Natural Products Insider

JUL-AUG 2018

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48 INSIDER July/August 2018 Astaxanthin Astaxanthin: A+ by Robin Koon Carotenoids belong to the category of lipid-soluble terpenes compounds (as a tetraterpenoid). There are more than 1,100 known carotenoid compounds, and they are split into two classes: carotenes (which are unoxygenated and include α-carotene, β-carotene and lycopene) and xanthophylls (which contain oxygen), such as astaxanthin, canthaxanthin, lutein and zeaxanthin. Carotenoids are found in high concentrations in plants, algae and microorganisms. Humans cannot synthesize them and therefore are required to ingest them in their diet. Astaxanthin (AX) Empirical formula: C40H52O4 Molecular weight: 596.84 g/mol (molar mass) Astaxanthin, a deep reddish-orange color compound, was fi rst identifi ed and isolated in 1938 by Richard Kuhn. He had a laboratory on the Neckar River (Germany). When studying lobsters to determine what gave them their color, he named the carotenoid astaxanthin—"asta" (from Astacus gammarus, the scientifi c name for lobster) and "xanthin" (from xanthophyll, which is the class in which astaxanthin belongs). Kuhn was awarded the 1938 Nobel Prize in chemistry for his work on carotenoids and vitamins. There are two forms of astaxanthin: free and esterifi ed. Astaxanthin may be esterifi ed with different fatty acids, such as palmitic, oleic, stearic or linoleic acid; it may also be free (with non-esterifi ed hydroxyl groups), but this makes it much more unstable and susceptible to oxidation. The esterifi ed form is reportedly the most predominant in nature and sold commercially; however, the free form can also be found. 1 Regardless of which form is ingested, only the free form is found in human blood. 2,3,4 Commercial astaxanthin is mainly derived from three sources: Xanthophyllomyces dendrorhous (yeast, formerly called Phaffi a rhodozyma), Haematococcus pluvialis (microalgae) and through chemical synthesis (synthetic). Natural astaxanthin is a carotenoid produced in microalgae, yeast, bacteria and fungi, and found in microalgae, yeast, salmon, trout, krill, lobster, shrimp, crayfi sh and crustaceans. In the aquatic environment, microalgae are consumed by zooplankton, insects or crustaceans, which accumulate astaxanthin and, in turn, are ingested by fi sh. Synthetic production of astaxanthin is not preferred in some cases because synthetic astaxanthin contains a racemic mixture of stereoisomers. It is produced chemically (synthesized by combining isophorone and C10-dialdehyde together in several reactive steps). Synthetic astaxanthin is non-esterifi ed, whereas astaxanthin in algae is always esterifi ed. Astaxanthin is primarily used as a dietary supplement for human consumption and as a feed supplement (pigmentation/ colorant) for salmon, crabs, shrimp, chickens and egg production. To date, more than 1,000 peer-reviewed papers published in scientifi c journals have studied the health effects of astaxanthin. Most of those research studies used dosages between 2 mg and 24 mg/d. Antioxidant Astaxanthin is a very strong antioxidant. The unique structure of astaxanthin allows it to span biological membranes and act as an antioxidant by reducing free radicals, therefore stabilizing them. 5,6 Astaxanthin as an antioxidant is 550 times stronger than vitamin E in singlet oxygen quenching. 7 Astaxanthin also improves plasma lipid antioxidant activity; the levels of blood plasma 12- and 15-hydroxy fatty acids lipids were reduced statistically and signifi cantly in the astaxanthin group. 8 Antihypertensive Effects In a double-blind, placebo-controlled study conducted in Japan, 20 healthy postmenopausal women who ingested 12 mg/d astaxanthin for four weeks experienced reductions of systolic and diastolic blood pressure by 7 percent and 4 percent, respectively. 9 Anti-infl ammatory Astaxanthin's anti-infl ammatory properties are closely related to its antioxidant activity. O OH OH O

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