/HRB-20059666 | | archive-url = https://web.archive.org/web/20170923043049/http://www.mayoclinic.org/drugs-supplements/lycopene/background/HRB-20059666 | ||
}}</ref> Lycopene may increase the risk of bleeding when taken with [[anticoagulant]] drugs.<ref name=mayo/> Because lycopene may cause low blood pressure, interactions with drugs that affect blood pressure may occur. Lycopene may affect the [[immune system]], the [[nervous system]], sensitivity to sunlight, or drugs used for stomach ailments.<ref name=mayo/> | }}</ref> Lycopene may increase the risk of bleeding when taken with [[anticoagulant]] drugs.<ref name=mayo/> Because lycopene may cause low blood pressure, interactions with drugs that affect blood pressure may occur. Lycopene may affect the [[immune system]], the [[nervous system]], sensitivity to sunlight, or drugs used for stomach ailments.<ref name=mayo/> | ||
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A 2020 review of [[randomized controlled trial]]s found conflicting evidence for lycopene having an effect on [[cardiovascular disease|cardiovascular]] [[Risk factor (epidemiology)|risk factor]]s,<ref>{{cite journal |last1=Tierney |first1=Audrey |last2=Rumble |first2=Chloe |last3=Billings |first3=Lauren |last4=George |first4=Elena |date=2020 |title=Effect of Dietary and Supplemental Lycopene on Cardiovascular Risk Factors: A Systematic Review and Meta-Analysis |url= |journal=Advances in Nutrition |volume=11 |issue=6 |pages=1453–1488 |doi=10.1093/advances/nmaa069 |pmid=32652029|pmc=7666898 }}</ref> whereas a 2017 review concluded that tomato products and lycopene supplementation reduced [[blood lipids]] and [[blood pressure]].<ref name="ChengKoutsidis2017">{{cite journal|last1=Cheng|first1=Ho Ming|last2=Koutsidis|first2=Georgios|last3=Lodge|first3=John K.|last4=Ashor|first4=Ammar|last5=Siervo|first5=Mario|last6=Lara|first6=José|title=Tomato and lycopene supplementation and cardiovascular risk factors: A systematic review and meta-analysis|journal=Atherosclerosis|volume=257|year=2017|pages=100–108|issn=0021-9150|doi=10.1016/j.atherosclerosis.2017.01.009|pmid=28129549|s2cid=19287598 |url=http://nrl.northumbria.ac.uk/29320/1/Cheng_etal_Atherosclerosis_January_2017_NRL.pdf}}</ref> | A 2020 review of [[randomized controlled trial]]s found conflicting evidence for lycopene having an effect on [[cardiovascular disease|cardiovascular]] [[Risk factor (epidemiology)|risk factor]]s,<ref>{{cite journal |last1=Tierney |first1=Audrey |last2=Rumble |first2=Chloe |last3=Billings |first3=Lauren |last4=George |first4=Elena |date=2020 |title=Effect of Dietary and Supplemental Lycopene on Cardiovascular Risk Factors: A Systematic Review and Meta-Analysis |url= |journal=Advances in Nutrition |volume=11 |issue=6 |pages=1453–1488 |doi=10.1093/advances/nmaa069 |pmid=32652029|pmc=7666898 }}</ref> whereas a 2017 review concluded that tomato products and lycopene supplementation reduced [[blood lipids]] and [[blood pressure]].<ref name="ChengKoutsidis2017">{{cite journal|last1=Cheng|first1=Ho Ming|last2=Koutsidis|first2=Georgios|last3=Lodge|first3=John K.|last4=Ashor|first4=Ammar|last5=Siervo|first5=Mario|last6=Lara|first6=José|title=Tomato and lycopene supplementation and cardiovascular risk factors: A systematic review and meta-analysis|journal=Atherosclerosis|volume=257|year=2017|pages=100–108|issn=0021-9150|doi=10.1016/j.atherosclerosis.2017.01.009|pmid=28129549|s2cid=19287598 |url=http://nrl.northumbria.ac.uk/29320/1/Cheng_etal_Atherosclerosis_January_2017_NRL.pdf}}</ref> | ||
