Carotenoids obi
All carotenoids     All organisms   Feedback
Carotenoids DB          Carotenoids DB: CA00322   
[   About  |   Help  |   Search carotenoid entry  |   Search organism entry  |   Search similar carotenoids  |   Predict biological activities of this carotenoid  |   Search possible pathways   ]
Entry
CA00322                                                            

Classification
Carotenoid Name
β-Cryptoxanthin;
beta-Cryptoxanthin
IUPAC name (3R)-beta,beta-Caroten-3-ol
Formula
C40H56O
Molecular Weight 
552.848 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Provitamin A activity - 30-50% of all-trans-β-carotene (Ref.408, Ref.415, Ref.467).
  • Anticarcinogenic activity - stronger than β-carotene, β-caroten-2-ol, and Isocryptoxanthin. C3 group one the β-end group enhanced the activity (Ref.409, Ref.414, Ref.491).
  • An antioxidant - 68.6 times stronger singlet oxygen quenching ability than that ofα-tocopherol - SOAC value: 68.6±2.0 (Ref.616, Ref.597, Ref.598, Ref.599, Ref.415).
  • Anti-obesity effects (Ref.416).
  • Stimulates the repair of DNA oxidation damage (Ref.419).
  • Yellow food coloring (Ref.468).
  • Number of
    conjugated double bonds 
    11
    Number of
    conjugated multiple bonds 
    11
    Isomers 
    InChI
    InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-/m1/s1
    InChIKey
    DMASLKHVQRHNES-FKKUPVFPSA-N
    Canonical SMILES
    O[C@@H]1CC(=C(C(C1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C)/C)/C)C
    XLogP
    12.649
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    1
    LipinskiFailures
    1
    Complexity of molecule
    0.309
    Number of heavy atoms
    41
    TPSA
    (Topological Polar Surface Area) 
    20.230 Å2
    Source organisms
    Thermus thermophilus (Ref.435) - Deinococcus-Thermus: Thermophilic bacterium
    Oscillantoria rubescens (Ref.1) - Cyanobacteria: other name is Planktothrix rubescens
    Oscillatoria agardhii (Ref.1) - Cyanobacteria: other name is Planktothrix agardhii
    Oscillatoria amoena (Ref.1) - Cyanobacteria
    Oscillatoria limosa (Ref.1) - Cyanobacteria
    Arthrospira sp. (Ref.1) - Cyanobacteria
    Phormidium foveolarum (Ref.1) - Cyanobacteria
    Anacystis nidulans (Ref.1) - Cyanobacteria: other name is Synechococcus elongatus PCC 7942
    Microcystis aeruginosa (Ref.1) - Cyanobacteria
    Merismopedia punctata (Ref.1) - Cyanobacteria: colony square or rectangular
    Synechococcus leopoliensis (Ref.8) - Cyanobacteria
    Planktothrix agardhii (Ref.8) - Cyanobacteria
    Porphyra perforata (conchocelis)  - Red alga: Bangiaceae
    Antithamnion plumula (Ref.11) - Red alga: Ceramiales
    Polysiphonia brodiae (Ref.9) - Red alga: Ceramiales
    Gelidium pusillum (Ref.10) - Red alga: Gelidiales
    Chondracanthus squarrulosus (Ref.10) - Red alga: Gigartinales
    Eucheuma uncinatum (Ref.10) - Red alga: Gigartinales
    Gracilaria gracilis (Ref.10) - Red alga: Gigartinales
    Gracilariopsis lemaneiformis (Ref.10) - Red alga: Gigartinales
    Centroceras clavulatum (Ref.10) - Red alga: Ceramiales
    Osmundea spectabilis (Ref.10) - Red alga: Ceramiales
    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
    Hymenomonas carterae (Ref.31) - Alga: Haptophyte
    Euglena gracilis (Ref.37, Ref.38) - Alga: Euglenoid
    Euglena gracilis var. bacillarus (Ref.41) - Alga: Euglenoid
    Euglena rubida mainx (Ref.42) - Alga: Euglenoid
    Gallus gallus (Ref.219) - Bird: chicken
    Acaryochloris marina strain MBIC 11017 (Ref.274) - Cyanobacteria: symbiotic species Unicellular Cyanobacterium, an epiphyte on red alga
    Prochloron sp. (Ref.274) - Cyanobacteria
    Averrhoa carambola (Ref.281) - Land plant: starfruit
    Diospyros kaki (Ref.282) - Land plant: kaki persimmon
    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
    Citrus sinensis L. Osbeck (Ref.373) - Land plant: orange
    Carica papaya (Ref.566) - Land plant: papaya
    Erythrobacter longus (Ref.364) - Alphaproteobacteria: marine anoxygenic phototroph with BChl a
    Protousnea sp. (Ref.388) - Fungi: lichen
    Passiflora edulis (Ref.129) - Land plant: yellow passion fruit
    Rhacophorus bipunctatus (Ref.421) - Himalaya flying frog
    Galleria mellonella (Ref.558) - Insect: greater wax moth
    Cladonia sp. (Ref.609) - Fungi: lichen, ascomycetes
    Clione limacina (Ref.635) - gastropods
    Paedoclione doliiformis (Ref.635) - gastropods
    Limacina helicina (Ref.635) - gastropods
    References
  • Ref.435 : Yokoyama A, Shizuri Y, Hoshino T, Sandmann G., Arch Microbiol. 1996 May 22;165(5):342-5., "Thermocryptoxanthins: novel intermediates in the carotenoid biosynthetic pathway of Thermus thermophilus".
