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Entry
CA00324                                                            
Classification
Carotenoid Name
Diatoxanthin
IUPAC name (3R,3'R)-7,8-Didehydro-beta,beta-carotene-3,3'-diol
Formula
C40H54O2
Molecular Weight 
566.832 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photoprotective activity (Ref.429).
  • Xanthophyll cycle pigment.
  • Anticarcinogenic activity (Ref.494).
    • Number of
    conjugated double bonds 
    9
    Number of
    conjugated multiple bonds 
    11
    Isomers 
    InChI

    InChIKey

    Canonical SMILES

    XLogP
    10.530
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    2
    LipinskiFailures
    1
    Complexity of molecule
    0.312
    Number of heavy atoms
    42
    TPSA
    (Topological Polar Surface Area) 
    40.460 Å2
    Reaction
  • Substrate: CR00144,  CR00194,  CR00396
  • Product: CR00143,  CR00395
    • Pathway
  • Pathway: CB000037,  CB000063,  CB000151
    • Major carotenoid information
    Major carotenoid of the Rosary Goby Gymnogobius castaneus (Ref.772).
    Minor carotenoid information
    Minor carotenoid in euglenophytes, diatoms, bolidophytes, haptophytes, dictyochophytes, pelagophytes and some dinoflagellates (Ref.707).
    Source organisms
    Euglena gracilis (Ref.38, Ref.8) - Alga: Euglena (Euglenida - Euglenaceae)
    Euglena sanguinea (Ref.43) - Alga: Euglena (Euglenida - Euglenaceae)
    Euglena viridis (Ref.44) - Alga: Euglena (Euglenida - Euglenaceae)
    Eutreptiella gymnastica (Ref.45) - Alga: Euglena (Euglenida - Eutreptiales)
    Hymenomonas carterae (Ref.31) - Alga: Haptophyte ((Haptophyceae) - Hymenomonadaceae)
    Isochrysis galbana (Ref.31) - Alga: Haptophyte ((Haptophyceae) - Isochrysidaceae)
    Pavlova lutheri (Ref.31) - Alga: Haptophyte ((Haptophyceae) - Pavlovaceae)
    Phaeocystis sp. (Ref.31) - Alga: Haptophyte ((Haptophyceae) - Phaeocystaceae)
    Prymnesium parvum (Ref.31) - Alga: Haptophyte ((Haptophyceae) - Prymnesiaceae)
    Pelagococcus subviridis (Ref.29) - Alga: Pelagophyceae ((Stramenopiles) - Pelagomonadales)
    Sarcinochrysis marina Getler (Ref.30) - Alga: Pelagophyceae ((Stramenopiles) - Sarcinochrysidaceae)
    Nitzschia sp. (Ref.36) - Alga: Diatom (Bacillariophyta - Bacillariaceae)
    Navicula pelliculosa (Ref.36) - Alga: Diatom (Bacillariophyta - Naviculaceae)
    Phaeodactylum tricornutum (Ref.36) - Alga: Diatom (Bacillariophyta - Phaeodactylaceae)
    Skeletonema menzelii (Ref.36) - Alga: Diatom (Bacillariophyta - Skeletonemataceae)
    Skeletonema costatum (Ref.36) - Alga: Diatom (Bacillariophyta - Skeletonemataceae)
    Thalassiosira oceanica (Ref.36) - Alga: Diatom (Bacillariophyta - Thalassiosiraceae)
    Thalassiosira pseudonana (Ref.36) - Alga: Diatom (Bacillariophyta - Thalassiosiraceae)
    Thalassiosira eccentrica (Ref.36) - Alga: Diatom (Bacillariophyta - Thalassiosiraceae)
    Thalassiosira rotula (Ref.36) - Alga: Diatom (Bacillariophyta - Thalassiosiraceae)
    Grammatophora oceanica (Ref.36) - Alga: Diatom (Bacillariophyta - Grammatophoraceae)
    Gymnodinum nelsoni (Ref.33) - Alga: Dinoflagellate ((Alveolata) - Gymnodiniaceae)
    Amphidinium carterae (Ref.33) - Alga: Dinoflagellate ((Alveolata) - Gymnodiniaceae)
    Tovellia sanguinea (Ref.34) - Alga: Dinoflagellate ((Alveolata) - Tovelliaceae)
    Peridinium bipes (Ref.494) - Alga: Dinoflagellate ((Alveolata) - Peridiniaceae)
    Corbicula clams (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Corbicula japonica (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Corbicula sandai (Ref.221) - Shellfish: bivalve (Mollusca - Corbiculidae)
    Fusinus perplexus (Ref.442) - Shellfish: univalve shell (Mollusca - Fasciolariidae)
    Clione limacina (Ref.635) - gastropods (Mollusca - Clionidae)
    Paedoclione doliiformis (Ref.635) - gastropods (Mollusca - Clionidae)
    Limacina helicina (Ref.635) - gastropods (Mollusca - Limacinidae)