A 2015 review found that dietary lycopene was associated with reduced risk of [[prostate cancer]],<ref name="Chen">{{cite journal|display-authors=3 | last1=Chen | first1=Ping | last2=Zhang | first2=Wenhao | last3=Wang | first3=Xiao | last4=Zhao | first4=Keke | last5=Negi | first5=Devendra Singh | last6=Zhuo | first6=Li | last7=Qi | first7=Mao | last8=Wang | first8=Xinghuan | last9=Zhang | first9=Xinhua | title=Lycopene and Risk of Prostate Cancer | journal=Medicine | volume=94 | issue=33 | date=2015-08-21 | issn=0025-7974 | pmid=26287411 | pmc=4616444 | doi=10.1097/md.0000000000001260 | | A 2015 review found that dietary lycopene was associated with reduced risk of [[prostate cancer]],<ref name="Chen">{{cite journal|display-authors=3 | last1=Chen | first1=Ping | last2=Zhang | first2=Wenhao | last3=Wang | first3=Xiao | last4=Zhao | first4=Keke | last5=Negi | first5=Devendra Singh | last6=Zhuo | first6=Li | last7=Qi | first7=Mao | last8=Wang | first8=Xinghuan | last9=Zhang | first9=Xinhua | title=Lycopene and Risk of Prostate Cancer | journal=Medicine | volume=94 | issue=33 | date=2015-08-21 | issn=0025-7974 | pmid=26287411 | pmc=4616444 | doi=10.1097/md.0000000000001260 | article-number=e1260}}</ref> whereas a 2021 [[meta-analysis]] found that dietary lycopene did not affect prostate cancer risk.<ref>{{Cite journal |last1=Luo |first1=Jie |last2=Ke |first2=Dandan |last3=He |first3=Qingwei |date=2021 |title=Dietary Tomato Consumption and the Risk of Prostate Cancer: A Meta-Analysis |journal=Frontiers in Nutrition |volume=8 |article-number=625185 |doi=10.3389/fnut.2021.625185 |issn=2296-861X |pmc=8129008 |pmid=34017849|doi-access=free }}</ref> Other reviews concluded that research has been insufficient to establish whether lycopene consumption affects human health.<ref>{{cite journal|pmc=3850026|year=2010|last1=Story|first1=EN|title=An Update on the Health Effects of Tomato Lycopene|journal=Annual Review of Food Science and Technology|volume=1|issue=1|pages=189–210|last2=Kopec|first2=R. E|last3=Schwartz|first3=S. J|last4=Harris|first4=G. K|doi=10.1146/annurev.food.102308.124120|pmid=22129335}}</ref> | ||
===Regulatory status in Europe and the United States=== | ===Regulatory status in Europe and the United States=== | ||
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In a review of literature on lycopene and its potential benefit in the diet, the [[European Food Safety Authority]] concluded there was insufficient evidence for lycopene having antioxidant effects in humans, particularly in skin, heart function, or vision protection from [[ultraviolet light]].<ref name="efsa">{{cite journal|journal=EFSA Journal|volume=9|issue=4|year=2011|title=Scientific Opinion on the substantiation of health claims related to lycopene and protection of DNA, proteins and lipids from oxidative damage (ID 1608, 1609, 1611, 1662, 1663, 1664, 1899, 1942, 2081, 2082, 2142, 2374), protection of the skin from UV-induced (including photo-oxidative) damage (ID 1259, 1607, 1665, 2143, 2262, 2373), contribution to normal cardiac function (ID 1610, 2372), and maintenance of normal vision (ID 1827) pursuant to Article 13(1) of Regulation (EC) No 1924/2006|doi=10.2903/j.efsa.2011.2031 |page=2031|doi-access=free}}</ref> | In a review of literature on lycopene and its potential benefit in the diet, the [[European Food Safety Authority]] concluded there was insufficient evidence for lycopene having antioxidant effects in humans, particularly in skin, heart function, or vision protection from [[ultraviolet light]].