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Carotenoid

DATA No : VCA0001 INFORMANT : Masayoshi Ito
NAME : b,b-Carotene
COMMON NAME: b-Carotene/ b,b-Carotene
SYMBOL: BC
FORMULA: C40H56 MOL.WT (average) : 536.873

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BIOLOGICAL ACTIVITY
Spinach D1-D2-cyt b559 complex contains 2 b-carotene, 6 chlorophyll a and 2 pheophytin a (Ref. 1137). Crystal structure of photosystem II from Thermosynechococcus vulcanus (cyanobacterium) contains 2 b-carotene and 36 chlorophyll a (Ref. 1289), and that from Thermosynechococcus elongatus contains 7 b-carotene and 36 chlorophyll a (Ref. 1290) and 9 b-carotene, 36 chlorophyll a and 2 pheophytin a (Ref. 1336). Crystal structure of photosystem I from Thermosynechococcus elongatus (cyanobacterium) contains 22 b-carotene and 96 chlorophyll a (Ref. 1288).
Purified cytochrome b6f complex from spinach contains 0.77 mol b-carotene and 0.97 mol chlorophyll a, Mastigocladau laminosus (cyanobacterium) 1.02 and 1.65, and Chlamydomonas reinhardtii (green alga) 0.55 and 1.37, respectively. (Ref. 1099)
Crystal structure of dimeric cytochrome b6f complex from M.laminosus (Ref. 1294) and C.reinhardtii (Ref. 1292) contain 2 mol b-carotene and 2 mol chlorophyll a.
Fucoxanthin-chlorophyll a/c-protein assembly (FCPA) with energy transfer activity from fucoxanthin to chlorophyll a and from chlorophyll c to chlorophyll a isolated from Dictyota dichotoma (brown alga); 10 fucoxanthin, 1 violaxanthin, no b-carotene, 3 chlorophyll c, 13 chlorophyll a and a 54 kDa protein to form a 4.8 S complex (Ref. 1115).

Pro-vitamin A(Ref. 0102/0216). Singlet oxygen-quenching activity (Ref. 0088/0230/0438/0441). Antioxidant activity (Ref. 0090/0091/0092/0093/0103/0214/0226/0437). Anti-tumor activity (Ref. 0099/0100/0101/0217/0229). Effects raising the incidence of lung cancer in smokers (Ref. 1006).
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). Palm carotene and b-carotene inhibited pancreatic carcinogenesis in hamsters, but a-carotene showed no effects (Ref. 1212).
A cellular carotenoid-binding protein of 67 kDa from ferret (mammalian) liver is purified and characterized with a high degree of specificity for binding only carotenoids with at least one unsubstituted b-end group (Ref. 1160).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:180-182degC (Ref. 0023)
177-180degC (Ref. 0024)
BOILING POINT:
REFRACTIVE INDEX:
OPTICAL ROTATION:
DENSITY:
SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): hexane 425, 450, 478
[Spectrum 0001] (Ref. 0060/0063); methanol 341, 429 (shoulder), 449, 475, %III/II=24.6
[Spectrum 1101] (Ref. 1052); acetonitrile/methanol/THF (58:35:7) 278, 353, 429 (shoulder), 453, 479, %III/II=26
[Spectrum 1001] (Ref. 1057); hexane, chloroform and CS2
[Spectrum 1052]
IR SPECTRA:nmax(KBr)/cm-1: 1629 and 1599w (C=C) and 965s (CH)
[Spectrum 0002] (Ref. 0065)
NMR SPECTRA:1H-NMR d(270 MHz, CDCl3): 6.16 (7, 7'-H), 6.15 (8, 8'-H), 6.15 (10, 10'-H), 6.65 (11, 11'-H), 6.35 (12, 12'-H), ca. 6.25 (14, 14'-H), ca. 6.63 (15, 15'-H), 1.028 (1, 1'-gem-Me), 1.719 (5, 5'-Me), 1.972 (9, 9', 13, 13'-Me) (Ref. 0062/0066)
13C-NMR d(CDCl3): 34.3 (1, 1'), 39.7 (2, 2'), 19.3 (3, 3'), 33.2 (4, 4'), 129.3 (5, 5'), 138.0 (6, 6'), 126.7 (7, 7'), 137.8 (8, 8'), 136.0 (9, 9'), 130.8 (10, 10'), 125.0 (11, 11'), 137.3 (12, 12'), 136.4 (13, 13'), 132.4 (14, 14'), 130.0 (15, 15'), 29.0 (1, 1'-gem-Me), 21.7 (5, 5'-Me), 12.7 (9, 9'-Me), 12.7 (13, 13'-Me) (Ref. 0061).
