Astaxantina
| Astaxantina | |
|---|---|
 | |
| Nomi alternativi | |
| 3,3'-diidrossi-β-carotene-4,4'-dione | |
| Caratteristiche generali | |
| Formula bruta o molecolare | C40H52O4 |
| Massa molecolare (u) | 596,84 |
| Aspetto | solido viola |
| Numero CAS | |
| Numero EINECS | 207-451-4 |
| PubChem | 5281224 |
| DrugBank | DBDB06543 |
| SMILES | CC1=C(C(CC(C1=O)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(C(=O)C(CC2(C)C)O)C)C)C |
| Proprietà chimico-fisiche | |
| Solubilità in acqua | insolubile |
| Indicazioni di sicurezza | |
| Frasi H | --- |
| Consigli P | --- [1] |
L'astaxantina (ASX) è un carotenoide di colore rosso-violaceo.
È presente, insieme ad altre molecole antiossidanti, nell'olio di krill (Euphausia superba) e nell'olio di Calanus finmarchicus.[2]
È responsabile del colore rosso della carne di alcuni pesci quali tonno, salmone, pesce spada, krill, gamberi.
Oltre alla funzione antiossidante[3][4] presenta proprietà di anti-infiammatorio e di protezione dai raggi UV. Come cantaxantina, luteina e zeaxantina, è fra i pochi carotenoidi in grado di superare la barriera ematoencefalica dei mammiferi – uomo incluso – nonché la barriera emato-retinica, fino a depositarsi nella retina[5]. Rispetto quindi alle altre forme di vitamina A, l'astaxantina è in grado di arrivare a svolgere la sua azione direttamente nell'occhio[6].
La prima fonte vegetale dell'astaxantina è l'Haematococcus pluvialis[7], un'alga unicellulare d'acqua dolce che, in condizioni ambientali che inducano stress ossidativo come acqua salata o elevata radiazione luminosa, produce autonomamente lipidi contenenti astaxantina naturale.
Note
- ^ Sigma Aldrich; rev. del 22.03.2013
- ^ Modifica del regolamento di esecuzione (UE) 2017/2470 per quanto riguarda le condizioni d’uso, i requisiti specifici di etichettatura e le specifiche del nuovo alimento olio di Calanus finmarchicus, su eur-lex.europa.eu.
- ^ H. D. Martin / C. Ruck / M. Schmidt / S. Sell / S. Beutner / B. Mayer / R. Walsh, Chemistry of carotenoid oxidation and free radical reactions, Pure and Applied Chemistry. Volume 71, Issue 12, Pages 2253–2262, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: 10.1351/pac199971122253, January 2009, Institute of Organic Chemistry and Macromolecular Chemistry presso University of Duesseldorf, D-40225 Duesseldorf, Germany, e Department of Chemistry, University of Reading, UK; pubblicato anche su 1999 IUPAC, Pure Appl. Chem. 71, 2253±2262, Great Britain
- ^ Quantitative assessment of antioxidantproperties of natural colorants andphytochemicals: carotenoids, flavonoids,phenols and indigoids. The role ofb-carotene inantioxidant functions, su Journal of the Science of Food and Agriculture, J Sci Food Agric 81:559±568 (online: 2001), 2001 Society of Chemical Industry. J Sci Food Agric 0022±5142/2001/: <<Three main categories of antioxidants may be classi®ed: (1) excellent antioxidants that perfectly quench excited states as well asground state radicals (eg actinioerythrol, astaxanthin); (2) good antioxidants that strongly inhibitperoxide formation but are less ef®cient in quenching excited states (eg ¯avonols, tocopherols) or leadto considerable degradation of the antioxidant itself (egb-carotene, lycopene); (3) moderateantioxidants that fail to excel in both reactivities (eg z-carotene, ¯avone)>>
- ^ Suppressive effect of astaxanthin on retinal injury induced by elevated intraocular pressure, su Regulatory Toxicology and Pharmacology, Volume 58, Issue 1, October 2010, Pages 121–130: condotto su topi a dosi di 5 mg/kg/day ASX per 8 settimane
- ^ Carotenoids in the retina — A review of their possible role in preventing or limiting damage caused by light and oxygen, su Chapter Free Radicals and Aging, Volume 62 of the series EXS pp 280-298, DOI 10.1007/978-3-0348-7460-1_29, Print ISBN 978-3-0348-7462-5: << This paper reviews the ideas that this concentration of dietary carotenoids in the macula is not accidental, but that their presence may prevent or limit damage due to their physicochemical properties and their capability to quench oxygen free radicals and singlet oxygen, which are generated in the retina as a consequence of the simultaneous presence of light and oxygen.>>
- ^ Haematococcus astaxanthin: applications for human health and nutrition, Mera Pharmaceuticals Inc., 73–4460 Queen Kaahumanu Hwy, Suite 110, Kailua-Kona, Hawaii 96740, USA, DOI: 10.1016/S0167-7799(03)00078-7
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