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Carotenoid


DATA No : VCA0007 INFORMANT : Masayoshi Ito

NAME : (3R,3'R)-b,b-Carotene-3,3'-diol

COMMON NAME: Zeaxanthin/ (3R,3'R)-Zeaxanthin
SYMBOL:
FORMULA: C40H56O2 MOL.WT (average) : 568.871


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BIOLOGICAL ACTIVITY
Antioxidant activity (Ref. 0092/0093/0215/0225/0226) Singlet oxygen quenching activity (Ref. 0215/0230) Reinforcement of phospholipid bilayer (Ref. 0237) Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217)
Zeaxanthin inhibited the development of mouse spontaneous liver cancer (Ref. 1207). Zeaxanthin showed anticarcinogenic activity in liver in mice (Ref. 1208).
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).

A water-soluble surface-associated complex from Prochlorothrix hallandica composed of two polypeptides of 56 and 58 kDa, zeaxanthin and lipopolysaccaride (Ref. 1161).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:207-208degC (Ref. 0014/0049)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) (e): hexane 452 (133692), 480 (116624) (Ref. 0014/0049); EPA (e) 273 (22000), 340 (7300), 450 (139300) (Ref. 0048); methanol 275, 341, 429 (shoulder), 448, 473, %III/II=22
[Spectrum 1105] (Ref. 1064)

IR SPECTRA:nmax(KBr)/cm-1:
[Spectrum 0013] (Ref. 0065)

NMR SPECTRA:1H-NMR d(CDCl3): 1.48 (2, 2'ax-H), 1.77 (2,2'eq-H), ca. 4.00 (3, 3'-H), 2.04 (4, 4'ax-H), 2.39 (4,4'eq-H), 6.11 (7, 7'-H), 6.13 (8, 8'-H), 6.16 (10, 10'-H), 6.64 (11, 11'-H), 6.36 (12, 12'-H), ca. 6.26 (14, 14'-H), ca. 6.63 (15, 15'-H), 1.074 (1, 1'-gem-Me), 1.736 (5, 5'-Me), 1.967, 1.972 (9, 9', 13, 13'-Me), ca. 1.35 (OH) (Ref. 0048) More precise data (Ref. 1080)
13C-NMR d(CDCl3): 37.1 (1, 1'), 48.2 (2, 2'), 65.1 (3, 3'), 42.4 (4, 4'), 126.1 (5, 5'), 137.6 (6, 6'), 125.5 (7, 7'), 138.5 (8, 8'), 135.7 (9, 9'), 131.3 (10, 10'), 124.9 (11, 11'), 137.6 (12, 12'), 136.5 (13, 13'), 132.6 (14, 14'), 130.0 (15, 15'), 28.7, 30.2 (1, 1'-gem-Me), 21.7 (5, 5'-Me), 12.8 (9, 9'-Me), 12.8 (13, 13'-Me) (Ref. 0061).

MASS SPECTRA:m/z: 568 (M, 100%), 550 (M-18, 84%), 532 (M-18-18, 5%), 489 (M-79, 1%), 476 (M-92, 13%), 462 (M-106, 1%), 458 (M-18-92, 11%), 444 (M-18-106, 1%), 410 (M-158, 5%) (Ref. 0058/0059)
FD-MS m/z: 568 (Ref. 1064)

