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DATA No : VCA0010 INFORMANT : Masayoshi Ito

NAME : y,y-Carotene

FORMULA: C40H56 MOL.WT (average) : 536.873

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Inhibitory effect on colonic aberrant crypt foci formation (anti-tumor promotion) (Ref. 0229/1019)
Effects on intrathymic T cell differentiation and peripheral CD4/CD8 ratio (Ref. 0231)
Singlet oxygen quenching activity (Ref. 0088/0441)
Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)
Effects lowering risk of prostate cancer (Ref. 1020)
Biological activities of lycopene are antioxidant activity (singlet oxygen quenching and peroxyl radical scavenging), induction of cell-cell communication, and growth control, but no provitamin A activity. Epidemiological studies suggest protective effects of lycopene on some types of cancer, e.g., prostate cancer (Ref. 1154).
Lycopene or tomato-rich diets decrease the prostate cancer risk. No study indicated that higher tomato consumption or lycopene blood levels statistically significantly increased the risk of cancer of any site (Ref. 1170).

The crystal structure of the light-harvesting complex II (B800-850) from Rhodospirillum molischianum (present name; Phaeospirillum molischianum) (purple bacterium): 8* (one lycopene, one B800 BChl, two B850 BChl, one a-polypeptide and one b-polypeptide) (Ref. 1152).
The administration of lycopene in drinking water inhibited the incidences and multiplicities of lung adenomas plus carcinomas combined in mouse multi-organ carcinogenesis model in male mice but not in females (Ref. 1197). The inhibitory effect of tomato juice rich in lycopene (17 ppm) was observed in rat colon carcinogenesis model (Ref. 1198). The tomato juice containing lycopene decreased the numbers, but not incidences, of urinary bladder transitional cell carcinomas in male rats (Ref. 1199). Lycopene (50 ppm in drinking water) had inhibitory effect on lung carcinogenesis in male mice (Ref. 1200). Long-term (6 to 76 weeks of age) administration of a diet containing 0.005% lycopene did not reduce the risk of hepatocarcinogenesis in a rat spontaneous liver carcinogenesis model (Ref. 1201). The inhibitory effect of lycopene containing diet was not seen in rat prostate carcinogenesis models (Ref. 1202). Fucoxanthin, lycopene and lutein decreased the number of aberrant crypt foci in colons in mice (Ref. 1206). Lycopene had anticarcinogenic activities in mammary gland, liver, skin and lung in mouse models, and also inhibited the development of aberrant crypt foci in rat colon (Ref. 1207). The moderate dose of a- and b-carotenes and lycopene enhanced gap-junctional intercellular communication (Ref. 1210). Both lycopene and b-carotene showed no inhibitory effect on the development of rat urinary bladder carcinomas, while combination of carotenoids with NSAID decreased numbers and incidences of cancers (Ref. 1211).
MELTING POINT:176degC (Ref. 0056>





UV SPECTRA:lmax (nm): hexane 286, 295, 425, 448, 476, 507 (Ref. 0056); methanol 293, 360, 442, 468, 499, %III/II=68.7
[Spectrum 1107] (Ref. 1052/1064); acetonitrile/methanol/THF (58:35:7) 296, 364, 447, 473, 504, %III/II=70
[Spectrum 1003]
[Spectrum 1051] (Ref. 1057); n-hexane 443.0, 470.5, 502.0 (Ref. 1132)

IR SPECTRA:KBr disc or pellet:
[Spectrum 0016] (Ref. 0065)

NMR SPECTRA:1H-NMR d(CDCl3): 5.11 (2, 2'-H), ca. 2.11 (3, 3'-H2), ca. 2.11 (4, 4'-H2), 5.95 (6, 6'-H), 6.49 (7, 7'-H), 6.25 (8, 8'-H), 6.18 (10, 10'-H), 6.64 (11, 11'-H), 6.35 (12, 12'-H), 6.25 (14, 14'-H), 6.62 (15, 15'-H), 1.688, 1.612 (1, 1'-gem-Me), 1.818 (5, 5'-Me), 1.968 (9, 9', 13, 13'-Me) (Ref. 0054)
13C-NMR d(CDCl3): 131.64 (1, 1'), 124.12 (2, 2'), 26.83 (3, 3'), 40.30 (4, 4'), 139.30 (5, 5'), 125.94 (6, 6'), 124.87 (7, 7'), 135.54 (8, 8'), 136.15 (9, 9'), 131.64 (10, 10'), 125.21 (11, 11'), 137.46 (12, 12'), 136.54 (13, 13'), 132.71 (14, 14'), 130.17 (15, 15'), 25.66, 17.70 (1, 1'-gem-Me), 16.97 (5, 5'-Me), 12.90 (9, 9'-Me), 12.81 (13, 13'-Me) (Ref. 0054)
(CDCl3) (Ref. 1132)
1H- and 13C-NMR in CDCl3 (Ref. 1251)

