Carotenoid
DATA No : VCA0009
INFORMANT : Masayoshi Ito
NAME : (6'R)-
b,
e-Carotene
| COMMON NAME | : | a-Carotene/ b,e-Carotene |
| SYMBOL | : | |
| FORMULA | : | C40H56 MOL.WT (average) : 536.873 |
Singlet oxygen quenching activity (
Ref. 0088)
Anti-tumor activity (
Ref. 0098/
0217/
0229)
Antioxidant activity (
Ref. 0092/
0093)
Preventive action against carcinogenesis (
Ref. 0236)
a-Carotene was more potent than
b-carotene in suppressing tumorigenesis in skin and lung of mouse (
Ref. 1204). The antitumorigenic activity of
a-carotene was stronger than that of
b-carotene, while both
a- and
b-carotene inhibited the tumorigenesis in skin, lung, liver and colon in mice (
Ref. 1208).
a-Carotene reduced the expression of N-myc gene and induced G0/G1 arrest in GOTO cells, and showed more potent inhibitory activity than
b-carotene in skin carcinogenesis (
Ref. 1209). The moderate dose of
a- and
b-carotenes and lycopene enhanced gap-junctional intercellular communication (
Ref. 1210). Palm carotene and
b-carotene inhibited pancreatic carcinogenesis in hamsters, but
a-carotene showed no effects (
Ref. 1212).
| PHYSICAL AND CHEMICAL PROPERTIES |
| MELTING POINT | : | 160-162 C (racemate) (Ref. 0082)
178C (optical active) (Ref. 0083) |
|
| BOILING POINT | : | |
|
| REFRACTIVE INDEX | : | |
|
| OPTICAL ROTATION | : | (6'S): [a]64318 = -400 (benzene) (Ref. 0083)
(6'S): [a] = -556 (benzene) (Ref. 0084)
(6'R): [a]64318 = +385 (benzene) (Ref. 0083) |
|
| DENSITY | : | |
|
| SOLUBILITY | : | |
| UV SPECTRA | : | lmax (nm): petro 420, 444, 473 (Ref. 0058/0079); methanol 335, 422 (shoulder), 442, 471, %III/II=61.2
[Spectrum 1106] (Ref. 1052); acetonitrile/methanol/THF (58:35:7) 272, 334, 426 (shoulder), 448, 476, %III/II=58
[Spectrum 1002] (Ref. 1057) |
|
| IR SPECTRA | : | KBr disc or pellet:
[Spectrum 0015] (Ref. 0065) |
|
| NMR SPECTRA | : | 1H-NMR d(400 MHz, CDCl3): 0.82 and 0.90 (each 3H, s, 1'-gem-Me), 1.03 (6H, s, 1-gem-Me), 1.58 (3H, br s, 5'-Me), 1.72 (3H, s, 5-Me), 1.91 (3H, s, 9'-Me), 1.96 and 1.97 (9H, s, 9-, 13-, 13'-Me), 2.18 (1H, d, J 9, 6'-H), 5.41 (1H, m, 4'-H), 5.52 (1H, dd, J 15.5, 9, 7'-H), 6.14 (2H, s, 7-, 8-H), 6.08-6.68 (ca. 11H, m, conj. olefinic). (Ref. 0079)
|
|
| MASS SPECTRA | : | m/z: 536 (M, 53%), 480 (M-56, 2%), 444 (M-92, 12%), 430 (M-106, 2%) (Ref. 0058/0079)
|
|
| OTHER SPECTRA | : | CD in EPA solution: De 238 (4.2), 266 (4.0), 298 (0.4), 330 (1.1), 362 (0.1) and 400 (2.0) (Ref. 0079)
|
TLC (silica gel-G-Ca(OH)2-MgO-CaSO4 (10:4:3:1), petrol-acetone 97:3) Rf = 0.84 (
Ref. 0079)
HPLC (column: Vydac 218TP54, acetonitrile-methanol-tetrahydrofuran 40:56:4, flow: 1 ml/min) tR = ca. 10 min
[
Chromatogram 0003] (
Ref. 0067)
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=17.7 min (
Ref. 1057)
Nemalion helminthoides, Bonnemaisonia hamifera, Rhodymenia palmata, Ceramium rubrum (red algae) (
Ref. 0058)
carrot, palm (higher plants) (
Ref. 0236)
Wittig reaction of dehydro-
b-apo-12'-carotenal (C25) with
a-ionylideneethyl-triphenylphosphonium chroride (C15) using NaOMe as base provided 15,15'-dehydro-
a-carotene, which was transformed by partial reduction and isomerization to racemic
a-carotene. (
Ref. 0082)
The enantiomerically pure
a-ionone obtained via resolution of racemic (2,6,6-trimethylcyclohex-2-enyl)prop-2-enoic acid was reacted with vinyl magnesium chloride to give the C15-alcohol. This was converted into the phosphonium salt and then condensed with
b-apo-12'-carotenel (C25) using NaOMe as base to give naturally occuring (6'R)-
a-carotene in 45% referred to (6'R)-
a-ionone. (6'S)-
a-carotene has been synthesized in an analogous way. (
Ref. 0019)
By use of enantiomeric (S)- and (R)-
a-ionones obtained by resolution of the racemate via the methylhydrazones, (6'S)- and (6'R)-
a-ionones was synthesized for the first time. (
Ref. 0019/
0083)
In Arabidopsis, lycopene is at first cyclized to
d-carotene by lycopene
e-cyclase, and then to
a-carotene by lycopene
b-cyclase (
Ref. 1015). CrtL-e from the marine cyanobacterium Prochlorococcus marinus MED4 has bifunctional activety (lycopene
e- and
b-cyclases), and poduces
a-carotene (
Ref. 1242).