OTHER SPECTRA:CD data in EPA solution (25degC): De 225 (-7.7), 254 (+8.1), 290 (-14.6), 348 (+3.7)
[Spectrum 0014] (Ref. 0048/0064/0078)
CD data in EPA solution (25degC): De 224 (-18.0), 236 (0), 245 (+18.0), 260 (0), 284 (-24.0), 325 (0), 350 (+4.0), 380 (+0.5) (Ref. 0405)
CHROMATOGRAM DATA
HPLC (column: Spherisorb S5W 0.31times50 cm, eluent: hexane-CH2Cl2-isopropyl alcohol-Hünig's base, 90.9:6.5:2.5:0.1)
[Chromatogram 0008] (Ref. 0048)
HPLC (columun: Sumipax OA-2000 (5mm) 0.8times30 cm, eluent: hexane-CH2Cl2-EtOH 90:10:0.1, flow: 1.5 ml/min) tR = ca. 40 min (meso), ca. 45 min (3R,3'R), ca. 50 min (3S,3'S)
[Chromatogram 0009] (Ref. 0069/0405)
A reversed-phase HPLC procedure for quantitative measurement in serum of seven carotenoids (lutein, zeaxanthin, canthaxanthin, b-cryptoxanthin, lycopene, a-carotene and b-carotene) has been developed (Ref. 0227).
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
Sea squirts (Halocynthia roretzi) (Ref. 0035) , Shell fishes (Ref. 0405/0410/0411) , Fishes (Ref. 0405/0410/0411)
Anacystis nidulans (Cyanobacterium) (Ref. 1077), Cyanophora paradoxa (Glaucocystophyte) (Takaichi Shinichi), Red algae (Bangia fucopurupurea, Gigartina stellata, Ceramium rubrum, Polysiphonia brodiaei, Polysiphonia urceolata) (Ref. 0058), Higher plants (Ref. 0409)
Paracoccus zeaxanthinifaciens R1534 (bacterium; previous name Flavobacterium sp.) (Ref. 1236)
Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1055)
CHEMICAL SYNTHESIS
The protected (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone was reacted with lithium acetylide and deprotected to give the acetylenic diol, which was acetylated and dehydrated to provide the 3-acetoxy-C11-terminal alkyne. This was converted into the C15-phosphonium salt via the intermediate vinyl carbinol in an overall yield of 72% from the starting hydroxyketone. Wittg condensation of the phosphonium salt with the C10-dialdehyde provided (3R,3'R)-zeaxanthin. (Ref. 0019/0053) (R)- and (S)-3-Hydroxy-b-cycloitrals prepared by hydroboration of safranol isopropenylether with (+)- and (-)-diisopinocampenylborane were transformed into (3R,3'R)-, (3S,3'S)- and (3R,3'S: meso)-zeaxanthin, via the Wittig condensation of the corresponding C15-phosphonium salt with the C10-dialdehyde. (Ref. 0019/0076)The protected (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone was reacted with dimethyl sulphonium methylide to give the allylic epoxide, which was transformed into (R)-3-hydroxy-b-cyclocitral. This was converted into the C15-phosphonium salt, then condensed with the C10-dialdehyde to give (3R,3'R)-zeaxanthin. (Ref. 0014/0057) The protected (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone was transformed with the protected (E)-3-methylpent-2-en-4-yn-1-ol into a C15-intermediate, which was converted into the C15-phosphonium salt. (Ref. 0049) The (R)-3-hydroxy-C15-sulphone was coupled with the C10-dialdehyde using BuLi as a base. The resulting dihydroxy compound was acetylated in situ and treated with aqueous NaOH to afford all-E-11,11'-bis-sulphonyl-zeaxanthin. Subsequent elimination of the sulphonyl group gave (3R,3'R)-zeaxanthin. (Ref. 0026)
METABOLISM
The gene product catalyzes the conversion of b-carotene to zeaxanthin by way of b-cryptoxanthin under the presence of O2, Fe2+, and 2-oxoglutarate (Ref. 0205).
Capsicum annuum (pepper) fruits contain two kinds of b-carotene hydroxylase. Both enzymes require iron, ferredoxin and NADPH for activity, use iron activated oxygen to break the C-H bond, and introduce a hydroxyl group (Ref. 1134).
Cofactors of zeaxanthin-epoxidase from spinach are FAD, NAD(P)H and O2 (Ref. 1153).
Zeaxanthin in Sphingobacterium multivorum is synthesized via non-mevalonate pathway (Ref. 1138).
Zeaxanthin is accumulated in the cytoplasmic membranes of Synechococcus sp. strain PCC 7942 (cyanobacteria) grown under high light condition (Ref. 1146).
[Table 1026]

Zeaxanthin is cleavated to crocetindial and hydroxy-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).
Carassius auratus (gold fish): Zeaxanthin -> b-carotene-3,4,3'-triol -> b-doradexanthin -> astaxanthin (Ref. 0415) Parasilurus asotus (Japanese common catfish): Zeaxanthin -> parasiloxanthin -> 7,8-dihydroparasiloxanthin (Ref. 0416) Tilapia nilotica (Tilapia): Zeaxanthin -> rhodoxanthin (Ref. 0417) Zeaxanthin -> 3,4-didehydroretinol (Ref. 0417/0216) Zeaxanthin -> e, e-carotene-3,3'-dione -> 3-hydroxy-e, e-caroten-3'-one (Ref. 0417) hen's egg yolk: zeaxanthin -> e,ee-carotene-3,3'-dione (Ref. 0428)
GENETIC INFORMATION
Genes required for the biosynthesis of zeaxanthin 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). Zeaxanthin is synthesized from FPP by five crt gene products, CrtE, CrtB, CrtI, CrtY, and CrtZ (Ref. 1002).
[Table 0003] Nowadays, the b-carotene hydroxylase gene is isolated from various organisms such as gram-negative bacteria (crtZ), cyanobacteria (crtR), and higher plants (crtR-b), and some higher plants contain two kinds of b-carotene hydroxylase genes (Ref. 0202/0204/1013/1014/1133/1134/1279).
Review of characteristics of zeaxanthin epoxidase and violaxanthin de-epoxidase (Ref. 1268)
CrtZ from Thermus thermophilus (Gram-negtive bacteria) is P450-type monooxygenase, while other CrtZ and CrtR are non-heme type (Ref. 1283).
NOTE
Highly deuterated zeaxanthin has recently been synthesized from fully deuterated mevalonolactone by using triply engineered Escherichia coli, which carries the five Erwinia crt genes from FPP to zeaxanthin and the genes involved in mevalonate pathway from mevalonate to isopentenyl diphosphate (IPP), by a Japanese group (Ref. 1084). This compound should be useful for various biological experiments for examining its metabolism.
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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