  • Ref.1 : S. Hertzberg, S. Liaaen-Jensen, and H. W. Siegelman, Phytochemistry, 1971, Vol. 10, pp. 3121 - 3127 "The carotenois of blue-green algae".
  • 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.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.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.31 : R. Berger, and S. Liaaen-Jensen, Biochemical Systematics and Ecology, 1977, Vol. 5, pp.71-75 "Carotenoids of Prymnesiophyceae (Haptophyceae)* ".
  • 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.38 : D. V. Heelis, W. Kernick, G. O. Philips, and K. Davies, Arch. Microbiol. 121, 207-211 (1979), "Separation and Identification of the Carotenoid Pigments of Stigmata Isolated from Light Grown Cells of Euglena gracilis Strain Z".
  • 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.219 : Brulc, Lucka; Simonovska, Breda; Vovk, Irena; Glavnik, Vesna, Journal of Chromatography A (2013), 1318, 134-141. "Determination of egg yolk xanthophylls by isocratic high-performance liquid chromatography".
  • Ref.274 : Shinichi Takaichi, Mari Mochimaru, Hiroko Uchida, Akio Murakami, Euichi Hirose, Takashi Maoka, Tohru Tsuchiya, and Mamoru Mimuro, Plant Cell Physiol. 53(11): 1881–1888 (2012) doi:10.1093/pcp/pcs126, "Opposite Chilarity of a-Carotene in Unusual Cyanobacteria with Unique Chlorophylls, Acaryochloris and Prochlorococcus".
  • Ref.281 : Jeana Gross, Raphael Ikan, Gert Eckhardt, Phytochemistry, Volume 22, Issue 6, 1983, Pages 1479-1481, "Carotenoids of the fruit of Averrhoa carambola".
  • 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.373 : Kudritskaya, S. E.; Fishman, G. M.; Zagorodskaya, L. M., Subtropicheskie Kul'tury (1977), (5-6), 154-8., "Identification of orange peel (Citrus sinensis Osb.) carotenoids".
  • Ref.566 : U Gamage Chandrika, Errol R Jansz, SMD Nalinie Wickramasinghe and Narada D Warnasuriya, J Sci Food Agric 83:1279–1282 (online: 2003), DOI: 10.1002/jsfa.1533, "Carotenoids in yellow- and red-fleshed papaya (Carica papaya L)".
  • Ref.364 : S. Takaichi, K. Shimada, and J. Ishidsu, Arch Microbiol.(1990) 153:118-122, "Carotenoids from the aerobic photosynthetic bacterium, Erythrobacter longus: β-Carotene and its hydroxyl derivatives".
  • 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.129 : da Silva, Sandra Regina; Mercadante, Adriana Z., Ciencia e Tecnologia de Alimentos (Campinas, Brazil) (2002), 22(3), 254-258., "Carotenoid composition of fresh yellow passion fruit (Passiflora edulis flavicarpa)".
  • Ref.421 : Pinky Baruah and Goswami UC., Journal of Research in Biology, pp.114-118, 2012, Vol.2, No.2, "Characterization of carotenoid pigments in amphibian, Rhacophorous bipunctatus".
  • Ref.558 : Vitus Oberhausera, Olaf Voolstraa, Annette Bangerta, Johannes von Lintigb, and Klaus Vogt, Proc Natl Acad Sci U S A. 2008 Dec 2;105(48):19000-5. doi: 10.1073/pnas.0807805105. Epub 2008 Nov 19., "NinaB combines carotenoid oxygenase and retinoid isomerase activity in a single polypeptide.".
