Nutritional aspects of phytoene and phytofluene, carotenoid precursors to lycopene

Advances in Nutrition

Volumn 2, Issue 1, 2011, Pages 51-61

  Engelmann, Nancy J ^a   Clinton, Steven K ^c   Erdman, John W ^a,b  

^a Division of Nutritional Sciences   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAROTENOID; LYCOPENE; PHYTOENE; PHYTOFLUENE;

ANIMAL; ARTICLE; BIOAVAILABILITY; BIOSYNTHESIS; CHEMISTRY; DIET; FRUIT; HUMAN; ISOTOPE LABELING; METABOLISM; NUTRITION; TOMATO;

ANIMALS; BIOLOGICAL AVAILABILITY; CAROTENOIDS; DIET; FRUIT; HUMANS; ISOTOPE LABELING; LYCOPERSICON ESCULENTUM; NUTRITIONAL PHYSIOLOGICAL PHENOMENA;

EID: 84855607399     PISSN: 21618313     EISSN: 21565376     Source Type: Journal    
DOI: 10.3945/an.110.000075     Document Type: Review

References (96)

1. Britton G, Liaaen-Jensen S, Pfander H. SpringerLink. Nutrition and health. Basel, London: Birkhauser; 2009. p. 5.
2. Canene-Adams K, Campbell JK, Zaripheh S, Jeffery EH, Erdman JW Jr. The tomato as a functional food. J Nutr. 2005;135:1226-30.
3. Giovannucci E. Tomato products, lycopene, and prostate cancer: a review of the epidemiological literature. J Nutr. 2005;135:S2030-1.
4. Etminan M, Takkouche B, Caamano-Isorna F. The role of tomato products and lycopene in the prevention of prostate cancer: a meta-analysis of observational studies. Cancer Epidemiol Biomarkers Prev. 2004;13:340-5.
5. Bramley PM. Regulation of carotenoid formation during tomato fruit ripening and development. J Exp Bot. 2002;53:2107-13.
6. Sandmann G. Evolution of carotene desaturation: the complication of a simple pathway. Arch Biochem Biophys. 2009;483:169-74.
7. Britton G. UV/visible spectroscopy. In: Britton G, Liaaen-Jensen S, Pfander H, editors. Carotenoids: spectroscopy. Basel: Birkhauser; 1995. p. 13.
8. Xianquan S, Shi J, Kakuda Y, Yueming J. Stability of lycopene during food processing and storage. J Med Food. 2005;8:413-22.
9. Britton G, Liaaen-Jensen S, Pfander H. SpringerLink. Natural functions. Basel, London: Birkhauser; 2007. p. 4.
10. Moran NA, Jarvik T. Lateral transfer of genes from fungi underlies carotenoid production in aphids. Science. 2010;328:624-7.
11. Edwards AJ, Vinyard BT, Wiley ER, Brown ED, Collins JK, Perkins-Veazie P, Baker RA, Clevidence BA. Consumption of watermelon juice increases plasma concentrations of lycopene and beta-carotene in humans. J Nutr. 2003;133:1043-50.
12. Khachik F, Beecher GR, Goli MB, Lusby WR. Separation, identification, and quantification of carotenoids in fruits, vegetables and human plasma by high-performance liquid-chromatography. Pure Appl Chem. 1991;63:71-80.
13. Khachik F, Carvalho L, Bernstein PS,Muir GJ, Zhao DY, Katz NB. Chemistry, distribution, and metabolism of tomato carotenoids and their impact on human health. Exp Biol Med (Maywood). 2002;227:845-51.
14. Kacjan Marsic N, Sircelj H, Kastelec D. Lipophilic antioxidants and some carpometric characteristics of fruits of ten processing tomato varieties, grown in different climatic conditions. J Agric Food Chem. 2010;58:390-7.
