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Carotenoid


DATA No : VCA0003 INFORMANT : Masayoshi Ito

NAME : (3S,5R,6S,3'S,5'R,6'R)-5,6-Epoxy-3'-ethanoyloxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-b,b-caroten-8-one

COMMON NAME: Fucoxanthin
SYMBOL:
FORMULA: C42H58O6 MOL.WT (average) : 658.906


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Singlet oxygen quenching activity (Ref. 0230/0441). Anti-tumor acitivity (Ref. 0095/0096/0217/0235). Fucoxanthin inhibited tumor development in skin and duodenal carcinogenesis models of mouse (Ref. 1204). Fucoxanthin, lycopene and lutein decreased the number of aberrant crypt foci in colons in mice (Ref. 1206). Fucoxanthin showed anti-tumor promoting activity in mouse skin carcinogenesis (Ref. 1213).
Fucoxanthin induces apoptosis and enhances the antiproliferative effect of the PPAR&gamma& ligand, troglitazone, on colon cancer cells (Ref. 1360). Fucoxanthin from edible seaweed, Undaria pinnatifida, shows antiobesity effect through UCP1 expression in white adipose tisues (Ref. 1361).

Light-harvesting pigment (Ref. 0008/0009/0046/0220)
Fucoxanthin-chlorophyll a/c-protein assembly (FCPA) with energy transfer activity from fucoxanthin to chlorophyll a and from chlorophyll c to chlorophyll a is 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).
Fucoxanthin-chlorophyll proteins are purified from the centric diatom Cyclotella meneghiniana. They contain 18 and 19 kDa subunits, fucoxanthin, chlorophyll a and c, and have energy transfer activity (Ref. 1327).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:164degC (evacuated tube) (Ref. 0027/0029)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): ethanol 266, 449, 467 sh; hexane 264, 426, 448, 477
[Spectrum 0005] (Ref. 0006); hexane 428 sh, 446, 475, %III/II=40; acetone 420 sh, 444, 467, %III/II=5; HPLC eluent 330, 427 sh, 445, 471, %III/II=6 (Ref. 0029); methanol
[Spectrum 1103]

IR SPECTRA:nmax(KBr)/cm-1: 3440 (OH), 1929 (allene), 1734 (OAc), 1658 (conj. CO) and 1608 (C=C) (Ref. 0006)
nmax(KBr)/cm-1: 3483(OH), 3030-2856 (CH), 1930 (allene), 1732 (C=O acetate), 1654 (conj. CO), 1607, 1576, 1530, 1471, 1456 (CH2), 1385 and 1367 (gem-Me), 1335, 1261, 1245 (C-O acetate), 1201, 1175-1157, 1071, 1053, 1032, 958 (trans disubstituted C=C), 917 (Ref. 0029/0033)

NMR SPECTRA:1H-NMR d(500 MHz, CDCl3): 0.96 (3H, s, 1eq-Me), 1.04 (3H, s, 1ax-Me), 1.07 (3H, s, 1'eq-Me), 1.22 (3H, s, 5-Me), ca. 1.35 (2ax-H), 1.35 (3H, s, 5'-Me), 1.39 (3H, s, 1'ax-Me), 1.41 (1H, t, J 12, 2'ax-H), ca. 1.49 (2eq-H), 1.51 (1H, t, J 13, 4'ax-H), 1.79 (1H, dd, J 14, 9, 4ax-H), 1.82 (3H, s, 9'-Me), 1.95 (3H, s, 9-Me), 1.99 (6H, s, 13-, 13'-Me), ca. 2.00 (2'eq-H), 2.04 (3H, s, OAc), 2.29 (1H, ddd, J 13, 4, 2, 4'eq-H), 2.32 (1H, br dd, J 14, 4.5, 4eq-H), 2.60 and 3.66 (each 1H, d, J 18, 7-H2), 3.82 (1H, m, 3-H), 5.38 (1H, m, 3'-H), 6.06 (1H, s, 8'-H), 6.13 (1H, dd-like, J 11, 1, 10'-H), 6.27 (1H, br d, J 11.5, 14'-H), 6.35 (1H, d, J 15, 12'-H), 6.41 (1H, br d, J 11.5, 14-H), 6.57 (1H, dd, J 15, 11, 11-H), 6.60 (1H, dd, J 15, 11, 11'-H), 6.64 (1H, dd, J 14.5, 11.5, 15-H), 6.67 (1H, d, J 15, 12-H), 6.75 (1H, dd, J 14.5, 11.5, 15'-H) and 7.15 (1H, br d, J 11, 10-H)
[Spectrum 0006] (Ref. 0006/0028/0029)
13C-NMR d(100.6 MHz, CDCl3): 35.79, 35.17 (1, 1'), 47.11, 45.45 (2, 2'), 64.35, 68.01 (3, 3'), 41.69, 45.25 (4, 4'), 66.16, 72.71 (5, 5'), 67.09, 117.53 (6, 6'), 40.83, 202.37 (7, 7'), 197.87, 103.39 (8, 8'), 134.55, 132.51 (9, 9'), 139.11, 128.55 (10, 10'), 123.40, 125.70 (11, 11'), 145.04, 137.16 (12, 12'), 135.55, 138.09 (13, 13'), 136.55, 132.19 (14, 14'), 129.44, 132.51 (15, 15'), 25.06, 29.21 (16-ax, 16'-ax), 28.15, 32.10 (17-eq, 17'-eq), 21.18, 31.31 (18, 18'), 11.84, 14.03 (19, 19'), 12.78, 12.93 (20, 20') (Ref. 0028/0061)

