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Entry
CA00043                                                            

Classification
Carotenoid Name
Lycopene;
(all-E)-Lycopene
IUPAC name psi,psi-Carotene
Formula
C40H56
Molecular Weight 
536.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Photoprotoection. (Ref.408)
  • Radioprotector against gamma-radiation-induced cellular damages (Ref.489).
  • Strong antioxidant. - strong singlet quenching ability - 141 times stronger than that of α-tocopherol - SOAC value: 141±7 (Ref.616, Ref.408, Ref.415, Ref.597, Ref.598, Ref.599).
  • Antiradical activity (Ref.477).
  • Anticarcinogenic activity - by reducing insulin growth factor 1 (IGF-1) stimulation with an increase in membrane-associated IGF binding proteins, and slow down IGF-1-stimulated cell cycle progression (Ref.408, Ref.414, Ref.415, Ref.491).
  • Anti-inflammation (Ref.408).
  • Antimicrobial activity against S. aureus, and E. coli O-157 (Ref.482).
  • Antifungal activity against C. albicans by aressting their cell cycle (Ref.482).
  • Cell differentioan and proliferation promoter by upregulating Connexin43 gene (Ref.412).
  • Bright pink/Brick red color (Ref.430).
  • Orange-red food coloring (Ref.468).
  • Non-Provitamin A (Ref.408).
  • Number of
    conjugated double bonds 
    11
    Number of
    conjugated multiple bonds 
    11
    Isomers 
    InChI
    InChI=1S/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
    InChIKey
    OAIJSZIZWZSQBC-GYZMGTAESA-N
    Canonical SMILES
    C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C=C(\CCC=C(C)C)/C)/C)/C)/C=C/C=C(/C=C/C=C(/CCC=C(C)C)\C)\C
    XLogP
    14.586
    Hydrogen Bond donors
    (Lipinski's definition)
    0
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    0
    LipinskiFailures
    2
    Complexity of molecule
    0.000
    Number of heavy atoms
    40
    TPSA
    (Topological Polar Surface Area) 
    0.000 Å2
    Source organisms
    Thermus thermophilus (Ref.435) - Deinococcus-Thermus: Thermophilic bacterium
    Rhodopseudomonas palustris (Ref.336, Ref.344) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Rhodobacter capsulatus (Ref.353) - Alphaproteobacteria: photosynthetic purple nonsulfur bacterium
    Halorubrum chaoviator Halo-G (Ref.333) - Archaea: Euryarchaeota
    Haloarcula japonica (Ref.621) - Archaea: Euryarchaeota, triangular, disc-shaped, extremely halophilic archaeon that requires high concentrations of NaCl for growth
    Phaeospirillum sp. (Ref.327) - Alphaproteobacteria: spiral-shaped phototrophic purple non-sulfur bacteria
    Roseospira sp. (Ref.327) - Alphaproteobacteria: phototrophic purple non-sulfur bacteria
    Nostoc sp. PCC 7120 (Ref.72) - Cyanobacteria: same as Anabaena sp. PCC 7120
    Oscillatoria princeps (Ref.1) - Cyanobacteria
    Staphylococcus aureus (Ref.540) - Firmicutes - Bacilli
    Cryptomonas ovata (Ref.26) - Alga: Cryptomonad
    Coccinella septempunctata (Ref.116) - Insect: seven-spotted ladybird
    Diospyros kaki (Ref.282) - Land plant: kaki persimmon
    Carica papaya (Ref.566) - Land plant: papaya
    Calendula officinalis (Ref.430) - Land plant: common marigold
    Elaeis spp. (Ref.431) - Land plant: palm oil
    Dunaliella salina (Ref.606) - Green alga: Dunaliellaceae
    Lamprocystis roseopersicina (Ref.351) - purple sulfur bacteria
    Thiodictyon strain 3011 (Ref.351) - purple sulfur bacteria
    Citrullus vulgaris (Ref.484) - Land plant: watermelon
    Homo sapiens (Ref.407) - Human
    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.336 : Zhang, Tong; Zhu, Rui-yan; Hui, Bo-di; Yang, Bo-yuan, Shipin Kexue (Beijing, China) (2013), 34(21), 283-291., "Lycopene biosynthesis in Rhodopseudomonas palustris".
  • Ref.344 : Zhao, Chun-gui; Fu, Qiao-ming; Zhuo, Min-quan; Yang, Su-ping, Weishengwuxue Tongbao (2014), 41(7), 1448-1455., "The relative polarity and stability of each carotenoid of spirilloxanthin biosynthesis pathway by thin-layer chromatography (TLC)".
  • Ref.353 : Maoka, Takashi; Matsumura, Akihiko; Ito, Yoshihiro; Okuda, Yoko; Mochida, Koichi, Jpn. Kokai Tokkyo Koho (1996), JP 08239658 A 19960917., "Antioxidants of Rhodobacter".
  • Ref.333 : Davood Naziri, Masoud Hamidi, Salar Hassanzadeh, Vahideh Tarhriz, Bahram Maleki Zanjani, Hossein Nazemyieh, Mohammd Amin Hejazi, Mohammad Saeid Hejazi, Advanced Pharmaceutical Bulletin, 2014, 4(1), 61-67, "Analysis of Carotenoid Production by Halorubrum sp. TBZ126; an Extremely Halophilic Archeon from Urmia Lake".
