World Library  
Flag as Inappropriate
Email this Article

Lycopene

Article Id: WHEBN0000018735
Reproduction Date:

Title: Lycopene  
Author: World Heritage Encyclopedia
Language: English
Subject: Carotene, Papaya, Carotenoids, E number, Biological pigment
Collection: Carotenoids, Dietary Antioxidants, Dietary Supplements, Food Antioxidants, Food Colorings, Hydrocarbons
Publisher: World Heritage Encyclopedia
Publication
Date:
 

Lycopene

Lycopene
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
UNII  YesY
EC number
ChEBI  YesY
ChEMBL  YesY
Jmol-3D images Image 1
Properties
Molecular formula C40H56
Molar mass 536.87 g mol−1
Appearance deep red solid
Density 0.889 g/cm3
Melting point 172–173 °C (342–343 °F; 445–446 K)
Boiling point 660.9 °C (1,221.6 °F; 934.1 K)
at 760 mmHg[1]
Solubility in water insoluble
Solubility soluble in CS2, CHCl3, THF, ether, C6H14, vegetable oil
insoluble in CH3OH, C2H5OH[1]
Solubility in hexane 1 g/L (14 °C)[1]
Vapor pressure 1.33·10-16 mmHg (25 °C)[1]
Hazards
MSDS External MSDS
Main hazards Combustible
NFPA 704
1
0
0
Flash point 350.7 °C (663.3 °F; 623.8 K) [1]
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/N?)

Lycopene from the neo-Latin lycopersicum, the tomato species, is a bright red carotene and carotenoid pigment and phytochemical found in tomatoes and other red fruits and vegetables, such as red carrots, watermelons, gac, and papayas, although not in strawberries, red bell peppers, or cherries.[2] Although lycopene is chemically a carotene, it has no vitamin A activity.[3] Foods that are not red may also contain lycopene, such as brown beans or parsley.[2]

In beta carotene, which is responsible for yellow, orange, or red pigmentation, photosynthesis, and photo-protection. Like all carotenoids, lycopene is a polyunsaturated hydrocarbon, i.e. an unsubstituted alkene. Structurally, lycopene is a tetraterpene and assembled from eight isoprene units that are composed entirely of carbon and hydrogen. It is insoluble in water. Lycopene's eleven conjugated double bonds give its deep red color and its antioxidant activity. Owing to the strong color and non-toxicity, lycopene is a useful food coloring (registered as E160d) and is approved for usage in the USA,[4] Australia and New Zealand (registered as 160d)[5] and the EU.[6]

Contents

  • Consumption by humans 1
  • Structure and physical properties 2
    • Staining and removal 2.1
  • Role in photosynthesis 3
    • Biosynthesis 3.1
  • Dietary sources 4
  • Pharmacokinetics 5
    • Adverse effects 5.1
  • Potential health effects 6
  • See also 7
  • References 8
    • Bibliography 8.1
  • External links 9

Consumption by humans

Lycopene is not an essential nutrient for humans, but it is commonly found in the diet mainly from dishes prepared from tomatoes.[2] When absorbed from the intestine, lycopene is transported in the blood by various lipoproteins and accumulates primarily in the blood, adipose tissue, skin, liver, and adrenal glands, but it can be found in most tissues.

Preliminary research has shown that people who consume tomatoes may have a lower cancer risk, possibly due to lycopene affecting mechanisms of prostate cancer.[3][7] However, this area of research and the relationship between lycopene and prostate cancer have been deemed insufficient of evidence for health claim approval by the US Food and Drug Administration.[8]

Skeletal formula of all-trans lycopene
Ball-and-stick model of all-trans lycopene

Structure and physical properties

Lycopene is a symmetrical tetraterpene assembled from eight isoprene units. It is a member of the carotenoid family of compounds, and because it consists entirely of carbon and hydrogen, is also a carotene.[9] 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 straight, constrained by its system of eleven conjugated double bonds. Each extension in this conjugated system reduces the energy required for electrons to transition to higher energy states, allowing the molecule to absorb visible light of progressively longer wavelengths. Lycopene absorbs all but the longest wavelengths of visible light, so it appears red.[10]