Biotechnological achievement has recently been made in relations with the supply of
a-carotene, by Calgene LLC, i. e., a transgenic canola (Brassica napus), which accumulates a great amount of
a-carotene as well as
b-carotene in seeds, has been constructed by over-expressing the Erwinia phytoene synthase gene crtB (
Ref. 1016).
Gel filtration of carrot root chromoplasts yields one major carotenoprotein, in which one unit contains one
a-carotene and two
b-carotene in 54-kDa peptide (
Ref. 1272).
[0019]
| AUTHOR | : | Pfander,H. and Bartels,B. (1996) Carotenoids Volume 2: Synthesis Chapter 3: Carotenoid Synthesis Part III: Synthesis of Cyclic Carotenoids (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp161-200, Birkhäuser Verlag,Basel,Boston,Berlin |
| TITLE | : | |
| JOURNAL | : | |
| VOL | : | PAGE : - () |
[0058]
| AUTHOR | : | Bjfrnland,T. and Aguilar-Martinez,M. |
| TITLE | : | Carotenoids in red algae |
| JOURNAL | : | Phytochemistry |
| VOL | : | 15 PAGE : 291 -296 (1976) |
[0065]
| 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 |
| TITLE | : | |
| JOURNAL | : | |
| VOL | : | PAGE : - () |
[0067]
| AUTHOR | : | Bushway,R.J. |
| TITLE | : | Determination of a- and b-Carotene in Some Raw Fruit and Vegetables by High-Performance Liquid Chromatography |
| JOURNAL | : | J. Agric. Food. Chem. |
| VOL | : | 34 PAGE : 409 -412 (1986) |
[0079]
| AUTHOR | : | Bjfrnland,T., Borch,G., and Liaaen-Jensen,S. |
| TITLE | : | Algal carotenoids: 29. Configurational studies on red algae carotenoids |
| JOURNAL | : | Phytochemistry |
| VOL | : | 23 PAGE : 1711 -1715 (1984) |
[0082]
| AUTHOR | : | Rüegg,R.,Schwieter,U.,Ryser,G.,Schudel,P., und Isler,O. |
| TITLE | : | Synthesen in der Carotinoid-Reihe g-Carotin sowie d,l-a- und b-Carotin aus Dehydro-b-apo-12'-carotenal (C25) |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 44 PAGE : 985 -993 (1961) |
[0083]
| AUTHOR | : | Tscharner,C.,Eugster,C.H., and Karrer,P. |
| TITLE | : | Synthese der optisch activen a-Carotin .Carotinoidsynthesen XX |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 40 PAGE : 1676 -1677 (1957) |
[0084]
| AUTHOR | : | Buchecker,R.,Egli,R.,Regel-Wild,H.,Tscharner,C.,Eugster,C.H.,Uhde,G., and Ohloff,G. |
| TITLE | : | Absolute Konfiguration der enantiomeren a-Cyclogeranium-säuren |
| JOURNAL | : | Helv. Chim. Acta |
| VOL | : | 56 PAGE : 2548 -2563 (1973) |
[0088]
| 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) |
[0092]
| AUTHOR | : | Lim, B. P., Nagao, A., Terao, J., Tanaka, K., Suzuki, T., and Takama, K. |
| TITLE | : | Antioxidant activity of xanthophylls on peroxyl radical-mediated phospholipid peroxidation PubMed ID:1627620 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 1126 PAGE : 178-184 (1992) |
[0093]
| AUTHOR | : | Terao, J. |
| TITLE | : | Antioxidant activity of beta-carotene-related carotenoids in solution PubMed ID:2779372 |
| JOURNAL | : | Lipids. |
| VOL | : | 24 PAGE : 659-661 (1989) |
[0098]
| AUTHOR | : | Murakoshi, M., Takayasu, J., Kimura, O., Kohmura, E., Nishino, H., Iwashima, A., Okuzumi, J., Sakai, T., Sugimoto, T., Imanishi, J., et al. |
| TITLE | : | Inhibitory effects of alpha-carotene on proliferation of the human neuroblastoma cell line GOTO PubMed ID:2795693 |
| JOURNAL | : | J Natl Cancer Inst. |
| VOL | : | 81 PAGE : 1649-1652 (1989) |
[0217]
