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Entry
CA00647                                                            
Classification
Carotenoid Name
Siphonaxanthin
IUPAC name (3R,3'R,6'R)-3,19,3'-Trihydroxy-7,8-dihydro-beta,epsilon-caroten-8-one
Formula
C40H56O4
Molecular Weight 
600.848 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Anticarcinogenic activity.
  • Effectively induces apoptosis in human leukemia (HL-60) cells via Bcl-2, caspase-3, GADD45α, and DR5 genes (Ref.682).
  • Anti-angiogenic activity (Ref.461).
  • Inhibitory effects on antigen-induced degranulation of mast cells (Ref.461).
  • The major carotenoid in the peripheral light­harvesting complexes (LHC) of photosystem II (PSII) in green algae (Ref.461).
    • Number of
    conjugated double bonds 
    9 including one ketone (9 in total)
    Number of
    conjugated multiple bonds 
    9 including one ketone (9 in total)
    Isomers 
    InChI

    InChIKey

    Canonical SMILES

    XLogP
    8.174
    Hydrogen Bond donors
    (Lipinski's definition)
    3
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    4
    LipinskiFailures
    2
    Complexity of molecule
    0.300
    Number of heavy atoms
    44
    TPSA
    (Topological Polar Surface Area) 
    77.760 Å2
    Reaction
  • Substrate: CR00285,  CR00286
  • Product: CR00246
    • Pathway
  • Pathway: CB000065,  CB000066
    • Major carotenoid information
    Dominant pigment in prasinophytes. (Ref.707).
    Minor carotenoid information
    Minor in chlorophytes. Also in siphonous green seaweeds (Ref.707).
    Source organisms
    Chlamydomonas parkeae (Ref.15) - Green alga: Chlamydomonadales, unicellular marine flagellate (Chlorophyta - Chlamydomonadaceae)
    Microdictyon boergesenii (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Anadyomenaceae)
    Cladophora coelothrix (Ref.24) - Green alga: Ulvophyceae (Chlorophyta - Cladophoraceae)
    References
  • 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.24: Y. Yoshii, I,. Wakana, K. Miriya, S. Arai, K. Ueda, and I. Inouye, J. Phycol. 40, 1170-1177 (2004) "Carotenoid comositions of Cladophora Balls (Aegagropila linnaei) and some members of the Cladophorales (Ulvophyceae, Chlorophyta): their taxonomic and evolutionary implication".
  • Ref.682: Ganesan P, Noda K, Manabe Y, Ohkubo T, Tanaka Y, Maoka T, Sugawara T, Hirata T., Biochim Biophys Acta. 2011 May;1810(5):497-503., "Siphonaxanthin, a marine carotenoid from green algae, effectively induces apoptosis in human leukemia (HL-60) cells.", PMID: 21371530 DOI: 10.1016/j.bbagen.2011.02.008.
  • Ref.461: Tatsuya Sugawara, Ponesakki Ganesan, Zhuosi Li, Yuki Manabe, and Takashi Hirata, Mar. Drugs 2014, 12(6), 3660-3668; doi:10.3390/md12063660, "Siphonaxanthin, a Green Algal Carotenoid, as a Novel Functional Compound".
  • 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.
    • CAS
    28526-44-5
    Links to other DB
    KNApSAcK: C00023022
    LipidBank: VCA1076

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