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Carotenoid


DATA No : VCA0059 INFORMANT : Masayoshi Ito

NAME : (3S,5R,6R,3'S,5'R,6'S)-5',6'-Epoxy-6,7-didehydro-5,6,5',6'-tetrahydro-b,b-carotene-3,5,3'-triol

COMMON NAME: Neoxanthin
SYMBOL:
FORMULA: C40H56O4 MOL.WT (average) : 600.870


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Component of LHC II in higher plants (Ref. 0154).
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).
A light-harvesting pigment-protein complex (LHC) of Pseudoscourfieldia marina (Micromonadophyceae = Pracinophyceae) contains 5 prasinoxanthin, 2 neoxanthin, 1 unknown carotenoid, 9 Chl b, 6 Chl a, 2 MgDV (mol) (Ref. 1136).

Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217).
Singlet oxygen quenching activity (Ref. 0441) .
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:136-139degC (Ref. 0153)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax all-E form (nm) (e): ethanol 471 (137900), 442, (142810), 418 (96180), 329 (10560), 265 (33930) (Ref. 0153); benzene 482 (111520), 452 (117070), 426 (77590), 336 (8172), 274 (16450) (Ref. 0153)
lmax 9'-cis form: MeOH/water (9/1) 413, 435, 464 ; all-trans form: 417, 440, 470
[Spectrum 1111] (Ref. 0154)
lmax 9'-cis form: benzene 418, 442, 472 nm, %III/II=84; acetone 414, 438, 466 nm, %III/II=73 (Ref. 1182)

IR SPECTRA:

NMR SPECTRA:1H-NMR d(400 MHz, CDCl3) all-E form: 4.32 (m, 3-H), 3.92 (m, 3'-H), 2.27 (ddd, J 12.8, 4.1, 2.1, 4eq-H), 2.39 (ddd, J 14.2, 5.0, 1.8, 4'eq-H), 5.88 (d, J 15.5, 7'-H), 6.04 (s, 8-H), 6.30 (d, J 15.5, 8'-H), 6.12 (d, J 11.3, 10-H), 6.20 (d, J 11.6, 10'-H), 6.34 (d, J 15.6, 12-H), 6.38 (d, J 14.5, 12'-H), 6.25 (d, J 11.1, 14-H), 6.25 (d, J 11.1, 14'-H), 6.63 (m, 15-H), 6.63 (m, 15'-H), 1.07 (16-Me), 0.98 (16'-Me), 1.34 (17-Me), 1.16 (17'-Me), 1.35 (18-Me), 1.19 (18'-Me), 1.81 (19-Me), 1.93 (19'-Me), 1.97 (20-Me), 1.97 (20'-Me) and 9'-Z form (Ref. 0153)
1H-NMR d(400 MHz, CDCl3 and CD3OD) 9'-E form (Ref. 1182)
1H-NMR d (500 MHz, CDCl3) 9'-cis form: ca. 1.93 (2eq-H), 1.63 (dd, 2'eq-H), 1.36 (2ax-H), 1.235 (d, J 3.0, 2'-ax-H), 4.32 (m, 3-H), 1.29 (d, J 1.5, 3-OH), 3.92 (m, 3'-H), ca. 1.26 (3'-OH), 2.263 (ddd, J 12.9, 4.1, 2.1, 4eq-H), 2.408 (ddd, J 14.3, 5.0, 1.8, 4'eq-H), 1.406 (4ax-H), 1.66 (dd, 4'ax-H), 5.935 (d, J 15.5, 7'-H), 6.032 (s, 8-H), 6.836 (d, J 15.5, 8'-H), 6.116 (d, J 10.5, 10-H), 6.075 (d, J 11.5, 10'-H), 6.544 (dd, J 11.5, 15.0, 11-H), 6.759 (dd, J 11.8, 14.8, 11'-H), 6.339 (d, J 15.0, 12-H), 6.292 (d, J 15.0, 12'-H), 6.242 (d, J 9.5, 14-H), 6.242 (d, J 9.5, 14'-H), 6.62 (m, 15-H), 6.62 (m, 15'-H), 1.068 (16-Me), 1.008 (16'-Me), 1.334 (17-Me), 1.165 (17'-Me), 1.350 (18-Me), 1.255 (18'-Me), 1.800 (19-Me), 1.933 (19'-Me), 1.957 (20-Me), 1.963 (20'-Me) (Ref. 0154)

MASS SPECTRA:FD-MS m/z: 600 (Ref. 0154)

