Carotenoid
DATA No : VCA0010
INFORMANT : Masayoshi Ito
NAME :
y,
y-Carotene
| COMMON NAME | : | Lycopene |
| SYMBOL | : | |
| FORMULA | : | C40H56 MOL.WT (average) : 536.873 |
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 | : | 176 C (Ref. 0056> |
|
| BOILING POINT | : | |
|
| REFRACTIVE INDEX | : | |
|
| OPTICAL ROTATION | : | |
|
| DENSITY | : | |
|
| SOLUBILITY | : | |
| 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 40-60
C)-acetonitrile-methanol ex: 1:6:3 Rf=0.16, 3:1:6 Rf=0.27 (
Ref. 0135)
HPLC (column: Nucleosil-300-5 0.4
50 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).
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