MASS SPECTRA:m/z: 536 (M, 22%), 467 (M-69), 444 (M-92), 430 (M-106), 378 (M-158), 361 (M-106-69) (Ref. 0059/0060)
FD-MS m/z: 536 (Ref. 1064)

OTHER SPECTRA:Fluoresence (Ref. 1062)
Raman spectrum in n-hexane (Ref. 1132)
RF-TLC on 0.25 mm RP-18 layers (Merck, Art. 15423) using several ratio of light petroleum (bp 40-60degC)-acetonitrile-methanol ex: 1:6:3 Rf=0.16, 3:1:6 Rf=0.27 (Ref. 0135)
HPLC (column: Nucleosil-300-5 0.4times50 cm, eluent: hexane-N-ethyldiisopropylamine, 2000:1, flow: 0.6 ml/min, detect : 469 nm) tR = ca. 27 min (all-E isomer)
[Chromatogram 0010] (Ref. 0054)
A reversed-phase HPLC procedure for quantitative measurement in serum of seven carotenoids (lutein, zeaxanthin, canthaxanthin, b-cryptoxanthin, lycopenes, a-c arotene and b-carotene) has been developed. (Ref. 0227)
Retinol, a-tocoherol, lutein, all-trans-lycopene, and a- and b-carotenes were determined in human plasma by reversed-phase HPLC. (Ref. 0228)
HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=11.4 min (Ref. 1057)
Phtosynthetic bacteria (Rhdospirillaceae, Chromatiaceae, Chrorobiaceae) (Ref. 0409)
Non-photosynthetic bacteria (Mycobacteriacea) (Ref. 0409)
Fungi (Phycomycetes, Axcomycetes, Deuteromycetes) (Ref. 0409)
Lycopersicon esculentum (tomato) (Ref. 0409)
Fruits, flowers, leaves, seeds of higher plant (Ref. 0409)
Rhabdochromatium marinum (purple photosynthetic bacterium) accumulates lycopene (Ref. 1119).
Reaction of y-ionone (C13) with propagyl bromide in the presence of zinc gave the acetylenic alcohol, which was acetylated followed by elimination of acetic acid by treatment with potassium t-butoxide to provide the C16-terminal alkyne. This was transformed to the Grignard reagent, which was coupled with the C8-diketone to give the C40-acetylenic diol. The dehydration with NBS gave lycopene in overall yield of 18%. (Ref. 0018)
Geranyl bromide, obtained from linalol and phosphorous tribromide, was converted with triphenylphosphine into the C10-phosphonium salt. The Wittig reaction with crocetindialdehyde (C20) and BuLi as base gave lycopene in an overall yield of 36%. (Ref. 0018/0055)
y-Ionone was reacted with lithium acetylide to give the a-acetylenic alcohol, which was reduced with H2 and Lindlar catalyst to provide vinyl-y-ionol. This was converted with triphenylphosphine hydrobromide with the C15-phosphonium salt, and condensed with the C10-dialdehyde using sodium methoxide as base to give lycopene in an overall yield of 20%. (Ref. 0018/0056)
Geranyldiethylamine was converted into geranylsulphone (C10) by reaction with ethyl chloroformate and sodium chlorophenylsulphate. Treatment of this sulphone with BuLi, crocetindialdehyde (C20), acetic anhydride and base led to the C40-disulphone with a di-cis configuration. Reduction with disodium dithionite gave all-E-lycopene. (Ref. 0018/0026)

