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Lycopene Metabolism And Its Biological Significance.

X. Wang
Published 2012 · Medicine, Biology

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The beneficial effects of a high intake of tomatoes and tomato products on the risk of certain chronic diseases have been presented in many epidemiologic studies, with the suggestion that lycopene (a major carotenoid in tomatoes) is a micronutrient with important health benefits. Within the past few years, we have gained greater knowledge of the metabolism of lycopene and the biological effects of lycopene derivatives. In particular, the characterization and study of β-carotene 9',10'-oxygenase has shown that this enzyme can catalyze the excentric cleavage of both provitamin and non-provitamin A carotenoids to form apo-10'-carotenoids, including apo-10'-lycopenoids from lycopene. This raised an important question of whether the effect of lycopene on various cellular functions and signaling pathways is a result of the direct actions of intact lycopene or its derivatives. Several reports, including our own, support the notion that the biological activities of lycopene can be mediated by apo-10'-lycopenoids. More research is clearly needed to identify and characterize additional lycopene metabolites and their biological activities, which will potentially provide invaluable insights into the mechanisms underlying the effects of lycopene in humans.
This paper references
10.1201/9781439822371
Carotenoids and retinoids : molecular aspects and health issues
L. Packer (2005)
10.1159/000410268
Mechanism of conversion of beta-carotene into vitamin A--central cleavage versus random cleavage.
J. Ganguly (1985)
10.3748/WJG.V16.I11.1330
Anti-inflammatory pathways and alcoholic liver disease: role of an adiponectin/interleukin-10/heme oxygenase-1 pathway.
P. Mandal (2010)
10.1016/0016-5085(95)90444-1
Vitamin E enhances the lymphatic transport of beta-carotene and its conversion to vitamin A in the ferret.
X. Wang (1995)
10.1016/j.abb.2010.11.005
Enzymatic formation of apo-carotenoids from the xanthophyll carotenoids lutein, zeaxanthin and β-cryptoxanthin by ferret carotene-9',10'-monooxygenase.
Jonathan R. Mein (2011)
10.1093/JNCI/91.2.151
Plasma levels of insulin-like growth factor-I and lung cancer risk: a case-control analysis.
H. Yu (1999)
10.3945/jn.111.150052
Apo-10'-lycopenoic acid, a lycopene metabolite, increases sirtuin 1 mRNA and protein levels and decreases hepatic fat accumulation in ob/ob mice.
J. Chung (2012)
10.1002/hep.23427
The anti‐inflammatory effects of adiponectin are mediated via a heme oxygenase‐1–dependent pathway in rat Kupffer cells
P. Mandal (2010)
10.1096/fj.09-150995
ISX is a retinoic acid‐sensitive gatekeeper that controls intestinal β,β‐carotene absorption and vitamin A production
G. P. Lobo (2010)
10.1016/J.BCP.2007.04.014
beta-Cryptoxanthin, a novel natural RAR ligand, induces ATP-binding cassette transporters in macrophages.
A. Matsumoto (2007)
10.1207/S15327914NC3601_14
Lycopene Interferes With Cell Cycle Progression and Insulin-Like Growth Factor I Signaling in Mammary Cancer Cells
M. Karas (2000)
10.7326/0003-4819-94-2-283_2
Modern nutrition in health and disease
R. S. Goodhart (1980)
10.2174/092986710791556041
Tomato Lycopene and Inflammatory Cascade: Basic Interactions and Clinical Implications
P. Palozza (2010)
10.1006/ABBI.1994.1371
Biosynthesis of 9-cis-retinoic acid from 9-cis-beta-carotene in human intestinal mucosa in vitro.
X. Wang (1994)
10.1086/399926
MANUAL of the international statistical classification of diseases, injuries, and causes of death. Addendum 1. Supplementary interpretations and instructions for coding causes of death.
B. Schneider (1953)
10.1021/JO050101L
Efficient syntheses of the keto-carotenoids canthaxanthin, astaxanthin, and astacene.
