Science.gov

Sample records for astaxanthin chiral isomers

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

    PubMed

    Holtin, Karsten; Kuehnle, Maximilian; Rehbein, Jens; Schuler, Paul; Nicholson, Graeme; Albert, Klaus

    2009-11-01

    The oily product ZANTHIN consists of natural astaxanthin, which is manufactured from the microalgae Haematococcus pluvialis by supercritical CO(2) extraction. An HPLC method was developed to separate all of the components of the complex astaxanthin extract using a C(30) 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, (1)H, and (1)H,(1)H COSY NMR spectroscopy. PMID:19466394

  2. Identification of geometrical isomers and comparison of different isomeric samples of astaxanthin.

    PubMed

    Qiu, Dan; Wu, Yue-Chan; Zhu, Wen-Li; Yin, Hong; Yi, Long-Tao

    2012-09-01

    A high-performance liquid chromatographic (HPLC) analysis system for isomeric astaxanthin was developed. The separation system consisted of a C(30) column and an elution system of methanol/MTBE/water/dichloromethane (77:13:8:2, v/v/v/v). Using the combination of HPLC diode array detector and HPLC atmospheric pressure chemical ionization mass spectrometry, 11 geometrical isomers and 4 epoxides of astaxanthin were successfully identified. Referred to crystal, only isomerization with different degrees was found for solvent dissolving and iodine catalysis, while melting of astaxanthin caused isomerization, slight oxidation, and more noticeable polymerization confirmed by gel permeation chromatography. Chemical changes in isomeric samples all caused a decrease in UV content. The vibrational spectra (infrared and Raman) showed that epoxide was the only new functional group generated for melting. Changes of several key bands and formations of new bands were found in iodine catalysis and melting samples because of isomerization. Practical Application:  Eleven geometrical isomers and 4 epoxides, which were normally generated for solvent dissolving, iodine catalysis, and melting of astaxanthin, have been identified by C(30) -HPLC-MS technology. Furthermore, different samples were measured by gel permeation chromatography, UV, infrared, and Raman, based on the analysis of messages, the effect of each processing was well understood. PMID:22900833

  3. Condensations of single DNA molecules induced by heptaplatin and its chiral isomer

    SciTech Connect

    Zhang, Hong-Yan; Liu, Yu-Ru; Li, Wei; Li, Hui; Dou, Shuo-Xing; Xie, Ping; Wang, Wei-Chi; Wang, Peng-Ye

    2014-08-15

    Heptaplatin is a third-generation platinum antitumor drug. It has a chiral isomer. We studied the interactions between the two isomers and DNA by using magnetic tweezers and atomic force microscopy (AFM) to investigate the effect of chiralities of the isomers on the interactions. We found that the extension curves and average condensation rates of DNA molecules incubated with heptaplatin were nearly the same as those incubated with its chiral isomer. In addition, the structures of DNA molecules incubated with heptaplatin were also similar to those incubated with its chiral isomer. These results indicate the difference in chirality of the two isomers does not induce different interactions of the isomers with DNA. Our study may facilitate the understanding of interactions of platinum complexes with DNA and the design of new antitumor platinum complexes.

  4. Enumeration of chiral and positional isomers of substituted fullerene cages (C[sub 20]-C[sub 70])

    SciTech Connect

    Balasubramanian, K. )

    1993-07-08

    Enumeration of chiral isomers of substituted fullerene cages (C[sub 20]-C[sub 70]) is considered using the generalized character cycle index (GCCI) of the alternating representation of the point group of the parent cage. It is shown that there are no chiral isomers for the monsubstituted C[sub 20], C[sub 24], C[sub 28], C[sub 30], C[sub 36], and C[sub 60] fullerene cages but there are chiral isomers for other monosubstituted cages. All cages considered here possess chiral isomers for disubstituted cages. It is shown that the number of positional isomers can be obtained using the GCCI of the totally symmetric representation. We also enumerate the [sup 13]C NMR signals of all fullerene cages C[sub 20]-C[sub 70]. 30 refs., 4 figs., 6 tabs.

