Synthesis, stability and bioavailability of astaxanthin succinate diester

Xiao, Qiao; Yang, Lu; Zhang, Ting; Qingxin, Zhou; Wang, Yuming; Xu, Jie; Xue, Changhu

doi:10.1002/jsfa.8824

Cited by 18 publications

(33 citation statements)

References 39 publications

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“…Therefore, in nature, it is either conjugated with proteins or esterified with one or two fatty acids (monoester or diester) to be more stable [11]. 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].…”

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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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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“…okada et al (38) showed that the metabolism of aST in a group of smokers was faster compared with the non-smokers group, which may be attributed to the antioxidant effect of aST. a previous study found that dietary oils may enhance the absorption of aST bioavailability in humans (39). in addition, Mercke et al (40) determined the bioavailability of aST from H. pluvialis dispersed in synthetic hydrophilic surfactant polysorbate 80 (B), which is a lipid-based formulation, was 1.7-3.7 times higher compared with the commercial formulation.…”

Section: Discussionmentioning

confidence: 98%

Attenuation of the Na/K‑ATPase/Src/ROS amplification signaling pathway by astaxanthin ameliorates myocardial cell oxidative stress injury

Zhang

et al. 2020

Mol Med Rep

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The 3S, 3'S-aSTaxanthin (3S, 3'S-aST) isomer has strong antioxidant activity; however, its protective roles and potential mechanisms against oxidative stress damage in cardiomyocytes have not been investigated. na + /K + -aTPase (nKa)/Src signal activation has an important role in increasing reactive oxygen species (roS) production. The aim of the present study was to investigate the protective effects and mechanism of 3S, 3'S-aST on hydrogen peroxide (H 2 o 2 )-induced oxidative stress injury in H9c2 myocardial cells. The protective effects of 3S, 3'S-aST on H 2 o 2 -induced H9c2 cell injury was observed by measuring lactate dehydrogenase and creatine kinase myocardial band content, cell viability and nuclear morphology. The antioxidant effect was investigated by analyzing roS accumulation and malondialdehyde, glutathione (GSH) peroxidase, GSH and glutathione reductase activity levels. The protein expression levels of Bax, Bcl-2, caspase-3 and cleaved caspase-3 were analyzed using western blotting to determine cardiomyocyte apoptosis. Western blot analysis of the phosphorylation levels of Src and erk1/2 were also performed to elucidate the molecular mechanism involved. The results showed that 3S, 3'S-aST reduced the release of ldH and promoted cell viability, and attenuated roS accumulation and cell apoptosis induced by H 2 o 2 . Furthermore, 3S, 3'S-aST also restored apoptosis-related Bax and Bcl-2 protein expression levels in H 2 o 2 -treated H9c2 cells. The phosphorylation levels of Src and Erk1/2 were significantly higher in the H 2 o 2 treatment group, whereas 3S, 3'S-AST pretreatment significantly decreased the levels of phosphorylated (p)-Src and p-erK1/2. The results provided evidence that 3S, 3'S-aST exhibited a cardioprotective effect against oxidative stress injury by attenuating NKA/Src/Erk1/2-modulated ROS amplification.

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“…Bioavailability of astaxanthin can be enhanced by the formation of an ester by conjugating it with succinic anhydride. Astaxanthin succinate diester is more thermally stable and bioavailable to the body tissues than ree astaxanthin (Qiao et al, 2018).…”

Section: B I O -Avail Ab Ilit Y and Source S Of A S Ta X Anthinmentioning

confidence: 98%

Mechanistic role of astaxanthin derived from shrimp against certain metabolic disorders

Yaqoob

Arshad

Imran

et al. 2021

Food Science & Nutrition

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Metabolic syndrome are a cluster of metabolic disorders in the same individual. The primary agreement concerning the description of the metabolic syndrome was established by the International Diabetes Federation (IDF) in the year of 2005. According to IDF, the main risk factor is obesity which is calculated based on body mass index (BMI) and waist circumference. The additional factors for the diagnosis of metabolic syndrome are reduced high-density lipoprotein (HDL) cholesterol, fasting plasma glucose, triglycerides, or blood pressure-. The patho physiology of metabolic syndrome is very composite and is not clearly established. The prevalence of metabolic syndrome is high among those individuals who are older, obese, having insulin resistance, and living a sedentary life style. The main risk factors are excess caloric intake, genetics, weight, lifestyle, and aging (Bonomini et al., 2015).Metabolic syndrome and the risk factors associated with this syndrome such as atherosclerosis, hypertension, dyslipidemia, and hyperglycemia are the main reasons for increasing medical issues in industrialized countries. The main risk factors for rising metabolic syndrome are physical immobility and a diet high in carbohydrates and fats (O'Neill & O'Driscoll, 2015). Oxidative stress is the main reason that causes metabolic syndrome (Furukawa et al., 2017).Oxidative stress leads elevationed intracellular stage reactive oxygen species (ROS) that causes damage to DNA, proteins, and lipids.Oxidative stress is associated with numerous pathologies (Schieber

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Synthesis, stability and bioavailability of astaxanthin succinate diester

Cited by 18 publications

References 39 publications

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

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

Attenuation of the Na/K‑ATPase/Src/ROS amplification signaling pathway by astaxanthin ameliorates myocardial cell oxidative stress injury

Mechanistic role of astaxanthin derived from shrimp against certain metabolic disorders

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