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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      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photosynthetic pigment in higher plants (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

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Substrate: CR00159,  CR00161,  CR00167,  CR00379,  CR00384,  CR00447
  • Product: CR00158,  CR00166
    • Pathway
  • Pathway: CB000038,  CB000040,  CB000042,  CB000064,  CB000069,  CB000071,  CB000080,  CB000081,  CB000147,  CB000148,  CB000150,  CB000131
    • Major carotenoid information
    Major carotenoid in a flower petal Mimulus lewisii (Lewis' monkeyflower) (Ref.706).
    Minor carotenoid information
    Minor carotenoid in chlorophytes, prasinophytes, trebouxiophytes, mesostigmatophytes, chlorarachniophytes, and some chrysophytes and eustigmatophytes (Ref.707).
    Source organisms
    Halomicronema hongdechloris (Ref.678) - A Chl f-containing filamentous cyanobacterium purified from stromatolites of Shark Bay, Wes-tern Australia. "hong-de-chloris" represents "red chlorophyll" in Chinese. (Ref.678) (Cyanobacteria - Leptolyngbyaceae)
    Antithamnion plumula (Ref.11) - Red alga: Ceramiales (Rhodophyta - Ceramiaceae)
    Ceramium rubrum (Ref.9) - Red alga: Ceramiales (Rhodophyta - Ceramiaceae)
    Laurencia gardneri (Ref.10) - Red alga: Ceramiales (Rhodophyta - Rhodomelaceae)
    Osmundea spectabilis (Ref.10) - Red alga: Ceramiales (Rhodophyta - Rhodomelaceae)
    Polysiphonia pacifica (Ref.10) - Red alga: Ceramiales (Rhodophyta - Rhodomelaceae)
    Polysiphonia hendryi (Ref.10) - Red alga: Ceramiales (Rhodophyta - Rhodomelaceae)
    Bossiella orbignyana (Ref.10) - Red alga: Corallinales (Rhodophyta - Corallinaceae)
    Corallina officinalis (Ref.10) - Red alga: Corallinales (Rhodophyta - Corallinaceae)
    Corallina vancouverensis (Ref.10) - Red alga: Corallinales (Rhodophyta - Corallinaceae)
    Jania tenella (Ref.10) - Red alga: Corallinales (Rhodophyta - Corallinaceae)
    Bossiella californica (Ref.10) - Red alga: Corallinales (Rhodophyta - Corallinaceae)
    Calliarthron tuberculosum (Ref.10) - Red alga: Corallinales (Rhodophyta - Corallinaceae)
    Gracilaria textorii (Ref.10) - Red alga: Gigartinales (Rhodophyta - Gracilariaceae)
    Gracilaria gracilis (Ref.10) - Red alga: Gigartinales (Rhodophyta - Gracilariaceae)
    Gracilariopsis lemaneiformis (Ref.10) - Red alga: Gigartinales (Rhodophyta - Gracilariaceae)
    Smithora naiadum (Ref.10) - Red alga: Compsopogonophyceae (Rhodophyta - Erythropeltidaceae)
    Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales (Chlorophyta - Chlamydomonadales)
    Ankistrodesmus spp. (Ref.16) - Green alga: Scenedesmaceae (Chlorophyta - Selenastraceae)
    Microdictyon boergesenii (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Anadyomenaceae)
    Basicladia sp. (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Chaetomorpha okamurae (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora horii (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora kosterae (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Aegagrophila linnaei (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Chaetomorpha crassa (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora conchopheria (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora albida (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora coelothrix (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora japonica (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora pellucida (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora sericea (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora vagabunda (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora ohkuboana (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Cladophora glomerata (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Rhizoclonium grande (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    Pithophora sp. (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Pithophoraceae)
    Wittrockiella lyallii (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Pithophoraceae)
    Wittrockiella paradoxa (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Pithophoraceae)
    Cladophoropsis vaucheriaeformis (Ref.24) - Green alga: Siphonocladaceae (Chlorophyta - Siphonocladaceae)
    Cladophoropsis fasciculatus (Ref.24) - Green alga: Siphonocladaceae (Chlorophyta - Siphonocladaceae)
    Cladophoropsis membranacea (Ref.24) - Green alga: Siphonocladaceae (Chlorophyta - Siphonocladaceae)