  5. Chiral separation of deprenyl-N-oxide isomers by capillary electrophoresis using various cyclodextrin derivatives.

    PubMed

    Tábi, Tamás; Halász, Attila Sándor; Pálfi, Melinda; Magyar, Kálmán; Szöko, Eva

    2004-01-01

    Chiral separation of deprenyl-N-oxide isomers is presented using capillary electrophoresis in the presence of various cyclodextrin (CD) derivatives. This recently identified metabolite of R-(-)-deprenyl may possess desirable pharmacological activities. The effect of the cavity size and the substituents of the CD are examined on the enantiomer resolution of the compound having an asymmetric center on a heteroatom. The importance of hydrophilic or hydrogen bonding interaction, as well as the position of the interacting groups is demonstrated. Outstanding selectivity and resolution values are achieved using the chargeable carboxymethyl-beta-CD. 2-Hydroxypropyl-beta-CD is also suitable for the enantiomer separation of the analyte. Native beta-CD and carboxyethyl-beta-CD provide only poor enantioselectivity, whereas heptakis-(2,6-di-O-methyl)-beta-CD is capable of separating only the diastereomers. No chiral resolution can be observed in the presence of gamma-CD. PMID:14965411

  6. Spectroscopic investigations of the chiral interactions of metolachlor and its (S)-isomer with lipase and phosphatase.

    PubMed

    Wen, Yue Z; Yuan, Yu L; Chen, Hui; Wang, He L; Liu, Hui J; Kang, Xiao D; Fu, Liu S

    2010-04-01

    Metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] is a chiral acetanilide herbicide. We investigated its enantioselective interactions, and that of its (S)-isomer, with Penicillium expansum alkaline lipase and phosphatase. UV differential spectroscopy and fluorescence spectrophotometry studies were conducted in phosphate buffered solution at pH 7. Chiral differences in the UV absorption and fluorescence spectra of lipase and phosphatase with metolachlor and its (S)-isomer were detected. The results showed that the interactions of metolachlor and its (S)-isomer with lipase and phosphatase occur statically through complex formation, and enantioselectivity was clearly observed. In addition, both UV absorption and fluorescence spectrophotometry showed that the (S)-isomer interacted more strongly with lipase and phosphatase than metolachlor. PMID:20390958

  7. Effect of thermal processing on astaxanthin and astaxanthin esters in pacific white shrimp Litopenaeus vannamei.

    PubMed

    Yang, Shu; Zhou, Qingxin; Yang, Lu; Xue, Yong; Xu, Jie; Xue, Changhu

    2015-01-01

    The red color of processed shrimp, one of the most attractive attributes and an important criterion for consumers, is often limited by thermal processing (microwaving, boiling and frying), due to astaxanthin degradation. The effect of thermal processing on astaxanthin in Pacific white shrimp (Litopenaeus vannamei) were investigated. A High-performance liquid chromatographic - atmospheric pressure chemical ionization mass spectrometry (LC-(APCI)-MS/MS) method was used to identify and quantify all-trans- and cis-isomers of astaxanthin, and molecular species of astaxanthin esters in fresh and thermal processed shrimps. Total astaxanthin loss ranged from 7.99% to 52.01% in first 3 min under three thermal processing. All-trans-astaxanthin was most affected, with a reduction from 32.81 to 8.72 μg kg(-1), while 13-cis-astxanthin had a rise (from 2.38 to 4.58 μg kg(-1)). Esterified astaxanthin was shown to hydrolyze and degrade, furthermore astaxanthin diesters had a better thermostability compare to astaxanthin monoesters. Astaxanthin monoesters with eicosapntemacnioc acid (EPA, C20:5) and docosahexaenoic acid (DHA, C22:6), had a lower thermal stability than those with saturated fatty acids, however, it was the opposite of astaxanthin diesters. The findings suggested that the method of thermal processing should be carefully used in the manufacturing and domestic cooking of shrimps. The results also could be useful in calculating the dietary intake of astaxanthin and in assessing astaxanthin profiles and contents of shrimp containing products. PMID:25757428

  8. Chirality at metal and helical ligand folding in optical isomers of chiral bis(naphthaldiminato)nickel(II) complexes.

    PubMed

    Enamullah, Mohammed; Quddus, Mohammad Abdul; Hasan, Mohammad Rezabul; Pescitelli, Gennaro; Berardozzi, Roberto; Makhloufi, Gamall; Vasylyeva, Vera; Janiak, Christoph