<ref name="efsa">{{cite journal|journal=EFSA Journal|volume=9|issue=4|year=2011|title=Scientific Opinion on the substantiation of health claims related to lycopene and protection of DNA, proteins and lipids from oxidative damage (ID 1608, 1609, 1611, 1662, 1663, 1664, 1899, 1942, 2081, 2082, 2142, 2374), protection of the skin from UV-induced (including photo-oxidative) damage (ID 1259, 1607, 1665, 2143, 2262, 2373), contribution to normal cardiac function (ID 1610, 2372), and maintenance of normal vision (ID 1827) pursuant to Article 13(1) of Regulation (EC) No 1924/2006|doi=10.2903/j.efsa.2011.2031 |page=2031|doi-access=free}}</ref> | ||
Although lycopene from tomatoes has been tested in humans for cardiovascular diseases and prostate cancer, no effect on any disease was found.<ref name="ReferenceA">{{cite web|title=Qualified Health Claims: Letter Regarding Tomatoes and Prostate Cancer (Lycopene Health Claim Coalition) (Docket No. 2004Q-0201) (Updated 9 July 2015)|publisher=US Food and Drug Administration|url=https://www.fda.gov/Food/IngredientsPackagingLabeling/LabelingNutrition/ucm072767.htm|date=8 November 2005|access-date=16 December 2019|archive-url=https://web.archive.org/web/20170722101944/https://www.fda.gov/Food/IngredientsPackagingLabeling/LabelingNutrition/ucm072767.htm|archive-date=22 July 2017 | Although lycopene from tomatoes has been tested in humans for cardiovascular diseases and prostate cancer, no effect on any disease was found.<ref name="ReferenceA">{{cite web|title=Qualified Health Claims: Letter Regarding Tomatoes and Prostate Cancer (Lycopene Health Claim Coalition) (Docket No. 2004Q-0201) (Updated 9 July 2015)|publisher=US Food and Drug Administration|url=https://www.fda.gov/Food/IngredientsPackagingLabeling/LabelingNutrition/ucm072767.htm|date=8 November 2005|access-date=16 December 2019|archive-url=https://web.archive.org/web/20170722101944/https://www.fda.gov/Food/IngredientsPackagingLabeling/LabelingNutrition/ucm072767.htm|archive-date=22 July 2017}}</ref> The US [[Food and Drug Administration]], in rejecting manufacturers' requests in 2005 to allow "qualified labeling" for lycopene and the reduction of various cancer risks, provided a conclusion that remains in effect {{Asof|2015|lc=y}}: | ||
{{blockquote |text=no studies provided information about whether lycopene intake may reduce the risk of any of the specific forms of cancer. Based on the above, FDA concludes that there is no credible evidence supporting a relationship between lycopene consumption, either as a food ingredient, a component of food, or as a dietary supplement, and any of these cancers.<ref name=ReferenceA/>}} | {{blockquote |text=no studies provided information about whether lycopene intake may reduce the risk of any of the specific forms of cancer. Based on the above, FDA concludes that there is no credible evidence supporting a relationship between lycopene consumption, either as a food ingredient, a component of food, or as a dietary supplement, and any of these cancers.<ref name=ReferenceA/>}} | ||
Latest revision as of 21:07, 15 October 2025
Template:Short description Template:Chembox
Lycopene is an organic compound classified as a tetraterpene and a carotene.[1] Lycopene (from the Neo-Latin Lycopersicon, the name of a former tomato genus) is a bright red carotenoid hydrocarbon found in tomatoes and other red fruits and vegetables.