S. Choi (2005)
10.1096/fj.10-173906
A mitochondrial enzyme degrades carotenoids and protects against oxidative stress
J. Amengual (2011)
10.1201/9780203026649.CH14
Carotenoid Oxidative/Degradative Products and Their Biological Activities
X. Wang (2004)
Intestinal absorption and metabolism of 9-cis-beta-carotene in vivo: biosynthesis of 9-cis-retinoic acid.
X. Hébuterne (1995)
10.1046/j.1464-410x.2001.02191.x
Are dietary influences on the risk of prostate cancer mediated through the insulin‐like growth factor system?
L. Mucci (2001)
Synthesis and biological activity of beta-ionone-derived alcohols for cancer chemoprevention.
M. Jung (1998)
Acyclo-retinoic acid induces apoptosis in human prostate cancer cells.
E. Kotake-Nara (2002)
10.1146/ANNUREV-NUTR-080508-141027
Colors with Functions: Elucidating the Biochemical and Molecular Basis of Carotenoid Metabolism
J. Lintig (2010)
10.1074/jbc.M707928200
Isx Participates in the Maintenance of Vitamin A Metabolism by Regulation of β-Carotene 15,15′-Monooxygenase (Bcmo1) Expression*
Y. Seino (2008)
10.1002/1521-3773(20010716)40:14<2613::AID-ANIE2613>3.0.CO;2-Z
The Reaction Mechanism of the Enzyme-Catalyzed Central Cleavage of β-Carotene to Retinal.
Michele G. Leuenberger (2001)
10.1006/ABBI.2001.2412
Effects of acyclo-retinoic acid and lycopene on activation of the retinoic acid receptor and proliferation of mammary cancer cells.
A. Ben-Dor (2001)
10.1186/1471-2156-11-10
A nonsense mutation in the beta-carotene oxygenase 2 (BCO2) gene is tightly associated with accumulation of carotenoids in adipose tissue in sheep (Ovis aries)
D. I. Våge (2009)
10.1111/j.1349-7006.2002.tb01235.x
Serum Insulin‐like Growth Factors, Insulin‐like Growth Factor‐binding Protein‐3, and Risk of Lung Cancer Death: A Case‐control Study Nested in the Japan Collaborative Cohort (JACC) Study
K. Wakai (2002)
10.1096/fj.03-1116fje
Lycopene and Vitamin E interfere with autocrine/paracrine loops in the Dunning prostate cancer model
Ulrich Siler (2004)
10.1152/AJPGI.1992.263.4.G480
Intestinal uptake and lymphatic absorption of beta-carotene in ferrets: a model for human beta-carotene metabolism.
X. Wang (1992)
10.1074/jbc.M706763200
CMO1 Deficiency Abolishes Vitamin A Production from β-Carotene and Alters Lipid Metabolism in Mice*
S. Hessel (2007)
10.1534/genetics.109.101741
Mutation in Bovine β-Carotene Oxygenase 2 Affects Milk Color
S. D. Berry (2009)
10.3109/10715762.2011.564168
Antioxidant and anti-proliferative properties of lycopene
Mareike Kelkel (2011)
10.1007/S00394-006-0595-X
Lycopene inhibition of IGF-induced cancer cell growth depends on the level of cyclin D1
A. Nahum (2006)
10.1002/ijc.22111
β‐Cryptoxanthin suppresses the growth of immortalized human bronchial epithelial cells and non‐small‐cell lung cancer cells and up‐regulates retinoic acid receptor β expression
F. Lian (2006)
10.1007/s10549-006-9405-7
Lycopene and other carotenoids inhibit estrogenic activity of 17β-estradiol and genistein in cancer cells
K. Hirsch (2006)
10.1007/978-3-7643-7501-0_7
Absorption, transport, distribution in tissues and bioavailability.
Kirstie Canene-Adams (2009)
10.1093/JN/132.6.1368
Excentric cleavage products of beta-carotene inhibit estrogen receptor positive and negative breast tumor cell growth in vitro and inhibit activator protein-1-mediated transcriptional activation.
E. Tibaduiza (2002)
10.1074/jbc.M512095200
The Biochemical Characterization of Ferret Carotene-9′, 10′-Monooxygenase Catalyzing Cleavage of Carotenoids in Vitro and in Vivo*
Kang-Quan Hu (2006)
10.1093/JN/129.6.1176
Cis-lycopene is more bioavailable than trans-lycopene in vitro and in vivo in lymph-cannulated ferrets.