    2016-01-14

    Enantiopure bis[{(R or S)-N-1-(Ar)ethyl-2-oxo-1-naphthaldiminato-κ(2)N,O}]nickel(ii) complexes {Ar = C6H5 ( or ), p-OMeC6H4 ( or ), and p-BrC6H4 ( or )} are synthesized from the reactions between (R or S)-N-1-(Ar)ethyl-2-oxo-1-naphthaldimine and nickel(ii) acetate. Circular-dichroism spectra and their density-functional theoretical simulation reveal the expected mirror image relationship between the enantiomeric pairs / and / in solution. CD spectra are dominated by the metal-centered Λ- or Δ-chirality of non-planar four-coordinated nickel, this latter being in turn dictated by the ligand chirality. Single crystal structure determination for and shows that there are two symmetry-independent molecules (A and B) in each asymmetric unit that give a Z' = 2 structure. Two asymmetric and chiral bidentate N^O-chelate Schiff base ligands coordinate to the nickel atom in a distorted square planar N2O2-coordination sphere. The conformational difference between the symmetry-independent molecules arises from the "up-or-down" folding of the naphthaldiminato ligand with respect to the coordination plane, which creates right- (P) or left-handed (M) helical conformations. Overall, the combination of ligand chirality, chirality at the metal and ligand folding gives rise to discrete metal helicates of preferred helicity in a selective way. Cyclic voltammograms (CV) show an oxidation wave at ca. 1.30 V for the [Ni(L)2]/[Ni(L)2](+) couple, and a reduction wave at ca. -0.35 V for the [Ni(L)2]/[Ni(L)2](-) couple in acetonitrile. PMID:26619269

  9. Perfluorooctane sulfonate: a review of human exposure, biomonitoring and the environmental forensics utility of its chirality and isomer distribution.

    PubMed

    Miralles-Marco, Ana; Harrad, Stuart

    2015-04-01

    Perfluorooctane sulfonate (PFOS) found extensive use for over 60 years up until its restriction in the early 2000s, culminating in its listing under the Stockholm Convention on Persistent Organic Pollutants (POPs) in 2009. Efforts to minimise human body burdens are hindered by uncertainty over their precise origins. While diet appears the principal source for the majority of western populations (with other pathways like dust ingestion, drinking water and inhalation also important contributors); the role played by exposure to PFOS-precursor compounds followed by in vivo metabolism to PFOS as the ultimate highly stable end-product is unclear. Such PFOS-precursor compounds include perfluorooctane sulfonamide derivates, e.g., perfluorooctane sulfonamides (FOSAs) and sulfonamidoethanols (FOSEs). Understanding the indirect contribution of such precursors to human body burdens of PFOS is important as a significant contribution from this pathway would render the margin of safety between the current exposure limits and estimates of external exposure to PFOS alone, narrower than hitherto appreciated. Estimates derived from mathematical modelling studies, put the contribution of so-called "precursor exposure" at between 10% and 40% of total PFOS body burdens. However, there are substantial uncertainties associated with such approaches. This paper reviews current understanding of human exposure to PFOS, with particular reference to recent research highlighting the potential of environmental forensics approaches based on the relative abundance and chiral signatures of branched chain PFOS isomers to provide definitive insights into the role played by "precursor exposure". PMID:25728452

  10. Capillary electrophoretic enantioseparation of basic drugs using a new single-isomer cyclodextrin derivative and theoretical study of the chiral recognition mechanism.

    PubMed

    Liu, Yongjing; Deng, Miaoduo; Yu, Jia; Jiang, Zhen; Guo, Xingjie

    2016-05-01

    A novel single-isomer cyclodextrin derivative, heptakis {2,6-di-O-[3-(1,3-dicarboxyl propylamino)-2-hydroxypropyl]}-β-cyclodextrin (glutamic acid-β-cyclodextrin) was synthesized and used as a chiral selector in capillary electrophoresis for the enantioseparation of 12 basic drugs, including terbutaline, clorprenaline, tulobuterol, clenbuterol, procaterol, carvedilol, econazole, miconazole, homatropine methyl bromide, brompheniramine, chlorpheniramine and pheniramine. The primary factors affecting separation efficiency, which include the background electrolyte pH, the concentration of glutamic acid-β-cyclodextrin and phosphate buffer concentration, were investigated. Satisfactory enantioseparations were obtained using an uncoated fused-silica capillary of 50 cm (effective length 40 cm) × 50 μm id with 120 mM phosphate buffer (pH 2.5-4.0) containing 0.5-4.5 mM glutamic acid-β-cyclodextrin as background electrolyte. A voltage of 20 kV was applied and the capillary temperature was kept at 20°C. The results proved that glutamic acid-β-cyclodextrin was an effective chiral selector for studied 12 basic drugs. Moreover, the possible chiral recognition mechanism of brompheniramine, chlorpheniramine and pheniramine on glutamic acid-β-cyclodextrin was investigated using the semi-empirical Parametric Method 3. PMID:26935589

  11. Chromatographic, NMR and vibrational spectroscopic investigations of astaxanthin esters: application to "Astaxanthin-rich shrimp oil" obtained from processing of Nordic shrimps.