Occurrence
Aside from tomatoes or tomato products like ketchup, it is found in watermelons, grapefruits, red guavas, and baked beans.[2] It has no vitamin A activity.[2]
In plants, algae, and other photosynthetic organisms, lycopene is an intermediate in the biosynthesis of many carotenoids, including beta-carotene, which is responsible for yellow, orange, or red pigmentation, photosynthesis, and photoprotection.[2]
Like all carotenoids, lycopene is a tetraterpene.[2] It is soluble in fat, but insoluble in water.[2] Eleven conjugated double bonds give lycopene its deep red color.[2]
Owing to the strong color, lycopene is used as a food coloring (registered as E160d) and is approved for use in the US,[3] Australia and New Zealand (registered as 160d),[4] and the European Union (E160d).[5]
Structure and physical properties
Lycopene is a symmetrical tetraterpene because it consists entirely of carbon and hydrogen and is derived from eight isoprene subunits.[2] Isolation procedures for lycopene were first reported in 1910, and the structure of the molecule was determined by 1931. In its natural, all-trans form, the molecule is long and somewhat flat, constrained by its system of 11 conjugated double bonds. The extended conjugation is responsible for its deep red color.[2]
Plants and photosynthetic bacteria produce all-trans lycopene.[2] When exposed to light or heat, lycopene can undergo isomerization to any of a number of cis-isomers, which have a less linear shape. Isomers distinct stabilities, with highest stability: 5-cis ≥ all-trans ≥ 9-cis ≥ 13-cis > 15-cis > 7-cis > 11-cis: lowest.[6][7] In human blood, various cis-isomers constitute more than 60% of the total lycopene concentration, but the biological effects of individual isomers have not been investigated.[8]
Carotenoids like lycopene are found in photosynthetic pigment-protein complexes in plants, photosynthetic bacteria, fungi, and algae.[2] They are responsible for the bright orange–red colors of fruits and vegetables, perform various functions in photosynthesis, and protect photosynthetic organisms from excessive light damage. Lycopene is a key intermediate in the biosynthesis of carotenoids, such as beta-carotene, and xanthophylls.[9]
Dispersed lycopene molecules can be encapsulated into carbon nanotubes enhancing their optical properties.[10] Efficient energy transfer occurs between the encapsulated dye and nanotube—light is absorbed by the dye and without significant loss is transferred to the nanotube. Encapsulation increases chemical and thermal stability of lycopene molecules; it also allows their isolation and individual characterization.[11]
Biosynthesis
The unconditioned biosynthesis of lycopene in eukaryotic plants and in prokaryotic cyanobacteria is similar, as are the enzymes involved.[2] Synthesis begins with mevalonic acid, which is converted into dimethylallyl pyrophosphate. This is then condensed with three molecules of isopentenyl pyrophosphate (an isomer of dimethylallyl pyrophosphate), to give the 20-carbon geranylgeranyl pyrophosphate. Two molecules of this product are then condensed in a tail-to-tail configuration to give the 40-carbon phytoene, the first committed step in carotenoid biosynthesis. Through several desaturation steps, phytoene is converted into lycopene. The two terminal isoprene groups of lycopene can be cyclized to produce beta-carotene, which can then be transformed into a wide variety of xanthophylls.[2]
Diet
Consumption by humans
Absorption of lycopene requires that it be combined with bile salts and fat to form micelles.[2] Intestinal absorption of lycopene is enhanced by the presence of fat and by cooking.[2] Lycopene dietary supplements (in oil) may be more efficiently absorbed than lycopene from food.[2]
Lycopene is not an essential nutrient for humans, but is commonly found in the diet mainly from dishes prepared from tomatoes.[2] The median and 99th percentile of dietary lycopene intake have been estimated to be 5.2 and 123 mg/d, respectively.[12]
Sources
| Source | mg wet weight |
|---|---|
| Gac aril | 2~6 per gram[13][14] |
| Raw tomato | 4.6 per cup |
| Tomato juice | 22 per cup |
| Tomato paste | 75 per cup |
| Tomato ketchup | 2.5 per tablespoon |
| Watermelon | 13 per wedge |
| Pink grapefruit | 2 per half grapefruit |