A. Boileau (1999)
10.1210/ME.2006-0225
Asymmetric cleavage of beta-carotene yields a transcriptional repressor of retinoid X receptor and peroxisome proliferator-activated receptor responses.
O. Ziouzenkova (2007)
10.3177/JNSV.41.575
Biological activity of (all-E)-beta-apo-12'-carotenoic acid and the geometrical isomers on human acute promyelocytic leukemia cell line HL-60.
T. Suzuki (1995)
10.1201/9781439822371.CH4
Chemical and Metabolic Oxidation of Carotenoids
F. Khachik (2005)
10.1089/ars.2010.3216
When NRF2 talks, who's listening?
N. Wakabayashi (2010)
10.1002/CHIN.199736209
Synthesis and biological activities of higher homologues of retinoic acid.
J. Y. Winum (1997)
10.3109/00498259609046688
Effects of canthaxanthin, astaxanthin, lycopene and lutein on liver xenobiotic-metabolizing enzymes in the rat.
S. Gradelet (1996)
10.1007/978-3-7643-7501-0_18
Biological Activities of Carotenoid Metabolites
X. Wang (2009)
10.1096/fj.04-1905fje
Lycopene reduced gene expression of steroid targets and inflammatory markers in normal rat prostate
A. Herzog (2005)
10.1074/jbc.M500409200
Key Role of Conserved Histidines in Recombinant Mouse β-Carotene 15,15′-Monooxygenase-1 Activity*
E. Poliakov (2005)
10.1002/ijc.23453
β‐Ionone suppresses mammary carcinogenesis, proliferative activity and induces apoptosis in the mammary gland of the Sprague‐Dawley rat
Jia-Ren Liu (2008)
10.1021/BI00105A003
Characterization of beta-apo-13-carotenone and beta-apo-14'-carotenal as enzymatic products of the excentric cleavage of beta-carotene.
G. Tang (1991)
10.1111/j.1472-765X.2009.02727.x
Effects of carotenoids from Deinococcus radiodurans on protein oxidation
B. Tian (2009)
10.1042/0264-6021:3540521
Expression pattern and localization of beta,beta-carotene 15,15'-dioxygenase in different tissues.
A. Wyss (2001)
10.1016/S0955-2863(97)00122-8
Biosynthesis of retinoic acid from β-apo-14'-carotenal in ferret in vivo
C. Liu (1997)
10.1074/JBC.271.43.26490
β-Oxidation in Rabbit Liver in Vitro and in the Perfused Ferret Liver Contributes to Retinoic Acid Biosynthesis from β-Apocarotenoic Acids*
X. Wang (1996)
10.1016/S0278-6915(03)00148-0
Lycopene oxidation product enhances gap junctional communication.
O. Aust (2003)
Lycopene supplementation inhibits lung squamous metaplasia and induces apoptosis via up-regulating insulin-like growth factor-binding protein 3 in cigarette smoke-exposed ferrets.
C. Liu (2003)
10.1093/AJCN/85.3.770
Excentral cleavage of β-carotene in vivo in a healthy man
C. C. Ho (2007)
10.1152/AJPHEART.00040.2001
Effects of oxygen tension on energetics of cultured vascular smooth muscle.
A. Lindqvist (2002)
10.1074/jbc.M202756200
Biochemical Properties of Purified Recombinant Human β-Carotene 15,15′-Monooxygenase*
A. Lindqvist (2002)
10.1093/JN/131.12.3303
Carotenoids affect proliferation of human prostate cancer cells.
E. Kotake-Nara (2001)
10.1016/J.FREERADBIOMED.2003.09.019
A novel cleavage product formed by autoxidation of lycopene induces apoptosis in HL-60 cells.
H. Zhang (2003)
10.1093/JN/136.6.1552
Apo-8'-lycopenal and apo-12'-lycopenal are metabolic products of lycopene in rat liver.
M. Gajić (2006)
10.1021/jf104092e
Organic synthesis of new putative lycopene metabolites and preliminary investigation of their cell-signaling effects.