    PubMed

    Subramanian, B; Thibault, M-H; Djaoued, Y; Pelletier, C; Touaibia, M; Tchoukanova, N

    2015-11-01

    Astaxanthin (ASTX) is a keto carotenoid, which possesses a non-polar linear central conjugated chain and polar β-ionone rings with ketone and hydroxyl groups at the extreme ends. It is well known as a super anti-oxidant, and recent clinical studies have established its nutritional benefits. Although it occurs in several forms, including free molecule, crystalline, aggregates and various geometrical isomers, in nature it exists primarily in the form of esters. Marine animals accumulate ASTX from primary sources such as algae. Nordic shrimps (P. borealis), which are harvested widely in the Atlantic Ocean, form a major source of astaxanthin esters. "Astaxanthin-rich shrimp oil" was developed as a novel product in a shrimp processing plant in Eastern Canada. A compositional analysis of the shrimp oil was performed, with a view to possibly use it as a nutraceutical product for humans and animals. Astaxanthin-rich shrimp oil contains 50% MUFAs and 22% PUFAs, of which 20% are omega-3. In addition, the shrimp oil contains interesting amounts of EPA and DHA, with 10%/w and 8%/w, respectively. Astaxanthin concentrations varied between 400 and 1000 ppm, depending on the harvesting season of the shrimp. Astaxanthin and its esters were isolated from the oil and analysed by NMR, FTIR and Micro-Raman spectroscopy. Astaxanthin mono- and diesters were synthesized and used as standards for the analysis of astaxanthin-rich shrimp oil. NMR and vibrational spectroscopy techniques were successfully used for the rapid characterization of monoesters and diesters of astaxanthin. Raman spectroscopy provided important intermolecular interactions present in the esterified forms of astaxanthin molecules. Also discussed in this paper is the use of NMR, FTIR and Micro-Raman spectroscopy for the detection of astaxanthin esters in shrimp oil. PMID:26393239

  12. Chiral recognition of pinacidil and its 3-pyridyl isomer by canine cardiac and smooth muscle: Antagonism by sulfonylureas

    SciTech Connect

    Steinberg, M.I.; Wiest, S.A.; Zimmerman, K.M.; Ertel, P.J.; Bemis, K.G.; Robertson, D.W. )

    1991-01-01

    Pinacidil, a potassium channel opener (PCO), relaxes vascular smooth muscle by increasing potassium ion membrane conductance, thereby causing membrane hyperpolarization. PCOs also act on cardiac muscle to decrease action potential duration (APD) selectively. To examine the enantiomeric selectivity of pinacidil, the stereoisomers of pinacidil (a 4-pyridylcyanoguanidine) and its 3-pyridyl isomer (LY222675) were synthesized and studied in canine Purkinje fibers and cephalic veins. The (-)-enantiomers of both pinacidil and LY222675 were more potent in relaxing phenylephrine-contracted cephalic veins and decreasing APD than were their corresponding (+)-enantiomers. The EC50 values for (-)-pinacidil and (-)-LY222675 in relaxing cephalic veins were 0.44 and 0.09 microM, respectively. In decreasing APD, the EC50 values were 3.2 microM for (-)-pinacidil and 0.43 microM for (-)-LY222675. The eudismic ratio was greater for the 3-pyridyl isomer than for pinacidil in both cardiac (71 vs. 22) and vascular (53 vs. 17) tissues. (-)-LY222675 and (-)-pinacidil (0.1-30 microM) also increased 86Rb efflux from cephalic veins to a greater extent than did their respective optical antipodes. The antidiabetic sulfonylurea, glyburide (1-30 microM), shifted the vascular concentration-response curve of (-)-pinacidil to the right by a similar extent at each inhibitor concentration. Glipizide also antagonized the response to (-)-pinacidil, but was about 1/10 as potent with a maximal shift occurring at 10 and 30 microM. Glyburide antagonized the vascular relaxant effects of 0.3 microM (-)-LY222675 (EC50, 2.3 microM) and reversed the decrease in APD caused by 3 microM (-)-LY222675 (EC50, 1.9 microM). Nitroprusside did not alter 86Rb efflux, and vascular relaxation induced by sodium nitroprusside was unaffected by sulfonylureas.

