Crocin

Last updated
Crocin
Crocin.png
Names
IUPAC name
Bis[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl] 8,8′-diapocarotene-8,8′-dioate
Systematic IUPAC name
Bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.050.783 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C44H64O24/c1-19(11-7-13-21(3)39(59)67-43-37(57)33(53)29(49)25(65-43)17-61-41-35(55)31(51)27(47)23(15-45)63-41)9-5-6-10-20(2)12-8-14-22(4)40(60)68-44-38(58)34(54)30(50)26(66-44)18-62-42-36(56)32(52)28(48)24(16-46)64-42/h5-14,23-38,41-58H,15-18H2,1-4H3/b6-5+,11-7+,12-8+,19-9+,20-10+,21-13+,22-14+/t23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37-,38-,41-,42-,43+,44+/m1/s1
    Key: SEBIKDIMAPSUBY-RTJKDTQDSA-N
  • InChI=1/C44H64O24/c1-19(11-7-13-21(3)39(59)67-43-37(57)33(53)29(49)25(65-43)17-61-41-35(55)31(51)27(47)23(15-45)63-41)9-5-6-10-20(2)12-8-14-22(4)40(60)68-44-38(58)34(54)30(50)26(66-44)18-62-42-36(56)32(52)28(48)24(16-46)64-42/h5-14,23-38,41-58H,15-18H2,1-4H3/b6-5+,11-7+,12-8+,19-9+,20-10+,21-13+,22-14+/t23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37-,38-,41-,42-,43+,44+/m1/s1
    Key: SEBIKDIMAPSUBY-RTJKDTQDBE
  • O=C(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)\C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(\C(=O)O[C@@H]4O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]4O)C)C)C)C
Properties
C44H64O24
Molar mass 976.972 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Crocin is a carotenoid chemical compound that is found in the flowers of crocus and gardenia. [1] Its oxygen content also chemically makes it a xanthene. Crocin is the chemical primarily responsible for the color of saffron.

Contents

Chemically, crocin is the diester formed from the disaccharide gentiobiose and the dicarboxylic acid crocetin. When isolated as a pure chemical compound, it has a deep red color and forms crystals with a melting point of 186 °C. When dissolved in water, it forms an orange solution.

The term crocins may also refer to members of a series of related hydrophilic carotenoids that are either monoglycosyl or diglycosyl polyene esters of crocetin. [2] The crocin underlying saffron's aroma is α-crocin (a carotenoid pigment that may compose more than 10% of dry saffron's mass): trans-crocetin di-(β-D-gentiobiosyl) ester; it bears the systematic (IUPAC) name 8,8-diapo-8,8-carotenoic acid. [2] :20

The major active component of saffron is the yellow pigment crocin 2 (three other derivatives with different glycosylations are known) containing a gentiobiose (disaccharide) group at each end of the molecule. The five major biologically active components of saffron, namely the four crocins and crocetin, can be measured with HPLC-UV. [3]

Research

Absorption

Crocin ingested orally is hydrolised to crocetin in the gut which is absorbed across the intestinal barrier, and that crocetin can permeate the blood–brain barrier. [4] [5]

Antioxidant

Crocin has been shown to be an antioxidant, [6] [7] and neural protective agent. [8] [9] Crocin can reduce oxidative stress and ROS (Reactive Oxygen Species) through enhancement of gene expression of Nrf2, HO-1, and anti-oxidant enzymes, such as CAT, GSH, and SOD. [10] [2] [7]

Neuroprotective

Crocin and its derivative crocetin may counteract oxidative stress, mitochondrial dysfunction and neuroinflammation, which are closely linked to initiation and progression of major brain pathologies such as Alzheimer's and Parkinson's disease. [11]

In an animal model of malathion-induced Parkinson's disease, crocin reduced the neurotoxic effect of malathion by its anti-apoptotic activity and it regulated the expression of proteins involved in Parkinson's disease pathogenesis. [12]

Crocins can suppress the active forms of GSK3β and ERK1/2 kinases, significantly reducing tau phosphorylation, thus suppressing key molecular pathways of Alzheimer's disease pathogenesis. [13]

Mood

Crocin displays possible antidepressant properties in mice [14] and humans. [15] [16] [17]

Cancer

Crocin has also shown antiproliferative action against cancer cells in vitro . [18] [19] [20] and in vivo . [21]

