Separation, Purification, and Identification of (3S,3′S)-trans-Astaxanthin fromHaematococcus pluvialis

Sun, Wenjing; Lin, Hong; Zhai, Yuxiu; Cao, Limin; Leng, Kailiang; Xing, Lihong

doi:10.1080/01496395.2014.976873

Cited by 25 publications

(20 citation statements)

References 26 publications

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“…For example, 3 S ,3′ S accounts for a large proportion of the isomers in H. pluvialis , whereas 3 R ,3′ R is more abundant than 3 S ,3′ S in Antarctic krill. 37,38 In the current study, hot-air drying decreased the 3 S ,3′ S ratio and increased the 3 S ,3′ R ratio. Liu et al 20 conducted in vitro and in vivo experiments and found that the antioxidation and antiageing activities of different stereoisomers of astaxanthin decreased in the order 3 S ,3′ S > 3 R ,3′ R > synthetic astaxanthin (3 S ,3′ S /3 S ,3′ R /3 R ,3′ R = 1:2:1).…”

Section: Resultssupporting

confidence: 50%

Effects of Drying Methods on the Content, Structural Isomers, and Composition of Astaxanthin in Antarctic Krill

Cong

Miao

Zhang³

et al. 2019

ACS Omega

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Antarctic krill (Euphausia superba) is one of the important bioresources in Antarctic waters, containing many bioactives (e.g., astaxanthin), which have a highly potential value for commercial exploitation. In this study, the effects of processing methods on the content, structural isomers, and composition of astaxanthins (free astaxanthin and astaxanthin esters) were studied. Three drying methods, comprising freeze-drying, microwave drying, and hot-air drying, were used. Free astaxanthin (Ast), astaxanthin monoesters (AM), and astaxanthin diesters (AD) in boiled krill (control) and dried krill were extracted and analyzed using high-resolution mass spectrometry with ultraviolet detection. After the three processes, total astaxanthin loss ranged from 8.6 to 64.9%, and the AM and AD contents ranged from 78.3 to 16.6 and 168.7 to 90.5 μg/g, respectively. Compared to other kinds of astaxanthin esters, astaxanthin esters, which linked to eicosapentaenoic acid and docosahexaenoic acid, as well as the Ast, were more easily degraded, and AM was more susceptible to degradation than AD. All-E-astaxanthin easily transformed to the 13Z-astaxanthin than to the 9Z-astaxanthin during the drying process, but the proportions of optical isomers changed due to drying by no more than 5%. The results suggested that freeze-drying, low-power microwave drying (≤1 kW), and low-temperature hot-air drying (≤60 °C) are optimal drying methods for ensuring the quality of krill products.

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Section: Resultssupporting

confidence: 50%

Effects of Drying Methods on the Content, Structural Isomers, and Composition of Astaxanthin in Antarctic Krill

Cong

Miao

Zhang³

et al. 2019

ACS Omega

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“…The one from H. pluvialis contains almost exclusively one isomer (3S,3′S-astaxanthin). 44 It was confirmed that this product contained 10% astaxanthin. The natural extract from H. pluvialis (sample 1 dissolved in acetone) was first converted to Ast-N by a transesterification reaction to remove the different fatty acids.…”

Section: Methodsmentioning

confidence: 82%

Chemical Transformation of Astaxanthin from Haematococcus pluvialis Improves Its Antioxidative and Anti-inflammatory Activities

Hwang

Kim

et al. 2020

ACS Omega

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Astaxanthin is a strong antioxidant, but the effect of esterification on its biological activities remains unclear. Here, we chemically synthesized three forms of astaxanthin (nonesterified (Ast-N), monoesterified (Ast-mE), and diesterified (Ast-dE) forms) using esterified astaxanthin (Ast-E) in natural extract from Haematococcus pluvialis and characterized them by spectrophotometry and high-performance liquid chromatography (HPLC). Additionally, the antioxidant and anti-inflammatory activities of the samples containing three forms of astaxanthin at different ratios were evaluated. The sample containing the maximum level of Ast-mE compared to those of Ast-N and Ast-dE showed the highest antioxidant and anti-inflammatory activities. We also observed the greatest increase in expression of genes related to antioxidant and anti-inflammatory effects in samples containing the highest Ast-mE. These results provide a foundation for in-depth investigation of astaxanthin and other antioxidant molecules, allowing for the development of a practical and cost-effective strategy to improve antioxidant or anti-inflammatory activities of natural extracts that can be used as dietary supplements.

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“…Astaxanthin has variable solubility in different organic solvents, in particular, in the order, from the highest to the lowest, dichloromethane > chloroform > acetonitrile > acetone (Mao et al ., ; Sun et al ., ) at room temperature. The comparison of the efficiency of different organic solvents for the extraction of astaxanthin esters and astaxanthin from the reaction medium was carried out by HPLC analysis and showed that ethyl acetate/ethanol mixture (1/1, v/v) allowed the highest extraction yield (Fig.…”

Section: Resultsmentioning

confidence: 97%

Highly efficient preparation of free all‐trans‐astaxanthin from Haematococcus pluvialis extract by a rapid biocatalytic method based on crude extracellular enzyme extract

Gao

Sun

Liu

et al. 2018

Int J of Food Sci Tech

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Summary A highly efficient, rapid, green and safe procedure for the preparation of free all‐trans‐astaxanthin from Haematococcus pluvialis algal extract, by a crude extracellular enzyme extract, was reported. The free all‐trans‐astaxanthin obtained by the biocatalysed method had fewer side products compared to the saponification procedure. Through single‐factor experiments and a Box–Behnken design, it was possible to find the optimal biocatalytic conditions for the hydrolysis of 2 mg of H. pluvialis oil with 14.7 mg (protein content) of lyophilised crude extracellular enzyme extract obtained from Pseudomonas aeruginosa. The reaction was carried out in 30 min at pH 9.16 and 36 °C, in 5.5 mL total reaction volume, under nitrogen atmosphere and dark conditions. The hydrolysis ratio of the astaxanthin esters was 98.72%, and the production of free all‐trans‐astaxanthin was 82.83 μg per mg of H. pluvialis oil. The method herein reported was simpler than other enzymatic methods previously described and allowed saving of time and costs.

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Separation, Purification, and Identification of (3S,3′S)-trans-Astaxanthin fromHaematococcus pluvialis

Cited by 25 publications

References 26 publications

Effects of Drying Methods on the Content, Structural Isomers, and Composition of Astaxanthin in Antarctic Krill

Effects of Drying Methods on the Content, Structural Isomers, and Composition of Astaxanthin in Antarctic Krill

Chemical Transformation of Astaxanthin from Haematococcus pluvialis Improves Its Antioxidative and Anti-inflammatory Activities

Highly efficient preparation of free all‐trans‐astaxanthin from Haematococcus pluvialis extract by a rapid biocatalytic method based on crude extracellular enzyme extract

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