Carotenoid
DATA No : VCA1001
INFORMANT : Norihiko Misawa
NAME : 15-cis-7,8,11,12,7',8',11'12'-Octahydro-
y,
y-carotene
| COMMON NAME | : | Phytoene |
| SYMBOL | : | |
| FORMULA | : | C40H64 MOL.WT (average) : 544.936 |
The transfer of crtB gene from Erwinia uredovora in mammalian cells produced phytoene, and the cells were protective against oxidative stress and H-ras induced transformation (
Ref. 1205).
The cancer preventive activity of phytoene was confirmed in phytoene producing mammalian cells (
Ref. 1207).
Transgenic mice carrying the phytoene synthase gene crtB produce phytoene and induce connexin 26 (
Ref. 1349).
| PHYSICAL AND CHEMICAL PROPERTIES |
| MELTING POINT | : | |
|
| BOILING POINT | : | |
|
| REFRACTIVE INDEX | : | |
|
| OPTICAL ROTATION | : | |
|
| DENSITY | : | |
|
| SOLUBILITY | : | |
HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=28.2 min (all-trans), 26.9 min (15-cis) (
Ref. 1057)
The crtI mutant of Rhodobacter sphaeroides (purple photosynthetic bacteria) (
Ref. 1089)
Myxococcus sp. MY-18 (fruiting gliding myxobacterium) accumulats (
Ref. 1353).
Phytoene is the first colorless carotenoid, which is formed form two molecules of geranylgeranyl diphosphate (GGPP) by phytoene synthase in all carotenogenic organisms (
Ref. 1001/
1029/
1030). This reaction is reported to be a rate-limiting step for carotenoid biosynthesis in a higher plant and a carotenogenic bacterium (
Ref. 1016/
1031). All carotenoids, except for C
30 special ones, are synthesized from phytoene as the starting carotenoid substrate (
Ref. 1003/
1004/
1005).
Chloroflexus aurantiacus (green filamentous photosynthetic bacterium) accumulates phytoene in the culture with 2-hydroxybiphenyl, and this compound inhibits carotenoid formation by inhibiting the flow of electrons liberated in the course of the desaturase reaction (
Ref. 1166).
The genes from Xanthophyllomyces dendrorhous (crtYB) (
Ref. 1172), Mucor circinelloides (carRP) (
Ref. 1173), and Phycomyces blakesleeanus (carRA) (
Ref. 1174) (fungus) encode a bifunctional protein involved phytoene synthase activity located in C-terminus domain and lycopene cyclase activity located in N-terminus domain.
An Escherichia coli transformant carrying the Erwinia uredovora crtE and crtB genes (
Ref. 0201/
1002).
[
Table 1019]
Phytoene desaturase (PDS) inhibitor (
Ref. 1252)
Phytoene synthase genes (crtB or psy), which mediate the formation of phytoene from GGPP, have been cloned from the photosynthetic bacteria Rhodobacter species (
Ref. 1032/
1033), the nonphotosynthetic bacteria Erwinia species (Erwinia uredovara and E. herbicola) (
Ref. 0201/
0233/
1034) and Thermus thermophilus (
Ref. 1031), the cyanobacterium Synechococcus PCC7942 (
Ref. 1029), the fungus Neurospora crassa (
Ref. 1035), and higher plants such as tomato and red pepper (
Ref. 1036/
1037/
1038/
1039).
In tomato, PSY1 transcripts predominate in seedlings and in late stages of fruit ripeing, whereas PSY2 transcripts are relatively more abundant in mature leaves (
Ref. 1036/
1186/
1190).
Biotechnological achievement has been made in metabolic engineering of caroteoids in animal cells, by the group of H. Nishino in 1995, i. e., a transgenic mammalian cells, which accumulates phytoene, has been constructed by expressing the Erwinia phytoene synthase gene crtB (
Ref. 1028).
