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Carotenoid


DATA No : VCA0010 INFORMANT : Masayoshi Ito

NAME : y,y-Carotene

COMMON NAME: Lycopene
SYMBOL:
FORMULA: C40H56 MOL.WT (average) : 536.873


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BIOLOGICAL ACTIVITY
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).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:176degC (Ref. 0056>

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
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)
CHROMATOGRAM DATA
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)
SOURCE
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).
CHEMICAL SYNTHESIS
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)
METABOLISM

[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).
GENETIC INFORMATION
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).
NOTE
Bond lengths, bond angles and dihedral angles determined by AM1 calculation (Ref. 1251).
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