[Table 1023] Lycopene is synthesized from phytoene and z-carotene through four-step (CrtI) and two-step (CrtQ, ZDS) dehydrogenation reactoins, by carotenogenic microorganisms such as bacteria Erwinia and Rhodobacter species and the fungus Neurospora crassa, and by plants including algae and cyanobacteria, respectively (Ref. 1002/1003/1004/1005).
Carotene isomerase, CrtH from Synechocystis sp. PCC 6803 (cyanobacterium) (Ref. 1177/1178) and Chlorobium tepidum (green sulfur bacterium) (Ref. 1295) and CrtISO from Arabidopsis (Ref. 1179) and tomato (Ref. 1180), is involved in the synthesis of all-trans lycopene from poly-cis lycopene (Ref. 1230), and under the light condition, this process is catalyzed by light, photoisomerization.
CrtI is inhibited by diphynylamine, and CrtQ/ZDS is inhibited by a herbicide J852 (Ref. 1004/1191). CrtQ is inhibited by 4-phenyl-3-(substituted benzylthio)-4H-1,2,4-triazoles in lettuse leaves (Ref. 1302).
A plastid terminal oxidase (PTOX) is a cofactor of PDS and ZDS in plants, such as Arabidopsis, tomato, peper and rice (Ref. 1187/1188/1189).

The first carotenoid in the normal spirilloxanthin pathway of purple photosynthetic bacteria (Ref. 1054). Rhabdochromatium marinum (purple photosynthetic bacterium) accumulates lycopene (Ref. 1119), and this may due to low activity of CrtC in the normal spirilloxanthin pathway (Ref. 1054).
Lycopene is a substrate of CrtC from Rubrivivax gelatinosus and Rhodobacter capsulatus (photosynthetic bacteria) to produce rhodopin (Ref. 1255).
Genes required for the biosynthesis of lycopene from farnesyl diphosphate (FPP) were clarified in epiphytic bacteria Erwinia species for the first time in the beginning of the 1990's (Ref. 0201/1001). Lycopene is synthesized from FPP by three crt gene products, CrtE, CrtB, and CrtI (Ref. 1002/1064).
[Table 0005] Nowadays, many corresponding genes are isolated from various organisms such as higher plants, cyanobacteria, fungi, and yeasts as well as bacteria, and the functions of the genes are elucidated (Ref. 0202/1002/1003/1004/1005). Phytoene is the direct substrate for the synthesis of lycopene, in the case catalyzed by phytoene desaturase (CrtI), which is derived from bacteria, fungi, and yeasts (Ref. 0206/1021). z-Carotene is the direct substrate for lycopene synthesis, in the case catalyzed by the plant-type desaturation enzyme, z-carotene desaturase (ZDS, CrtQ) (Ref. 1022/1131/1287).
[Table 0004]
Neurosporene is the major product of CrtI from Rubrivivax gelatinosus (purple photosynthetic bacterium) resulting in the synthesis of spheroidene, and lycopene is the minor resulting in the synthesis of spirilloxanthin (Ref. 1107).
The crtI mutants by random and site-directed mutagenesis of Rhodobacter sphaeroides, which produces only neurosporene, change to prodece also lycopene (Ref. 1116).
Bond lengths, bond angles and dihedral angles determined by AM1 calculation (Ref. 1251).
AUTHOR:Pfander,H. and Traber,B. (1996) Carotenoids Volume 2: Synthesis Chapter 3: Carotenoid Synthesis Part II: Acyclic Carotenoids (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp132-159, Birkhäuser Verlag,Basel,Boston,Berlin
VOL: PAGE : - ()

AUTHOR:Bernhard,K. and Mayer,H.
TITLE:Recent advances in the synthesis of achiral carotenoids
JOURNAL:Pure Appl. Chem.
VOL:63 PAGE : 35 -44 (1991)

AUTHOR:Hengartner,U.,Bernhard,K.,Meyer,K.,Englert,G., and Glinz,E.
TITLE:Synthesis, Isolation, and NMR-Spectroscopic Characterization of Fourteen (Z)-Isomers of Lycopene and Some Acetylenic Didehydro- and Tetrahydrolycopenes
JOURNAL:Helv. Chim. Acta
VOL:75 PAGE : 1848 -1865 (1992)

AUTHOR:Isler,O.,Gutmann,H.,Lindlar,H.,Montavon,M.,Rüegg,R., and Zeller,P.
TITLE:Synthesen in der Carotinoid-Reihe. Synthese von Crocetindialdehyd und Lycopin
JOURNAL:Helv. Chim. Acta
VOL:39 PAGE : 463 -473 (1956)

