C50 carotenoids
    1.1 psi,psi Carotene
            C50 Hydroxycarotenoids

C50H76O4

741.108 g/mol

  Predict biological activities of this carotenoid
(2S,2'S), 3,4--H, 3',4'--H, 1-OH, 1'-OH, psi,psi, 2-isoprene-3-OH, 2'-isoprene-3-OH
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Antioxidant activity - much better radical scavenger than that of β-carotene as it contains 13 pairs of conjugated double bonds (Ref.575, Ref.576).

Also resist from H2O2 exposure (Ref.577, Ref.578).

Photoprotective activity - resist oxidative DNA damage from UV irradiation (Ref.577, Ref.578).

Radio protective activity - resist oxidative DNA damage from gamma irradiation (Ref.577, Ref.578).

13

13

4

4

2

0.000

54

80.920 Å²

Product: CR00210,  CR00354

Pathway: CB000097,  CB000098

Major carotenoid in extremely halophilic Archaea (Halobacterium salinarum strains NRC-1 and R1, Halorubrum sodomense, Haloarcula valismortis) and in Salinibacter ruber, a red extremely halophilic member of the Bacteria (Ref.737).

Ref.332: SUI Liying, LIU Liangsen, DENG Yuangao, Chinese Journal of Oceanology and Limnology, Vol. 32 No. 6, P. 1280-1287, 2014, "Characterization of halophilic C50 carotenoid-producing archaea isolated from solar saltworks in Bohai Bay, China".

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.389: Mandelli, Fernanda; Miranda, Viviane S.; Rodrigues, Eliseu; Mercadante, Adriana Z., World Journal of Microbiology & Biotechnology (2012), 28(4), 1781-1790., "Identification of carotenoids with high antioxidant capacity produced by extremophile microorganisms".

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.387: Strand, Aase; Shivaji, Sisinthy; Liaaen-Jensen, Synnove, Biochemical Systematics and Ecology (1997), 25(6), 547-552., "Bacterial carotenoids 55. C50-carotenoids 25. Revised structures of carotenoids associated with membranes in psychrotrophic Micrococcus roseus".

Ref.575: Yatsunami, R.; Ando, A.; Yang, Y.; Takaichi, S.; Kohno, M.; Matsumura, Y.; Ikeda, H.; Fukui, T.; Nakasone, K.; Fujita, N.; et al. Identification of carotenoids from the extremely halophilic archaeon Haloarcula japonica. Front. Microbiol. 2014, 5, 100–105..

Ref.576: Saito, T.; Miyabe, Y.; Ide, H.; Yamamoto, O. Hydroxyl radical scavenging ability of bacterioruberin. Radiat. Phys. Chem. 1997, 50, 267–269..

Ref.577: Shahmohammadi, H.R.; Asgarani, E.; Terato, H.; Saito, T.; Ohyama, Y.; Gekko, K.; Yamamoto, O.; Ide, H. Protective roles of bacterioruberin and intracellular KCl in the resistance of Halobacterium salinarium against DNA-damaging agents. J. Radiat. Res. 1998, 39, 251–262..

Ref.578: Kottemann, M.; Kish, A.; Iloanusi, C.; Bjork, S.; DiRuggiero, J. Physiological responses of the halophilic archaeon Halobacterium sp. strain NRC1 to desiccation and gamma irradiation. Extremophiles 2005, 9, 219–227..

Ref.737: Jehlička J, Edwards HG, Oren A., Spectrochim Acta A Mol Biomol Spectrosc. 2013 Apr;106:99-103., "Bacterioruberin and salinixanthin carotenoids of extremely halophilic Archaea and Bacteria: a Raman spectroscopic study.",doi: 10.1016/j.saa.2012.12.081.

32719-43-0

KNApSAcK: C00023099
ProCarDB: C1753