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Entry
CA00414                                                            

Classification
Carotenoid Name
Neoxanthin;
(all-E)-Neoxanthin
IUPAC name (3S,5R,6R,3'S,5'R,6'S)-5',6'-Epoxy-6,7-didehydro-5,6,5',6'-tetrahydro-beta,beta-carotene-3,5,3'-triol
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photosynthetic pigment of higher plants (Ref.503).
  • Antimicrobial activity - anti-H. pylori (Ref.492).
  • Anticarcinogenic activity - a concentration of 1 microgram/mL was sufficient to avoid the formation of tumors (Ref.493).
  • Non-provitamin A (Ref.466).
  • Number of
    conjugated double bonds 
    9
    Number of
    conjugated multiple bonds 
    9
    Isomers 
    InChI
    InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-35-36(5,6)25-33(41)27-38(35,9)43)15-11-12-16-30(2)18-14-20-32(4)23-24-40-37(7,8)26-34(42)28-39(40,10)44-40/h11-21,23-24,33-34,41-43H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20+/t22-,33-,34-,38+,39+,40-/m0/s1
    InChIKey
    PGYAYSRVSAJXTE-MTYISEJWSA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O)/C)/C)/C=C/C=C(/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C
    XLogP
    10.319
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    1
    Complexity of molecule
    0.310
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    73.220 Å2
    Source organisms
    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
    Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae
    Chlorella pyrenoidosa (Ref.21) - Green alga: Trebouxiophyceae
    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
    Ochromonas sp. (Ref.30) - Golden alga: Chrysophyceae
    Poterioochromonas malhamensis (Ref.30) - Golden alga: Synurophyceae
    Olisthodiscus luteus (Ref.30) - Alga: unclassified stramenopiles
    Gonyostomum semen (Ref.35) - Alga: Raphidophyceae
    Euglena gracilis (Ref.37, Ref.8) - Alga: Euglenoid
    Euglena gracilis var. bacillarus (Ref.41) - Alga: Euglenoid
    Euglena rubida mainx (Ref.42) - Alga: Euglenoid
    Euglena sanguinea (Ref.43) - Alga: Euglenoid
    Euglena viridis (Ref.44) - Alga: Euglenoid
    Eutreptiella gymnastica (Ref.45) - Alga: Euglenoid
    Bathycoccus prasinos (Ref.46) - Green alga: Prasinophyte
    Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte
    Micromonas pusilla (Ref.46, Ref.47) - Green alga: Prasinophyte
    Arousa sp. (Ref.46) - Green alga: Prasinophyte
    Prasinococcus capsulatus (Ref.46) - Green alga: Prasinophyte
    Pycnococcus provasolii (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
    Pseudoscourfieldia marina (Ref.46) - Green alga: Prasinophyte
    Tetraselmis wettsteinii (Ref.46, Ref.47) - Green alga: Chlorodendraceae
    Tetraselmis sp. (Ref.46, Ref.47) - Green alga: Chlorodendraceae
    Pyramimonas amylifera (Ref.46) - 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 saccharina (Ref.53) - Brown alga: Laminariaceae
    Mangifera indica (Ref.284) - Land plant: mango
    Citrus reticulata (Ref.292) - Land plant: mandarin orange, tangerine
    Boronia megastigma (Ref.297) - Land plant: brown boronia
    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
    Persea americana (Ref.202) - Land plant: avocado
    Solorina crocea (Ref.374) - Fungi: lichen
    Protousnea sp. (Ref.388) - Fungi: lichen
    Calendula officinalis (Ref.430) - Land plant: common marigold
    Citrullus vulgaris (Ref.484) - Land plant: watermelon
    Malus domestica (Ref.492) - Land plant: Rosaceae: apple peel extract
    Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes
    References
  • 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.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.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.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.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.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.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.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.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.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.297 : Cooper, Chris M.; Davies, Noel W.; Menary, Robert C., Journal of Agricultural and Food Chemistry (2009), 57(4), 1513-1520., "Changes in Some Carotenoids and Apocarotenoids during Flower Development in Boronia megastigma (Nees)".
  • 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.202 : Gross, Jeana; Gabai, Michaela; Lifshitz, Abraham; Sklarz, Benjamin, Phytochemistry (Elsevier) (1974), 13(9), 1917-21., "Structures of some carotenoids from pulp of Persea americana".
  • 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.430 : T. W. GOODWIN, Biochem J. 1954 Sep;58(1):90-4., "Studies in carotenogenesis. 13. The carotenoids of the flower petals of Calendula officinalis.".
  • Ref.484 : Wen’en Zhao, Pin Lv, Huihui Gu, Agricultural Sciences Vol.4, No.7A, 13-20 (2013), http://dx.doi.org/10.4236/as.2013.47A003, "Studies on carotenoids in watermelon flesh".
  • 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.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 " .
  • CAS
    14660-91-4
    Links to other DB
    KEGG COMPOUND: C08606
    KNApSAcK: C00003780
    LipidBank: VCA0059
    MassBank: CA000089

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