AUTHOR:Manchand,P.S.,Rüegg,R.,Schwieter,U.,Siddons,P.T., and Weedon,B.C.L.
TITLE:Carotenoid and Related Compounds. Part XI. Syntheses of d-Carotene and e-Carotene
JOURNAL:J. Chem. Soc., Pert II
VOL: PAGE : 2019 -2026 (1965)

AUTHOR:Enzell,C.R.,Francis,G.W., and Liaaen-Jensen,S.
TITLE:Mass Spectrometric Studies of Carotenoids 2. A Survey of Fragmentation Reactions
JOURNAL:Acta Chim. Scand.
VOL:23 PAGE : 727 -750 (1969)

AUTHOR:Schwieter,U.Englert,G.,Rigassi,N., and Vetter,W.
TITLE:Physical organic methods in carotenid research
JOURNAL:Pure Appl. Chem.
VOL:20 PAGE : 365 -420 (1969)

AUTHOR:Bernhard,K., and Grosjean,M. (1995) Carotenoids Volume 1B: Spectroscopy Chapter 4: Infrared Spectroscopy (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp117-146, Birkhäuser Verlag,Basel,Boston,Berlin
VOL: PAGE : - ()

AUTHOR:Di Mascio, P., Kaiser, S., and Sies, H.
TITLE:Lycopene as the most efficient biological carotenoid singlet oxygen quencher PubMed ID:2802626
JOURNAL:Arch Biochem Biophys.
VOL:274 PAGE : 532-538 (1989)

AUTHOR:Isaksen,M., and Francis,G.W.
TITLE:Reversed-phase thin-layer chromatography of carotenoids
JOURNAL:J. Chromatogr.
VOL:355 PAGE : 358 -362 (1986)

AUTHOR:Misawa, N., Nakagawa, M., Kobayashi, K., Yamano, S., Izawa, Y., Nakamura, K., and Harashima, K.
TITLE:Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli PubMed ID:2254247
JOURNAL:J Bacteriol.
VOL:172 PAGE : 6704-6712 (1990)

AUTHOR:Misawa, N., Satomi, Y., Kondo, K., Yokoyama, A., Kajiwara, S., Saito, T., Ohtani, T., and Miki, W.
TITLE:Structure and functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin biosynthetic pathway proposed at the gene level PubMed ID:7592436
JOURNAL:J Bacteriol.
VOL:177 PAGE : 6575-6584 (1995)

AUTHOR:Fraser, P. D., Misawa, N., Linden, H., Yamano, S., Kobayashi, K., and Sandmann, G.
TITLE:Expression in Escherichia coli, purification, and reactivation of the recombinant Erwinia uredovora phytoene desaturase PubMed ID:1400305
JOURNAL:J Biol Chem.
VOL:267 PAGE : 19891-19895 (1992)

AUTHOR:Tsushima, M., Maoka, T., Katsuyama, M., Kozuka, M., Matsuno, T., Tokuda, H., Nishino, H., and Iwashima, A.
TITLE:Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters PubMed ID:7742789
JOURNAL:Biol Pharm Bull.
VOL:18 PAGE : 227-233 (1995)

AUTHOR:Steghens, J. P., van Kappel, A. L., Riboli, E., and Collombel, C.
TITLE:Simultaneous measurement of seven carotenoids, retinol and alpha-tocopherol in serum by high-performance liquid chromatography PubMed ID:9234850
JOURNAL:J Chromatogr B Biomed Sci Appl.
VOL:694 PAGE : 71-81 (1997)

TITLE:Simple determination of retinol, alpha-tocopherol and carotenoids (lutein, all-trans-lycopene, alpha- and beta-carotenes) in human plasma by isocratic liquid chromatography PubMed ID:8004234
JOURNAL:J Chromatogr B Biomed Appl.
VOL:654 PAGE : 129-133 (1994)

AUTHOR:Narisawa, T., Fukaura, Y., Hasebe, M., Ito, M., Aizawa, R., Murakoshi, M., Uemura, S., Khachik, F., and Nishino, H.
TITLE:Inhibitory effects of natural carotenoids, alpha-carotene, beta-carotene, lycopene and lutein, on colonic aberrant crypt foci formation in rats PubMed ID:8913278
JOURNAL:Cancer Lett.
VOL:107 PAGE : 137-142 (1996)