Eric Reynaud (2011)
10.1093/JN/122.1.96
Plasma carotenoid levels in human subjects fed a low carotenoid diet.
C. Rock (1992)
10.1369/jhc.5A6705.2005
Cell Type-specific Expression of β-Carotene 9', 10'-Monooxygenase in Human Tissues
A. Lindqvist (2005)
10.1074/JBC.M009030200
Identification, Expression, and Substrate Specificity of a Mammalian β-Carotene 15,15′-Dioxygenase*
T Michael Redmond (2001)
10.1111/j.1753-4887.2008.00120.x
Biological activity of lycopene metabolites: implications for cancer prevention.
Jonathan R. Mein (2008)
10.1093/PS/84.1.143
Skin pigmentation evaluation in broilers fed natural and synthetic pigments.
M. Castañeda (2005)
10.1016/J.ABB.2006.09.012
Lycopenoids: are lycopene metabolites bioactive?
Brian L Lindshield (2007)
10.1016/j.freeradbiomed.2009.06.008
Structure activity relationship of carotenoid derivatives in activation of the electrophile/antioxidant response element transcription system.
Karin Linnewiel (2009)
10.1016/0006-291X(68)90791-2
The specificity of a partially purified carotenoid cleavage enzyme of rabbit intestine.
M. Lakshmanan (1968)
10.1074/jbc.M011510200
Identification and Characterization of a Mammalian Enzyme Catalyzing the Asymmetric Oxidative Cleavage of Provitamin A*
C. Kiefer (2001)
10.1371/journal.pgen.1000010
Identification of the Yellow Skin Gene Reveals a Hybrid Origin of the Domestic Chicken
J. Eriksson (2008)
10.1074/JBC.275.16.11915
Filling the Gap in Vitamin A Research
J. von Lintig (2000)
10.1002/ijc.23696
Enzymatic metabolites of lycopene induce Nrf2‐mediated expression of phase II detoxifying/antioxidant enzymes in human bronchial epithelial cells
F. Lian (2008)
10.1006/ABBI.1999.1510
Stimulation of gap junctional communication: comparison of acyclo-retinoic acid and lycopene.
W. Stahl (2000)
10.1016/J.ABB.2004.03.024
Intestinal absorption and metabolism of carotenoids: insights from cell culture.
Alexandrine During (2004)
10.1007/s00253-010-2823-9
Biotransformation of carotenoids to retinal by carotenoid 15,15′-oxygenase
Y. Kim (2010)
10.1093/JNCI/94.10.749
Insulin-like growth factor I, IGF-binding protein 3, and lung cancer risk in a prospective study of men in China.
S. London (2002)
10.1093/JN/135.8.2053S
Can smoke-exposed ferrets be utilized to unravel the mechanisms of action of lycopene?
X. Wang (2005)
10.1002/ijc.24689
Dietary lycopene and tomato extract supplementations inhibit nonalcoholic steatohepatitis‐promoted hepatocarcinogenesis in rats
Y. Wang (2010)
10.1021/jf100415z
Identification and quantification of apo-lycopenals in fruits, vegetables, and human plasma.
R. Kopec (2010)
10.1093/carcin/bgp231
Nrf2: friend or foe for chemoprevention?
T. Kensler (2010)
10.1093/CARCIN/BGM076
Apo-10'-lycopenoic acid inhibits lung cancer cell growth in vitro, and suppresses lung tumorigenesis in the A/J mouse model in vivo.
F. Lian (2007)
Carotenoids activate the antioxidant response element transcription system.
A. Ben-Dor (2005)
10.1016/J.BCP.2004.06.022
Geraniol and beta-ionone inhibit proliferation, cell cycle progression, and cyclin-dependent kinase 2 activity in MCF-7 breast cancer cells independent of effects on HMG-CoA reductase activity.
Robin E. Duncan (2004)
10.1207/S15327914nc392_18
Acyclic Carotenoids and Their Oxidation Mixtures Inhibit the Growth of HL-60 Human Promyelocytic Leukemia Cells
E. Nara (2001)
10.1002/mnfr.201000399
CD36 is involved in lycopene and lutein uptake by adipocytes and adipose tissue cultures.
