TITLE

Determination of astaxanthin and astaxanthin esters in the microalgae Haematococcus pluvialis by LC-(APCI)MS and characterization of predominant carotenoid isomers by NMR spectroscopy

AUTHOR(S)
Holtin, Karsten; Kuehnle, Maximilian; Rehbein, Jens; Schuler, Paul; Nicholson, Graeme; Albe, Klaus
PUB. DATE
November 2009
SOURCE
Analytical & Bioanalytical Chemistry;Nov2009, Vol. 395 Issue 6, p1613
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
The oily product ZANTHIN® consists of natural astaxanthin, which is manufactured from the microalgae Haematococcus pluvialis by supercritical CO2 extraction. An HPLC method was developed to separate all of the components of the complex astaxanthin extract using a C30 column. The separation resulted in different isomers of astaxanthin accompanied by two other carotenoids. The main component consisted of astaxanthin singly esterified with several different fatty acids. C18:3, C18:2, C18:1 and C16:0 were identified as the most commonly occurring fatty acids. Doubly esterified astaxanthin was also found, although in lower concentrations compared to singly esterified astaxanthin. After performing a detailed fatty acid analysis by GC-MS, the peaks from the extract were assigned via HPLC-MS. A trans to cis transmutation of the all- trans compound was performed by thermal treatment in order to obtain an enrichment of cis isomers as the basis for unambiguous identification via NMR experiments. The all- trans as well as the 9- and 13- cis isomers of astaxanthin were characterized in detail by UV/Vis, 1H, and 1H,1H COSY NMR spectroscopy.
ACCESSION #
44917212

 

Related Articles

  • Temperature-dependent molecular motions of saturated acyl cholesteryl esters: A 13C NMR study. Croll, David H.; Small, Donald M.; Hamilton, James A. // Journal of Chemical Physics;12/15/1986, Vol. 85 Issue 12, p7380 

    High resolution 13C NMR spectra were obtained vs temperature in the isotropic liquid and liquid-crystalline phases of four cholesteryl esters with saturated acyl chains [(6:0), (14:0), (16:0), and (18:0)] and a mixture rich in cholesteryl esters with unsaturated acyl chains [10% 16:0, 45% 18:1,...

  • Phylogenetic and molecular analysis of hydrogen-producing green algae. Timmins, Matthew; Thomas-Hall, Skye R.; Darling, Aaron; Zhang, Eugene; Hankamer, Ben; Marx, Ute C.; Schenk, Peer M. // Journal of Experimental Botany;Apr2009, Vol. 60 Issue 6, p1691 

    A select set of microalgae are reported to be able to catalyse photobiological H2 production from water. Based on the model organism Chlamydomonas reinhardtii, a method was developed for the screening of naturally occurring H2-producing microalgae. By purging algal cultures with N2 in the dark...

  • Preparation and Spectroscopic Characterization of 3'-Oxolutein. Molnár, Péter; Deli, József; Ősz, Erzsébet; Tóth, Gyula; Zsila, Ferenc; Herrero, Christian; Landrum, John T. // Letters in Organic Chemistry;Oct2006, Vol. 3 Issue 10, p723 

    In this study we report on the preparation of 3'-oxolutein (1) by MnO2- and NiO2-oxidation of lutein (2) and the complete structure elucidation of this carotenoid by spectroscopic (UV/VIS, IR, 1H-NMR, 13C-NMR, CD, MS) methods and chemical reaction (NaBH4 reduction). The complete assignment of...

  • Synthesis of Derivatives of 1-(9-Alkyl-9H-carbazol-3-yl)-4-carboxy-2-pyrrolidinones. Sapiyanskaite, B.; Mickevicius, V.; Mikulskene, G. // Chemistry of Heterocyclic Compounds;Sep2003, Vol. 39 Issue 9, p1142 

    Derivatives of 1-(9-alkyl-9H-carbazol-3-yl)-4-carboxy-2-pyrrolidinones (methyl esters, hydrazides) were synthesized. The condensation of the synthesized hydrazides with aromatic aldehydes, acetylacetone, and acetoacetic ester was studied. Structure of the obtained compounds was confirmed by IR...

  • Triterpene glycosides from Cussonia paniculata. III. Structure of glycosides I1, I2, J1a, J1b, J2, K, L1, and L2 from C. paniculata leaves. Dovgii, I. I.; Grishkovets, V. I.; Kachala, V. V.; Shashkov, A. S. // Chemistry of Natural Compounds;Mar2006, Vol. 42 Issue 2, p182 

    Structures of eight triterpene glycosides, of which the 28- O-(2- O-acetyl-and 3- O-acetyl- α-L-rhamnopyranosyl)-(1→4)- O- β-D-glucopyranosyl-(1→ 6)- O- β-D-glucopyranosyl esters of hederagenin 3- O- β-D-glucopyranosyl-(1→ 2)- O- α-L-arabinopyranoside (J1a and...

  • New long-chained feruloyl ester from the bark of Cedrelinga catenaeformis. El-Seedi, H. R. // Chemistry of Natural Compounds;May2007, Vol. 43 Issue 3, p256 

    Tetradecyl ferulate and a new n-alkyl ester of 3-hydroxy-4-methoxy- trans-cinnamate (hexacosanylisoferulate) have been isolated from Cedrelinga catenaeformis Duke (Leguminoseae). The structures were determined by 1D- and 2D-NMR spectroscopy, mass spectrometry, chemical transformations and...

  • Structural Characterization and Comparison of Switchgrass Ball-milled Lignin Before and After Dilute Acid Pretreatment. Samuel, Reichel; Pu, Yunqiao; Raman, Babu; Ragauskas, Arthur J. // Applied Biochemistry & Biotechnology;Sep2010, Vol. 162 Issue 1, p62 

    To reduce the recalcitrance and enhance enzymatic activity, dilute H2SO4 pretreatment was carried out on Alamo switchgrass ( Panicum virgatum). Ball-milled lignin was isolated from switchgrass before and after pretreatment. Its structure was characterized by 13C, HSQC, and 31P NMR spectroscopy....

  • Regioselectivity of Meisenheimer complexation in reaction of oxygen-centred nucleophiles with picryl aryl ethers: Polar vs. SET mechanisms. Buncel, Erwin; Dust, Julian M; Manderville, Richard A; Tarkka, Richard M // Canadian Journal of Chemistry;Jun2003, Vol. 81 Issue 6, p443 

    Picryl alkyl ethers react with hydroxide and methoxide ions to give regioisomeric Meisenheimer (anionic σ-) adducts; the C-3 adduct is kinetically favoured and the C-1 adduct is thermodynamically favoured (K3T1 behaviour). In the current 400 MHz NMR spectroscopic study of the reactions of two...

  • A new tigliane-type diterpene ester from Wikstroemia scytophylla. Jiang, He-Zhong; Ma, Qing-Yun; Huang, Sheng-Zhuo; Liang, Wen-Juan; Wang, Peng-Cheng; Zhao, You-Xing // Chemistry of Natural Compounds;Sep2012, Vol. 48 Issue 4, p587 

    A new tigliane-type diterpene ester, wiksphyllamin B ( 1), and one known compound, 12- O-benzoylphorbol 13-octanoate ( 2), were isolated from the stems of Wikstroemia scytophylla Diels. Their structures were identified using spectroscopic methods. The incorrect assignment of C NMR data of...

Share

Read the Article

Courtesy of THE LIBRARY OF VIRGINIA

Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics