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Entry
CA00407                                                            

Classification
Carotenoid Name
Antheraxanthin;
Antheraxanthin A
IUPAC name (3S,5R,6S,3'R)-5,6-Epoxy-5,6-dihydro-beta,beta-carotene-3,3'-diol
Formula
C40H56O3
Molecular Weight 
584.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photosynthetic pigment (Ref.415, Ref.428, Ref.503).
  • Photoprotective activity (Ref.428).
  • Xanthophyll cycle pigment.
  • Membrane stabilizer in chloroplasts - decreases the membrane fluidity, increases the membrane thermostability, and lowers susceptibility to lipid peroxidation (Ref.498).
  • Number of
    conjugated double bonds 
    10
    Number of
    conjugated multiple bonds 
    10
    Isomers 
    InChI
    InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39-,40+/m1/s1
    InChIKey
    OFNSUWBAQRCHAV-OYQUVCAXSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)C[C@H](CC1(C)C)O)\C
    XLogP
    9.764
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    1
    Complexity of molecule
    0.313
    Number of heavy atoms
    43
    TPSA
    (Topological Polar Surface Area) 
    52.990 Å2
    Source organisms
    Smithora naiadum (Ref.10) - Red alga: Compsopogonophyceae
    Antithamnion plumula (Ref.11) - Red alga: Ceramiales
    Ceramium rubrum (Ref.9) - Red alga: Ceramiales
    Gracilaria gracilis (Ref.10) - Red alga: Gigartinales
    Gracilaria textorii (Ref.10) - Red alga: Gigartinales
    Gracilariopsis lemaneiformis (Ref.10) - Red alga: Gigartinales
    Laurencia gardneri (Ref.10) - Red alga: Ceramiales
    Osmundea spectabilis (Ref.10) - Red alga: Ceramiales
    Polysiphonia hendryi (Ref.10) - Red alga: Ceramiales
    Polysiphonia pacifica (Ref.10) - Red alga: Ceramiales
    Bossiella californica (Ref.10) - Red alga: Corallinales
    Bossiella orbignyana (Ref.10) - Red alga: Corallinales
    Calliarthron tuberculosum (Ref.10) - Red alga: Corallinales
    Corallina officinalis (Ref.10) - Red alga: Corallinales
    Corallina vancouverensis (Ref.10) - Red alga: Corallinales
    Jania tenella (Ref.10) - Red alga: Corallinales
    Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales
    Ankistrodesmus spp. (Ref.16) - Green alga: Scenedesmaceae
    Pleurastrum paucicellulare (Ref.16) - Green alga: Ulvophyceae
    Oedogonium cardiacum (Ref.16) - Green alga: Chlorophyceae
    Chara foetida (Ref.16) - Green plants: Charophyceae
    Aegagrophila linnaei (Ref.24) - Green alga: Ulvophyceae
    Basicladia sp. (Ref.24) - Green alga: Ulvophyceae
    Chaetomorpha okamurae (Ref.24) - Green alga: Ulvophyceae
    Cladophora conchopheria (Ref.24) - Green alga: Ulvophyceae
    Cladophora horii (Ref.24) - Green alga: Ulvophyceae
    Cladophora kosterae (Ref.24) - Green alga: Ulvophyceae
    Pithophora sp. (Ref.24) - Green alga: Ulvophyceae
    Wittrockiella lyallii (Ref.24) - Green alga: Ulvophyceae
    Wittrockiella paradoxa (Ref.24) - Green alga: Ulvophyceae
    Microdictyon boergesenii (Ref.24) - Green alga: Ulvophyceae
    Cladophoropsis fasciculatus (Ref.24) - Green alga: Ulvophyceae
    Cladophoropsis membranacea (Ref.24) - Green alga: Ulvophyceae
    Cladophoropsis vaucheriaeformis (Ref.24) - Green alga: Ulvophyceae
    Siphonocladus tropicus (Ref.24) - Green alga: Ulvophyceae
    Chaetomorpha crassa (Ref.24) - Green alga: Ulvophyceae
    Cladophora ohkuboana (Ref.24) - Green alga: Ulvophyceae
    Cladophora albida (Ref.24) - Green alga: Ulvophyceae
    Cladophora coelothrix (Ref.24) - Green alga: Ulvophyceae
    Cladophora glomerata (Ref.24) - Green alga: Ulvophyceae
    Cladophora japonica (Ref.24) - Green alga: Ulvophyceae
    Cladophora ohkuboana (Ref.24) - Green alga: Ulvophyceae
    Cladophora pellucida (Ref.24) - Green alga: Ulvophyceae
    Cladophora sericea (Ref.24) - Green alga: Ulvophyceae
    Cladophora vagabunda (Ref.24) - Green alga: Ulvophyceae