Plants and photosynthetic bacteria naturally produce all-trans lycopene, but a total of 72 geometric isomers of the molecule are sterically possible.[11] When exposed to light or heat, lycopene can undergo isomerization to any of a number of these cis-isomers, which have a bent rather than linear shape. Different isomers were shown to have different stabilities due to their molecular energy (highest stability: 5-cis ≥ all-trans ≥ 9-cis ≥ 13-cis > 15-cis > 7-cis > 11-cis: lowest).[12] In the human bloodstream, various cis-isomers constitute more than 60% of the total lycopene concentration, but the biological effects of individual isomers have not been investigated.[13]

Staining and removal

Lycopene is insoluble in water, and can be dissolved only in organic solvents and oils. Because of its non-polarity, lycopene in food preparations will stain any sufficiently porous material, including most plastics. While a tomato stain can be fairly easily removed from fabric (provided the stain is fresh), lycopene diffuses into plastic, making it impossible to remove with hot water or detergent. If lycopene is oxidized (for example, by reacting with bleaches or acids), the double bonds between the carbon atoms will be broken; cleaving the molecule, breaking the conjugated double bond system, and eliminating the chromophore.

Role in photosynthesis

Lycopene is a key intermediate in the biosynthesis of many carotenoids.

Carotenoids like lycopene are important pigments found in photosynthetic pigment-protein complexes in plants, photosynthetic bacteria, fungi, and algae. They are responsible for the bright 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 many important carotenoids, such as beta-carotene, and xanthophylls.[14]

Biosynthesis

The unconditioned biosynthesis of lycopene in eukaryotic plants and in prokaryotic cyanobacteria is similar, as are the enzymes involved.[15] 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 twenty-carbon geranylgeranyl pyrophosphate. Two molecules of this product are then condensed in a tail-to-tail configuration to give the forty-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.[16]

Dietary sources

Dietary sources of lycopene[17]
Source μg/g wet weight
Gac 2,000–2,300
Raw tomato 8.8–42
Tomato juice 86–100
Tomato sauce 63–131
Tomato ketchup 124
Watermelon 23–72
Pink grapefruit 3.6–34
Pink guava 54
Papaya 20–53
Rosehip puree 7.8
Apricot < 0.1

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. Although gac (Momordica cochinchinensis Spreng) has the highest content of lycopene of any known fruit or vegetable, up to 70 times more than tomatoes for example,[18] due to gac's rarity outside its native region of southeast Asia, tomatoes and tomato-based sauces, juices, and ketchup account for more than 85% of the dietary intake of lycopene for most people.[19] The lycopene content of tomatoes depends on species and increases as the fruit ripens.[20]

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.[21] Lycopene in tomato paste is up to four times more bioavailable than in fresh tomatoes.[22]

While most green leafy vegetables and other sources of lycopene are low in fats and oils, lycopene is insoluble in water and is tightly bound to vegetable fiber. Processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain the highest concentrations of bioavailable lycopene from tomato-based sources.

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 is a notable exception, containing high concentrations of lycopene and also saturated and unsaturated fatty acids.[23]

Lycopene may be obtained from vegetables and fruits such as the tomato, but another source of lycopene is the fungus Blakeslea trispora. Gac is a possible commercial source of lycopene for the purposes of extraction and purification, as its seed content of lycopene is high.[24]

The cis-lycopene from some varieties of tomato is more bioavailable.[25]

Note that there are some resources which make the mistaken assumption that all red fruits contain lycopene, when in fact many are pigmented by other chemicals. An example is the blood orange, which is colored by anthocyanins,[26] while other red colored oranges, such as the Cara cara navel, and other citrus fruit, such as pink grapefruit, are colored by lycopene.[2][27]