| 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) |
[0227]
| 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) |
[0228]
| AUTHOR | : | Bui, M. H. |
| 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) |
[0229]
| 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) |
[0236]
| AUTHOR | : | Murakoshi, M., Nishino, H., Satomi, Y., Takayasu, J., Hasegawa, T., Tokuda, H., Iwashima, A., Okuzumi, J., Okabe, H., Kitano, H., et al. |
| TITLE | : | Potent preventive action of alpha-carotene against carcinogenesis: spontaneous liver carcinogenesis and promoting stage of lung and skin carcinogenesis in mice are suppressed more effectively by alpha-carotene than by beta-carotene PubMed ID:1423303 |
| JOURNAL | : | Cancer Res. |
| VOL | : | 52 PAGE : 6583-6587 (1992) |
[1015]
| AUTHOR | : | Cunningham, F. X., Jr., Pogson, B., Sun, Z., McDonald, K. A., DellaPenna, D., and Gantt, E. |
| TITLE | : | Functional analysis of the beta and epsilon lycopene cyclase enzymes of Arabidopsis reveals a mechanism for control of cyclic carotenoid formation PubMed ID:8837512 |
| JOURNAL | : | Plant Cell. |
| VOL | : | 8 PAGE : 1613-1626 (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) |
[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) |
[1204]
| AUTHOR | : | Nishino, H. |
| TITLE | : | Cancer chemoprevention by natural carotenoids and their related compounds PubMed ID:8538203 |
| JOURNAL | : | J Cell Biochem Suppl. |
| VOL | : | 22 PAGE : 231-235 (1995) |
[1208]
| AUTHOR | : | Nishino, H., Tokuda, H., Murakoshi, M., Satomi, Y., Masuda, M., Onozuka, M., Yamaguchi, S., Takayasu, J., Tsuruta, J., Okuda, M., et al. |
| TITLE | : | Cancer prevention by natural carotenoids PubMed ID:11237205 |
| JOURNAL | : | Biofactors. |
| VOL | : | 13 PAGE : 89-94 (2000) |
[1209]
| AUTHOR | : | Nishino, H., Murakoshi, M., Kitano, H., Iwasaki, R., Tanaka, Y., Tsushima, M., Matsuno, T., Okabe, H., Okuzumi, J., hasegawa, T., Takayasu, J., Satomi, Y., Tokuda, H., Nishino, A., and Iwashima, A. (1992) Anti-tumor and anti-tumor promoting activity of a- and b-carotene. in Lipid-Soluble Antioxidants: Biochemistry and Clinical Applications (Ong, A.S.H. and Packer, L. eds.) pp.228-242, Birkhäuser, Basel, Switzerland |
| TITLE | : | |
| JOURNAL | : | |
| VOL | : | PAGE : - () |
[1210]
| 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) |
[1212]
| AUTHOR | : | Majima, T., Tsutsumi, M., Nishino, H., Tsunoda, T., and Konishi, Y. |
| TITLE | : | Inhibitory effects of beta-carotene, palm carotene, and green tea polyphenols on pancreatic carcinogenesis initiated by N-nitorsobis(2-oxopropyl)amine in Syrian golden hamsters PubMed ID:9436857 |
| JOURNAL | : | Pancreas. |
| VOL | : | 16 PAGE : 13-18 (1998) |
[1242]
| AUTHOR | : | Stickforth, P., Steiger, S., Hess, W. R., and Sandmann, G. |
| TITLE | : | A novel type of lycopene epsilon-cyclase in the marine cyanobacterium Prochlorococcus marinus MED4 PubMed ID:12712234 |
| JOURNAL | : | Arch Microbiol. |
| VOL | : | 179 PAGE : 409-415 (2003) |
[1272]
| AUTHOR | : | Bryant, J.D., McCord, J.D., Unlu, L. K., Erdman, Jr., J.W. |
| TITLE | : | Isolation and partial characterization of a- and b-carotene-containing carotenoprotein from carrot (Daucus carota L.) root chromoplasts |
| JOURNAL | : | J. Agric. Food Chem. |
| VOL | : | 40 PAGE : 545 -549 (1992) |
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