M. Moussa (2011)
10.1016/j.abb.2010.05.010
Hepatic stellate cells are an important cellular site for β-carotene conversion to retinoid.
I. Shmarakov (2010)
10.1002/ijc.22320
The effects of combined antioxidant (β‐carotene, α‐tocopherol and ascorbic acid) supplementation on antioxidant capacity, DNA single‐strand breaks and levels of insulin‐like growth factor‐1/IGF‐binding protein 3 in the ferret model of lung cancer
Y. Kim (2007)
Biogenesis of retinoic acid from beta-carotene. Differences between the metabolism of beta-carotene and retinal.
J. Napoli (1988)
10.1210/EDRV-16-1-3
Insulin-like growth factors and their binding proteins: biological actions.
J. I. Jones (1995)
10.1080/01635581.2011.523494
Lycopene and Apo-12′-Lycopenal Reduce Cell Proliferation and Alter Cell Cycle Progression in Human Prostate Cancer Cells
Nikki A. Ford (2011)
10.1016/j.abb.2010.07.025
The eccentric cleavage product of β-carotene, β-apo-13-carotenone, functions as an antagonist of RXRα.
Abdulkerim Eroglu (2010)
10.1146/annurev.food.102308.124120
An update on the health effects of tomato lycopene.
Erica N Story (2010)
Lifestyle correlates of plasma insulin-like growth factor I and insulin-like growth factor binding protein 3 concentrations.
M. Holmes (2002)
10.1093/JN/134.3.667
β-Carotene and β-Apo-14′-Carotenoic Acid Prevent the Reduction of Retinoic Acid Receptor β in Benzo[a]pyrene-Treated Normal Human Bronchial Epithelial Cells
Pankaj Prakash (2004)
10.1038/343177A0
Identification of a retinoic acid responsive element in the retinoic acid receptor & beta;gene
H. Thé (1990)
10.1016/0003-9861(91)90322-A
Enzymatic conversion of β-carotene into β-apo-carotenals and retinoids by human, monkey, ferret, and rat tissues
X. Wang (1991)
10.1080/01635589509514415
Lycopene is a more potent inhibitor of human cancer cell proliferation than either alpha-carotene or beta-carotene.
J. Levy (1995)
10.1080/01635580903191510
Effects of β-Ionone on Mammary Carcinogenesis and Antioxidant Status in Rats Treated With DMBA
Jia-Ren Liu (2010)
10.1201/9780203026649
Carotenoids in Health and Disease
N. Krinsky (2004)



This paper is referenced by
Nutritional and postharvest quality attributes of commercial tomato varieties
Rachel Mwendwa Kubai (2017)
10.21608/JHIPH.2015.20262
Effect of Two Carotenoids (Lycopene and β-Carotene) Supplementation on Hyperlipidemia and Lipid Peroxidation in Experimental Albino Rats
S. A. Salem (2015)
Provisional chapter Biofunctionality of Carotenoid Metabolites : An Insight into Qualitative and Quantitative Analysis
Bangalore Prabhashankar Arathi (2017)
Molecular aspects of β , β-carotene-9 ’ , 10 ’-oxygenase 2 in carotenoid metabolism and beyond
Lei Wu (2016)
10.1080/07352689.2014.929929
Environmentally Modified Organisms – Expanding Genetic Potential with Light
S. D. Carvalho (2014)
10.1038/s41598-017-15222-x
Targeted Metabolomics Reveals Abnormal Hepatic Energy Metabolism by Depletion of β-Carotene Oxygenase 2 in Mice
L. Wu (2017)
10.21873/invivo.12133
Tomato Juice Consumption Could Improve Breast Skin Adverse Effects of Radiotherapy in Breast Cancer Patients
Yasuyo Fukushi (2020)
10.1017/S0007114514004103
Evaluation of dietary patterns among Norwegian postmenopausal women using plasma carotenoids as biomarkers.