AUTHOR:Kobayashi, T., Iijima, K., Mitamura, T., Toriizuka, K., Cyong, J. C., and Nagasawa, H.
TITLE:Effects of lycopene, a carotenoid, on intrathymic T cell differentiation and peripheral CD4/CD8 ratio in a high mammary tumor strain of SHN retired mice PubMed ID:8740725
JOURNAL:Anticancer Drugs.
VOL:7 PAGE : 195-198 (1996)

AUTHOR:Goodwin T. W. (1980) The biochemistry of the carotenoids, Volume I, Plants, Chapman and Hall, London and New York
VOL: PAGE : - ()

AUTHOR:Hirayama, O., Nakamura, K., Hamada, S., and Kobayasi, Y.
TITLE:Singlet oxygen quenching ability of naturally occurring carotenoids PubMed ID:8152349
VOL:29 PAGE : 149-150 (1994)

AUTHOR:Sandmann, G., and Misawa, N.
TITLE:New functional assignment of the carotenogenic genes crtB and crtE with constructs of these genes from Erwinia speicies
JOURNAL:FEMS Microbiol. Lett.
VOL:90 PAGE : 253 -258 (1992)

AUTHOR:Misawa, N., and Shimada, H.
TITLE:Metabolic engineering for the production of carotenoids in non-carotenogenic bacteria and yeasts PubMed ID:9519479
JOURNAL:J Biotechnol.
VOL:59 PAGE : 169-181 (1997)

AUTHOR:Misawa, N., Masamoto, K., Hori, T., Ohtani, T., Böger, P., and Sandmann, G.
TITLE:Expression of an Erwinia phytoene desaturase gene not only confers multiple resistance to herbicides interfering with carotenoid biosynthesis but also alters xanthophyll metabolism in transgenic plants
VOL:6 PAGE : 481 -489 (1994)

AUTHOR:Sandmann, G.
TITLE:Carotenoid biosynthesis in microorganisms and plants PubMed ID:8033911
JOURNAL:Eur J Biochem.
VOL:223 PAGE : 7-24 (1994)

AUTHOR:Armstrong, G. A., and Hearst, J. E.
TITLE:Carotenoids 2: Genetics and molecular biology of carotenoid pigment biosynthesis PubMed ID:8641556
VOL:10 PAGE : 228-237 (1996)

AUTHOR:Arimochi, H., Kataoka, K., Kuwahara, T., Nakayama, H., Misawa, N., and Ohnishi, Y.
TITLE:Effects of beta-glucuronidase-deficient and lycopene-producing Escherichia coli strains on formation of azoxymethane-induced aberrant crypt foci in the rat colon PubMed ID:10462473
JOURNAL:Biochem Biophys Res Commun.
VOL:262 PAGE : 322-327 (1999)

AUTHOR:Giovannucci, E., Ascherio, A., Rim, E.B., Stampfer, M.J., Colditz, G.A., and Willet, W.C.
TITLE:Intake of carotenids and retinol in relation to risk of prostate cancer
JOURNAL:J. National Cancer Institute
VOL:87 PAGE : 1767 -1776 (1995)

AUTHOR:Verdoes, J. C., Misawa, N., and van Ooyen, A. J.
TITLE:Cloning and characterization of the astaxanthin biosynthetic gene encoding phytoene desaturase of Xanthophyllomyces dendrorhous PubMed ID:10397832
JOURNAL:Biotechnol Bioeng.
VOL:63 PAGE : 750-755 (1999)

AUTHOR:Breitenbach, J., Kuntz, M., Takaichi, S., and Sandmann, G.
TITLE:Catalytic properties of an expressed and purified higher plant type zeta-carotene desaturase from Capsicum annuum PubMed ID:10491195
JOURNAL:Eur J Biochem.
VOL:265 PAGE : 376-383 (1999)

AUTHOR:Takaichi, S. and Shimada, K.
TITLE:Characterization of carotenoids in photosynthetic bacteria
JOURNAL:Methods Enzymol.
VOL:213 PAGE : 374 -385 (1992)

AUTHOR:Takaichi, S. (1999) Carotenoids and Carotenogenesis in Anoxygenic Photosynthetic Bacteria, in The Photochemistry of Carotenoids (Frank, H. A., Young, A., Britton G., and Cogdell, R. J., eds.) pp. 39-69, Kluwer Academic Publishers, Dordrecht, The Netherlands
VOL: PAGE : - ()