MASS SPECTRA:m/z: 536 (M, 100%), 444 (M-92, 10%), 430 (M-106, 0.6%) (Ref. 0058/0060)
(70 eV) m/z (ion, intensity relative to base peak in %): 536 (M, 45), 444 (16), 430 (4), 219 (13),197 (12), 157 (26), 145 (34), 133 (32), 119 (72), 105 (62), 95 (51), 91 (45), 81 (48), 69 (100), 55 (60), 41 (48) (Ref. 0066)
FD-MS m/z: 536 (100%) (Ref. 1053)
OTHER SPECTRA:
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=0.09, 3:1:6 Rf=0.20 (Ref. 0135)
HPLC (column: calcium hydroxide (Nakarai) 0.4times30 cm, eluent: acetone-hexane 99.9:0.1, flow: 0.5 ml/min) tR = ca. 28 min (all-E isomer)
[Chromatogram 0001] (Ref. 0062)
HPLC (column: Spherisorb A5Y (alumina) 0.28times25 cm, eluent: hexane with controlled water content) tR = ca. 32 min (all-E isomer)
[Chromatogram 0002] (Ref. 0066)
HPLC (column: Vydac 218TP54, acetonitrile-methanol-tetrahydrofuran 40:56:4, flow: 1 ml/min) tR = ca. 11 min (all-E isomer)
[Chromatogram 0003] (Ref. 0067)
HPLC (columun: TSK gel ODS-80Ts (Tosoh) 0.46times15 cm, eluent and flow: 1.0 ml/min, H2O-MeOH 5:95 for 5 min, follwed by 5 min-linear gradient MeOH-THF 7:3, and then MeOH-THF 7:3 for 5 min) b-carotene, echinenone, b-cryptoxanthin, 3-hydroxy-echinenone, cantaxanthin, 3'-hydroxy-echinenone, cis-adonixanthin, adonirubin, adonixanthin and astaxanthin were separated. tR = 14.98 min for b-carotene (Ref. 0208)
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=19.5 min (Ref. 1057)
SOURCE
Bacteria, algae, higher plants (Ref. 0409) Animals (Ref. 0410)
Bangia fucopurupurea, Nemalion helminthoides, Bonnemaisonia hamifera, Gigartina stellata, Rhodymenia palmata, Ceramium rubrum, Polysiphonia brodiaei, Polysiphonia urceolata (Red algae) (Ref. 0058)
Anacystis nidulans (Cyanobacterium) (Ref. 1077)
Chloroflexus aurantiacus (Ref. 1105) and Chloroflexus aggregans (S. Takaichi) (Ref. 1106) (green filamentous bacteria)
CHEMICAL SYNTHESIS
The Wittig olefination of the C10-dialdehyde with 2 equivalents of the C15-phosphonium salt and of the retinlylphosphonium salt with retinal is described. b-Carotene is obtained in 80-85% yield after thermal isomerisation. (Ref. 0020)
Retinyl phosphonate was condensed with retinal to afford b-carotene in good yield. (Ref. 0021)
The di-Grignard reagent of acetylene was reacted with 2 equivalents of the C19-aldehyde to give the C40-acetylenic diol, from which b-carotene was obtained by dehydration, Lindlar hydrogenation, and isomerisation. (Ref. 0015/0020/0022)
The reductive coupling of retinal on treatment with low-valent titanium species, formed in situ TiCl3 and LiAlH4, provided b-carotene in high yield. (Ref. 0015/0023)
The reductive coupling of retinal to give b-carotene is also possible with TiCl4 and LiAlH4 in the presence of 1,8-bis(dimethylamino)naphthalene as a proton sponge. (Ref. 0015/0024)
2 Equivalents of the C15-sulphone was coupled with the C10-dialdehyde using BuLi as a base, acetylated in situ, and treated with aqueous NaOH to provide all-E-11,11'-bis[(p-chlorophenyl)-sulphonyl]-b,b-carotene in high yield. Subsequent elimination of the sulphonyl group then gave all-E-b-carotene. (Ref. 0014/0017/0026)
2 Equivalents of the C13-sulphone was reacted with the C14-acetylenic dichloride to give 15,15'-didehydro-b-carotene, which was transformed by a twofold isomerisation and partial reduction to b-carotene. (Ref. 0014/0017/0026)
Crystalline all-trans-b-carotene was obtained in 65% yield by simply refluxing a mixture of 2.6 equivalents of b-ionylideneethanol (C15-alcohol), phenyl isocyanate and tributylphosphine, 1 equivalent of the C10-dialdehyde, and 10 mol% of Pd(PPh3)4 in CH3CN for 5 h. (Ref. 0015/0025)
METABOLISM
b-Carotene is synthesized from lycopene through two-step cyclization reactions by way of g-carotene by carotenogenic organisms such as higher plants (CrtL-b), algae, cyanobacteria (CrtL), and bacteria Erwinia species (CrtY) (Ref. 1002/1003/1004/1005).
