Indicaxanthin

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Indicaxanthin
Indicaxanthin.svg
Names
IUPAC name
4-[2-(2-Carboxy-pyrrolidin-1-yl)-vinyl]-2,3-dihydro-pyridine-2,6-dicarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
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 Yes check.svgY
    Key: RJIIQBYZGJSODH-QWRGUYRKSA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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

Related Research Articles

Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. This can lead to polymerization and other chain reactions. They are frequently added to industrial products, such as fuels and lubricants, to prevent oxidation, and to foods to prevent spoilage, in particular the rancidification of oils and fats. In cells, antioxidants such as glutathione, mycothiol or bacillithiol, and enzyme systems like superoxide dismutase, can prevent damage from oxidative stress.

<span class="mw-page-title-main">Nopal</span> Fruit of the Opuntia cactus

Nopal is a common name in Spanish for Opuntia cacti, as well as for its pads.

<i>Mirabilis jalapa</i> Species of flower

Mirabilis jalapa, the marvel of Peru or four o'clock flower, is the most commonly grown ornamental species of Mirabilis plant, and is available in a range of colors. Mirabilis in Latin means wonderful and Jalapa is the state capital of Veracruz in México. Mirabilis jalapa was cultivated by the Aztecs for medicinal and ornamental purposes.

<i>Opuntia ficus-indica</i> Species of cactus

Opuntia ficus-indica, the Indian fig opuntia, fig opuntia, or prickly pear, is a species of cactus that has long been a domesticated crop plant grown in agricultural economies throughout arid and semiarid parts of the world. O. ficus-indica is the most widespread and most commercially important cactus. It is grown primarily as a fruit crop, and also for the vegetable nopales and other uses. Cacti are good crops for dry areas because they convert water into biomass efficiently. O. ficus-indica, as the most widespread of the long-domesticated cactuses, is as economically important as maize and blue agave in Mexico. Opuntia species hybridize easily, but the wild origin of O. ficus-indica is likely to have been in central Mexico where its closest genetic relatives are found.

<span class="mw-page-title-main">ABTS</span> Chemical compound

In biochemistry, ABTS is a chemical compound used to observe the reaction kinetics of specific enzymes. A common use for it is in the enzyme-linked immunosorbent assay (ELISA) to detect the binding of molecules to each other.

Oxygen radical absorbance capacity (ORAC) was a method of measuring antioxidant capacities in biological samples in vitro. Because no physiological proof in vivo existed in support of the free-radical theory or that ORAC provided information relevant to biological antioxidant potential, it was withdrawn in 2012.

Hemoglobin C is an abnormal hemoglobin in which glutamic acid residue at the 6th position of the β-globin chain is replaced with a lysine residue due to a point mutation in the HBB gene. People with one copy of the gene for hemoglobin C do not experience symptoms, but can pass the abnormal gene on to their children. Those with two copies of the gene are said to have hemoglobin C disease and can experience mild anemia. It is possible for a person to have both the gene for hemoglobin S and the gene for hemoglobin C; this state is called hemoglobin SC disease, and is generally more severe than hemoglobin C disease, but milder than sickle cell anemia.

<span class="mw-page-title-main">Antioxidant effect of polyphenols and natural phenols</span>

A polyphenol antioxidant is a hypothetical type of antioxidant containing a polyphenolic substructure and studied in vitro. Numbering over 4,000 distinct species mostly from plants, polyphenols may have antioxidant activity in vitro, but are unlikely to be antioxidants in vivo. Hypothetically, they may affect cell-to-cell signaling, receptor sensitivity, inflammatory enzyme activity or gene regulation, although high-quality clinical research has not confirmed any of these possible effects in humans as of 2020.

<span class="mw-page-title-main">Hemoglobin subunit beta</span> Mammalian protein found in Homo sapiens

Hemoglobin subunit beta is a globin protein, coded for by the HBB gene, which along with alpha globin (HBA), makes up the most common form of haemoglobin in adult humans, hemoglobin A (HbA). It is 147 amino acids long and has a molecular weight of 15,867 Da. Normal adult human HbA is a heterotetramer consisting of two alpha chains and two beta chains.

<i>Opuntia engelmannii</i> Species of cactus

Opuntia engelmannii is a prickly pear common across the south-central and Southwestern United States and northern Mexico. It goes by a variety of common names, including desert prickly pear, discus prickly pear, Engelmann's prickly pear in the US, and nopal, abrojo, joconostle, and vela de coyote in Mexico.

<span class="mw-page-title-main">Folin–Ciocalteu reagent</span>

The Folin–Ciocâlteu reagent (FCR) or Folin's phenol reagent or Folin–Denis reagent, is a mixture of phosphomolybdate and phosphotungstate used for the colorimetric in vitro assay of phenolic and polyphenolic antioxidants, also called the gallic acid equivalence method (GAE). It is named after Otto Folin, Vintilă Ciocâlteu, and Willey Glover Denis. The Folin-Denis reagent is prepared by mixing sodium tungstate and phosphomolybdic acid in phosphoric acid. The Folin–Ciocalteu reagent is just a modification of the Folin-Denis reagent. The modification consisted of the addition of lithium sulfate and bromine to the phosphotungstic-phosphomolybdic reagent.