  • Ref.621 : Ying Yang, Rie Yatsunami, Ai Ando, Nobuhiro Miyoko, Toshiaki Fukui, Shinichi Takaichi, Satoshi Nakamura, "Complete Biosynthetic Pathway of the C50 Carotenoid Bacterioruberin from Lycopene in the Extremely Halophilic Archaeon Haloarcula japonica", Journal of Bacteriology, May 2015 Volume 197 Number 9.
  • Ref.327 : Takaichi, Shinichi; Maoka, Takashi; Sasikala, Ch.; Ramana, Ch. V.; Shimada, Keizo, Current Microbiology (2011), 63(1), 75-80., "Genus specific unusual carotenoids in purple bacteria, Phaeospirillum and Roseospira: Structures and biosyntheses".
  • Ref.72 : Heo, Jinsol; Kim, Se Hyeuk; Lee, Pyung Cheon, Applied and Environmental Microbiology (2013), 79(11), 3336-3345., "New insight into the cleavage reaction of Nostoc sp. strain PCC 7120 carotenoid cleavage dioxygenase in natural and nonnatural carotenoids".
  • 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.540 : Benjamin N. Mijts, Pyung Cheon Lee, Claudia Schmidt-Dannert, Chemistry & Biology, Volume 12, Issue 4, April 2005, Pages 453–460, "Identification of a Carotenoid Oxygenase Synthesizing Acyclic Xanthophylls: Combinatorial Biosynthesis and Directed Evolution".
  • Ref.26 : F. C. Pennington, F. T. Haxo, G. Borch, and Liaaen-Jensen, Biochemical Systematics and Ecology, Vol. 13, No. 3, pp. 215-219, 1985 "Carotenoids of Cryptophyceae".
  • Ref.116 : Britton, George; Lockley, William J. S.; Harriman, Garry A.; Goodwin, Trevor W., Nature (London, United Kingdom) (1977), 266(5597), 49-50., "Pigmentation of the ladybird beetle Coccinella septempunctata by carotenoids not of plant origin".
  • Ref.282 : A. L. Curl, Volume 25, Issue 5, Article first published online: 25 AUG 2006, "The Carotenoids of Jappanese persimmons".
  • 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.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.431 : R. F. Hunter and R. M. Krakenberger, Biochem Jv.40(4); 1946PMC1258385, "Palm-oil carotenoids".
  • Ref.606 : K.N. Chidambara Murthy, A. Vanitha, J. Rajesha, M. Mahadeva Swamy, P.R. Sowmya, Gokare A. Ravishankar, Life Sciences 76 (2005) 1381 – 1390, "In vivo antioxidant activity of carotenoids from Dunaliella salina — a green microalga".
  • Ref.351 : Francis, G. W.; Liaaen Jensen, Synnoeve, Acta Chemica Scandinavica (1947-1973) (1970), 24(8), 2705-12., "Bacterial carotenoids.  XXXIII.  Carotenoids of thiorhodaceae.  9.  Structures of the carotenoids of the rhodopinal series".
  • 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.407 : Wilhelm Stahl and Helmut Sies, 2012 American Society for Nutrition, "β-Carotene and other carotenoids in protection from sunlight".
  • 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.489 : Srinivasan M, Devipriya N, Kalpana KB, Menon VP., Toxicology. 2009 Jul 28;262(1):43-9. doi: 10.1016/j.tox.2009.05.004. Epub 2009 May 18., "Lycopene: An antioxidant and radioprotector against gamma-radiation-induced cellular damages in cultured human lymphocytes.".
  • 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.415 : Takuji Tanaka, Masahito Shnimizu, and Hisataka Moriwaki, Molecules 2012, 17, 3202-3242; doi:10.3390/molecules17033202, "Cancer Chemoprevention by Carotenoids".
  • 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.477 : Marıa D. Mendez-Robles, Herry H. Permady, Marıa E. Jaramillo-Flores, Eugenia C. Lugo-Cervantes, Anaberta Cardador-Martınez, Alejandro A. Canales-Aguirre, Fernando Lopez-Dellamary, Carlos M. Cerda-Garcı´a-Rojas, and Joaquın Tamariz, J. Nat. Prod. 2006, 69, 1140-1144, "C-26 and C-30 Apocarotenoids from Seeds of Ditaxis heterantha with Antioxidant Activity and Protection against DNA Oxidative Damage".
  • 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.482 : Sung Woo Sang, In-Seon-Lee, and Dong Gun Lee, J. Microbiol. Biotechnol. (2007), 17(11), 1797-1804, "Damage to the Cytoplasmic Membrane and Cell Death Caused by Lycopene in Candida albicans".
  • Ref.412 : Li-Xin Zhang, Robert V. Cooney, and John S. Bertram, CANCER RESEARCH 52, 5707-5712, October 15, 1992, "Carotenoids Up-Regulate Connexin43 Gene Expression Independent of Their Provitamin A or Antioxidant Properties1".
  • 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
    502-65-8
    Links to other DB
    KEGG COMPOUND: C05432
    KNApSAcK: C00000911
    LipidBank: VCA0010
    MassBank: CA000154
    ProCarDB: C1913

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