15. Jesus Periago M, Garcia-Alonso J, Jacob K, Belen Olivares A, Jose Bernal M, Dolores Iniesta M, Martinez C, Ros G. Bioactive compounds, folates and antioxidant properties of tomatoes (Lycopersicum esculentum) during vine ripening. Int J Food Sci Nutr. 2009;60:694-708.
16. Choi SH, Lee SH, Kim HJ, Lee IS, Kozukue N, Levin CE, Friedman M. Changes in free amino acid, phenolic, chlorophyll, carotenoid, and glycoalkaloid contents in tomatoes during 11 stages of growth and inhibition of cervical and lung human cancer cells by green tomato extracts. J Agric Food Chem. 2010;58:7547-56.
17. National Center for Health Statistics. FastStats: leading causes of death. Version current December 31, 2009 [cited 2010 Jul 27]. Available from: http://www.cdc.gov/nchs/fastats/lcod.htm.
18. American Cancer Society. Cancer facts and figures 2009. Version current 2009 [2010 25 Oct]. Available from: http://www.cancer.org/Research/CancerFactsFigures/index2009.
19. WCRF/AICR. Summary: food, nutrition, physical activity and the prevention of cancer: a global perspective. Second Expert Report ed.Washington, DC: American Institute for Cancer Research; 2007.
20. Mosca L, Banka CL, Benjamin EJ, Berra K, Bushnell C, Dolor RJ, Ganiats TG, Gomes AS, Gornik HL, et al. Evidence-based guidelines for cardiovascular disease prevention in women: 2007 update. J Am Coll Cardiol. 2007;49:1230-50.
21. Riccioni G. Carotenoids and cardiovascular disease. Curr Atheroscler Rep. 2009;11:434-9.
22. Voutilainen S, Nurmi T, Mursu J, Rissanen TH. Carotenoids and cardiovascular health. Am J Clin Nutr. 2006;83:1265-71.
23. Hadley CW, Clinton SK, Schwartz SJ. The consumption of processed tomato products enhances plasma lycopene concentrations in association with a reduced lipoprotein sensitivity to oxidative damage. J Nutr. 2003;133:727-32.
24. Erdman JW Jr, Ford NA, Lindshield BL. Are the health attributes of lycopene related to its antioxidant function? Arch Biochem Biophys. 2009;483:229-35.
25. Sesso HD. Carotenoids and cardiovascular disease: what research gaps remain? Curr Opin Lipidol. 2006;17:11-6.
26. Goralczyk R. Beta-carotene and lung cancer in smokers: review of hypotheses and status of research. Nutr Cancer. 2009;61:767-74.
27. Wang XD. Can smoke-exposed ferrets be utilized to unravel the mechanisms of action of lycopene? J Nutr. 2005;135:S2053-6.
28. Miller EC, Giovannucci E, Erdman JW Jr, Bahnson R, Schwartz SJ, Clinton SK. Tomato products, lycopene, and prostate cancer risk. Urol Clin North Am. 2002;29:83-93.
29. Kavanaugh CJ, Trumbo PR, Ellwood KC. The U.S. Food and Drug Administration's evidence-based review for qualified health claims: tomatoes, lycopene, and cancer. J Natl Cancer Inst. 2007;99:1074-85.
30. Canene-Adams K, Lindshield BL, Wang S, Jeffery EH, Clinton SK, Erdman JW Jr. Combinations of tomato and broccoli enhance antitumor activity in dunning r3327-h prostate adenocarcinomas. Cancer Res. 2007;67:836-43.
31. Boileau TW, Liao Z, Kim S, Lemeshow S, Erdman JW Jr, Clinton SK. Prostate carcinogenesis in N-methyl-N-nitrosourea (NMU)-testosterone-treated rats fed tomato powder, lycopene, or energy-restricted diets. J Natl Cancer Inst. 2003;95:1578-86.
32. Konijeti R, Henning S, Moro A, Sheikh A, Elashoff D, Shapiro A, Ku M, Said JW, Heber D, et al. Chemoprevention of prostate cancer with lycopene in the TRAMP model. Prostate. 2010;70:1547-54.