    Rhizoclonium grande (Ref.24) - Green alga: Ulvophyceae
    Chara tomentosa (Ref.25) - Green plants: Charophyceae
    Chara vulgaris (Ref.25) - Green plants: Charophyceae
    Chara contraria (Ref.25) - Green plants: Charophyceae
    Chara gymnophylla (Ref.25) - Green plants: Charophyceae
    Chara hispida (Ref.25) - Green plants: Charophyceae
    Chara polyacantha (Ref.25) - Green plants: Charophyceae
    Chara rudis (Ref.25) - Green plants: Charophyceae
    Chara intermedia (Ref.25) - Green plants: Charophyceae
    Chara globularis (Ref.25) - Green plants: Charophyceae
    Chara aspera (Ref.25) - Green plants: Charophyceae
    Nitella opaca (Ref.25) - Green plants: Charophyceae
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Nannochloropsis gaditana (Ref.28) - Alga: Eustigmatophyceae
    Olisthodiscus luteus (Ref.30) - Alga: unclassified stramenopiles
    Euglena gracilis (Ref.37) - Alga: Euglenoid
    Euglena gracilis var. bacillarus (Ref.41) - Alga: Euglenoid
    Euglena rubida mainx (Ref.42) - Alga: Euglenoid
    Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte
    Prasinococcus capsulatus (Ref.46) - Green alga: Prasinophyte
    Nephroselmis olivace (Ref.46) - Green alga: Prasinophyte
    Pyramimonas amylifera (Ref.46) - Green alga: Prasinophyte
    Tetraselmis chui (Ref.48) - Green alga: Chlorodendraceae
    Tetraselmis marina (Ref.48) - Green alga: Chlorodendraceae
    Tetraselmis rubens (Ref.48) - Green alga: Chlorodendraceae
    Tetraselmis subcordiformis (Ref.48) - Green alga: Chlorodendraceae
    Tetraselmis suecica (Ref.48) - Green alga: Chlorodendraceae
    Tetraselmis tetrathele (Ref.48) - Green alga: Chlorodendraceae
    Pyramimonas parkeae (Ref.48) - Green alga: Prasinophyte
    Capsicum annuum var. lycopersiciforme flavum (Ref.283) - Land plant: yellow paprika
    Rhinogobius brunneus (Ref.290) - Bony fish: Amur goby
    Citrus reticulata (Ref.292) - Land plant: mandarin orange, tangerine
    Solorina crocea (Ref.374) - Fungi: lichen
    Protousnea sp. (Ref.388) - Fungi: lichen
    Malus domestica (Ref.492) - Land plant: Rosaceae: apple peel extract
    Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes
    References
  • Ref.10 : N. Schubert, E. Garcia-Mendoza, and I. Pachecho-Ruiz, J. Phycol. 42, 1208-1216 (2006) "Carotenoid composition of marine red algae".
  • Ref.11 : T. Bjornland, G. Borch, and S. Liaaen-Jensen, Phytochemistry, Vol. 23, No 8, pp.1711-1715, 1984. "Configurational studies on red algae carotenoids".
  • Ref.9 : T. Bjoernland and M. Aguilar-Martinez, Phytochemistry, 1976, Vol.15 pp.291-296, "Carotenoids in red algae".
  • Ref.16 : M. Orosa, E. Torres, P. Fidalgo, J. Abalde, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 553-556 "Production and analysis of secondary carotenoids in green algae".
  • Ref.17 : H. Kleinig and F. C. Czygan (1969), Z Naturforsch B. 1969 Jul;24(7):927-30. "Lipids of Protosiphon (Chlorophyta) Carotenoids and Carotenoid Esters of five Strains of Protosiphon botryoides Klebs" .
  • Ref.24 : Y. Yoshii, I,. Wakana, K. Miriya, S. Arai, K. Ueda, and I. Inouye, J. Phycol. 40, 1170-1177 (2004) "Carotenoid comositions of Cladophora Balls (Aegagropila linnaei) and some members of the Cladophorales (Ulvophyceae, Chlorophyta): their taxonomic and evolutionary implication".
  • Ref.25 : M. Schagerl, and Clemens Pichler, Aquatic Botany 67 (2000) 117–129 "Pigment composition of freshwater charophyceae".
  • Ref.27 : N. J. Antial, and J.Y. Cheng, British Phycological Journal, Volume 17, Issue 1, 1982 "The Keto carotenoids of two marine cocoid members of the eustimaphyceae" DOI:10.1080/00071618200650061 .
  • Ref.28 : Luis M. Lubián, Olimpio Montero, Ignacio Moreno-Garrido, I. Emma Huertas, Cristina Sobrino, Manuel González-del Valle, Griselda Parés, Journal of Applied Phycology, October 2000, Volume 12, Issue 3-5, pp 249-255 "Nannochloropsis (Eustigmatophyceae) as source of commercially valuable pigments".
