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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


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BIOLOGICAL ACTIVITY
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:160-162degC (racemate) (Ref. 0082)
178degC (optical active) (Ref. 0083)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:(6'S): [a]64318 = -400 (benzene) (Ref. 0083)
(6'S): [a]d-22 = -556 (benzene) (Ref. 0084)
(6'R): [a]64318 = +385 (benzene) (Ref. 0083)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
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)
CHROMATOGRAM DATA
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)
SOURCE
Nemalion helminthoides, Bonnemaisonia hamifera, Rhodymenia palmata, Ceramium rubrum (red algae) (Ref. 0058)
carrot, palm (higher plants) (Ref. 0236)
CHEMICAL SYNTHESIS
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)
METABOLISM

[Table 1027]
GENETIC INFORMATION
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).
NOTE
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).
REFERENCES
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[0058]
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[0067]
AUTHOR:Bushway,R.J.
TITLE:Determination of a- and b-Carotene in Some Raw Fruit and Vegetables by High-Performance Liquid Chromatography
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VOL:34 PAGE : 409 -412 (1986)
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[0079]
AUTHOR:Bjfrnland,T., Borch,G., and Liaaen-Jensen,S.
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VOL:23 PAGE : 1711 -1715 (1984)
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[0082]
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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
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[0083]
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[0084]
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VOL:56 PAGE : 2548 -2563 (1973)
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[0088]
AUTHOR:Di Mascio, P., Kaiser, S., and Sies, H.
TITLE:Lycopene as the most efficient biological carotenoid singlet oxygen quencher PubMed ID:2802626
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VOL:274 PAGE : 532-538 (1989)
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[0092]
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VOL:1126 PAGE : 178-184 (1992)
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[0093]
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JOURNAL:Lipids.
VOL:24 PAGE : 659-661 (1989)
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[0098]
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TITLE:Inhibitory effects of alpha-carotene on proliferation of the human neuroblastoma cell line GOTO PubMed ID:2795693
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VOL:81 PAGE : 1649-1652 (1989)
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[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
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VOL:18 PAGE : 227-233 (1995)
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VOL:694 PAGE : 71-81 (1997)
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[0228]
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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
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[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)
[TOP]

[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)
[TOP]

[1015]
AUTHOR:Cunningham, F. X., Jr., Pogson, B., Sun, Z., McDonald, K. A., DellaPenna, D., and Gantt, E.
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JOURNAL:Plant Cell.
VOL:8 PAGE : 1613-1626 (1996)
[TOP]

[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
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VOL:20 PAGE : 401-412X (1999)
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[1052]
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TITLE:Characterization of carotenoids in photosynthetic bacteria
JOURNAL:Methods Enzymol.
VOL:213 PAGE : 374 -385 (1992)
[TOP]

[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)
[TOP]

[1204]
AUTHOR:Nishino, H.
TITLE:Cancer chemoprevention by natural carotenoids and their related compounds PubMed ID:8538203
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VOL:22 PAGE : 231-235 (1995)
[TOP]

[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
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VOL:13 PAGE : 89-94 (2000)
[TOP]

[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
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VOL: PAGE : - ()
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[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)
[TOP]

[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)
[TOP]

[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)
[TOP]

[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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