33. Gitenay D, Lyan B, Rambeau M, Mazur A, Rock E. Comparison of lycopene and tomato effects on biomarkers of oxidative stress in vitamin E deficient rats. Eur J Nutr. 2007;46:468-75.
34. Gitenay D, Lyan B, Talvas J, Mazur A, George S, Caris-Veyrat C, Rock E. Serum from rats fed red or yellow tomatoes induces Connexin43 expression independently from lycopene in a prostate cancer cell line. Biochem Biophys Res Commun. 2007;364:578-82.
35. Brown MJ, Ferruzzi MG, Nguyen ML, Cooper DA, Eldridge AL, Schwartz SJ, White WS. Carotenoid bioavailability is higher from salads ingested with full-fat than with fat-reduced salad dressings as measured with electrochemical detection. Am J Clin Nutr. 2004;80:396-403.
36. Huo T, Ferruzzi MG, Schwartz SJ, Failla ML. Impact of fatty acyl composition and quantity of triglycerides on bioaccessibility of dietary carotenoids. J Agric Food Chem. 2007;55:8950-7.
37. Unlu NZ, Bohn T, Clinton SK, Schwartz SJ. Carotenoid absorption from salad and salsa by humans is enhanced by the addition of avocado or avocado oil. J Nutr. 2005;135:431-6.
38. van Het Hof KH, West CE, Weststrate JA, Hautvast JG. Dietary factors that affect the bioavailability of carotenoids. J Nutr. 2000;130:503-6.
39. van Bennekum A, Werder M, Thuahnai ST, Han CH, Duong P, Williams DL, Wettstein P, Schulthess G, Phillips MC, et al. Class B scavenger receptor-mediated intestinal absorption of dietary beta-carotene and cholesterol. Biochemistry. 2005;44:4517-25.
40. During A, Dawson HD, Harrison EH. Carotenoid transport is decreased and expression of the lipid transporters SR-BI, NPC1L1, and ABCA1 is downregulated in Caco-2 cells treated with ezetimibe. J Nutr. 2005;135:2305-12.
41. Borel P, Moussa M, Reboul E, Lyan B, Defoort C, Vincent-Baudry S, Maillot M, Gastaldi M, Darmon M, et al. Human plasma levels of vitamin E and carotenoids are associated with genetic polymorphisms in genes involved in lipid metabolism. J Nutr. 2007;137:2653-9.
42. Paetau I, Khachik F, Brown ED, Beecher GR, Kramer TR, Chittams J, Clevidence BA. Chronic ingestion of lycopene-rich tomato juice or lycopene supplements significantly increases plasma concentrations of lycopene and related tomato carotenoids in humans. Am J Clin Nutr. 1998;68:1187-95.
43. Paetau I, Rao D, Wiley ER, Brown ED, Clevidence BA. Carotenoids in human buccal mucosa cells after 4 wk of supplementation with tomato juice or lycopene supplements. Am J Clin Nutr. 1999;70:490-4.
44. Diwadkar-Navsariwala V, Novotny JA, Gustin DM, Sosman JA, Rodvold KA, Crowell JA, Stacewicz-Sapuntzakis M, Bowen PE. A physiological pharmacokinetic model describing the disposition of lycopene in healthy men. J Lipid Res. 2003;44:1927-39.
45. Clinton SK, Emenhiser C, Schwartz SJ, Bostwick DG, Williams AW, Moore BJ, Erdman JW Jr. Cis-trans lycopene isomers, carotenoids, and retinol in the human prostate. Cancer Epidemiol Biomarkers Prev. 1996;5:823-33.
46. Khachik F, Pfander H, Traber B. Proposed mechanisms for the formation of synthetic and naturally occurring metabolites of lycopene in tomato products and human serum. J Agric Food Chem. 1998;46:4885-90.
47. Lindshield BL, Canene-Adams K, Erdman JW Jr. Lycopenoids: are lycopene metabolites bioactive? Arch Biochem Biophys. 2007;458:136-40.