  • 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.37 : N. I. Krinsky, and T. H. Goldsmith, Archives of Biochemistry and Biophysics 91, 271-279 (1960), "The Carotenoids of the Flagellated Alga, Euglena gracilis".
  • Ref.41 : N. I. Krinsky, A. Gordon, and A. I. Stern, Plant Physiol 39: 441-445 1964, "The appearance of Neoxanthin during the Regreenin g of Dark-grown Euglena".
  • Ref.42 : B.Czeczuga, Comp. Biochem. Physiol., 1974, Vol. 48B, pp. 349-354, "Carotenoids in Euglena rubida mainx".
  • Ref.46 : E. S. Egeland, R. R. L. Guillard, and S. Liaaen-Jensen, Phytochemistry, Vol. 44, No. 6, pp.1087-1097, 1997, "Additional carotenoid prototype representatices and general chemosystematic evaluation of carotenoids in prasinophyceae (chlorophyta)".
  • Ref.47 : E. S. Egeland, W. Eikrem, J. Throndsen, C. Wilhelm, M. Zapata, and S. Liaaen-Jensen, Biochemical systematics and Ecology, Vol. 23, NO. 7/8, pp. 747-755, 1995 "Carotenoids from Further Prasinophytes".
  • Ref.48 : Jose L. Carrido, Francisco Rodriguez, and Mannuel Zapata J. Phycol. 15, 366-374 (2009) "Occurrence of Loroxanthin, Loroxanthin decenoate, and Loroxanthin dodecenoate in Tetraselmis species (Prasinophyceae, Chlorophyta)".
  • Ref.283 : Zoltan Matus, Jozsef Deli, Jozsef Szabolcs, J. Agric. Food Chem., 1991, 39 (11), pp 1907–1914, "Carotenoid composition of yellow pepper during ripening: isolation of .beta.-cryptoxanthin 5,6-epoxide".
  • Ref.290 : Miyuki Tsushima ,Eisaku Mune , Takashi Maoka , and Takao Matsuno, J. Nat. Prod., 2000, 63 (7), pp 960–964, "Prev. Article Next Article Table of Contents Isolation of Stereoisomeric Epoxy Carotenoids and New Acetylenic Carotenoid from the Common Freshwater Goby Rhinogobius brunneus".
  • Ref.292 : Thomas Wingerath ,Wilhelm Stahl ,Dieter Kirsch, Raimund Kaufmann, and Helmut Sies, J. Agric. Food Chem., 1996, 44 (8), pp 2006–2013, DOI: 10.1021/jf960057y, "Fruit Juice Carotenol Fatty Acid Esters and Carotenoids As Identified by Matrix-Assisted Laser Desorption Ionization (MALDI) Mass Spectrometry".
  • 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.388 : B. Czeczuga, E. Czeczuga-Semeniuk, S. Calvelo, and S. Liberatore, Journal of Botanical Taxonomy and Geobotany, Volume 116, Issue 3-4, pages 195–200, August 2005, "Carotenoids in representatives of the Protousnea (Parmeliaceae), endemic genus from South America".
  • Ref.492 : Péter Molnár, József Deli, Toru Tanaka,Yoshiyuki Kann, Satoru Tani, Nóra Gyémánt, Joseph Molnár ,and Masami Kawase, Phytotherapy Research, Volume 24, Issue 5, pages 644–648, May 2010, “Carotenoids with anti-Helicobacter pylori activity from Golden deliciousapple”.
  • Ref.609 : Prof. Dr. B. Czeczuga and Doz. Dr. R. Doll, Journal of Botanical Taxonomy and Geobatany, Volume 102, Issue 5-6, pages 431–436, 1991, DOI: 10.1002/fedr.19911020518, "The carotenoid content of lichens of the Cladonia genus from Mecklenburg".
  • Ref.415 : Takuji Tanaka, Masahito Shnimizu, and Hisataka Moriwaki, Molecules 2012, 17, 3202-3242; doi:10.3390/molecules17033202, "Cancer Chemoprevention by Carotenoids".
  • Ref.428 : Peter Jahns, Dariusz Latowski, Kazimierz Strzalka, Biochimica et Biophysica Acta 1787 (2009) 3–14, "Mechanism and regulation of the violaxanthin cycle: The role of antenna proteins and membrane lipids".
  • Ref.503 : Javier de las Rivas, Anunciacion Abadia, and Javier Abadia, Plant Physiol. (1989) 91, 190-192, “A New Reversed Phase-HPLC Method Resolving All Major Higher Plant Photosynthetic Pigments1”.
  • Ref.498 : Michel Havaux, Trends in Plant science, Volume 3, Issue 4, 1 April 1998, Pages 147–151, "Carotenoids as membrane stabilizers in chloroplasts".
  • CAS
    640-03-9
    Links to other DB
    KEGG COMPOUND: C08579
    KNApSAcK: C00003760
    LipidBank: VCA1012
    MassBank: CA000003

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