Chemical Synthesis of Astaxanthin n-Octanoic Acid Monoester and Diester and Evaluation of Their Oral Absorbability

Fukami, Hironobu; Namikawa, Koshi; Sugiura-Tomimori, Namino; Sumida, Motoo; Katano, Kenji; Nakao, Masahiro

doi:10.5650/jos.55.653

Cited by 24 publications

(24 citation statements)

References 9 publications

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“…Also, upon complexation, the electron-withdrawing effect of the positively charged metal ions should decrease the electron density on the cyclohexene ring. This decreased electron density increases the acidity of the astaxanthin, facilitating proton loss52 and the formation of mono and di-esters 53…”

Section: Discussionmentioning

confidence: 99%

Free Radical Formation in Novel Carotenoid Metal Ion Complexes of Astaxanthin

et al. 2010

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The carotenoid astaxanthin forms novel metal ion complexes with Ca2+, Zn2+ and Fe2+. MS and NMR measurements indicate that the two oxygen atoms on the terminal cyclohexene ring of astaxanthin chelate the metal to form 1:1 complexes with Ca2+ and Zn2+ at low salt concentrations < 0.2 mM. The stability constants of these complexes increased by a factor of 85 upon changing the solvent from acetonitrile to ethanol for Ca2+ and by a factor of 7 for Zn2+ as a consequence of acetonitrile being a part of the complex. Optical studies showed that at high concentrations (> 0.2 mM) of salt 2:1 metal:astaxanthin complexes were formed in ethanol. In the presence of Ca2+ and Zn2+ salts the lifetime of the radical cation and dication formed electrochemically decreased relative to that of the carotenoid neutral radical. DFT calculations showed that the deprotonation of the radical cation at the carbon C3 position resulted in the lowest energy neutral radical while proton loss at the C5, C9 or C13 methyl groups was less favorable. Pulsed EPR measurements were carried out on UV-produced radicals of astaxanthin supported on silica-alumina, MCM-41 or Ti-MCM-41. The pulsed EPR measurements detected the radical cation and neutral radicals formed by proton loss at 77 K from the C3, C5, C9, and C13-methyl groups and a radical anion formed by deprotonation of the neutral radical at C3. There was more than an order of magnitude increase in the concentration of radicals on Ti-MCM-41 relative to MCM-41, and the radical cation concentration exceeded that of the neutral radicals.

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Section: Discussionmentioning

confidence: 99%

Free Radical Formation in Novel Carotenoid Metal Ion Complexes of Astaxanthin

et al. 2010

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“…A similar degradation behavior was observed in other monoester species during boiling and frying in this study, confirming that the astaxanthin monoesters with saturated fatty acids have a better stability than those with EPA and DHA. Esterified carotenoids, including astaxanthin, composed of saturated fatty acids are more stable, being less prone to photo-and thermo-oxidative degradation and enzyme assisted decomposition 39 .…”

Section: Effects Of Thermal Processing On Astaxanthin Estersmentioning

confidence: 99%

Effect of Thermal Processing on Astaxanthin and Astaxanthin Esters in Pacific White Shrimp <i>Litopenaeus v</i><i>annamei</i>

et al. 2015

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“…AST esters are better absorbed in the small intestine than AST, have higher bioavailability, and accumulate more in various tissues [12][13][14]. Fukami et al synthesized astaxanthin n-octanoic acid esters, a type of medium-chain fatty acid esters, through chemical and enzymatic methods [10,15]. The metabolism of astaxanthin n-octanoic acid esters in blood and liver has been investigated, and it was found that the oral absorption of astaxanthin n-octanoic acid esters was better than that of AST or astaxanthin long-chain fatty acid ester mixture extracted from Haematococcus algae [15].…”

Section: Introductionmentioning

confidence: 99%

Astaxanthin n-Octanoic Acid Diester Ameliorates Insulin Resistance and Modulates Gut Microbiota in High-Fat and High-Sucrose Diet-Fed Mice

Gao

Yang

Chin

et al. 2020

IJMS

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Astaxanthin n-octanoic acid diester (AOD) is a type of astaxanthin connecting medium-chain fatty acids with a more stable structure. In this study, we examined the role of AOD in ameliorating insulin resistance (IR) induced by a high-fat and high-sucrose diet (HFD) as well as its effect on modulating gut microbiota in mice, with free astaxanthin (AST) as a comparison. Four groups of male C57BL/6J mice (6 weeks old; n = 10 per group) were fed with a normal control diet (NC), HFD orally administered with AOD, AST (50 mg/kg body weight), or vehicle for 8 weeks. AOD improved glucose tolerance, IR, systematic and intestinal inflammation, and intestinal integrity better than AST. Further, both AOD and AST modulated gut microbiota. A significantly higher abundance of Bacteroides and Coprococcus was found in AOD than in AST, and the predicted pathway of carbohydrate metabolism was significantly impacted by AOD. Overall, AOD may play a role in alleviating IR and inflammation with the modulating effect on microbiota in HFD-fed mice. Our findings could facilitate the development of AOD as a bioactive nutraceutical and more stable alternative to AST.

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Chemical Synthesis of Astaxanthin n-Octanoic Acid Monoester and Diester and Evaluation of Their Oral Absorbability

Cited by 24 publications

References 9 publications

Free Radical Formation in Novel Carotenoid Metal Ion Complexes of Astaxanthin

Free Radical Formation in Novel Carotenoid Metal Ion Complexes of Astaxanthin

Effect of Thermal Processing on Astaxanthin and Astaxanthin Esters in Pacific White Shrimp <i>Litopenaeus v</i><i>annamei</i>

Astaxanthin n-Octanoic Acid Diester Ameliorates Insulin Resistance and Modulates Gut Microbiota in High-Fat and High-Sucrose Diet-Fed Mice

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