AUTHOR:Takaichi, S.
TITLE:Characterization of carotenes in a combination of a C18 HPLC column with isocratic elution and absorption spectra with a photodiode-array detector
JOURNAL:Photosynth. Res.
VOL:65 PAGE : 93 -99 (2000)

AUTHOR:Akimoto, S., Yamazaki, I., Takaichi, S., and Mimuro, M.
TITLE:Excitation relaxation dynamics of linear carotenoids
JOURNAL:J. Luminescence
VOL:8789 PAGE : 797 -799 (2000)

AUTHOR:Kuwabara, T., Hasegawa, M., Kawano, M., and Takaichi, S.
TITLE:Characterization of violaxanthin de-epoxidase purified in the presence of Tween 20: effects of dithiothreitol and pepstatin A PubMed ID:10635115
JOURNAL:Plant Cell Physiol.
VOL:40 PAGE : 1119-1126 (1999)

AUTHOR:Harada, J., Nagashima, K. V., Takaichi, S., Misawa, N., Matsuura, K., and Shimada, K.
TITLE:Phytoene desaturase, CrtI, of the purple photosynthetic bacterium, Rubrivivax gelatinosus, produces both neurosporene and lycopene PubMed ID:11673627
JOURNAL:Plant Cell Physiol.
VOL:42 PAGE : 1112-1118 (2001)

AUTHOR:Wang, C. W., and Liao, J. C.
TITLE:Alteration of product specificity of Rhodobacter sphaeroides phytoene desaturase by directed evolution PubMed ID:11526111
JOURNAL:J Biol Chem.
VOL:276 PAGE : 41161-41164 (2001)

AUTHOR:Dilling, W., Liesack, W., and Pfennig, N.
TITLE:Rhabdochromatium marinum gen. nom. rev., sp. nov., a purple sulfur bacteium from a salt march microbial mat
JOURNAL:Arch. Microbiol.
VOL:164 PAGE : 125 -131 (1995)

AUTHOR:Breitenbach, J., Fernandez-Gonzalez, B., Vioque, A., and Sandmann, G.
TITLE:A higher-plant type zeta-carotene desaturase in the cyanobacterium Synechocystis PCC6803 PubMed ID:9526505
JOURNAL:Plant Mol Biol.
VOL:36 PAGE : 725-732 (1998)

AUTHOR:Qian, P., Saiki, K., Mizoguchi, T., Hara, K., Sashima, T., Fujii, R., and Koyama, Y.
TITLE:Time-dependent changes in the carotenoid composition and preferential binding of spirilloxanthin to the reaction center and anhydrorhodovibrin to the LH1 antenna complex in Rhodobium marinum PubMed ID:11594059
JOURNAL:Photochem Photobiol.
VOL:74 PAGE : 444-452 (2001)

AUTHOR:Koepke, J., Hu, X., Muenke, C., Schulten, K., and Michel, H.
TITLE:The crystal structure of the light-harvesting complex II (B800-850) from Rhodospirillum molischianum PubMed ID:8736556
VOL:4 PAGE : 581-597 (1996)

AUTHOR:Stahl, W., and Sies, H.
TITLE:Lycopene: a biologically important carotenoid for humans? PubMed ID:8951028
JOURNAL:Arch Biochem Biophys.
VOL:336 PAGE : 1-9 (1996)

AUTHOR:Schmitz-Drager, B. J., Eichholzer, M., Beiche, B., and Ebert, T.
TITLE:Nutrition and prostate cancer PubMed ID:11464107
VOL:67 PAGE : 1-11 (2001)

AUTHOR:Breitenbach, J., Vioque, A., and Sandmann, G.
TITLE:Gene sll0033 from Synechocystis 6803 encodes a carotene isomerase involved in the biosynthesis of all-E lycopene PubMed ID:11724407
JOURNAL:Z Naturforsch [C].
VOL:56 PAGE : 915-917 (2001)

AUTHOR:Masamoto, K., Wada, H., Kaneko, T., and Takaichi, S.
TITLE:Identification of a gene required for cis-to-trans carotene isomerization in carotenogenesis of the cyanobacterium Synechocystis sp. PCC 6803 PubMed ID:11773533
JOURNAL:Plant Cell Physiol.
VOL:42 PAGE : 1398-1402 (2001)