In addition, some foods that do not appear red also contain lycopene, e.g., asparagus, which contains approximately 30μg of lycopene per 100 gram serving[2] and dried parsley and basil, which contain approximately 3.5-7 μg of lycopene per gram.[2]

Pharmacokinetics

Distribution of lycopene[28]
Tissue nmol/g wet weight
Liver 1.28–5.72
Kidney 0.15–0.62
Adrenal 1.9–21.6
Testes 4.34–21.4
Ovary 0.25–0.28
Adipose 0.2–1.3
Lung 0.22–0.57
Colon 0.31
Breast 0.78
Skin 0.42

After ingestion, lycopene is incorporated into lipid micelles in the small intestine. These micelles are formed from dietary fats and bile acids, and help to solubilize the hydrophobic lycopene and allow it to permeate the intestinal mucosal cells by a passive transport mechanism. Little is known about the liver metabolism of lycopene, but like other carotenoids, lycopene is incorporated into chylomicrons and released into the lymphatic system. In blood plasma, lycopene is eventually distributed into the very low and low density lipoprotein fractions.[29] Lycopene is mainly distributed to fatty tissues and organs such as the adrenal glands, liver, prostate and testes.

Adverse effects

Photograph of a test tube containing a dichloromethane solution of lycopene

Lycopene is non-toxic and is commonly found in the diet, but cases of excessive carotenoid intake have been reported. In a middle-aged woman who had prolonged and excessive consumption of tomato juice, her skin and liver were colored orange-yellow and she had elevated levels of lycopene in her blood. After three weeks on a lycopene-free diet her skin color returned to normal.[29] This discoloration of the skin is known as lycopenodermia[30] and is non-toxic.

There are also cases of intolerance or allergic reaction to dietary lycopene, which may cause diarrhea, nausea, stomach pain or cramps, gas, vomiting, and loss of appetite.[31]

Potential health effects

Given its potential properties in vivo, substantial research has been devoted to a possible correlation between lycopene consumption and general health. In 2005, the United States Food and Drug Administration allowed a limited, highly qualified claim to be used for tomatoes and tomato products which contain lycopene, as a guide that would not mislead consumers, namely: "Very limited and preliminary scientific research suggests that eating one-half to one cup of tomatoes and/or tomato sauce a week may reduce the risk of prostate cancer. FDA concludes that there is little scientific evidence supporting this claim."[8] A 2011 Cochrane review found insufficient evidence to come to any conclusion about what effect lycopene might have on prostate symptoms, PSA levels or prostate cancer.[32] A 2013 review concluded that lycopene appears to be negatively associated with prostate cancer risk.[33]