The photophysics of two lowest lying singlet excited states in 15-cis-phytoene and 15-cis-phytofluene by means of steady-state fluorescence spectroscopy (
Ref. 1113)
[0061]
| AUTHOR | : | Moss,G.P. |
| TITLE | : | Carbon-13 NMR spectra of carotenoids |
| JOURNAL | : | Pure Appl. Chem. |
| VOL | : | 2047 PAGE : 97 -102 (1976) |
[0201]
| 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) |
[0233]
| AUTHOR | : | To, K. Y., Lai, E. M., Lee, L. Y., Lin, T. P., Hung, C. H., Chen, C. L., Chang, Y. S., and Liu, S. T. |
| TITLE | : | Analysis of the gene cluster encoding carotenoid biosynthesis in Erwinia herbicola Eho13 PubMed ID:8180698 |
| JOURNAL | : | Microbiology. |
| VOL | : | 140 (Pt 2) PAGE : 331-339 (1994) |
[1001]
| 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) |
[1002]
| 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) |
[1003]
| 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 |
| JOURNAL | : | Plant J. |
| VOL | : | 6 PAGE : 481 -489 (1994) |
[1004]
| AUTHOR | : | Sandmann, G. |
| TITLE | : | Carotenoid biosynthesis in microorganisms and plants PubMed ID:8033911 |
| JOURNAL | : | Eur J Biochem. |
| VOL | : | 223 PAGE : 7-24 (1994) |
[1005]
| AUTHOR | : | Armstrong, G. A., and Hearst, J. E. |
| TITLE | : | Carotenoids 2: Genetics and molecular biology of carotenoid pigment biosynthesis PubMed ID:8641556 |
| JOURNAL | : | Faseb J. |
| VOL | : | 10 PAGE : 228-237 (1996) |
[1016]
| AUTHOR | : | Shewmaker, C. K., Sheehy, J. A., Daley, M., Colburn, S., and Ke, D. Y. |
| TITLE | : | Seed-specific overexpression of phytoene synthase: increase in carotenoids and other metabolic effects PubMed ID:10607293 |
| JOURNAL | : | Plant J. |
| VOL | : | 20 PAGE : 401-412X (1999) |
[1028]
| AUTHOR | : | Satomi, Y., Yoshida, T., Aoki, K., Misawa, N., Masuda, M., Murakoshi, M., Takasuka, N., Sugimura, T., and Nishino, H. |
| TITLE | : | Production of phytoene, an oxidative stress protective carotenoid, in mammalian cells by introduction of phytoene synthase gene crtB isolated from a bacterium Erwinia uredovora |
| JOURNAL | : | Proc. Japan Academy |
| VOL | : | 71 PAGE : 236 -240 (1995) |
[1029]
| AUTHOR | : | Chamovitz, D., Misawa, N., Sandmann, G., and Hirschberg, J. |
| TITLE | : | Molecular cloning and expression in Escherichia coli of a cyanobacterial gene coding for phytoene synthase, a carotenoid biosynthesis enzyme PubMed ID:1537409 |
| JOURNAL | : | FEBS Lett. |
| VOL | : | 296 PAGE : 305-310 (1992) |
[1030]
| AUTHOR | : | Misawa, N., Truesdale, M. R., Sandmann, G., Fraser, P. D., Bird, C., Schuch, W., and Bramley, P. M. |
| TITLE | : | Expression of a tomato cDNA coding for phytoene synthase in Escherichia coli, phytoene formation in vivo and in vitro, and functional analysis of the various truncated gene products PubMed ID:7896759 |
| JOURNAL | : | J Biochem (Tokyo). |
| VOL | : | 116 PAGE : 980-985 (1994) |
[1031]
| AUTHOR | : | Hoshino, T., Fujii, R., and Nakahara, T. |
| TITLE | : | Molecular cloning and sequence analysis of the crtB gene of Thermus thermophilus HB27, an extreme thermophile producing carotenoid pigments PubMed ID:8215386 |
| JOURNAL | : | Appl Environ Microbiol. |
| VOL | : | 59 PAGE : 3150-3153 (1993) |
[1032]
| AUTHOR | : | Armstrong, G. A., Alberti, M., Leach, F., and Hearst, J. E. |
