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Carotenoid

DATA No : VCA0016 INFORMANT : Masayoshi Ito
NAME : (3R,3'R,6'R)-b,e-Carotene-3,3'-diol
COMMON NAME: Lutein/ Lutein A
SYMBOL:
FORMULA: C40H56O2 MOL.WT (average) : 568.871

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BIOLOGICAL ACTIVITY
Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217). Inhibitory effect on colonic aberrant crypt foci formation (anti-tumor promotion) (Ref. 0229). Singlet oxygen quenching activity (Ref. 0088/0230/0441). Scavenging effect against free radical (Ref. 0215).
Lycopene and lutein showed the anti-tumor promoting activities in mouse two-stage skin carcinogenesis and decreased the number of aberrant crypt foci in rat colon (Ref. 1205). Fucoxanthin, lycopene and lutein decreased the number of aberrant crypt foci in colons in mice (Ref. 1206). Lutein and b-cryptoxanthin suppressed tumorigenesis in skin and colon in mice (Ref. 1208).
A carotenoid binding protein is isolated from silk glands of Bombyx mori larvae. The Y (yellow hemolymph) gene (AF309498) encods this 33 kDa protein, and one lutein bonds (Ref. 1183).
Typical lutein and zeaxanthin levels in the human eye (Ref. 1301). (3R,3'R)-Zeaxanthin, meso-zeaxanthin and (3R,3'R,6'R)-lutein are located in human macular (Ref. 1168/1169). A membrane-associated xanthophyll-binding protein, which is a Pi isoform of human glutathione S-transferase (GSTP1), is purified from hman macula. It binds (3R,3'R)-zeaxanthin and (3R,3'S-meso)-zeaxanthin, but not lutein A (Ref. 1326).

Crystal structure of spinach major light-harvesting complex (LHCII) contains 2 lutein, 1 9'-cis neoxanthin, 1 (violaxanthin, antheraxanthin or zeaxanthin), 8 chlorophyll a, and 6 chlorophyll b per monomer (Ref. 1291).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:183-185degC (Ref. 0086) 174-178degC (Ref. 1078)
BOILING POINT:
REFRACTIVE INDEX:
OPTICAL ROTATION:
DENSITY:
SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) (e): dioxane 429 (1680), 453 (2515), 482 (2259) (Ref. 0086); methanol 330, 422 (shoulder), 443, 470, %III/II=61.7
[Spectrum 1108] (Ref. 1052)
IR SPECTRA:
NMR SPECTRA:1H-NMR d(270 MHz, CDCl3): 0.849, 0.998 (6H, s, 1'-gem-Me), 1.074 (6H, s, 1-gem-Me), 1.37 (1H, dd, J 13, 7, 2'ax-H), 1.48 (1H, t, J 12, 2ax-H), 1.626 (3H, s, 5'-Me), 1.739 (3H, s, 5-Me), 1.84 (1H, dd, J 13, 6, 2'eq-H), 1.912 (3H, s, 9'-Me), 1.970 (9H, s, 9-, 13-, 13'-Me), 2.04 (1H, dd, J 17, 10, 4ax-H), ca. 2.33-2.45 (2H, m, 6'-, 4eq-H), ca. 4.0 (1H, m, 3-H), 4.25 (1H, 3'-H), 5.43 (1H, dd, J 15.5, 10, 7'-H), 5.55 (1H, s, 4'-H), ca. 6.12 (2H, s, 7-, 8-H), ca. 6.15 (3H, m, 8'-, 10-, 10'-H), ca. 6.26 (2H, m, 14-, 14'-H), 6.36 (2H, d, J 15, 12-, 12'-H), ca. 6.55-6.71 (4H, m, 11-, 11'-, 15-, 15'-H) (Ref. 0086/0128/1080)
13C-NMR d(CDCl3): 37.1 (C1), 48.4 (C2), 65.1 (C3), 42.5 (C4), 126.2 (C5), 137.6 (C6), 125.6 (C7), 138.5 (C8), 135.6 (C9), 131.3 (C10), 124.9 (C11), 137.6 (C12), 136.5 (C13), 132.6 (C14), 130.0 (C15), 28.7, 30.2 (1-gem-Me), 21.6 (5-Me), 12.7 (9-Me), 12.7 (13-Me), 34.0 (C1'), 44.7 (C2'), 65.9 (C3'), 125.6 (C4'), 137.8 (C5'), 55.0 (C6'), 128.6 (C7'), 137.8 (C8'), 135.0 (C9'), 130.8 (C10'), 124.5 (C11'), 137.6 (C12'), 136.5 (C13'), 132.6 (C14'), 130.0 (C15'), 24.3, 29.5 (1'-gem-Me), 22.8 (5'-Me), 13.2 (9'-Me), 12.7 (13'-Me) (Ref. 0061).
MASS SPECTRA:(Ref. 0059)
OTHER SPECTRA:CD: 247.5 (+6.33), 288 (-2.39) (Ref. 0086)
CD data in EPA solution (25degC): De 220 (+2.0), 245 (+8.0), 275 (0), 284 (-4.5), 370 (-0.5) (Ref. 0117/0116)
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=0.30, 3:1:6 Rf=0.63 (Ref. 0135)
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: Spherisorb 5S, eluent: hexane-CH2Cl2-2-Propanol-NEt(iso-Pr)2 90.9:6.5:2.5:0.1) (Ref. 0128)
Separation of zeaxanthin and lutein by Novapak C18 HPLC column (8 times 100 mm, RCM-type, Waters) (Ref. 1150) and by Spherisorb ODS-1 HPLC column (4.6 times 250 mm) (Ref. 1151).
SOURCE
Algae (Chlorophyta) (Ref. 0409)
Fruits, flowers, leaves, seeds of higher plant (Ref. 0409)
Birds, birds' egg yolk, fish, fish eggs, shellfish, insect, reptiles (Ref. 0410)
Parnus major (bird) (Ref. 0429)
Lutein is the major carotenoid in the yellow facial skin of Egyptian vulture (bird), which includes ungulate faeces in its diet for cosmetic purposes (Ref. 1184).
CHEMICAL SYNTHESIS
Reaction of (S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-one with mesyl chloride followed by treatment with tetrabutylammonium acetate gave the acetoxyketone with complete inversion of configuration, which was readily transformed into the protected (R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-one. Diastereoselective epoxidation of this protected hydroxyketone with dimethyl sulphonium methylide followed by stereoselective opening of the epoxide with Grignard reagent gave the protected hydroxy-a-cyclocitral. This was converted into the C15-phosphonium chloride, which was condensed with C25-apocarotenal by use of KOH as base to give (3R,3'R,6'R)-lutein in 25% yield referred to apocarotenal. (Ref. 0014/0019/0086)
METABOLISM
Carassius auratus (gold fish): Lutein a_right 3'-epilutein a_right a-carotene-3,4,3'-triol a_right a-doradexanthin (Ref. 0415)
Hen's egg yolk: Lutein a_right e,e-carotene-3,3'-dione (Ref. 0427/0428)
Tilapia (Tilapia nilotica): Lutein a_right tunaxanthin (Ref. 0417)
Lutein a_right 3,4-didehydroretinol (Ref. 0417/0217)
[Table 1028]
GENETIC INFORMATION
From a-carotene, b-carotene hydroxylase (CrtR-b) and e-carotene hydroxylase (LUT1, CrtR-e) produce lutein A (Ref. 1280>.
NOTE

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