  • 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.408 : Jonathan R Mein, Fuzhi Lian, Xiang-Dong Wang, Nutr Rev. 2008 Dec;66(12):667-83. doi: 10.1111/j.1753-4887.2008.00120.x., PMID: 19019036, "Biological activity of lycopene metabolites: implications for cancer prevention".
  • Ref.415 : Takuji Tanaka, Masahito Shnimizu, and Hisataka Moriwaki, Molecules 2012, 17, 3202-3242; doi:10.3390/molecules17033202, "Cancer Chemoprevention by Carotenoids".
  • Ref.467 : Abdulkerim Eroglu and Earl H. Harrison, Journal of Lipid Research Volume 54, 2013, "Carotenoid metabolism in mammals, including man: formation, occurrence, and function of apocarotenoids".
  • Ref.409 : Hoyoku Nishino, Michiaki Murakoshi, Harukuni Tokuda, Yoshiko Satomi, Archives of Biochemistry and Biophysics, Volume 483, Issue 2, 15 March 2009, Pages 165–168, "Cancer prevention by carotenoids".
  • Ref.414 : Nishino H, Murakosh M, Ii T, Takemura M, Kuchide M, Kanazawa M, Mou XY, Wada S, Masuda M, Ohsaka Y, Yogosawa S, Satomi Y, Jinno K., Cancer Metastasis Rev. 2002;21(3-4):257-64., "Carotenoids in cancer chemoprevention.".
  • Ref.491 : Tsushima M, Maoka T, Katsuyama M, Kozuka M, Matsuno T, Tokuda H, Nishino H, Iwashima A., Biol Pharm Bull. 1995 Feb;18(2):227-33., PMID: 7742789, "Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters.".
  • Ref.616 : Takahashi S., Iwasaki-Kino Y., and Terao J., and Mukai K., FOOD COMPOSITION AND ADDITIVES, Journal of AOAC International Vol. 99, no.1, 2016 pp.193-197, "Development of Singlet Oxygen Absorption Capacity (SOAC) Assay Method Using a Microplate Reader".
  • Ref.597 : Kazuo MUKAI, Aya OUCHI, Oleoscience, Vol. 13 (2013) No. 8 p. 371-378, "Antioxidant Activity of Foods Development of Singlet Oxygen Absorption Capacity (SOAC) Assay Method".
  • Ref.598 : Ouchi, A., Aizawa, K., Iwasaki, Y., Inakuma, T., Terao, J., Nagaoka, S., Mukai, K., 2010. Kinetic study of the quenching reaction of singlet oxygen by carotenoids and food extracts in solution. Development of a singlet oxygen absorption capacity (SOAC) assay method. J. Agric. Food Chem. 58, 9967–78. doi:10.1021/jf101947a.
  • Ref.599 : Aizawa, K., Iwasaki, Y., Ouchi, A., Inakuma, T., Nagaoka, S., Terao, J., Mukai, K., 2011. Development of singlet oxygen absorption capacity (SOAC) assay method. 2. Measurements of the SOAC values for carotenoids and food extracts. J. Agric. Food Chem. 59, 3717–29. doi:10.1021/jf104955a .
  • Ref.416 : Takayanagi K, Morimoto S, Shirakura Y, Mukai K, Sugiyama T, Tokuji Y, Ohnishi M., J Agric Food Chem. 2011 Dec 14;59(23):12342-51. doi: 10.1021/jf202821u. Epub 2011 Nov 15., "Mechanism of visceral fat reduction in Tsumura Suzuki obese, diabetes (TSOD) mice orally administered β-cryptoxanthin from Satsuma mandarin oranges (Citrus unshiu Marc).".
  • Ref.419 : Yolanda Lorenzo, Amaia Azqueta, Luisa Luna, Félix Bonilla, Gemma Domínguez and Andrew R. Collins, Carcinogenesis vol.30 no.2 pp.308–314, 2009, doi:10.1093/carcin/bgn270, "The carotenoid β-cryptoxanthin stimulates the repair of DNA oxidation damage in addition to acting as an antioxidant in human cells".
  • 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
    472-70-8
    Links to other DB
    KEGG COMPOUND: C08591
    KNApSAcK: C00000920
    LipidBank: VCA1013
    MassBank: CA000038
    ProCarDB: C1922

       Search other references with Google Scholar