48. von Lintig J, Vogt K. Filling the gap in vitamin A research. Molecular identification of an enzyme cleaving beta-carotene to retinal. J Biol Chem. 2000;275:11915-20.
49. Kiefer C, Hessel S, Lampert JM, Vogt K, Lederer MO, Breithaupt DE, von Lintig J. Identification and characterization of a mammalian enzyme catalyzing the asymmetric oxidative cleavage of provitamin A. J Biol Chem. 2001;276:14110-6.
50. Mein JR, Lian F, Wang XD. Biological activity of lycopene metabolites: implications for cancer prevention. Nutr Rev. 2008;66:667-83.
51. Kopec RE, Riedl KM, Harrison EH, Curley RW, Hruszkewycz DP, Clinton SK, Schwartz SJ. Identification and quantification of apo-lycopenals in fruits, vegetables, and human plasma. J Agric Food Chem. 2010;58: 3290-6.
52. Gajic M, Zaripheh S, Sun F, Erdman JW Jr. Apo-89-lycopenal and apo-12'-lycopenal are metabolic products of lycopene in rat liver. J Nutr. 2006;136:1552-7.
53. Lindqvist A, He YG, Andersson S. Cell type-specific expression of betacarotene 99,10'-monooxygenase in human tissues. J Histochem Cytochem. 2005;53:1403-12.
54. Ford NA, Clinton SK, von Lintig J, Wyss A, Erdman JW Jr. Loss of carotene-99,10'-monooxygenase expression increases serum and tissue lycopene concentrations in lycopene-fed mice. J Nutr 2010;140:2134-8.
55. Nara E, Hayashi H, Kotake M, Miyashita K, Nagao A. Acyclic carotenoids and their oxidation mixtures inhibit the growth of HL-60 human promyelocytic leukemia cells. Nutr Cancer. 2001;39:273-83.
56. Campbell JK, Rogers RB, Lila MA, Erdman JW Jr. Biosynthesis of 14Cphytoene from tomato cell suspension cultures (Lycopersicon esculentum) for utilization in prostate cancer cell culture studies. J Agric Food Chem. 2006;54:747-55.
57. Campbell JK, Engelmann NJ, Lila MA, Erdman JW Jr. Phytoene, phytofluene, and lycopene from tomato powder differentially accumulate in tissues of male Fisher 344 rats. Nutr Res. 2007;27:794-801.
58. Werman MJ, Mokady S, Ben-Amotz A. Bioavailability of the isomer mixture of phytoene and phytofluene-rich alga Dunaliella bardawil in rat plasma and tissues. J Nutr Biochem. 2002;13:585-91.
59. Boileau TW, Boileau AC, Erdman JW Jr. Bioavailability of all-trans and cis-isomers of lycopene. Exp Biol Med (Maywood). 2002;227:914-9.
60. Liu AG, Volker SE, Jeffery EH, Erdman JW Jr. Feeding tomato and broccoli powders enriched with bioactives improves bioactivity markers in rats. J Agric Food Chem. 2009;57:7304-10.
61. Huang CS, Chuang CH, Hu ML. Effects of lycopene supplementation on plasma and tissue lycopene levels in various rodent strains. Int J Vitam Nutr Res. 2006;76:377-84.
62. Mills JP, Simon PW, Tanumihardjo SA. Beta-carotene from red carrot maintains vitamin A status, but lycopene bioavailability is lower relative to tomato paste in Mongolian gerbils. J Nutr. 2007;137:1395-400.
63. Lee CM, Boileau AC, Boileau TW, Williams AW, Swanson KS, Heintz KA, Erdman JW Jr. Review of animal models in carotenoid research. J Nutr. 1999;129:2271-7.
64. Howe JA, Maziya-Dixon B, Tanumihardjo SA. Cassava with enhanced beta-carotene maintains adequate vitamin A status in Mongolian gerbils (Meriones unguiculatus) despite substantial cis-isomer content. Br J Nutr. 2009;102:342-9.