Crocin through the PI3K/AKT/mTOR, MAPK, VEGF, Wnt/β-catenin, and JAK-STAT suppression has antiproliferative properties. Also, the Nrf2 and p53 signaling pathway activation may be effective in the antiproliferative effect of crocin. [22]

Behavior

Aphrodisiac properties of crocin in male rats has been observed at very high doses. [23]

Retinal diseases

Emerging evidence highlights the cytoprotective, antioxidative, and anti-inflammatory potential of crocin in retinal tissue, which positions it as a promising candidate for enhancing vision and eye health. [24] Nevertheless, it's important to note that the majority of research has primarily focused on animal models, and there remains a shortage of robust clinical data to firmly establish the benefits of crocin in addressing eye health and related diseases. [25]

Related Research Articles

<span class="mw-page-title-main">Saffron</span> Spice made from crocus flowers

Saffron is a spice derived from the flower of Crocus sativus, commonly known as the "saffron crocus". The vivid crimson stigma and styles, called threads, are collected and dried for use mainly as a seasoning and colouring agent in food. The saffron crocus was slowly propagated throughout much of Eurasia and was later brought to parts of North Africa, North America, and Oceania.

<i>Crocus</i> Genus of flowering plants in the family Iridaceae

Crocus is a genus of seasonal flowering plants in the family Iridaceae comprising about 100 species of perennials growing from corms. They are low growing plants, whose flower stems remain underground, that bear relatively large white, yellow, orange or purple flowers and then become dormant after flowering. Many are cultivated for their flowers, appearing in autumn, winter, or spring. The flowers close at night and in overcast weather conditions. The crocus has been known throughout recorded history, mainly as the source of saffron. Saffron is obtained from the dried stigma of Crocus sativus, an autumn-blooming species. It is valued as a spice and dyestuff, and is one of the most expensive spices in the world. Iran is the center of saffron production. Crocuses are native to woodland, scrub, and meadows from sea level to alpine tundra from the Mediterranean, through North Africa, central and southern Europe, the islands of the Aegean, the Middle East and across Central Asia to Xinjiang in western China. Crocuses may be propagated from seed or from daughter cormels formed on the corm, that eventually produce mature plants. They arrived in Europe from Turkey in the 16th century and became valued as an ornamental flowering plant.

<span class="mw-page-title-main">Aminolevulinic acid</span> Endogenous non-proteinogenic amino acid

δ-Aminolevulinic acid, an endogenous non-proteinogenic amino acid, is the first compound in the porphyrin synthesis pathway, the pathway that leads to heme in mammals, as well as chlorophyll in plants.

In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups. The general molecular formula for dicarboxylic acids can be written as HO2C−R−CO2H, where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids.

<span class="mw-page-title-main">Neuroprotection</span> Relative preservation of neurons

Neuroprotection refers to the relative preservation of neuronal structure and/or function. In the case of an ongoing insult the relative preservation of neuronal integrity implies a reduction in the rate of neuronal loss over time, which can be expressed as a differential equation.

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

Zeaxanthin is one of the most common carotenoids in nature, and is used in the xanthophyll cycle. Synthesized in plants and some micro-organisms, it is the pigment that gives paprika, corn, saffron, goji (wolfberries), and many other plants and microbes their characteristic color.

mTOR Mammalian protein found in humans

The mammalian target of rapamycin (mTOR), also referred to as the mechanistic target of rapamycin, and sometimes called FK506-binding protein 12-rapamycin-associated protein 1 (FRAP1), is a kinase that in humans is encoded by the MTOR gene. mTOR is a member of the phosphatidylinositol 3-kinase-related kinase family of protein kinases.

<i>Crocus sativus</i> Species of flowering plant

Crocus sativus, commonly known as saffron crocus or autumn crocus, is a species of flowering plant in the iris family Iridaceae. A cormous autumn-flowering cultivated perennial, unknown in the wild, it is best known for the culinary use of its floral stigmas as the spice saffron. Human cultivation of saffron crocus and the trade and use of saffron have endured for more than 3,500 years and span different cultures, continents, and civilizations.

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

Safranal is an organic compound isolated from saffron, the spice consisting of the stigmas of crocus flowers. It is the constituent primarily responsible for the aroma of saffron.

