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Entry
CA01225                                                            
Classification
Carotenoid Name
Loliolide
IUPAC name 1,3-dihydroxy-3,5,5-trimethylcyclohexylidene-4-acetic acid lactone
Formula
C11H16O3
Molecular Weight 
196.238 g/mol
Structure      Search similar carotenoids

Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
  • Variety of biological properties such as anti-cancer, antibacterial, antifungal and antioxidant. Also used in alternative medicine in treatment of diabetes and depression (Ref.770).
  • Anti-inflammatory and antiaging activity (Ref.768).
  • Antiapoptosis and antiscratching effects on skin (Ref.768).
  • An allelochemical plant–plant communication (Ref.767).
  • Loliolide induce resistance to multiple herbivore pests through the activation of JA-independent defense responses (Ref.767).
  • A biomarker for photo-oxidative alterations of phytoplankton (Ref.769).
  • It is also regarded as monoterpenoid (Ref.770).
  • Loliolide was found in animals (insects) and plants (flowers, shrubs, trees) both terrestrial and marine, such as algae and corals. One of the most ubiquitous lactone (Ref.770).
    • Number of
    conjugated double bonds 
    2 including one lactone (2 in total)
    Number of
    conjugated multiple bonds 
    2 including one lactone (2 in total)
    Isomers 
    InChI

    InChIKey

    Canonical SMILES

    XLogP
    0.952
    Hydrogen Bond donors
    (Lipinski's definition)
    1
    Hydrogen Bond Acceptors
    (Lipinski's definition)
    3
    LipinskiFailures
    0
    Complexity of molecule
    0.300
    Number of heavy atoms
    14
    TPSA
    (Topological Polar Surface Area) 
    46.530 Å2
    Reaction
    Pathway
    Major carotenoid information

    Minor carotenoid information

    Source organisms
    Corallina pilulifera (Ref.769) - Red alga: Corallinaceae (Rhodophyta - Corallinaceae)
    Undaria pinnatifida (Ref.769) - Brown alga: Alariaceae ((Phaeophyceae) - Alariaceae)
    Padina tetrastromatica (Ref.769) - Brown alga: Dictyotaceae; ((Phaeophyceae) - Dictyotaceae)
    Cystophora moniliformis (Ref.769) - Brown alga: Sargassaceae ((Phaeophyceae) - Sargassaceae)
    Sargassum crassifolium (Ref.769) - Brown alga: Sargassaceae ((Phaeophyceae) - Sargassaceae)
    Dictyota dichotoma (Ref.769) - Brown alga: Dictyotaceae ((Phaeophyceae) - Dictyotaceae)
    Cladostephus spongiosus f. verticillatus (Ref.769) - Brown alga: Cladostephaceae ((Phaeophyceae) - Cladostephaceae)
    Fumaria officinalis (Ref.769) - Land plant: flowering plant, common fumitory, earth-smoke, wax-dolls (Streptophyta - Papaveraceae)
    References
  • Ref.769: Aline Percota, Ahmet Yalcin, Veysel Aysel, Huseyin Erdugan, Berrin Dural and Kas|m Cemal Guvenb, Natural Product Research Vol. 23, No. 5, 20 March 2009, 460–465, “Loliolide in marine algae”.
  • Ref.770: Malgorzata Grabarczyk et al., Folia Biologica et Oecologica 11: (2015), DOI: 10.1515/fobio-2015-0001, “Loliolide - the most ubiquitous lactone”.
  • Ref.768: Sang Hee Park et al., Int. J. Mol. Sci. 2019, 20, 651; doi:10.3390/ijms20030651, “Loliolide Presents Antiapoptosis and Antiscratching Effects in Human Keratinocytes”.
  • Ref.767: Mika Murata, Tetsuya Kobayashi and Shigemi Seo, Molecules 2020, 25, 17; doi:10.3390/molecules25010017, “α-Ionone, an Apocarotenoid, Induces Plant Resistance to Western Flower Thrips, Frankliniella occidentalis, Independently of Jasmonic Acid”.
    • CAS

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