65. Davis CR, Howe JA, Rocheford TR, Tanumihardjo SA. The xanthophyll composition of biofortified maize (Zea mays Sp.) does not influence the bioefficacy of provitamin a carotenoids in Mongolian gerbils (Meriones unguiculatus). J Agric Food Chem. 2008;56:6745-50.
66. Howe JA, Tanumihardjo SA. Carotenoid-biofortified maize maintains adequate vitamin a status in Mongolian gerbils. J Nutr. 2006;136: 2562-7.
67. Tanumihardjo SA, Howe JA. Twice the amount of alpha-carotene isolated from carrots is as effective as beta-carotene in maintaining the vitamin A status of Mongolian gerbils. J Nutr. 2005;135:2622-6.
68. Deming DM, Baker DH, Erdman JW Jr. The relative vitamin A value of 9-cis beta-carotene is less and that of 13-cis beta-carotene may be greater than the accepted 50% that of all-trans beta-carotene in gerbils. J Nutr. 2002;132:2709-12.
69. Shapira N. Nutritional approach to sun protection: a suggested complement to external strategies. Nutr Rev. 2010;68:75-86.
70. Aust O, StahlW, Sies H, Tronnier H, Heinrich U. Supplementation with tomato-based products increases lycopene, phytofluene, and phytoene levels in human serum and protects against UV-light-induced erythema. Int J Vitam Nutr Res. 2005;75:54-60.
71. Fuller B, Smith D, Howerton A, Kern D. Anti-inflammatory effects of CoQ10 and colorless carotenoids. J Cosmet Dermatol. 2006;5:30-8.
72. Shaish A, Harari A, Kamari Y, Soudant E, Harats D, Ben-Amotz A. A carotenoid algal preparation containing phytoene and phytofluene inhibited LDL oxidation in vitro. Plant Foods Hum Nutr. 2008;63:83-6.
73. Campbell JK, Stroud CK, Nakamura MT, Lila MA, Erdman JW Jr. Serum testosterone is reduced following short-term phytofluene, lycopene, or tomato powder consumption in F344 rats. J Nutr. 2006;136: 2813-9.
74. Nishino H, Murakosh M, Ii T, Takemura M, Kuchide M, Kanazawa M, Mou XY, Wada S, Masuda M, et al. Carotenoids in cancer chemoprevention. Cancer Metastasis Rev. 2002;21:257-64.
75. Satomi Y, Misawa N, Maoka T, Nishino H. Production of phytoene, a carotenoid, and induction of connexin 26 in transgenic mice carrying the phytoene synthase gene crtB. Biochem Biophys Res Commun. 2004;320:398-401.
76. Ben-Dor A, Steiner M, Gheber L, Danilenko M, Dubi N, Linnewiel K, Zick A, Sharoni Y, Levy J. Carotenoids activate the antioxidant response element transcription system. Mol Cancer Ther. 2005;4:177-86.
77. Novotny JA, Kurilich AC, Britz SJ, Clevidence BA. Plasma appearance of labeled beta-carotene, lutein, and retinol in humans after consumption of isotopically labeled kale. J Lipid Res. 2005;46:1896-903.
78. Kurilich AC, Britz SJ, Clevidence BA, Novotny JA. Isotopic labeling and LC-APCI-MS quantification for investigating absorption of carotenoids and phylloquinone from kale (Brassica oleracea). J Agric Food Chem. 2003;51:4877-83.
79. Kelm MA, Flanagan VP, Pawlosky RJ, Novotny JA, Clevidence BA, Britz SJ. Quantitative determination of 13C-labeled and endogenous betacarotene, lutein, and vitamin A in human plasma. Lipids. 2001;36: 1277-82.
80. Tang G, Qin J, Dolnikowski GG, Russell RM, Grusak MA. Golden Rice is an effective source of vitamin A. Am J Clin Nutr. 2009;89:1776-83.