See also

References

  1. ^ a b c d e "Lycopene from Tomato CAS No.: 502-65-8". http://www.ec21.com. Fuxing Technology Co., Ltd. Retrieved 2014-05-27. 
  2. ^ a b c d e f "Foods highest in lycopene, Nutrition Data, USDA Nutrient Database, version SR-21". nutritiondata.com. Conde Nast. 2014. Retrieved 2014-08-19. 
  3. ^ a b Journal of the American College of Nutrition: Role of Antioxidant Lycopene in Cancer and Heart Disease
  4. ^ 21 CFR 73.585
  5. ^ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27. 
  6. ^ UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27. 
  7. ^ Sharoni, Y; Linnewiel-Hermoni, K; Zango, G; Khanin, M; Salman, H; Veprik, A; Danilenko, M; Levy, J (2012). "The role of lycopene and its derivatives in the regulation of transcription systems: Implications for cancer prevention". American Journal of Clinical Nutrition 96 (5): 1173S–8S.  
  8. ^ a b "Summary of Qualified Health Claims Subject to Enforcement Discretion". FDA. 11 August 2005. Retrieved 25 September 2013. 
  9. ^ Grossman et al. (2004) p. 129
  10. ^ Rao et al. (2007) p. 210
  11. ^ 1054 isomers are theoretically possible, but only 72 are possible due to steric hindrance. IARC Handbook, (1998) p. 25
  12. ^ Chasse et al. Journal of Molecular Structure: THEOCHEM, Volume 571, Number 1, 27 August 2001 , pp. 27-37(11)[1]
  13. ^ Lycopene: Its role in human health and disease, Rao 'et al.', AGROFood industry hi-tech, July/August 2003 [2]
  14. ^ NDSU Agriculture. "What Color is Your Food?". Retrieved 10 May 2012. 
  15. ^ Cunningham (2007) p. 533
  16. ^ Armstrong (1996) p. 229
  17. ^ Rao and Rao (2007) pp. 209–210
  18. ^ USDA study on Cartenoid content of gac fruit
  19. ^ Rao (2007) p.
  20. ^ Khan et al. (2008) p. 495
  21. ^ Perdomo F, Cabrera Fránquiz F, Cabrera J, Serra-Majem L (2012). "Influence of cooking procedure on the bioavailability of lycopene in tomatoes". Hospital Nutrition (Madrid) 27 (5): 1542–6.  
  22. ^ Kamiloglu, S.; Demirci, M.; Selen, S.; Toydemir, G.; Boyacioglu, D.; Capanoglu, E. (2014). "Home processing of tomatoes (Solanum lycopersicum): Effects onin vitrobioaccessibility of total lycopene, phenolics, flavonoids, and antioxidant capacity". Journal of the Science of Food and Agriculture 94 (11): 2225.  
  23. ^ Ishida BK, Turner C, Chapman MH, McKeon TA (January 2004). "Fatty acid and carotenoid composition of gac (Momordica cochinchinensis Spreng) fruit".  
  24. ^ Aoki, H; Kieu, N. T.; Kuze, N; Tomisaka, K; Van Chuyen, N (2002). "Carotenoid pigments in GAC fruit (Momordica cochinchinensis SPRENG)". Bioscience, Biotechnology and Biochemistry 66 (11): 2479–82.  
  25. ^ "Unique Tomatoes Tops In Disease-Fighting Antioxidants". Medical News Today. March 5, 2007. Retrieved 2014-08-19. 
  26. ^ Hillebrand, S; Schwarz, M; Winterhalter, P (2004). "Characterization of anthocyanins and pyranoanthocyanins from blood orange Citrus sinensis (L.) Osbeck juice". Journal of Agricultural and Food Chemistry 52 (24): 7331–8.  
  27. ^ Alquezar, B; Rodrigo, M. J.; Zacarías, L (2008). "Regulation of carotenoid biosynthesis during fruit maturation in the red-fleshed orange mutant Cara Cara". Phytochemistry 69 (10): 1997–2007.  
  28. ^ Stahl (1996) p. 7
  29. ^ a b Stahl (1996) p. 6
  30. ^ Institute of Medicine, Food and Nutrition Board. Beta-carotene and other carotenoids. Dietary reference intakes for vitamin C, vitamin E, selenium, and carotenoids. Washington, D.C.: National Academy Press; 2000:325-400.
  31. ^ "Lycopene". Mayo Clinic. October 1, 2011. Retrieved December 17, 2011. 
  32. ^ Ilic, D.; Forbes, KM.; Hassed, C. (2011). "Lycopene for the prevention of prostate cancer.". Cochrane Database Syst Rev (11): CD008007.  
  33. ^ Vance, Terrence M.; Su, Joseph; Fontham, Elizabeth T. H.; Koo, Sung I.; Chun, Ock K. (August 2013). "Dietary Antioxidants and Prostate Cancer: A Review". Nutrition and Cancer 65 (6): 793–801.  