M. S. Markussen (2015)
10.1194/jlr.M069021
Genetic dissection in a mouse model reveals interactions between carotenoids and lipid metabolism[S]
Grzegorz Palczewski (2016)
10.3233/JAD-161216
Dietary Lycopene Supplementation Improves Cognitive Performances in Tau Transgenic Mice Expressing P301L Mutation via Inhibiting Oxidative Stress and Tau Hyperphosphorylation.
Lixia Yu (2017)
10.17140/aftnsoj-6-163
Lycopene: Implications for Human Health–A Review
Lynda M. Doyle (2020)
10.3389/fmicb.2020.558747
Active Transposition of Insertion Sequences by Oxidative Stress in Deinococcus geothermalis
Chanjae Lee (2020)
10.3390/molecules25194378
The Role of Circulating Lycopene in Low-Grade Chronic Inflammation: A Systematic Review of the Literature
Hidde P van Steenwijk (2020)
10.1186/s13018-018-0944-5
Effect of lycopene on titanium implant osseointegration in ovariectomized rats
X. Li (2018)
10.3390/ijms21197119
Potential Role of Lycopene in the Prevention of Postmenopausal Bone Loss: Evidence from Molecular to Clinical Studies
Umani S Walallawita (2020)
10.15562/bmj.v8i2.1145
Administration of pismatom juice increasing of potassium serum levels and faster of recovery in middle run athletes PASI Denpasar, Bali-Indonesia
I. W. Juniarsana (2019)
10.1016/j.foodchem.2017.11.055
Can lycopene be considered an effective protection against cardiovascular disease?
J. Costa-Rodrigues (2018)
10.1007/978-3-642-45195-9_13
Lycopene for the prevention and treatment of prostate disease.
D. Ilic (2014)
10.1016/J.FBP.2015.12.006
Production of solid lipid microparticles loaded with lycopene by spray chilling: Structural characteristics of particles and lycopene stability
J. R. Pelissari (2016)
10.1556/AALIM.43.2014.1.11
Visible reflectance and content of isomeric ratio of lycopene in commercial and elevated lycopene tomato varieties by different technological traits
Z. Pék (2014)
10.1002/mnfr.201600031
Lycopene supplementation restores vitamin A deficiency in mice and possesses thereby partial pro-vitamin A activity transmitted via RAR signaling.
G. Aydemir (2016)
10.3390/ijms21165775
The Remedial Potential of Lycopene in Pancreatitis through Regulation of Autophagy
Suyun Choi (2020)
Phytochemicals, polyunsaturated fatty acids and selenium in prostate cancer : - a randomized controlled trial
Roland Björn Erik Hulander (2013)
10.1002/jobm.201300920
Lycopene cyclase and phytoene synthase activities in the marine yeast Rhodosporidium diobovatum are encoded by a single gene crtYB
W. Guo (2014)
10.3892/ijmm.2017.2960
Lycopene inhibits NF-κB activation and adhesion molecule expression through Nrf2-mediated heme oxygenase-1 in endothelial cells.
Po-Min Yang (2017)
10.1017/S0007114519000606
The association between intake of dietary lycopene and other carotenoids and gestational diabetes mellitus risk during mid-trimester: a cross-sectional study.
Q. Gao (2019)
10.1093/ajcn/nqy177
Limited appearance of apocarotenoids is observed in plasma after consumption of tomato juices: a randomized human clinical trial.
J. Cooperstone (2018)
10.1111/IJFS.14260
Lycopene – a bioactive carotenoid offering multiple health benefits: a review
S. Przybylska (2020)
Działanie likopenu na układ kostny Effects of lycopene on the skeletal system
Zakład Farmakologii (2015)
10.1093/ajcn/nqy099
Serum untargeted metabolomic profile of the Dietary Approaches to Stop Hypertension (DASH) dietary pattern.
C. Rebholz (2018)
10.1158/1940-6207.CAPR-13-0178
Lycopene Metabolite, Apo-10′-Lycopenoic Acid, Inhibits Diethylnitrosamine-Initiated, High Fat Diet–Promoted Hepatic Inflammation and Tumorigenesis in Mice
Blanche C Ip (2013)
10.3978/J.ISSN.2304-3881.2013.07.04
Effect of tomato extract supplementation against high-fat diet-induced hepatic lesions.
A. J. Meléndez-Martínez (2013)
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