AUTHOR:Park, H., Kreunen, S. S., Cuttriss, A. J., DellaPenna, D., and Pogson, B. J.
TITLE:Identification of the carotenoid isomerase provides insight into carotenoid biosynthesis, prolamellar body formation, and photomorphogenesis PubMed ID:11884677
JOURNAL:Plant Cell.
VOL:14 PAGE : 321-332 (2002)

AUTHOR:Isaacson, T., Ronen, G., Zamir, D., and Hirschberg, J.
TITLE:Cloning of tangerine from tomato reveals a carotenoid isomerase essential for the production of beta-carotene and xanthophylls in plants PubMed ID:11884678
JOURNAL:Plant Cell.
VOL:14 PAGE : 333-342 (2002)

AUTHOR:Carol, P., Stevenson, D., Bisanz, C., Breitenbach, J., Sandmann, G., Mache, R., Coupland, G., and Kuntz, M.
TITLE:Mutations in the Arabidopsis gene IMMUTANS cause a variegated phenotype by inactivating a chloroplast terminal oxidase associated with phytoene desaturation PubMed ID:9878632
JOURNAL:Plant Cell.
VOL:11 PAGE : 57-68 (1999)

AUTHOR:Josse, E. M., Simkin, A. J., Gaffe, J., Laboure, A. M., Kuntz, M., and Carol, P.
TITLE:A plastid terminal oxidase associated with carotenoid desaturation during chromoplast differentiation PubMed ID:10938359
JOURNAL:Plant Physiol.
VOL:123 PAGE : 1427-1436 (2000)

AUTHOR:Carol, P., and Kuntz, M.
TITLE:A plastid terminal oxidase comes to light: implications for carotenoid biosynthesis and chlororespiration PubMed ID:11164375
JOURNAL:Trends Plant Sci.
VOL:6 PAGE : 31-36 (2001)

AUTHOR:Simkin, A. J., Breitenbach, J., Kuntz, M., and Sandmann, G.
TITLE:In vitro and in situ inhibition of carotenoid biosynthesis in Capsicum annuum by bleaching herbicides PubMed ID:11052718
JOURNAL:J Agric Food Chem.
VOL:48 PAGE : 4676-4680 (2000)

AUTHOR:Kim, D. J., Takasuka, N., Kim, J. M., Sekine, K., Ota, T., Asamoto, M., Murakoshi, M., Nishino, H., Nir, Z., and Tsuda, H.
TITLE:Chemoprevention by lycopene of mouse lung neoplasia after combined initiation treatment with DEN, MNU and DMH PubMed ID:9570381
JOURNAL:Cancer Lett.
VOL:120 PAGE : 15-22 (1997)

AUTHOR:Narisawa, T., Fukaura, Y., Hasebe, M., Nomura, S., Oshima, S., Sakamoto, H., Inakuma, T., Ishiguro, Y., Takayasu, J., and Nishino, H.
TITLE:Prevention of N-methylnitrosourea-induced colon carcinogenesis in F344 rats by lycopene and tomato juice rich in lycopene PubMed ID:9849577
JOURNAL:Jpn J Cancer Res.
VOL:89 PAGE : 1003-1008 (1998)

AUTHOR:Okajima, E., Tsutsumi, M., Ozono, S., Akai, H., Denda, A., Nishino, H., Oshima, S., Sakamoto, H., and Konishi, Y.
TITLE:Inhibitory effect of tomato juice on rat urinary bladder carcinogenesis after N-butyl-N-(4-hydroxybutyl)nitrosamine initiation PubMed ID:9510471
JOURNAL:Jpn J Cancer Res.
VOL:89 PAGE : 22-26 (1998)

AUTHOR:Kim, D. J., Takasuka, N., Nishino, H., and Tsuda, H.
TITLE:Chemoprevention of lung cancer by lycopene PubMed ID:11237207
VOL:13 PAGE : 95-102 (2000)

AUTHOR:Watanabe, S., Kitade, Y., Masaki, T., Nishioka, M., Satoh, K., and Nishino, H.
TITLE:Effects of lycopene and Sho-saiko-to on hepatocarcinogenesis in a rat model of spontaneous liver cancer PubMed ID:11588908
JOURNAL:Nutr Cancer.
VOL:39 PAGE : 96-101 (2001)

