Indicaxanthin

Indicaxanthin
Names
IUPAC name
4-[2-(2-Carboxy-pyrrolidin-1-yl)-vinyl]-2,3-dihydro-pyridine-2,6-dicarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C14H16N2O6/c17-12(18)9-6-8(7-10(15-9)13(19)20)3-5-16-4-1-2-11(16)14(21)22/h3,5-6,10-11H,1-2,4,7H2,(H3,17,18,19,20,21,22)/t10-,11-/m0/s1 checkY
    Key: RJIIQBYZGJSODH-QWRGUYRKSA-N checkY
  • InChI=1/C14H16N2O6/c17-12(18)9-6-8(7-10(15-9)13(19)20)3-5-16-4-1-2-11(16)14(21)22/h3,5-6,10-11H,1-2,4,7H2,(H3,17,18,19,20,21,22)/t10-,11-/m0/s1
    Key: RJIIQBYZGJSODH-QWRGUYRKBB
  • O=C(O)\C2=C\C(=C\C=[N+]1/[C@H](C([O-])=O)CCC1)C[C@@H](C(=O)O)N2
Properties
C14H16N2O6
Molar mass 308.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Indicaxanthin is a type of betaxanthin, a plant pigment present in beets, in Mirabilis jalapa flowers,[1] in cacti such as prickly pears (Opuntia sp.) or the red dragonfruit (Hylocereus costaricensis). It is a powerful antioxidant.

Medical uses

It has been shown in a spectrophotometric study for patients with thalassemia, that indicaxanthin can reduce perferryl-Hb generated in solution from met-Hb and hydrogen peroxide, more effectively than either trolox (a vitamin E derivative) or vitamin C, possibly interfering with perferryl-Hb, a reactive intermediate in the hydroperoxide-dependent Hb degradation.[2]

Indicaxanthin in antioxidant studies was more effective than Trolox at scavenging the ABTS cation radical.[3]

See also

References

  1. ^ Piattelli, M.; Minale, L.; Nicolaus, R.A. (1965). "Pigments of centrospermae—V. : Betaxanthins from Mirabilis jalapa L.". Phytochemistry. 4 (6): 817–23. doi:10.1016/S0031-9422(00)86258-5.
  2. ^ Tesoriere, L.; Allegra, M.; Butera, D.; Gentile, C.; Livrea, M. A. (2006). "Cytoprotective effects of the antioxidant phytochemical indicaxanthin in β-thalassemia red blood cells". Free Radical Research. 40 (7): 753–61. doi:10.1080/10715760600554228. PMID 16984002.
  3. ^ Butera, Daniela; Tesoriere, Luisa; Di Gaudio, Francesca; Bongiorno, Antonino; Allegra, Mario; Pintaudi, Anna Maria; Kohen, Rohn; Livrea, Maria A. (2002). "Antioxidant Activities of Sicilian Prickly Pear (Opuntia ficus indica) Fruit Extracts and Reducing Properties of Its Betalains: Betanin and Indicaxanthin". Journal of Agricultural and Food Chemistry. 50 (23): 6895–901. doi:10.1021/jf025696p. hdl:10447/107910. PMID 12405794.