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Entry
CA00519                                                            

Classification
Carotenoid Name
Fucoxanthin
IUPAC 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-beta,beta-caroten-8-one
Formula
C42H58O6
Molecular Weight 
658.884 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photosynthetic pigment - Coulomb coupling as a mechanism for carotenoid to Chl A energy transfer (Ref.501).
  • Antiproliferative, and chemopreventive activity (Ref.493).
  • Anticarcinogenic activity - induces apoptosis in various cancer cell (Ref.414, Ref.493).
  • Anti-inflammatory activity (Ref.512, Ref.513).
  • Antioxidant activity as an electron donor (Ref.415).
  • Free-radical quencher (Ref.453).
  • Anti-obese property (Ref.417, Ref.453).
  • Antidiabetes agent (Ref.511).
  • Brown/Orange color (Ref.415).
  • Non-provitamin A (Ref.415).
  • Photoprotective activity - protective effect of UV-B induced cell damage (Ref.496).
  • Number of
    conjugated double bonds 
    9 including one ketone (9 in total)
    Number of
    conjugated multiple bonds 
    9 including one ketone (9 in total)
    Isomers 
  • Constitutional isomer: CA00518
  • InChI
    InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23-,34-,35-,40+,41+,42-/m0/s1
    InChIKey
    SJWWTRQNNRNTPU-XJUZQKKNSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(=O)C)\C
    XLogP
    9.874
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    6
    LipinskiFailures
    2
    Complexity of molecule
    0.292
    Number of heavy atoms
    48
    TPSA
    (Topological Polar Surface Area) 
    96.360 Å2
    Source organisms
    Pelagococcus subviridis (Ref.29) - Alga: Pelagophyceae
    Ochromonas sp. (Ref.30) - Golden alga: Chrysophyceae
    Poterioochromonas malhamensis (Ref.30) - Golden alga: Synurophyceae
    Olisthodiscus luteus (Ref.30) - Alga: unclassified stramenopiles
    Synura petersenii (Ref.30) - Golden alga: Synurophyceae
    Chromulina ochromonoides (Ref.30) - Golden alga: Chrysophyceae
    Sarcinochrysis marina Getler (Ref.30) - Alga: Pelagophyceae
    Hymenomonas carterae (Ref.31) - Alga: Haptophyte
    Isochrysis galbana (Ref.31) - Alga: Haptophyte
    Pavlova lutheri (Ref.31) - Alga: Haptophyte
    Pavlova sp. (NEP)  - Alga: Haptophyte
    Phaeocystis sp. (Ref.31) - Alga: Haptophyte
    Prymnesium parvum (Ref.31) - Alga: Haptophyte
    Chattonella japonica (Ref.35) - Alga: Raphidophyceae
    Fibrocapsa japonica (Ref.35) - Alga: Raphidophyceae
    Skeletonema costatum (Ref.36) - Alga: Diatom
    Skeletonema menzelii (Ref.36) - Alga: Diatom
    Thalassiosira eccentrica (Ref.36) - Alga: Diatom
    Thalassiosira oceanica (Ref.36) - Alga: Diatom
    Thalassiosira pseudonana (Ref.36) - Alga: Diatom
    Thalassiosira rotula (Ref.36) - Alga: Diatom
    Grammatophora oceanica (Ref.36) - Alga: Diatom
    Navicula pelliculosa (Ref.36) - Alga: Diatom
    Nitzschia sp. (Ref.36) - Alga: Diatom
    Phaeodactylum tricornutum (Ref.36) - Alga: Diatom
    Fucus serratus (Ref.53) - Brown alga: Fucaceae
    Fucus vesiculosus (Ref.53) - Brown alga: Fucaceae
    Pelvetia canaliculata (Ref.53) - Brown alga: Fucaceae
    Ascophyllum nodosum (Ref.53) - Brown alga: Fucaceae
    Laminaria saccharina (Ref.53) - Brown alga: Laminariaceae
    Gelliodes callista (Ref.253) - Sea sponge
    Corbicula japonica (Ref.221) - Shellfish: bivalve
    Corbicula sandai (Ref.221) - Shellfish: bivalve
    Corbicula clam (Ref.221) - Shellfish: bivalve
    Solorina crocea (Ref.374) - Fungi: lichen
    Echinoidea sp. (Ref.375) - Sea urchin
    Limacina helicina (Ref.635) - gastropods
    References
  • Ref.29 : T.Bjoernland, S. Liaaen-Jensen, and J. Throndsen, Phytochemistry, Vol. 28, No. 12, pp. 3347-3353, 1989; "Carotenoids of the marine chrysophyte Pelagococcus subviridis".
  • Ref.30 : N. W. Withers, A. Fiksdahl, R.C. Tuttle, and S. Liaaen-Jense, Comp. Biochem. Physiol. Vol. 68B, pp. 345 to 349, 1979, "Carotenoids of the Chrysophyceae".
  • Ref.31 : R. Berger, and S. Liaaen-Jensen, Biochemical Systematics and Ecology, 1977, Vol. 5, pp.71-75 "Carotenoids of Prymnesiophyceae (Haptophyceae)* ".
  • Ref.35 : A.Fiksdahl, N. Withers, R. R. L. Guillard, and S. Liaaen-Jensen, Comp. Biochem. Physiol. Vol. 78B, No. 1, pp. 265-271, 1984, "Carotenoids of the Raphidophyceae - a chemosystematic contribution ".