Bibliography

  • Armstrong GA, Hearst JE (1996). "Carotenoids 2: Genetics and molecular biology of carotenoid pigment biosynthesis". FASEB J. 10 (2): 228–37.  
  • Basu A, Imrhan V (2007). "Tomatoes versus lycopene in oxidative stress and carcinogenesis: conclusions from clinical trials". Eur J Clin Nutr 61 (3): 295–303.  
  • Berneburg M, Grether-Beck S, Kurten V, Ruzicka T, Briviba K, Sies H, Krutmann J (1999). "Singlet oxygen mediates the UVA-induced generation of the photoaging-associated mitochondrial common deletion". The Journal of Biological Chemistry 274 (22): 15345–15349.  
  • Britton, George; Synnove Liaaen-Jensen; Hanspeter Pfander; (1996). Carotenoids : Synthesis (Carotenoids). Boston: Birkhauser.  
  • Cunningham FX, Lee H, Gantt E (2007). "Carotenoid biosynthesis in the primitive red alga Cyanidioschyzon merolae". Eukaryotic Cell 6 (3): 533–45.  
  • Di Mascio P, Kaiser S, Sies H (1989). "Lycopene as the most efficient biological carotenoid singlet oxygen quencher". Arch. Biochem. Biophys. 274 (2): 532–8.  
  • Gerster H (1997). "The potential role of lycopene for human health". J Am Coll Nutr 16 (2): 109–26.  
  • Giovannucci E, Ascherio A, Rimm EB, Stampfer MJ, Colditz GA, Willett WC (1995). "Intake of carotenoids and retinol in relation to risk of prostate cancer". J. Natl. Cancer Inst. 87 (23): 1767–76.  
  • Grossman AR, Lohr M, Im CS (2004). "Chlamydomonas reinhardtii in the landscape of pigments". Annu. Rev. Genet. 38 (1): 119–73.  
  • IARC Working Group on the Evaluation of Cancer Preventive Agents (1998). IARC Handbooks of Cancer Prevention: Volume 2: Carotenoids (IARC Handbooks of Cancer Prevention). Oxford University Press, USA. p. 25.  
  • Khan N, Afaq F, Mukhtar H (2008). "Cancer chemoprevention through dietary antioxidants: progress and promise". Antioxid. Redox Signal. 10 (3): 475–510.  
  • Rao AV, Rao LG (March 2007). "Carotenoids and human health". Pharmacol. Res. 55 (3): 207–16.  
  • Stahl W, Sies H (1996). "Lycopene: a biologically important carotenoid for humans?". Arch. Biochem. Biophys. 336 (1): 1–9.  
  • Giovannucci E, Willett WC, Stampfer MJ, Liu Y, Rimm EB (2002). "A prospective study of tomato products, lycopene, and prostate cancer risk". J. Natl Cancer Inst 94 (5): 391–396.  
  • Levy J, Sharoni Y, Danilenko M, Miinster A, Bosin E, Giat Y, Feldman B (1995). "Lycopene is a more potent inhibitor of human cancer cell proliferation than either alpha-carotene or beta-carotene". Nutr Cancer 24 (3): 257–266.  
  • Pollack A, Madar Z, Eisner Z, Nyska A, Oren,P (1997). "Inhibitory effect of lycopene on cataract development in galactosemic rats". Metab Pediatr Syst Ophthalmol 19 (20): 31–36. 
  • Nahum A, Sharoni Y, Prall OW, Levy J, Hirsch K, Watts CK, Danilenko M (2001). "Lycopene inhibition of cell cycle progression in breast and endometrial cancer cells is associated with reduction in cyclin D levels and retention of p27(Kip1) in the cyclin E-cdk2 complexes". Oncogene 20 (26): 3428–436.  
  • Narisawa T, Fukaura Y, Hasebe M, Ito M, Nishino H, Khachik F, Murakoshi M, Uemura S, Aizawa R (1996). "Ihibitory effects of natural carotenoids, alpha-carotene, beta-carotene, lycopene and lutein, on colonic aberrant crypt foci formation in rats". Cancer Lett 107 (1): 137–142.  

External links

  • Phytochemicals as Nutraceuticals-Lycopene
  • USDA Webpage on Lycopene Content of Gac - Fatty Acids and Carotenoids in Gac (Momordica Cochinchinensis Spreng) Fruit.
  • Food Sources of Lycopene - Based on USDA (US Department of Agriculture) National Nutrient Database Release 21 (SR21).
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 


Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.