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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      Search similar carotenoids

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

    InChIKey

    Canonical SMILES

    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
    Reaction
  • Substrate: CR00088,  CR00101,  CR00141,  CR00180,  CR00290,  CR00291,  CR00355,  CR00359,  CR00402
  • Product: CR00382
    • Pathway
  • Pathway: CB000040,  CB000042,  CB000064,  CB000080,  CB000081,  CB000147,  CB000148,  CB000150,  CB000124,  CB000131
    • Major carotenoid information
    Dominant pigment in mesostigmatophytes (Ref.707). Major in a flower petal Mimulus lewisii (Lewis' monkeyflower) (Ref.706), and in a citrus fruit ponkan mandarin (Ref.723).
    Minor carotenoid information

    Source organisms
    Pouteria sapota (Ref.773)  - Land plant: red mamey sapote, species of tree native to Cuba and Central America. Fruit is commonly eaten in many Latin American countries. It is is about 10 to 25 cm (4 to 10 in) long and 8 to 12 cm (3 to 4.5 in) wide and has flesh ranging in color from pink to orange to red. The fruit's texture is creamy and soft, the flavor is a mix of sweet potato, pumpkin, honey, prune, peach, apricot, cantaloupe, cherry, and almond. (Streptophyta - Chrysophylloideae)
    Chlamydomonas parkeae (Ref.15) - Green alga: Chlamydomonadales, unicellular marine flagellate (Chlorophyta - Chlamydomonadaceae)
    Chlamydomonas reinhardtii (Ref.12, Ref.13, Ref.14) - Green alga: Chlamydomonadales, unicellular green alga (Chlorophyta - Chlamydomonadaceae)
    Protosiphon botryoides (Ref.16, Ref.17) - Green alga: Chlamydomonadales (Chlorophyta - Chlamydomonadales)
    Ankistrodesmus spp. (Ref.16) - Green alga: Scenedesmaceae (Chlorophyta - Selenastraceae)
    Pleurastrum paucicellulare (Ref.16) - Green alga: Ulvophyceae (Chlorophyta - Ulotrichales incertae sedis)
    Tetraselmis wettsteinii (Ref.46, Ref.47) - Green alga: Chlorodendraceae (Chlorophyta - Chlorodendraceae)
    Tetraselmis sp. (Ref.46, Ref.47) - 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)
    Bathycoccus prasinos (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Bathycoccaceae)
    Mantoniella squamata (Ref.46, Ref.47) - Green alga: Prasinophyte (Chlorophyta - Mamiellaceae)
    Micromonas pusilla (Ref.46, Ref.47) - Green alga: Prasinophyte (Chlorophyta - Mamiellaceae)
    Nephroselmis olivace (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Nephroselmidophyceae)
    Nephroselmis rotunda (Ref.46, Ref.47) - Green alga: Prasinophyte (Chlorophyta - Nephroselmidophyceae)
    Nephroselmis pyriformis (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Nephroselmidophyceae)
    Prasinococcus capsulatus (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Prasinococcales)
    Pseudoscourfieldia marina (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Pycnococcaceae)
    Pycnococcus provasolii (Ref.46) - Green alga: Prasinophyte (Chlorophyta - Pycnococcaceae)
    Pyramimonas amylifera (Ref.46) - Green alga: Prasinophyte same as Polyblepharides amylifera (Chlorophyta - Pyramimonadales)
    Arousa sp. (Ref.46) - Green alga: Prasinophyte (Unclassified chlorophyta - Unclassified chlorophyta)
    Chlorella pyrenoidosa (Ref.21) - Green alga: Trebouxiophyceae (Chlorophyta - Chlorellaceae)
    Botryococcus braunii (Ref.19) - Green alga: Trebouxiophyceae (Chlorophyta - Botryococcaceae)
    Botryococcus braunii Kawaguchi-1 (Ref.301) - Green alga: Trebouxiophyceae (Chlorophyta - Botryococcaceae)
    Euglena rubida mainx (Ref.42) - Alga: Euglena (Euglenida - Euglenaceae)
    Euglena gracilis var. bacillarus (Ref.41) - Alga: Euglena (Euglenida - Euglenaceae)
    Euglena gracilis (Ref.37, 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)
    Ochromonas sp. (Ref.30) - Golden alga: Chrysophyceae ((Stramenopiles) - Chromulinaceae)
    Poterioochromonas malhamensis (Ref.30) - Golden alga: Synurophyceae ((Stramenopiles) - Ochromonadaceae)
    Olisthodiscus luteus (Ref.30) - Alga: unclassified stramenopiles ((Stramenopiles) - Unclassified stramenopiles)
    Ascophyllum nodosum (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Fucus serratus (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Fucus vesiculosus (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Pelvetia canaliculata (Ref.53) - Brown alga: Fucaceae ((Phaeophyceae) - Fucaceae)
    Laminaria saccharina (Ref.53) - Brown alga: Laminariaceae ((Phaeophyceae) - Laminariaceae)
    Laminaria digitata (Ref.53) - Brown alga: Laminariaceae ((Phaeophyceae) - Laminariaceae)
    Gonyostomum semen (Ref.35) - Alga: Raphidophyceae ((Raphidophyceae) - Chattonellaceae)
    Spinacia oleracea L. (Ref.601) - Land plant: spinach (Streptophyta - Chenopodiaceae)
    Arabidopsis thaliana (Ref.762) - Land plant: thale-cress, a model organism (Streptophyta - Brassicaceae)
    Coffea canephora (Ref.323) - Land plant: robusta coffee (Streptophyta - Rubiaceae)
    Coffea arabica (Ref.323) - Land plant: arabica coffee (Streptophyta - Rubiaceae)
    Malus domestica (Ref.492) - Land plant: Rosaceae: peel and flesh of apple fruits (Streptophyta - Rosaceae)
    Mangifera indica (Ref.284) - Land plant: mango (Streptophyta - Anacardiaceae)
    Boronia megastigma (Ref.297) - Land plant: brown boronia (Streptophyta - Rutaceae)
    Citrus reticulata (Ref.292) - Land plant: mandarin orange, tangerine (Streptophyta - Rutaceae)
    Citrullus vulgaris (Ref.484) - Land plant: watermelon (Streptophyta - Cucurbitaceae)
    Calendula officinalis (Ref.430) - Land plant: common marigold (Streptophyta - Asteraceae)
    Persea americana (Ref.202) - Land plant: avocado (Streptophyta - Lauraceae)
    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)
    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.762: Kerry L. Taylor, Anika E. Brackenridge, Melane A. Vivier, Anita Oberholster, Journal of Chromatography A, 1121 (2006) 83–91, "High-performance liquid chromatography profiling of the major carotenoids in Arabidopsis thaliana leaf tissue".
  • Ref.773: Attila Agócs et al., Journal of Food Composition and Analysis 65 (2018) 1–5, “Isolation of allene carotenoids from mamey”, http://dx.doi.org/10.1016/j.jfca.2017.04.004.
  • 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.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.
  • 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.723: S.D. Lin and .O. Chen (2007) Journal of Food Biochemistry 18(4):273 - 283 "Major carotenoids in juice of ponkan mandarin and liucheng orange", DOI: 10.1111/j.1745-4514.1994.tb00502.x.
    • CAS
    14660-91-4
    Links to other DB
    KEGG COMPOUND: C08606
    KNApSAcK: C00003780
    LipidBank: VCA0059
    MassBank: CA000089

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