OTHER SPECTRA:CD in EPA all-E form: De 219 (0), 225 (-1.8), 243 (-0.7), 265 (-2.8), 293 (-0.6), 311 (-0.8), ca. 350 (+0.1) (Ref. 0153)
CD in EtOH: De 227 (-2.7), 241 (-1.28), 266 (-4.77), 303 (-0.57), 313 (-0.77), 335 (0), 341 (+2.4), ca. 359 (0), 377 (+3.9), 400 (+0.68), 419 (+0.79), 441 (+1.17), 463 (+0.71) ca. 479 (0) (Ref. 0153)
Excited-state dynamics of all-trans and 9'-cis neoxanthin were investigated using the fluorescence up-conversion method: their absorption spectra and the fluorescence lifetimes of the second singlet excited-state were the same (Ref. 1112).
CHROMATOGRAM DATA
HPLC, mBondapak C18 column (8*100 mm, RCM type, Waters), eluent methanol/water 9/1, 2.0 ml/min: all-trans form 7.9 min, 9'-cis form 8.5 min (Ref. 0154)
HPLC of Mesostigma viride (Prasinophyceae) (Ref. 1250)
SOURCE
Major carotenoids of oxygenic phototrophs: the 9'-cis form, but not the all-trans form, is found in chloroplasts of seed plants, ferns, mosses and green algae, all of which contain chlorophylls a and b. In contrast, neoxanthin is not found in other algal classes, such as Heterokontophyta, Rhodophyta and onygenic phototrophic prokaryotes. In non-photosynthetic organs, such as petals and fruits, the presence of neoxanthin is classified into four types; those having only the 9'-cis form, those with only the all-trans form, those with both forms, and those without either form (Ref. 0154).
Botryococcus braunii (Green algae) (Ref. 1081) Higher plants (Ref. 0409) green algae (Ref. 0409) Prasinophytes (algae) (Ref. 0513)
CHEMICAL SYNTHESIS
The optically active 3-hydroxy-5,6-epoxy-C15-aldehyde was reacted with the acetylenic C10-diphosphonate and the resulting C25-phosphonate was next condensed with the optically active C15-allenic aldehyde to give the 15,15'-didehydro-neoxanthin which, after partial hydrogenation and isomerization, gave all-E neoxanthin. (Ref. 0019)
METABOLISM
All-trans neoxanthin is the substrate of violaxanthin de-epoxidase, but 9'-cis neoxanthin is not (Ref. 1143/1144).
9-Cis epoxy-carotenoids (9'-cis neoxanthin and 9-cis violaxanthin) are cleaved to xanthoxin, which is a precursor of abscisic acid (plant hormone), by nine-cis epoxy-carotenoid dioxygenase (NCED) or neoxanthin cleavage enzyme (NCE) of maize and tomato (Ref. 1157/1158/1159). Similar enzyme, carotenoid cleavage dioxygenase (CCD), cleaves carotenoids symmetrically to produce a C14 dialdehyde and two C13 products (Ref. 1159).
[Table 1029]
GENETIC INFORMATION
A gene for neoxanthin synthase (NSY and NXS) is cloned and functionaly identified from Lycopersicum esculentum (tomato) and Solanum tuberosum (potato), respectively, and both have homology to lycopene b-cyclase (CrtL-b or LCY-b) and capsanthin capsorubin synthase (CCS) (Ref. 1125/1126). This enzyme synthesises neoxanthin from violaxanthin, but it seems not to have isomerise activity, all-trans form to 9-cis form (S. Takaichi).
NOTE
All-trans form is isolated from pumpkin fruit, and 9'-cis from leaves (Ref. 0154/1112).
Mesostigma viride (Prasinophyceae) has only all-trans form not 9'-cis form (Ref. 1250).
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]

[0153]
AUTHOR:Baumeler,A., and Eugster,C.H.
TITLE:Synthese von (6R,all-E)-Neoxanthin und verwandten Allen-Carotinoiden
JOURNAL:Helv. Chim. Acta
VOL:75 PAGE : 773 -790 (1992)
[TOP]

[0154]
AUTHOR:Takaichi,S., and Mimuro,M.
TITLE:Distribution and Geometric Isomerization of Neoxanthin in Oxygenic Phototrophs: 9'-Cis, a Sole Molecular Form
JOURNAL:Plant Cell Physiol.
VOL:39 PAGE : 968 -977 (1998)
[TOP]

[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
JOURNAL:Biol Pharm Bull.
VOL:18 PAGE : 227-233 (1995)
[TOP]

[0409]
AUTHOR:Goodwin T. W. (1980) The biochemistry of the carotenoids, Volume I, Plants, Chapman and Hall, London and New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0441]
AUTHOR:Hirayama, O., Nakamura, K., Hamada, S., and Kobayasi, Y.
TITLE:Singlet oxygen quenching ability of naturally occurring carotenoids PubMed ID:8152349
JOURNAL:Lipids.
VOL:29 PAGE : 149-150 (1994)
[TOP]

[0513]
AUTHOR:Egeland,E.S., Eikrem,W., Throndsen,J., Wilhelm,C., Zapata,M., Liaaen-Jensen,S.
TITLE:Algal carotenoids 61: Carotenoids from Prasinophyceae 6: Carotenpids from Further Prasinophytes (Erratum 24: 179-180 (1996))
JOURNAL:Biochem. Syst. Ecol.
VOL:23 PAGE : 747 -755 (1995)
[TOP]