| TITLE | : | Nucleotide sequence, organization, and nature of the protein products of the carotenoid biosynthesis gene cluster of Rhodobacter capsulatus PubMed ID:2747617 |
| JOURNAL | : | Mol Gen Genet. |
| VOL | : | 216 PAGE : 254-268 (1989) |
[1033]
| AUTHOR | : | Lang, H. P., Cogdell, R. J., Gardiner, A. T., and Hunter, C. N. |
| TITLE | : | Early steps in carotenoid biosynthesis: sequences and transcriptional analysis of the crtI and crtB genes of Rhodobacter sphaeroides and overexpression and reactivation of crtI in Escherichia coli and R. sphaeroides PubMed ID:8021167 |
| JOURNAL | : | J Bacteriol. |
| VOL | : | 176 PAGE : 3859-3869 (1994) |
[1034]
| AUTHOR | : | Armstrong, G. A., Alberti, M., and Hearst, J. E. |
| TITLE | : | Conserved enzymes mediate the early reactions of carotenoid biosynthesis in nonphotosynthetic and photosynthetic prokaryotes PubMed ID:2263648 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 87 PAGE : 9975-9979 (1990) |
[1035]
| AUTHOR | : | Schmidhauser, T. J., Lauter, F. R., Schumacher, M., Zhou, W., Russo, V. E., and Yanofsky, C. |
| TITLE | : | Characterization of al-2, the phytoene synthase gene of Neurospora crassa. Cloning, sequence analysis, and photoregulation PubMed ID:8163509 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 269 PAGE : 12060-12066 (1994) |
[1036]
| AUTHOR | : | Bartley, G. E., Viitanen, P. V., Bacot, K. O., and Scolnik, P. A. |
| TITLE | : | A tomato gene expressed during fruit ripening encodes an enzyme of the carotenoid biosynthesis pathway PubMed ID:1544888 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 267 PAGE : 5036-5039 (1992) |
[1037]
| AUTHOR | : | Ray, J., Bird, C., Maunders, M., Grierson, D., and Schuch, W. |
| TITLE | : | Sequence of pTOM5, a ripening related cDNA from tomato PubMed ID:3697097 |
| JOURNAL | : | Nucleic Acids Res. |
| VOL | : | 15 PAGE : 10587- (1987) |
[1038]
| AUTHOR | : | Romer, S., Hugueney, P., Bouvier, F., Camara, B., and Kuntz, M. |
| TITLE | : | Expression of the genes encoding the early carotenoid biosynthetic enzymes in Capsicum annuum PubMed ID:8250898 |
| JOURNAL | : | Biochem Biophys Res Commun. |
| VOL | : | 196 PAGE : 1414-1421 (1993) |
[1039]
| AUTHOR | : | Scolnik, P. A., and Bartley, G. E. |
| TITLE | : | Nucleotide sequence of an Arabidopsis cDNA for phytoene synthase PubMed ID:8016277 |
| JOURNAL | : | Plant Physiol. |
| VOL | : | 104 PAGE : 1471-1472 (1994) |
[1052]
| AUTHOR | : | Takaichi, S. and Shimada, K. |
| TITLE | : | Characterization of carotenoids in photosynthetic bacteria |
| JOURNAL | : | Methods Enzymol. |
| VOL | : | 213 PAGE : 374 -385 (1992) |
[1057]
| 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) |
[1089]
| AUTHOR | : | Lang, H. P., Cogdell, R. J., Takaichi, S., and Hunter, C. N. |
| TITLE | : | Complete DNA sequence, specific Tn5 insertion map, and gene assignment of the carotenoid biosynthesis pathway of Rhodobacter sphaeroides PubMed ID:7721699 |
| JOURNAL | : | J Bacteriol. |
| VOL | : | 177 PAGE : 2064-2073 (1995) |
[1113]
| AUTHOR | : | Andersson, P. O., Takaichi, S., Cogdell, R. J., and Gillbro, T. |
| TITLE | : | Photophysical characterization of natural cis-carotenoids PubMed ID:11683034 |
| JOURNAL | : | Photochem Photobiol. |
| VOL | : | 74 PAGE : 549-557 (2001) |
[1166]
