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Carotenoid


DATA No : VCA0011 INFORMANT : Masayoshi Ito

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

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


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BIOLOGICAL ACTIVITY
(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).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:212-213 degC (Ref. 0076)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) (e): hexane 273 (360), 403 (902), 430sh (1710), 449 (2410), 477 (2130) (Ref. 0076)

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

NMR SPECTRA:1H-NMR d(CDCl3, 270 MHz): 1.073 (12H, s, 1,1'-gem-Me), 1.415 (2H, d, J 4, OH), 1.47 (2H, t, J 12, 2,2'ax-H), 1.738 (6H, s, 5,5'-Me), 1.765 (2H, dt, J 12, 2.5, 2,2'eq-H), 1.972 (12H, s, 9',9',13,13'-Me), 2.035 (2H, dd, J 17, 9.5, 4,4'ax-H), 2.385 (2H, dd, J 17, 5.5, 4,4'eq-H), 3.98 (2H, m, 3,3'-H), 6.117 (4H, s, 7,7',8,8'-H), 6.155 (2H, d, J 11, 10, 10,10'-H), 6.255 (2H, d, J 9, 14,14'-H), 6.360 (2H, d, J 15, 12,12'-H), 6.55-6.74 (4H, m, 11,11',15,15'-H) (Ref. 0076)

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)

OTHER SPECTRA:CD data in EPA solution (25degC): no optical activity (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] --- (3R,3'R)-zeaxanthin (Ref. 0048)
HPLC columun: Sumipax OA-2000 (5mm) 0.8times30 cmeluent: hexane-CH2Cl2-EtOH 90:10:0.1, flow: 1.5 ml/min tR = ca. 40 min (meso)-zeaxamthin, ca. 45 min (3R,3'R), ca. 50 min (3S3'S)
[Chromatogram 0009] (Ref. 0069/0405)
SOURCE
Shrimp (Paratya compressa compressa) (Ref. 0405)
Fish (Oncorhynchus keta, Seriola quinqueraduata, Micropterus salmoides, Tilapia nilotica, Stephanolepis cirrhifer, Salmo gairdneri) (Ref. 0405)
Fish (Salmo salar, Salmo gairdneri) (Ref. 0406/0407)
Human macular (Ref. 1168/1169).
CHEMICAL SYNTHESIS
(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)
METABOLISM

GENETIC INFORMATION

NOTE
Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) were performed in order to predict their stable structures (Ref. 1337).
REFERENCES
[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 : - ()
[TOP]

[0048]
AUTHOR:Englert,G., Noack,K., Broger,E.A., Glinz,E., Vecchi,M., and Zell,R.
TITLE:Synthesis, Isolation, and Full Spectroscopic Characterization of Eleven (Z)-Isomers of (3R,3'R)-Zeaxanthin
JOURNAL:Helv. Chim. Acta
VOL:74 PAGE : 969 -982 (1991)
[TOP]

[0058]
AUTHOR:Bjfrnland,T. and Aguilar-Martinez,M.
TITLE:Carotenoids in red algae
JOURNAL:Phytochemistry
VOL:15 PAGE : 291 -296 (1976)
[TOP]

[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 : - ()
[TOP]

[0069]
AUTHOR:Pfander,H., and Riesen,R. (1995) Carotenoids Volume 1A: Isolation and Analysis Chapter 6: Chromatography: Part IV High-Performance Liquid Chromatography (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp145-190, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0076]
AUTHOR:Rüttimann,A., and Mayer,H.
TITLE:Synthese von optisch aktiven, natürlichen Carotenoiden und strukturell verwandten Naturprodukten V. Synthese von (3R,3'R)-, (3S,3'S)- und (3R,3'S;meso)-Zeaxanthin durch asymmetrische Hydroborierung. Ein neuer Sugang zu optisch aktiven Carotinoidbausteinen
JOURNAL:Helv. Chim. Acta
VOL:63 PAGE : 1456 -1462 (1980)
[TOP]

[0405]
AUTHOR:Maoka,T.,Arai,A.,Shimizu,M., and Matsuno,T.
TITLE:The first isolation of enantiomeric and meso-zeaxanthin in nature
JOURNAL:Comp. Biochem. Physiol.
VOL:83 PAGE : 121 -124 (1986)
[TOP]

[0406]
AUTHOR:Schiedt,K.,Leuenberger,F.J.,Vecchi,M., and Glinz,E.
TITLE:Absorption, retention and metabolic transformations of carotenoids in rainbow trout, salmon and chicken
JOURNAL:Pure Appl. Chem.
VOL:57 PAGE : 685 -692 (1985)
[TOP]

[0407]
AUTHOR:Schiedt,K.,Vecchi,M.,Glinz,E., and Storebakken,T.
TITLE:Metabolism of carotenoids in salmonids Metabolism of astaxanthin and canthaxanthin in the skin of atlantic salmon (Salmo salar, L.)
JOURNAL:Helv. Chim. Acta
VOL:71 PAGE : 887 -896 (1988)
[TOP]

[1168]
AUTHOR:Bone, R. A., Landrum, J. T., Hime, G. W., Cains, A., and Zamor, J.
TITLE:Stereochemistry of the human macular carotenoids PubMed ID:8491553
JOURNAL:Invest Ophthalmol Vis Sci.
VOL:34 PAGE : 2033-2040 (1993)
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[1169]
AUTHOR:Landrum, J. T., and Bone, R. A.
TITLE:Lutein, zeaxanthin, and the macular pigment PubMed ID:11361022
JOURNAL:Arch Biochem Biophys.
VOL:385 PAGE : 28-40 (2001)
[TOP]

[1326]
AUTHOR:Bhosale, P., Larson, A. J., Frederick, J. M., Southwick, K., Thulin, C. D., and Bernstein, P. S.
TITLE:Identification and characterization of a Pi isoform of glutathione S-transferase (GSTP1) as a zeaxanthin-binding protein in the macula of the human eye PubMed ID:15355982
JOURNAL:J Biol Chem.
VOL:279 PAGE : 49447-49454 (2004)
[TOP]

[1337]
AUTHOR:Hashimoto, H., Yoda, T., Kobayashi, T., Young, A.J.
TITLE:Molecular structures of carotenoids as predicted by MNDO-AM1 molecular orbital calculations
JOURNAL:J. Mol. Struct.
VOL:604 PAGE : 125 -146 (2002)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.