AUTHOR:Imaida, K., Tamano, S., Kato, K., Ikeda, Y., Asamoto, M., Takahashi, S., Nir, Z., Murakoshi, M., Nishino, H., and Shirai, T.
TITLE:Lack of chemopreventive effects of lycopene and curcumin on experimental rat prostate carcinogenesis PubMed ID:11238188
VOL:22 PAGE : 467-472 (2001)

AUTHOR:Kim, J. M., Araki, S., Kim, D. J., Park, C. B., Takasuka, N., Baba-Toriyama, H., Ota, T., Nir, Z., Khachik, F., Shimidzu, N., et al.
TITLE:Chemopreventive effects of carotenoids and curcumins on mouse colon carcinogenesis after 1,2-dimethylhydrazine initiation PubMed ID:9472697
VOL:19 PAGE : 81-85 (1998)

AUTHOR:Nishino, H., Tokuda , H., Satomi, Y., Masuda, M., Bu, P., Onozuka, M., Yamaguchi, S., Okuda, Y., Takayasu, J., Tsurata, J., Okada, M., Ichiishi, E., Murakoshi, M., Kato, T., Misawa, N., Narisawa, T., Takasuka, N., and Yano, M.
TITLE:Cancer prevention by carotenoids
JOURNAL:Pure Appl. Chem.
VOL:71 PAGE : 2273 -2278 (1999)

AUTHOR:Krutovskikh, V., Asamoto, M., Takasuka, N., Murakoshi, M., Nishino, H., and Tsuda, H.
TITLE:Differential dose-dependent effects of alpha-, beta-carotenes and lycopene on gap-junctional intercellular communication in rat liver in vivo PubMed ID:9473727
JOURNAL:Jpn J Cancer Res.
VOL:88 PAGE : 1121-1124 (1997)

AUTHOR:Okajima, E., Ozono, S., Endo, T., Majima, T., Tsutsumi, M., Fukuda, T., Akai, H., Denda, A., Hirao, Y., Okajima, E., et al.
TITLE:Chemopreventive efficacy of piroxicam administered alone or in combination with lycopene and beta-carotene on the development of rat urinary bladder carcinoma after N-butyl-N-(4-hydroxybutyl)nitrosamine treatment PubMed ID:9263531
JOURNAL:Jpn J Cancer Res.
VOL:88 PAGE : 543-552 (1997)

AUTHOR:Giuliano, G., Giliberto, L., and Rosati, C.
TITLE:Carotenoid isomerase: a tale of light and isomers PubMed ID:12399171
JOURNAL:Trends Plant Sci.
VOL:7 PAGE : 427-429 (2002)

AUTHOR:Qian, P., Mizoguchi, T., Fujii, R., and Hara, K.
TITLE:Conformation analysis of carotenoids in the purple bacterium Rhodobium marinum based on NMR spectroscopy and AM1 calculation PubMed ID:12444727
JOURNAL:J Chem Inf Comput Sci.
VOL:42 PAGE : 1311-1319 (2002)

AUTHOR:Steiger, S., Mazet, A., and Sandmann, G.
TITLE:Heterologous expression, purification, and enzymatic characterization of the acyclic carotenoid 1,2-hydratase from Rubrivivax gelatinosus PubMed ID:12745254
JOURNAL:Arch Biochem Biophys.
VOL:414 PAGE : 51-58 (2003)

AUTHOR:Conti, A., Pancaldi, S., Fambrini, M., Michelotti, V., Bonora, A., Salvini, M., and Pugliesi, C.
TITLE:A deficiency at the gene coding for zeta-carotene desaturase characterizes the sunflower non dormant-1 mutant PubMed ID:15111719
JOURNAL:Plant Cell Physiol.
VOL:45 PAGE : 445-455 (2004)

AUTHOR:Frigaard, N. U., Maresca, J. A., Yunker, C. E., Jones, A. D., and Bryant, D. A.
TITLE:Genetic manipulation of carotenoid biosynthesis in the green sulfur bacterium Chlorobium tepidum PubMed ID:15292122
JOURNAL:J Bacteriol.
VOL:186 PAGE : 5210-5220 (2004)

AUTHOR:Yamada, N., Kusano, D., and Kuwano, E.
TITLE:Bleaching activity of 4-phenyl-3-(substituted benzylthio)-4H-1,2,4-triazoles PubMed ID:12353626
JOURNAL:Biosci Biotechnol Biochem.
VOL:66 PAGE : 1671-1676 (2002)

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