| AUTHOR | : | Foidl, M., Golecki, J.R., and Oelze, J. |
| TITLE | : | Phototrophic growth and chlorosome formation in Chloroflexus aurantiacus under conditions of carotenoid deficienct |
| JOURNAL | : | Photosynth. Res. |
| VOL | : | 54 PAGE : 219 -226 (1997) |
[1172]
| AUTHOR | : | Verdoes, J. C., Krubasik, K. P., Sandmann, G., and van Ooyen, A. J. |
| TITLE | : | Isolation and functional characterisation of a novel type of carotenoid biosynthetic gene from Xanthophyllomyces dendrorhous PubMed ID:10589832 |
| JOURNAL | : | Mol Gen Genet. |
| VOL | : | 262 PAGE : 453-461 (1999) |
[1173]
| AUTHOR | : | Velayos, A., Eslava, A. P., and Iturriaga, E. A. |
| TITLE | : | A bifunctional enzyme with lycopene cyclase and phytoene synthase activities is encoded by the carRP gene of Mucor circinelloides PubMed ID:10951210 |
| JOURNAL | : | Eur J Biochem. |
| VOL | : | 267 PAGE : 5509-5519 (2000) |
[1174]
| AUTHOR | : | Arrach, N., Fernandez-Martin, R., Cerda-Olmedo, E., and Avalos, J. |
| TITLE | : | A single gene for lycopene cyclase, phytoene synthase, and regulation of carotene biosynthesis in Phycomyces PubMed ID:11172012 |
| JOURNAL | : | Proc Natl Acad Sci U S A. |
| VOL | : | 98 PAGE : 1687-1692 (2001) |
[1186]
| AUTHOR | : | Bartley, G. E., and Scolnik, P. A. |
| TITLE | : | cDNA cloning, expression during development, and genome mapping of PSY2, a second tomato gene encoding phytoene synthase PubMed ID:8245008 |
| JOURNAL | : | J Biol Chem. |
| VOL | : | 268 PAGE : 25718-25721 (1993) |
[1190]
| AUTHOR | : | Fraser, P. D., Kiano, J. W., Truesdale, M. R., Schuch, W., and Bramley, P. M. |
| TITLE | : | Phytoene synthase-2 enzyme activity in tomato does not contribute to carotenoid synthesis in ripening fruit PubMed ID:10480392 |
| JOURNAL | : | Plant Mol Biol. |
| VOL | : | 40 PAGE : 687-698 (1999) |
[1205]
| AUTHOR | : | Nishino, H. |
| TITLE | : | Cancer prevention by natural carotenoids PubMed ID:9591197 |
| JOURNAL | : | J Cell Biochem Suppl. |
| VOL | : | 27 PAGE : 86-91 (1997) |
[1207]
| 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) |
[1252]
| AUTHOR | : | Ohki, S., Miller-Sulger, R., Wakabayashi, K., Pfleiderer, W., and Boger, P. |
| TITLE | : | Phytoene desaturase inhibition by O-(2-phenoxy)ethyl-N-aralkylcarbamates PubMed ID:12720390 |
| JOURNAL | : | J Agric Food Chem. |
| VOL | : | 51 PAGE : 3049-3055 (2003) |
[1265]
| AUTHOR | : | Granger, P., Maudinas, B., Herber, R., Villoutreix, J. |
| TITLE | : | 1H and 13C NMR of cis and trans phytoene isomers |
| JOURNAL | : | J. Magnet. Reso. |
| VOL | : | 10 PAGE : 43 -50 (1973) |
[1349]
| AUTHOR | : | Satomi, Y., Misawa, N., Maoka, T., Nishino, H. |
| TITLE | : | Production of phytoene, a carotenoid, and induction of conexin 26 in transgenic mice carrying the phytoene synthase gene crtB PubMed ID:15219841 |
| JOURNAL | : | Biochem. Biophys. Res. Commun. |
| VOL | : | 320 PAGE : 398 -401 (2004) |
[1353]
| AUTHOR | : | Takaichi, S., Yazawa, H., Yamamoto, Y. |
| TITLE | : | Carotenoids of the fruiting gliding myxobacterium, Myxococcus sp. MY-18, isolated from lake sediment: accumulation of phytoene and keto-myxocoxanthin glucoside ester |
| JOURNAL | : | Biosci. Biotech. Biochem. |
| VOL | : | 59 PAGE : 464 -468 (1995) |
Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.