[1081]
AUTHOR:Grung, M., Metzger, P., and Liaaen-Jensen, S.
TITLE:Primary and secondary carotenoids in two races of the green alga Botryococcus braunii
JOURNAL:Biochem. System. Ecol.
VOL:17 PAGE : 263 -269 (1989)
[TOP]

[1112]
AUTHOR:Mimuro, M., Akimoto, S., Takaichi, S., and Yamazaki, I.
TITLE:Relaxation processes from the excited states and physiological functions of carotenoids: comparison of two molecular forms of neoxanthin
JOURNAL:Photomed. Photobiol.
VOL:20 PAGE : 95 -97 (1998)
[TOP]

[1125]
AUTHOR:Bouvier, F., D'Harlingue, A., Backhaus, R. A., Kumagai, M. H., and Camara, B.
TITLE:Identification of neoxanthin synthase as a carotenoid cyclase paralog PubMed ID:11029576
JOURNAL:Eur J Biochem.
VOL:267 PAGE : 6346-6352 (2000)
[TOP]

[1126]
AUTHOR:Al-Babili, S., Hugueney, P., Schledz, M., Welsch, R., Frohnmeyer, H., Laule, O., and Beyer, P.
TITLE:Identification of a novel gene coding for neoxanthin synthase from Solanum tuberosum PubMed ID:11094161
JOURNAL:FEBS Lett.
VOL:485 PAGE : 168-172 (2000)
[TOP]

[1136]
AUTHOR:Fawley, M.W.
TITLE:Structure of a prasinoxanthin-chlorophyll a/b light-harvesting complex of the green flagellate Pseudoscourfieldia marina (Micromonadophyceae)
JOURNAL:Biochim. Biophys. Acta
VOL:1183 PAGE : 85 -90 (1993)
[TOP]

[1143]
AUTHOR:Grotz, B., Molnár, P, Stransky, H., and Hager, A.
TITLE:Substrate specificity and functional aspects of violaxanthin-de-epoxidase, an enzyme of the xanthophyll cycle
JOURNAL:J. Plant Physiol.
VOL:154 PAGE : 437 -446 (1999)
[TOP]

[1144]
AUTHOR:Yamamoto, H. Y., and Higashi, R. M.
TITLE:Violaxanthin de-epoxidase. Lipid composition and substrate specificity PubMed ID:102251
JOURNAL:Arch Biochem Biophys.
VOL:190 PAGE : 514-522 (1978)
[TOP]

[1157]
AUTHOR:Schwartz, S. H., Tan, B. C., Gage, D. A., Zeevaart, J. A., and McCarty, D. R.
TITLE:Specific oxidative cleavage of carotenoids by VP14 of maize PubMed ID:9188535
JOURNAL:Science.
VOL:276 PAGE : 1872-1874 (1997)
[TOP]

[1158]
AUTHOR:Burbidge, A., Grieve, T., Jackson, A., Thompson, A., and Taylor, I.
TITLE:Structure and expression of a cDNA encoding a putative neoxanthin cleavage enzyme (NCE), isolated from a wilt-related tomato (Lycopersicon esculentum Mill.) library
JOURNAL:J. Exp. Botany
VOL:47 PAGE : 2111 -2112 (1997)
[TOP]

[1159]
AUTHOR:Schwartz, S. H., Qin, X., and Zeevaart, J. A.
TITLE:Characterization of a novel carotenoid cleavage dioxygenase from plants PubMed ID:11316814
JOURNAL:J Biol Chem.
VOL:276 PAGE : 25208-25211 (2001)
[TOP]

[1182]
AUTHOR:Strand, A., Kvernberg, K., A, M. Karlsen, and Liaaen-Jensen, S.
TITLE:Geometrical E/Z isomers of (6R)- and (6S)-neoxanthin and biological implications PubMed ID:10725601
JOURNAL:Biochem Syst Ecol.
VOL:28 PAGE : 443-455 (2000)
[TOP]

[1250]
AUTHOR:Yoshii, Y., Takaichi, S., Maoka, T., Inouye, I.
TITLE:Photosynthetic pigment composition in the premitive green alga Mesostigma viride (Prasinophyceae): phylogenetic and evolutionary implications
JOURNAL:J. Phycol.
VOL:39 PAGE : 570 -576 (2003)
[TOP]

[1291]
AUTHOR:Liu, Z., Yan, H., Wang, K., Kuang, T., Zhang, J., Gui, L., An, X., and Chang, W.
TITLE:Crystal structure of spinach major light-harvesting complex at 2.72 A resolution PubMed ID:15029188
JOURNAL:Nature.
VOL:428 PAGE : 287-292 (2004)
[TOP]

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