Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00416   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00416                                                            

Classification
Carotenoid Name
Violaxanthin
IUPAC name (3S,5R,6S,3'S,5'R,6'S)-5,6:5',6'-Diepoxy-5,6,5',6'-tetrahydro-beta,beta-carotene-3,3'-diol
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photoprotective activity (Ref.428).
  • Photosynthetic pigment (Ref.415, Ref.428, Ref.503).
  • Xanthophyll cycle pigment.
  • Anticarcinogenic activity - antiproliferative alone, early apoptosis effect in MCF-7 cell (Ref.493).
  • Non-proviramin A (Ref.466).
  • Yellow food coloring (Ref.468).
  • Effective MDR modulator (Ref.493).
  • Number of
    conjugated double bonds 
    9
    Number of
    conjugated multiple bonds 
    9
    Isomers 
    InChI
    InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1
    InChIKey
    SZCBXWMUOPQSOX-WVJDLNGLSA-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/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C
    XLogP
    8.964
    Hydrogen Bond donors
    (Lipinski's definition)
    2
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.320
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    65.520 Å2
    Source organisms
    Nannochloropsis oculata (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Nannochloropsis salina (Ref.27, Ref.28) - Alga: Eustigmatophyceae
    Smithora naiadum (Ref.10) - Red alga: Compsopogonophyceae
    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
    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
    Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga
    Chlamydomonas parkeae (Ref.15) - Green alga: Chlamydomonadales, unicellular marine flagellate
    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
    Chlorella fusca (Ref.18) - Green alga: Scenedesmaceae
    Chlorella zofingiensis (Ref.18) - Green alga: Scenedesmaceae
    Chlorococcum citriforme (Ref.18) - Green alga: Chlamydomonadales
    Coelastrum proboscideum (Ref.18) - Green alga: Scenedesmaceae
    Muriella aurantiaca (Ref.18) - Green alga: Scenedesmaceae
    Muriella decolor (Ref.18) - Green alga: Trebouxiophyceae
    Muriellopsis sp. (Ref.18) - Green alga: Trebouxiophyceae
    Neospongiococcum gelatinosum (Ref.18) - Green alga: Chlamydomonadales
    Tetracystis aplanosporum (Ref.18) - Green alga: Chlamydomonadales
    Tetracystis intermidium (Ref.18) - Green alga: Chlamydomonadales
    Tetracystis tetrasporum (Ref.18) - Green alga: Chlamydomonadales
    Tetracystis sp. (Ref.18) - Green alga: Chlamydomonadales
    Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae
    Chlorella pyrenoidosa (Ref.21) - Green alga: Trebouxiophyceae
    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 ohkuboana (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 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 gaditana (Ref.28) - Alga: Eustigmatophyceae
    Olisthodiscus luteus (Ref.30) - Alga: unclassified stramenopiles
    Chattonella japonica (Ref.35) - Alga: Raphidophyceae
    Euglena rubida mainx (Ref.42) - Alga: Euglenoid
    Bathycoccus prasinos (Ref.46) - Green alga: Prasinophyte
    Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte
    Arousa sp. (Ref.46) - Green alga: Prasinophyte
    Prasinococcus capsulatus (Ref.46) - Green alga: Prasinophyte
    Nephroselmis olivace (Ref.46) - Green alga: Prasinophyte
    Nephroselmis pyriformis (Ref.46) - Green alga: Prasinophyte
    Nephroselmis rotunda (Ref.46, Ref.47) - Green alga: Prasinophyte
    Tetraselmis sp. (Ref.46, Ref.47) - Green alga: Chlorodendraceae
    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
    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 digitata (Ref.53) - Brown alga: Laminariaceae
    Laminaria digitata (Ref.53) - Brown alga: Laminariaceae
    Laminaria saccharina (Ref.53) - Brown alga: Laminariaceae
    Diospyros kaki (Ref.282) - Land plant: kaki persimmon
    Capsicum annuum var. lycopersiciforme flavum (Ref.283) - Land plant: yellow paprika
    Capsicum annuum var. lycopersiciforme flavum (Ref.283) - Land plant: yellow paprika
    Mangifera indica (Ref.284) - Land plant: mango
    Citrus reticulata (Ref.292) - Land plant: mandarin orange, tangerine
    Botryococcus braunii Kawaguchi-1 (Ref.301) - Green alga: Trebouxiophyceae
    Spinacia oleracea L. (Ref.601) - Land plant: spinach
    Coffea arabica (Ref.323) - Land plant: arabica coffee
    Coffea canephora (Ref.323) - Land plant: robusta coffee
    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.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.10 : N. Schubert, E. Garcia-Mendoza, and I. Pachecho-Ruiz, J. Phycol. 42, 1208-1216 (2006) "Carotenoid composition of marine red algae".