  • Ref.36 : F. Pennington, R. R. L. Guillard and S. Liaaen-Jensen, Biochemical Systematics and Ecology, Vol.16, No.7/8, pp. 589-592, 1988, "Carotenoid Distribution Patterns in Bacillariophyceae (Diatoms)".
  • Ref.53 : G. Nybraaten, and S. L. Jensen, Acta Chem. Scand. Ser. B, 28,(1974), 485, "Algal Carotenoids. XII. * Chemical Reactions of Carotenoids with 2-Hydroxylated beta-Rings".
  • Ref.253 : Tanaka, Yoshito; Inoue, Tsuyoshi, Nippon Suisan Gakkaishi (1987), 53(7), 1271-3., "new aldehydic carotenoid gelliodesxanthin from sea sponge Gelliodes callista".
  • Ref.221 : Maoka, Takashi; Fujiwara, Yasuhiro; Hashimoto, Keiji; Akimoto, Naoshige, Journal of Agricultural and Food Chemistry (2005), 53(21), 8357-8364. "Carotenoids in Three Species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam)".
  • Ref.374 : Czeczuga, Bazyli; Olech, Maria, Phyton (Horn, Austria) (1990), 30(2), 235-45., "Investigations on carotenoids in lichens.  XXV.  Studies of carotenoids in lichens from Spitsbergen".
  • Ref.375 : Galasko, Gail; Hora, J.; Toube, T. P.; Weedon, B. C. L.; Andre, D.; Barbier, M.; Lederer, E.; Villanueva, V. R., Journal of the Chemical Society [Section] C:  Organic (1969), (9), 1264-5., "Carotenoids and related compounds.  XXII.  Allenic carotenoids in sea urchins".
  • Ref.635 : Takashi Maoka, Takashi Kuwahara, and Masanao Narita, Mar. Drugs 2014, 12, 1460-1470, "Carotenoids of Sea Angels Clione limacina and Paedoclione doliiformis from the Perspective of the Food Chain", doi:10.3390/md12031460.
  • Ref.501 : A.P. Shreve, J.K. Trautman, T.G. Owens, A.C. Albrecht, Chemical Physics, Volume 154, Issue 1, 15 June 1991, Pages 171-178, "A femtosecond study of electronic state dynamics of fucoxanthin and implications for photosynthetic carotenoid-to-chlorophyll energy transfer mechanisms".
  • Ref.493 : Anne-Laure Gagez, Valérie Thiery, Virginie Pasquet, Jean-Paul Cadoret, and Laurent Picot, Current Bioactive Compounds 2012, 8, 000-000, "Epoxycarotenoids and Cancer. Review".
  • Ref.414 : Nishino H, Murakosh M, Ii T, Takemura M, Kuchide M, Kanazawa M, Mou XY, Wada S, Masuda M, Ohsaka Y, Yogosawa S, Satomi Y, Jinno K., Cancer Metastasis Rev. 2002;21(3-4):257-64., "Carotenoids in cancer chemoprevention.".
  • Ref.512 : K.-N. Kim, S.-J. Heo, W.-J. Yoon et al., “Fucoxanthin inhibits the inflammatory response by suppressing the activation of NF-𝜅B and MAPKs in lipopolysaccharide-induced RAW 264.7 macrophages,” European Journal of Pharmacology, vol. 649, no.1–3, pp. 369–375, 2010.
  • Ref.513 : S. Sakai, T. Sugawara, K. Matsubara, and T. Hirata, “Inhibitory effect of carotenoids on the degranulation of mast cells via suppression of antigen-induced aggregation of high affinity IgE receptors,” The Journal of Biological Chemistry, vol. 284, no. 41, pp. 28172–28179, 2009..
  • Ref.415 : Takuji Tanaka, Masahito Shnimizu, and Hisataka Moriwaki, Molecules 2012, 17, 3202-3242; doi:10.3390/molecules17033202, "Cancer Chemoprevention by Carotenoids".
  • Ref.453 : Graziano Riccioni, Nicolantonio D’Orazio, Sara Franceschelli, and Lorenza Speranza, Marine Drugs 2011, 9(7), 1166-1175; doi:10.3390/md9071166, "Marine Carotenoids and Cardiovascular Risk Markers".
  • Ref.417 : Woo MN, Jeon SM, Shin YC, Lee MK, Kang MA, Choi MS., Mol Nutr Food Res. 2009 Dec;53(12):1603-11. doi: 10.1002/mnfr.200900079., "Anti-obese property of fucoxanthin is partly mediated by altering lipid-regulating enzymes and uncoupling proteins of visceral adipose tissue in mice.".
  • Ref.511 : H. Maeda, M. Hosokawa, T. Sashima, K. Murakami-Funayama,and K. Miyashita, “Anti-obesity and anti-diabetic effects of fucoxanthin on diet-induced obesity conditions in a murine model,” Molecular Medicine Reports, vol. 2, no. 6, pp. 897–902,2009..
  • Ref.496 : Soo-Jin Heoa, You-Jin Jeon, Journal of Photochemistry and Photobiology B: Biology, Volume 95, Issue 2, 4 May 2009, Pages 101–107, "Protective effect of fucoxanthin isolated from Sargassum siliquastrum on UV-B induced cell damage".
  • CAS
    3351-86-8
    Links to other DB
    KNApSAcK: C00003773
    LipidBank: VCA0003
    MassBank: CA000057

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