<span class="mw-page-title-main">Betalain</span> Class of chemical compounds

Betalains are a class of red and yellow tyrosine-derived pigments found in plants of the order Caryophyllales, where they replace anthocyanin pigments. Betalains also occur in some higher order fungi. They are most often noticeable in the petals of flowers, but may color the fruits, leaves, stems, and roots of plants that contain them. They include pigments such as those found in beets.

<span class="mw-page-title-main">Cochineal</span> Species of insect producing the crimson dye carmine

The cochineal (, , is a scale insect in the suborder Sternorrhyncha, from which the natural dye carmine is derived. A primarily sessile parasite native to tropical and subtropical South America through North America, this insect lives on cacti in the genus Opuntia, feeding on plant moisture and nutrients. The insects are found on the pads of prickly pear cacti, collected by brushing them off the plants, and dried.

<span class="mw-page-title-main">Vulgaxanthin</span>

Vulgaxanthins are a group of betaxanthins, or the predominant yellow plant pigments found in red beets, among other plants like Mirabilis jalapa and swiss chard. They are antioxidant pigments, types I, II, III, IV, and V. Like all betaxanthins, they cannot be hydrolyzed by acid to aglycone without degradation. Water activity also affects stability of this antioxidant. It has been studied as a natural nutritional additive but instability remains a problem.

The Trolox equivalent antioxidant capacity (TEAC) assay measures the antioxidant capacity of a given substance, as compared to the standard, Trolox. Most commonly, antioxidant capacity is measured using the ABTS Decolorization Assay. Other antioxidant capacity assays which use Trolox as a standard include the diphenylpicrylhydrazyl (DPPH), oxygen radical absorbance capacity (ORAC) and ferric reducing ability of plasma (FRAP) assays. The TEAC assay is often used to measure the antioxidant capacity of foods, beverages and nutritional supplements.

<i>Opuntia</i> Genus of cactus

Opuntia, commonly called prickly pear or pear cactus, is a genus of flowering plants in the cactus family Cactaceae. Prickly pears are also known as tuna (fruit), sabra, nopal from the Nahuatl word nōpalli for the pads, or nostle, from the Nahuatl word nōchtli for the fruit; or paddle cactus. The genus is named for the Ancient Greek city of Opus, where, according to Theophrastus, an edible plant grew and could be propagated by rooting its leaves. The most common culinary species is the Indian fig opuntia (O. ficus-indica).

<span class="mw-page-title-main">Isorhamnetin</span> Chemical compound

Isorhamnetin is an O-methylated flavon-ol from the class of flavonoids. A common food source of this 3'-methoxylated derivative of quercetin and its glucoside conjugates are pungent yellow or red onions, in which it is a minor pigment, quercetin-3,4'-diglucoside and quercetin-4'-glucoside and the aglycone quercetin being the major pigments. Pears, olive oil, wine and tomato sauce are rich in isorhamnetin. Others sources include the spice, herbal medicinal and psychoactive Mexican tarragon (Tagetes lucida), which is described as accumulating isorhamnetin and its 7-O-glucoside derivate. Nopal is also a good source of isorhamnetin, which can be extracted by supercritical fluid extraction assisted by enzymes.

<i>Opuntia macrocentra</i> Species of cactus

Opuntia macrocentra, the long-spined purplish prickly pear or purple pricklypear, is a cactus found in the lower Southwestern United States and Northwestern Mexico. A member of the prickly pear genus, this species of Opuntia is most notable as one of a few cacti that produce a purple pigmentation in the stem. Other common names for this plant include black-spined pricklypear, long-spine prickly pear, purple pricklypear, and redeye prickly pear.

Opuntia matudae, or xoconostle, is a cactus native to Mexico. It is sometimes treated as a synonym of Opuntia hyptiacantha. In 2019, a genetic study supported keeping the taxa distinct.

Treatment of the inherited blood disorder thalassemia depends upon the level of severity. For mild forms of the condition, advice and counseling are often all that are necessary. For more severe forms, treatment may consist in blood transfusion; chelation therapy to reverse iron overload, using drugs such as deferoxamine, deferiprone, or deferasirox; medication with the antioxidant indicaxanthin to prevent the breakdown of hemoglobin; or a bone marrow transplant using material from a compatible donor, or from the patient's mother. Removal of the spleen (splenectomy) could theoretically help to reduce the need for blood transfusions in people with thalassaemia major or intermedia but there is currently no reliable evidence from clinical trials about its effects. Population screening has had some success as a preventive measure.

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.