  • Ref.12 : N.I. Krinsky and R. P. Levine, Plant Physiol. Jul 1964; 39(4): 680–687. "Carotenoids of Wild Type and Mutant Strains of the Green Alga, Chlamydomonas reinhardi".
  • Ref.13 : PMID: 1190948: Francis GW, Strand LP, Lien T, Knutsen G., Arch Microbiol. 1975 Aug 28;104(3):249-54. "Variations in the Carotenoid Content of Chlamydomonas reinhardii throughout the Cell cycle".
  • Ref.14 : S. Tkaichi, and M. Mimuro, Plant Cell Physiol. 39(9): 968-977 (1998) "Distribution and Geometric Isomerism of Neoxanthin in Oxygenic Phototrophs: 9'-Cis, a Sole Molecular Form".
  • Ref.15 : T. Sasa, S. Suda, M. M. Watanabe, S. Takaichi, Plant Cell Physiol. 33(5): 527-534(1992) "A novel carotenoid ester, Loroxanthin dodecenoate, from Pyramimonas parkeae (Prasinophyceae) and Chlorarachniophycean alga".
  • 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.18 : PMID: 10784296 : Del Campo JA1, Moreno J, Rodríguez H, Vargas MA, Rivas J, Guerrero MG., J Biotechnol. 2000 Jan 7;76(1):51-9. "Carotenoid content of chlorophycean microalgae: factors determining Lutein accumulation in Muriellopsis sp. (Chlorophyta).".
  • Ref.19 : Merete Grunga, Pierre Metzger, Synnove Liaaen-jensen, Biochemical Systematics and Ecology, Volume 17, Issue 4, 28 July 1989, Pages 263–269 "Primary and Secondary Carotenoids in Two Races of the Green Alga Botryocossu braunii".
  • Ref.21 : B. Stephen Inbaraj, J.T. Chien, B. H. Chen. (2005); "Improved high performance liquid chromatographic method for determination of carotenoids in the microalga Chlorella pyrenoidosa".
  • 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.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.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.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.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.282 : A. L. Curl, Volume 25, Issue 5, Article first published online: 25 AUG 2006, "The Carotenoids of Jappanese persimmons".
  • 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.284 : Adriana Z. Mercadante ,Délia B. Rodriguez-Amaya, George Britton, J. Agric. Food Chem., 1997, 45 (1), pp 120–123, "HPLC and Mass Spectrometric Analysis of Carotenoids from Mango".
  • 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.301 : Tonegawa, Izumi; Okada, Shigeru; Murakami, Masahiro; Yamaguchi, Katsumi, Fisheries Science (1998), 64(2), 305-308., "Pigment composition of the green microalga Botryococcus braunii Kawaguchi-1".
  • Ref.601 : Andrea Bunea, Mirjana Andjelkovic, Carmen Socaciu, Otilia Bobis, Madalina Neacsu, Roland Verhe, John Van Camp, Food Chemistry 108 (2008) 649–656, "Total and individual carotenoids and phenolic acids content in fresh, refrigerated and processed spinach (Spinacia oleracea L.)".
  • Ref.323 : Andrew J. Simkin, Marcel Kuntz, Helene Moreau, James McCarthy, Plant Physiology and Biochemistry 48 (2010) pp.434-442, "Carotenoid profiling and the expression of carotenoid biosynthetic genes in developing coffee grain".
  • 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.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.415 : Takuji Tanaka, Masahito Shnimizu, and Hisataka Moriwaki, Molecules 2012, 17, 3202-3242; doi:10.3390/molecules17033202, "Cancer Chemoprevention by Carotenoids".
  • 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.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.466 : Torsten Bohn, Current Nutrition & Food Science, 2008, 4, 240-258, "Bioavailability of Non-Provitamin A Carotenoids " .
  • Ref.468 : Gerard P. Moss, Herbert Baxter, J.B. Harborne, Gerald P. Moss, CRC Press; 1 edition (February 15, 1993), ISBN-10: 0850667364, ISBN-13: 978-0850667363, "Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants".
  • CAS
    126-29-4
    Links to other DB
    KEGG COMPOUND: C08614
    KNApSAcK: C00003787
    LipidBank: VCA0060
    MassBank: CA000114, CA000105

       Search other references with Google Scholar