Crocin
| Crocin | |
|---|---|
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| IUPAC name Bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioate | |
| Identifiers | |
| CAS number | 42553-65-1 |
| PubChem | 5281233 |
| ChemSpider | 4444645 |
| Jmol-3D images | {{#if: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|Image 1 |
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| Properties | |
| Molecular formula | C44H64O24 |
| Molar mass | 976.96 g mol−1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Crocin is a natural carotenoid chemical compound that is found in the flowers crocus and gardenia.[1] It is the diester formed from the disaccharide gentiobiose and the dicarboxylic acid crocetin. 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.
Crocin is the chemical ingredient primarily responsible for the color of saffron.
Physiological effects in mammalian tissues and organisms
Crocin has been shown to be a potent antioxidant.[2][3][4] It has also been shown to have an antiproliferative action against cancer cells in vitro.[5][6][7] Limited evidence suggests possible antidepressant properties of crocin in mice[8] and humans.[9] One study reports aphrodisiac properties in male rats at very high doses.[10]
References
- ↑ "Chemical Information". sun.ars-grin.gov. Retrieved 2008-03-02.
- ↑ Papandreou MA, Kanakis CD, Polissiou MG, Efthimiopoulos S, Cordopatis P, Margarity M, Lamari FN. (2006). "Inhibitory activity on amyloid-beta aggregation and antioxidant properties of Crocus sativus stigmas extract and its crocin constituents". J Agric Food Chem. 54 (23): 8762–8. doi:10.1021/jf061932a. PMID 17090119.
- ↑ Ochiai T et al. (2006). "Protective effects of carotenoids from saffron on neuronal injury in vitro and in vivo". Biochim Biophys Acta. 1770 (4): 578–584. doi:10.1016/j.bbagen.2006.11.012. PMID 17215084.
- ↑ Zheng YQ, Liu JX, Wang JN, Xu L. (2006). "Effects of crocin on reperfusion-induced oxidative/nitrative injury to cerebral microvessels after global cerebral ischemia". Brain Res. 1138: 86–94. doi:10.1016/j.brainres.2006.12.064. PMID 17274961.
- ↑ Escribano J, Alonso GL, Coca-Prados M, Fernandez JA. (1996). "Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro". Cancer Letters 100 (1–2): 22–30. doi:10.1016/0304-3835(95)04067-6. PMID 8620447.
- ↑ Chryssanthi DG, Lamari FN, Iatrou G, Pylara A, Karamanos NK, Cordopatis P. (2007). "Inhibition of breast cancer cell proliferation by style constituents of different Crocus species". Anticancer Research 27 (1A): 357–62. PMID 17352254.
- ↑ Abdullaev Jafarova F, Caballero-Ortega H, Riverón-Negrete L, Pereda-Miranda R, Rivera-Luna R, Manuel Hernández J, Pérez-López I, Espinosa-Aguirre JJ. (2002). "In vitro evaluation of the chemopreventive potential of saffron". Rev. Invest. Clin. 54 (5): 430–6. PMID 12587418.
- ↑ Hosseinzadeh, H; Jahanian, Z (2010). "Effect of Crocus sativus L. (saffron) stigma and its constituents, crocin and safranal, on morphine withdrawal syndrome in mice". Phytotherapy research : PTR 24 (5): 726–30. doi:10.1002/ptr.3011. PMID 19827024.
- ↑ Akhondzadeh, S; Fallah-Pour, H; Afkham, K; Jamshidi, AH; Khalighi-Cigaroudi, F (2004). "Comparison of Crocus sativus L. And imipramine in the treatment of mild to moderate depression: A pilot double-blind randomized trial ISRCTN45683816". BMC Complementary and Alternative Medicine 4: 12. doi:10.1186/1472-6882-4-12. PMC 517724. PMID 15341662.
- ↑ Hosseinzadeh H, Ziaee T, Sadeghi A (June 2008). "The effect of saffron, Crocus sativus stigma, extract and its constituents, safranal and crocin on sexual behaviors in normal male rats". Phytomedicine 15 (6–7): 491–5. doi:10.1016/j.phymed.2007.09.020. PMID 17962007.
See also
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