MASS SPECTRA:(210degC, 70 eV) m/z (ion, intensity relative to base peak in %): 658 (M, 23), 640 (M-18, 37), 622 (M-18-18, 26), 580 (M-18-60, 21), 578 (M-80, 7), 562 (M-18-18-60, 13), 560 (M-18-80, 6), 488 (9), 484 (7), 482 (8), 237 (27), 221 (43), 212 (51), 197 (100)
[Spectra 0007 ] (Ref. 0029)

OTHER SPECTRA:CD data in EPA solution:
[Spectrum 0008] (Ref. 0006/0028/0029)
Fluorescence properties (Ref. 1162)
CHROMATOGRAM DATA
TLC (silica plates, 0.5 mm, Kieselgel 60 Merck, hexane-acetone 7:3) Rf = 0.26 (Ref. 0029)
HPLC (column: Spherisorb S 5-W, eluent: hexane-isopropyl acetate-isopropyl alcohol-N-ethyl-diisopropylamine 83.9:14:2:0.1, flow: 1.5 ml/min) tR = ca. 35 min
[Chromatogram 0006] (Ref. 0002/0030)
HPLC (column: CHIRALCEL OD; DAICEL IND., LTD., 1.0times25 cm, eluent: EtOH-hexane 15:85, temp.: 37degC, flow: 2.2 ml/min) tR = 20 min
[Chromatogram 0007] (Ref. 0005/0006)
SOURCE
Brown algae (Fucus serratus) (Ref. 0027/0033)
Macroalgae (Pheophyceae) (Ref. 0033)
Marine Phytoplankton (Bacilliarophyceae, Dinophyceae, Prymnesiophyceae, Prasinophyceae, Chlorophyceae, Cryptophyceae, Rhodophyceae, Cyanophyceae) (Ref. 0033/0034)
Sea squirts (Halocynthia roretzi) (Ref. 0035/0401/0402/0411)
Shell fish (Tapes philippinarum) (Ref. 0403) (Mytilus edulis) (Ref. 0426)
Shell fish (Ref. 0411)
All-E (3S,5R,6S,3'S,5'R,6'R)-fucoxanthin is the only naturally occurring stereoisomer in brown algae (Ref. 1163).
CHEMICAL SYNTHESIS
Double Wittig condensations of the C10-dialdehyde with the 8-oxo-C15-phosphonium salt and the allenic C15-phosphonium salt provided the C40-skeletal compound, which was treated with MCPBA to afford fucoxanthin. These phosphonium salts were derived from the common intermediate, the C15-a-acetytlenic alcohol, which was synthesized via the coupling reaction of protected (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone with the protected (E)-3-methylpent-2-en-4-yn-1-ol. Key step was effective conversion of the C15-a-acetytlenic alcohol into the C15-8-oxo-compound using oxo-metallic catalyst and subsequent iodine-catalysed double-bond shift. (Ref. 0005/0006)
METABOLISM
Sea squirt: Fucoxanthin a_right fucoxanthinol a_right halocynthiaxanthin a_right mytiloxanthin a_right mytiloxanthinone (Ref. 0401)
Fucoxanthin a_right fucoxanthinol a_right amarouciaxanthin A a_right amarouciaxanthin B (Ref. 0401)
Shell fish (Mytilus edulis): Fucoxanthin a_right fucoxanthinol a_right halocynthiaxanthin a_right mytiloxanthin (Ref. 0404)
In lying hens, fucoxanthin in Fucus serratus (brown algae) is metabolized to fucoxanthinol, and then fucoxanthinol 3'-sulphate and paracentrone (Ref. 1309).
GENETIC INFORMATION

NOTE
The keto group at C-8 of fucoxanthin is single-bond trans-conformation for the conjugated double bond determined by NMR (Ref. 0028).
REFERENCES
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VOL:68 PAGE : 159 -168 (1993)
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[0217]
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[1115]
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[1163]
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[1204]
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[1206]
AUTHOR:Kim, J. M., Araki, S., Kim, D. J., Park, C. B., Takasuka, N., Baba-Toriyama, H., Ota, T., Nir, Z., Khachik, F., Shimidzu, N., et al.
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[1213]
AUTHOR:Satomi, Y., Tokuda, H., Fujii, H., Shimidzu, N., Tanaka, Y., and Nishino, H.
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[1309]
AUTHOR:Strand, A., Herstad, O., Liaaen-Jensen, S.
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[1327]
AUTHOR:Buchel, C.
TITLE:Fucoxanthin-chlorophyll proteins in diatoms: 18 and 19 kDa subunits assemble into different oligomeric states PubMed ID:14596618
JOURNAL:Biochemistry.
VOL:42 PAGE : 13027-13034 (2003)
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[1360]
AUTHOR:Hosokawa, M., Kudo, M., Maeda, H., Kohno, H., Tanaka, T., Miyashita, K.
TITLE:Fucoxanthin induces apoptosis and enhances the antiproliferative effect of the PPAR&gamma& ligand, troglitazone, on colon cancer cells PubMed ID:15535974
JOURNAL:Biochim. Biophys. Acta
VOL:1675 PAGE : 113 -119 (2004)
[TOP]

[1361]
AUTHOR:Maeda, H., Hosokawa, M., Sashima, t., Funayama, K., Miyashita, K.
TITLE:Fucoxanthin from edible seaweed, Undaria pinnatifida, shows antiobesity effect through UCP1 expression in white adipose tisues PubMed ID:15896707
JOURNAL:Biochem. Biophys. Res. Commun.
VOL:332 PAGE : 392 -397 (2005)
[TOP]

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