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

Picrocrocin is a monoterpene glycoside precursor of safranal. It is found in the spice saffron, which comes from the crocus flower. Picrocrocin has a bitter taste, and is the chemical most responsible for the taste of saffron.

<i>Crocus cartwrightianus</i> Species of flowering plant

Crocus cartwrightianus is a species of flowering plant in the family Iridaceae. It is native to mainland Greece, Euboea, Crete, Skyros and some islands of the Cyclades. It is a cormous perennial growing to 5 cm (2 in). The flowers, in shades of lilac or white with purple veins and prominent red stigmas, appear with the leaves in autumn and winter.

<span class="mw-page-title-main">Crocetin</span> Carotenoid chemical compound

Crocetin is a natural apocarotenoid dicarboxylic acid that is found in the crocus flower together with its glycoside, crocin, and Gardenia jasminoides fruits. It is also known as crocetic acid. It forms brick red crystals with a melting point of 285 °C.

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

Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen.

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

Betulinic acid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch from which it gets its name, same as the bracket fungus Fomitopsis betulina, but also the ber tree, selfheal, the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas, a member of the persimmon family, Tetracera boiviniana, the jambul, flowering quince, rosemary, and Pulsatilla chinensis.

<span class="mw-page-title-main">NFE2L2</span> Human protein and coding gene

Nuclear factor erythroid 2-related factor 2 (NRF2), also known as nuclear factor erythroid-derived 2-like 2, is a transcription factor that in humans is encoded by the NFE2L2 gene. NRF2 is a basic leucine zipper (bZIP) protein that may regulate the expression of antioxidant proteins that protect against oxidative damage triggered by injury and inflammation, according to preliminary research. In vitro, NRF2 binds to antioxidant response elements (AREs) in the promoter regions of genes encoding cytoprotective proteins. NRF2 induces the expression of heme oxygenase 1 in vitro leading to an increase in phase II enzymes. NRF2 also inhibits the NLRP3 inflammasome.

<span class="mw-page-title-main">CUL3</span> Protein-coding gene in humans

Cullin 3 is a protein that in humans is encoded by the CUL3 gene.

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

Valorphin, also known as VV-hemorphin-5, is a naturally occurring, endogenous opioid heptapeptide of the hemorphin family with the amino acid sequence H-Val-Val-Tyr-Pro-Trp-Thr-Gln-OH (VVYPWTQ). It is produced in the body via proteolyic cleavage of residues 33-39 of the β-chain of hemoglobin. Valorphin binds preferentially to the μ-opioid receptor and produces effects such as analgesia and self-administration in animals. It also possesses cytotoxic and antiproliferative properties against tumor cells, the mediation of which, because they are reversed by naloxone, appears to be dependent on the opioid receptors.

An oxygen diffusion-enhancing compound is any substance that increases the availability of oxygen in body tissues by influencing the molecular structure of water in blood plasma and thereby promoting the movement (diffusion) of oxygen through plasma. Oxygen diffusion-enhancing compounds have shown promise in the treatment of conditions associated with hypoxia and ischemia. Such conditions include hemorrhagic shock, myocardial infarction, and stroke.

Crocetin glucosyltransferase is an enzyme with systematic name UDP-glucose:crocetin 8-O-D-glucosyltransferase. This enzyme catalyses the following chemical reaction

Saffron is one of the world's most expensive spices by weight due to its difficulty to harvest. Saffron consists of stigmas plucked from the vegetatively propagated and sterile Crocus sativus, known popularly as the saffron crocus. The resulting dried "threads" are distinguished by their bitter taste, hay-like fragrance, and slight metallic notes. The saffron crocus is unknown in the wild; its most likely precursor, Crocus cartwrightianus, originated in Crete or Central Asia; The saffron crocus is native to Southwest Asia, and is believed to have been first cultivated in Iran. Greece, Turkey, and India have also been suggested as possible sites of origin.

"Saffron, for example, was once less regarded than it is today because the crocus from which it is extracted was not particularly mysterious. It flourished in European locations extending from Asia Minor, where it originated, to Saffron Walden in England, where it was naturalised. Only subsequently, when its labour-intensive cultivation became largely centred in Kashmir, did it seem sufficiently exotic to qualify as one of the most precious of spices."

References

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Bibliography