    Siphonocladus tropicus (Ref.24) - Green alga: Siphonocladaceae (Chlorophyta - Siphonocladaceae)
    Pleurastrum paucicellulare (Ref.16) - Green alga: Ulvophyceae (Chlorophyta - Ulotrichales incertae sedis)
    Tetraselmis suecica (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
    Tetraselmis tetrathele (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
    Tetraselmis chui (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
    Tetraselmis marina (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
    Tetraselmis rubens (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
    Tetraselmis subcordiformis (Ref.48) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
    Oedogonium cardiacum (Ref.16) - Green alga: Chlorophyceae (Chlorophyta - Oedogoniales)
    Chara gymnophylla (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Chara tomentosa (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Chara contraria (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Chara hispida (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Chara rudis (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Chara globularis (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Chara intermedia (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Chara polyacantha (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Chara aspera (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Chara foetida (Ref.16) - Green plants: Charophyceae (Streptophyta - Characeae)
    Chara vulgaris (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Nitella opaca (Ref.25) - Green plants: Charophyceae (Streptophyta - Characeae)
    Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte (Chlorophyta - Mamiellaceae)
    Nephroselmis olivace (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Nephroselmidophyceae)
    Prasinococcus capsulatus (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Prasinococcales)
    Pyramimonas amylifera (Ref.46) - Green alga: Prasinophyte same as Polyblepharides amylifera (Chlorophyta - Pyramimonadales)
    Pyramimonas parkeae (Ref.48) - Green alga: Prasinophyte (Chlorophyta - Pyramimonadales)
    Euglena rubida mainx (Ref.42) - Alga: Euglena (Euglenida - Euglenaceae)
    Euglena gracilis var. bacillarus (Ref.41) - Alga: Euglena (Euglenida - Euglenaceae)
    Euglena gracilis (Ref.37) - Alga: Euglena (Euglenida - Euglenaceae)
    Olisthodiscus luteus (Ref.30) - Alga: unclassified stramenopiles ((Stramenopiles) - Unclassified stramenopiles)
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae ((Eustigmatophyceae) - Monodopsidaceae)
    Nannochloropsis gaditana (Ref.28) - Alga: Eustigmatophyceae ((Eustigmatophyceae) - Monodopsidaceae)
    Lepidodinium chlorophorum (Ref.673) - Alga: Green dinoflagellate, same as Gymnodinium chlorophorum ((Alveolata) - Gymnodiniaceae)
    Capsicum annuum var. lycopersiciforme flavum (Ref.283) - Land plant: yellow paprika (Streptophyta - Solanaceae)
    Malus domestica (Ref.492) - Land plant: Rosaceae: peel and flesh of apple fruits (Streptophyta - Rosaceae)
    Citrus reticulata (Ref.292) - Land plant: mandarin orange, tangerine (Streptophyta - Rutaceae)
    Protousnea sp. (Ref.388) - Fungi: lichen (Ascomycota - Lecanorineae)
    Solorina crocea (Ref.374) - Fungi: lichen (Ascomycota - Peltigeraceae)
    Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes (Ascomycota - Cladoniaceae)
    Rhinogobius brunneus (Ref.290) - Bony fish: Amur goby (Chordata - Gobiidae)
    References
  • Ref.678: Chen M1, Li Y, Birch D, Willows RD., FEBS Lett. 2012 Sep 21;586(19):3249-54., "A cyanobacterium that contains chlorophyll f--a red-absorbing photopigment.", PMID: 22796191 DOI: 10.1016/j.febslet.2012.06.045.
  • 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.673: Antonio Gavalas-Olea, Susana Alvarez, Pilar Riobo, Francisco Rodriguez, Jose L. Garrido, and Belen Vaz, Org Lett. 2016 Sep 16;18(18):4642-5. Epub 2016 Sep 1., "19,19’-diacyloxy signature: an atypical level of structural evolution in carotenoid pigments", doi: 10.1021/acs.orglett.6b02272.
  • 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".
  • Ref.706: Amy M. LaFountain, Harry A. Frank, Yao-Wu Yuan, Archives of Biochemistry and Biophysics 573 (2015) 32–39, “Carotenoid composition of the flowers of Mimulus lewisii and related species: Implications regarding the prevalence and origin of two unique, allenic pigments”.
  • 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
    640-03-9
    Links to other DB
    KEGG COMPOUND: C08579
    KNApSAcK: C00003760
    LipidBank: VCA1012
    MassBank: CA000003

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