[Table 1025]
b-Carotene is metabolized to retinal by b,b-carotene-15,15'-dioxygenase in animals. The gene encoding this enzyme has been cloned and functionally identified from chicken (Ref. 1044), Drosophila melanogaster (fly) (Ref. 1122), mouse (Ref. 1123/1233) and human (Ref. 1231).
b,b-Carotene-9',10'-dioxygenase is functionally identified from mouse, and its homolog is found from human and zebrafish (Ref. 1185).
b-Carotene is cleaved to crocetindial and b-cyclocitral by b-carotene 7,8(7',8') oxygenase of Microcystis (cyanobacterium) by freezing the cell pellet. The enzyme requires O2 and iron, but is sensitive to sulfhydryl reagents, antioxidants and chelation reagents, and is membrane bound (Ref. 1266).
GENETIC INFORMATION
Genes required for the biosynthesis of b-carotene 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). b-Carotene is synthesized from FPP by four crt gene products, CrtE, CrtB, CrtI, and CrtY (Ref. 1002).
[Table 0001] 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. 0202/0233/1002/1003/1004/1005). Lycopene is the direct substrate for the synthesis of b-carotene by the way of g-carotene, catalyzed by lycopene cyclase (CrtY, LCY) (Ref. 0232/0234/1018).
Lycopene cyclases are divided into three types (Ref. 1258).
(1) CrtY and CrtL type: Higher plants (Lcy-b, CrtL-b), cyanobacteria (CrtL), purple bacteria, and bacteria including Erwinia and Paracoccus species (CrtY) (Ref. 1002/1003/1004/1005). They and also lycopene e-cyclase (CrtL-e, plants), lycopene b-monocyclase (CrtLm and CrtYm, bacteria) and capsanthin-caprorubin synthase (CCS, plants) have homology and five conserved regions (Ref. 1258). Erwinia CrtY has NADPH binding domain, but hydrogen atom introduced at C-2 comes from water not from NADPH (Ref. 1313).

(2) CrtYc and CrtYd type: They are divided into three groups, and they among threegroups have homology (Ref. 1310/1311). A heterodimer of two peptides (CrtYc and CrtYd) is found in Brevibacterium linens (Ref. 1124) and Mycobacterium aurum A+ (Ref. 1127) (Actinomycetales). A fusion-type of CrtYc and CrtYd is found in Halobacterim salinarum (CrtY) (Ref. 1310) and Sulfolobus solfataricus (Ref. 1311) (archaeon). A bifunctional enzyme involved lycopene cyclase activity (CrtY) located in N-terminus domain and phytoene synthase activity (CrtB) located in C-terminus domain is found Xanthophyllomyces dendrorhous (crtYB) (Ref. 1172), Mucor circinelloides (carRP) (Ref. 1173), Phycomyces blakesleeanus (carRA) (Ref. 1174), Neurospora crassa (al-2) (Ref. 1176), and Blakeslea trispora (CarRA) (Ref. 1312) (fungus). CrtY region is also a fusion of CrtYc and CrtYd.
(3) CruA type: Recently, a new type CruA is found in Chlorobium tepidum (green sulfur bacteria). From sequence homology, this is also found in some cyanobacteria.
NOTE
Biotechnological achievement has recently been made for purposes of supplying b-carotene (provitamin A) to vitamin A-deficient children, by a Swiss and German group, i. e., transgenic rice plants 'Golden rice', which accumulate b-carotene in the endosperm, have been constructed by using the plant- and Erwinia-derived carotenogenic genes (Ref. 1017). Transgenic tomato plants, in which the b-carotene content has increased about threefold to 45% of the total carotenoid content, have also been constructed using the Erwinia crtI gene by an English, German, and Japanese group (Ref. 1066).
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).
Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337)
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