    Gymnogobius castaneus (Ref.772) - Bony fish: Rosary goby, small goby（4～6 cm body length）that inhabits the middle stretches of rivers, lakes, and lagoons in North Eastern Japan. Its tail fin is bright orange in color. (Chordata - Gobiidae)
    Carassius auratus (Ref.365) - Bony fish: gold fish (Chordata - Cyprinidae)
    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.33: J. E. Joansen, W. A. Svec, and S. Liaaen-Jensen, Phytochemistry, 1974, Vol.13 pp.2261-2271, "Carotenoids of the Dinophyceae".
  • Ref.494: Takashi MAOKA, Miyuki TSUSHIMA, and Hoyoku NISHINO, Chem. Pharm. Bull. 50(12) 1630—1633 (2002), "Isolation and Characterization of Dinochrome A and B, Anti-carcinogenic Active Carotenoids from the Fresh Water Red Tide Peridinium bipes".
  • Ref.34: R. Frassanito G. Flaim, I. Mancini, G. Guella, Biochemical Systematics and Ecology 34 (2006) pp.843-853, "High production of unexpected carotenoids in Dinophyceae. Astaxanthin esters from freshwater dinoflagellate Tovellia sanguinea".
  • 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.38: D. V. Heelis, W. Kernick, G. O. Philips, and K. Davies, Arch. Microbiol. 121, 207-211 (1979), "Separation and Identification of the Carotenoid Pigments of Stigmata Isolated from Light Grown Cells of Euglena gracilis Strain Z".
  • Ref.8: L. Schlueter, T. L. Lauridsen, G. Krogh, and Joergensen, Freshwater Biology, 2006, 51, 1474-1485 " Identification and quantification of phytoplankton groups in lakes using new pigment ratios – a comparison between pigment analysis by HPLC and microscopy".
  • Ref.43: Merte grung et.al, S. Liaaen-Jensen, Biochemical Systematics and Ecology, Vol. 21, No. 8, pp. 757-763, 1993 "Algal Carotenoids52*; Secondary carotenoids of Algae 3; Carotenoids in natural bloom of Euglena sanguinea".
  • Ref.44: A. Fiksdahl, S. Liaaen-Jensen, Phytochemistry, Vol.27, No.5, pp. 1447 - 1450, 1988 "Diacetylenic carotenoids from Euglena viridis".
  • Ref.45: A. Fiksdahl, T. Bjoernland, and S. Liaaen-Jensen, Phytochemistry, Vol. 23, No.3, pp. 649-655, 1984, "Algal carotenoids with novel end groups".
  • 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.365: Masahiro Ohkubo, Miyuki Tsushima, Takashi Maoka, Takao Matsuno, Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology, Volume 124, Issue 3, November 1999, Pages 333–340, "Carotenoids and their metabolism in the goldfish Carassius auratus (Hibuna)".
  • Ref.442: Kiyoshi Katagiri, Takashi Maoka, Takao Matsuno, COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY. B, COMPARATIVE BIOCHEMISTRY, 84(4):473-476 · JANUARY 1986, "Carotenoids of shell fishes-VIII. Comparative biochemical studies of carotenoids in three species of spindleshell, Fusinus perplexus, F.p. ferrugineus and F. forceps".
  • 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.772: Takashi Maoka, J. Oleo Sci. 67, (10) 1259-1263 (2018), “New Acetylenic Carotenoid 6’-Epimonadoxanthin from the Rosary Goby Gymnogobius castaneus”, doi: 10.5650/jos.ess18153.
  • Ref.429: Reimund Goss, Elizabeth Ann Pinto, Christian Wilhelm, Michael Richter, Journal of Plant Physiology, Volume 163, Issue 10, 5 October 2006, Pages 1008–1021, "The importance of a highly active and ΔpH-regulated diatoxanthin epoxidase for the regulation of the PS II antenna function in diadinoxanthin cycle containing algae".
  • Ref.707: Suzanne Roy et al., Phytoplankton Pigments Characterization, Chemotaxonomy and Applications in Oceanography, October 2011, Cambridge University Press, pp 665-674, "Part VII - Data sheets aiding identification of phytoplankton carotenoids and chlorophylls", available at http://www.cambridge.org/gb/files/2013/6697/5826/Data_sheets_part_3_Xanthophylls.pdf, ISBN: 9781107000667.
    • CAS
    31063-73-7
    Links to other DB
    KNApSAcK: C00022863
    LipidBank: VCA0052
    MassBank: CA000052

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