Fruits and vegetables that are high in lycopene include autumn olive, gac, tomatoes, watermelon, pink grapefruit, pink guava, papaya, seabuckthorn, wolfberry (goji, a berry relative of tomato), and rosehip.[2] Ketchup is a common dietary source of lycopene.[2] Although gac (Momordica cochinchinensis Spreng) has the highest content of lycopene of any known fruit or vegetable (multiple times more than tomatoes),[15][16] tomatoes and tomato-based sauces, juices, and ketchup account for more than 85% of the dietary intake of lycopene for most people.[2] The lycopene content of tomatoes depends on variety and increases as the fruit ripens.[17]
Unlike other fruits and vegetables, where nutritional content such as vitamin C is diminished upon cooking, processing of tomatoes increases the concentration of bioavailable lycopene.[2][18] Lycopene in tomato paste is up to four times more bioavailable than in fresh tomatoes.[19] Processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain a higher concentration of bioavailable lycopene compared to raw tomatoes.[2][20]
Cooking and crushing tomatoes (as in the canning process) and serving in oil-rich dishes (such as spaghetti sauce or pizza) greatly increases assimilation from the digestive tract into the bloodstream. Lycopene is fat-soluble, so the oil is said to help absorption. Gac has high lycopene content derived mainly from its seed coats.[21] Cara Cara navel oranges, and other citrus fruit, such as pink grapefruits, also contain lycopene.[2][22] Some foods that do not appear red also contain lycopene, e.g., baked beans.[2] When lycopene is used as a food additive (E160d), it is usually obtained from tomatoes.[2][23]
Adverse effects
Lycopene is non-toxic and commonly found in the diet, mainly from tomato products.[2] There are cases of intolerance or allergic reaction to dietary lycopene, which may cause diarrhea, nausea, stomach pain or cramps, gas, and loss of appetite.[24] Lycopene may increase the risk of bleeding when taken with anticoagulant drugs.[24] Because lycopene may cause low blood pressure, interactions with drugs that affect blood pressure may occur. Lycopene may affect the immune system, the nervous system, sensitivity to sunlight, or drugs used for stomach ailments.[24]
Lycopenemia is an orange discoloration of the skin that is observed with high intakes of lycopene.[12] The discoloration is expected to fade after discontinuing excessive lycopene intake.[12]
Research and potential health effects
A 2020 review of randomized controlled trials found conflicting evidence for lycopene having an effect on cardiovascular risk factors,[25] whereas a 2017 review concluded that tomato products and lycopene supplementation reduced blood lipids and blood pressure.[26]
A 2015 review found that dietary lycopene was associated with reduced risk of prostate cancer,[27] whereas a 2021 meta-analysis found that dietary lycopene did not affect prostate cancer risk.[28] Other reviews concluded that research has been insufficient to establish whether lycopene consumption affects human health.[29]
Regulatory status in Europe and the United States
In a review of literature on lycopene and its potential benefit in the diet, the European Food Safety Authority concluded there was insufficient evidence for lycopene having antioxidant effects in humans, particularly in skin, heart function, or vision protection from ultraviolet light.[30]
Although lycopene from tomatoes has been tested in humans for cardiovascular diseases and prostate cancer, no effect on any disease was found.[31] The US Food and Drug Administration, in rejecting manufacturers' requests in 2005 to allow "qualified labeling" for lycopene and the reduction of various cancer risks, provided a conclusion that remains in effect Template:Asof:
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no studies provided information about whether lycopene intake may reduce the risk of any of the specific forms of cancer. Based on the above, FDA concludes that there is no credible evidence supporting a relationship between lycopene consumption, either as a food ingredient, a component of food, or as a dietary supplement, and any of these cancers.[31]
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In a review of research through 2024, the US National Cancer Institute concluded that the FDA has not approved the use of lycopene as effective for treating any medical condition, including various types of cancer.[32]
See also
References
Template:Sister project Template:Carotenoids Template:Terpenoids Template:Dietary supplement
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