81. Wang J, Wang Y, Wang Z, Li L, Qin J, Lai W, Fu Y, Suter PM, Russell RM, et al. Vitamin A equivalence of spirulina beta-carotene in Chinese adults as assessed by using a stable-isotope reference method. Am J Clin Nutr. 2008;87:1730-7.
82. Parker RS, Brenna JT, Swanson JE, Goodman KJ, Marmor B. Assessing metabolism of beta-[13C]carotene using high-precision isotope ratio mass spectrometry. Methods Enzymol. 1997;282:130-40.
83. Parker RS, Swanson JE, Marmor B, Goodman KJ, Spielman AB, Brenna JT, Viereck SM, Canfield WK. Study of beta-carotene metabolism in humans using 13C-beta-carotene and high precision isotope ratio mass spectrometry. Ann N Y Acad Sci. 1993;691:86-95.
84. Tang G, Ferreira AL, Grusak MA, Qin J, Dolnikowski GG, Russell RM, Krinsky NI. Bioavailability of synthetic and biosynthetic deuterated lycopene in humans. J Nutr Biochem. 2005;16:229-35.
85. Zaripheh S, Erdman JW Jr. The biodistribution of a single oral dose of [14C]-lycopene in rats prefed either a control or lycopene-enriched diet. J Nutr. 2005;135:2212-8.
86. Zaripheh S, Boileau TW, Lila MA, Erdman JW Jr. 14C]-lycopene and [14C]-labeled polar products are differentially distributed in tissues of F344 rats prefed lycopene. J Nutr. 2003;133:4189-95.
87. Engelmann NJ, Campbell JK, Rogers RB, Rupassara SI, Garlick PJ, Lila MA, Erdman JW Jr. Screening and selection of high carotenoid producing in vitro tomato cell culture lines for [(13)C]-carotenoid production. J Agric Food Chem. 2010;58:9979-87.
88. Engelmann NJ, Rogers RB, Lila MA, Erdman JW Jr. Herbicide treatments alter carotenoid profiles for 14C tracer production from tomato (Solanum lycopersicum cv. VFNT cherry) cell cultures. J Agric Food Chem. 2009;57:4614-9.
89. Yousef GG, Seigler DS, Grusak MA, Rogers RB, Knight CT, Kraft TF, Erdman JW Jr, Lila MA. Biosynthesis and characterization of 14C-enriched flavonoid fractions from plant cell suspension cultures. J Agric Food Chem. 2004;52:1138-45.
90. Reppert A, Yousef GG, Rogers RB, Lila MA. Isolation of radiolabeled isoflavones from kudzu (Pueraria lobata) root cultures. J Agric Food Chem. 2008;56:7860-5.
91. Engelmann NJ, Reppert A, Yousef GG, Rogers RB, Lila MA. In vitro production of radiolabeled red clover (Trifolium pratense) isoflavones. Plant Cell Tissue Organ Cult. 2009;98:147-56.
92. Ishida BK, Mahoney NE, Ling LC. Increased lycopene and flavor volatile production in tomato calyces and fruit cultured in vitro and the effect of 2-(4-chlorophenylthio)triethylamine. J Agric Food Chem. 1998; 46:4577-82.
93. Robertson GH, Mahoney NE, Goodman N, Pavlath AE. Regulation of lycopene formation in cell suspension culture of VFNT tomato (Lycopersicon esculentum) by CPTA, growth regulators, sucrose, and temperature. J Exp Bot. 1995;46:667-73.
94. Fosket DE, Radin DN. Induction of carotenogenesis in cultured cells of Lycopersicon Esculentum cultivar Ep-7. Plant Sci Lett. 1983;30:165-76.
95. Bramley PM. Carotenoid biosynthesis: a target site for bleaching herbicides. Biochem Soc Trans. 1994;22:625-9.
96. Windhovel U, Sandmann G, Boger P. Genetic engineering of resistance to bleaching herbicides affecting phytoene desaturase and lycopene cyclase in cyanobacterial carotenogenesis. Pestic Biochem Physiol. 1997; 57:68-78.