  13. Preferential selection of isomer binding from chiral mixtures: alternate binding modes observed for the E and Z isomers of a series of 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines as ternary complexes with NADPH and human dihydrofolate reductase

    SciTech Connect

    Cody, Vivian; Piraino, Jennifer; Pace, Jim; Li, Wei; Gangjee, Aleem

    2010-12-01

    The structures of six chirally mixed E/Z-isomers of 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines reveals only one isomer is bound in the active site of human DHFR. The configuration of all but one C9-analogue is observed as the E-isomer. The crystal structures of six human dihydrofolate reductase (hDHFR) ternary complexes with NADPH and a series of mixed E/Z isomers of 5-substituted 5-[2-(2-methoxyphenyl)-prop-1-en-1-yl]furo[2,3-d]pyrimidine-2,4-diamines substituted at the C9 position with propyl, isopropyl, cyclopropyl, butyl, isobutyl and sec-butyl (E2–E7, Z3) were determined and the results were compared with the resolved E and Z isomers of the C9-methyl parent compound. The configuration of all of the inhibitors, save one, was observed as the E isomer, in which the binding of the furopyrimidine ring is flipped such that the 4-amino group binds in the 4-oxo site of folate. The Z3 isomer of the C9-isopropyl analog has the normal 2,4-diaminopyrimidine ring binding geometry, with the furo oxygen near Glu30 and the 4-amino group interacting near the cofactor nicotinamide ring. Electron-density maps for these structures revealed the binding of only one isomer to hDHFR, despite the fact that chiral mixtures (E:Z ratios of 2:1, 3:1 and 3:2) of the inhibitors were incubated with hDHFR prior to crystallization. Superposition of the hDHFR complexes with E2 and Z3 shows that the 2′-methoxyphenyl ring of E2 is perpendicular to that of Z3. The most potent inhibitor in this series is the isopropyl analog Z3 and the least potent is the isobutyl analog E6, consistent with data that show that the Z isomer makes the most favorable interactions with the active-site residues. The isobutyl moiety of E6 is observed in two orientations and the resultant steric crowding of the E6 analog is consistent with its weaker activity. The alternative binding modes observed for the furopyrimidine ring in these E/Z isomers suggest that new templates can be designed to probe these binding

  14. Synthesis of cationic single-isomer cyclodextrins for the chiral separation of amino acids and anionic pharmaceuticals.

    PubMed

    Tang, Weihua; Ng, Siu-Choon

    2007-01-01

    We describe a protocol for the synthesis of mono-6(A)-(1-butyl-3-imidazolium)-6(A)-deoxy-beta-cyclodextrin chloride (BIMCD), a cationic, water-soluble cyclodextrin used in the chiral separation of amino acids and anionic pharmaceuticals by capillary electrophoresis. Starting from commercially available chemicals, BIMCD is synthesized in five steps. The first step involves a nucleophilic substitution between p-toluenesulfonyl chloride and imidazole to afford 1-(p-toluenesulfonyl)imidazole (A). In the second step, a nucleophilic substitution between beta-cyclodextrin and A affords mono-6(A)-(p-toluenesulfonyl)-6(A)-deoxy-beta-cyclodextrin (B). In the third step, a nucleophilic substitution between 1-bromobutane and imidazole affords 1-butylimidazole (C). In the fourth step, a nucleophilic addition between A and C affords BIMCD tosylate. In the final step, anion exchange using an ion-exchange resin yields BIMCD as a highly water-soluble solid. Each step takes up to 2 d, including the time required for product purification. The overall protocol requires approximately 6 d. PMID:18079719

  15. Development and validation of a chiral high-performance liquid chromatography assay for rogletimide and rogletimide-N-oxide isomers in plasma.

    PubMed

    Etienne, M C; Oster, W; Milano, G

    1996-01-01

    The purpose of the present study was to develop and validate a stereo-specific high-performance liquid chromatography (HPLC) assay for rogletimide (Rog) and rogletimide-N-oxide (Nox) isomers in plasma. The assay was performed with a chiral cellulose-[4-methylbenzoate]ester column (Chiracel OJ). Optimal separation was achieved isocratically with a mobile phase consisting of n-hexane/anhydrous ethanol (65/35, v/v) at a flow rate of 0.9 ml/min, with the column being thermostated at +35 degrees C (UV detection at 257 nm). Under these conditions, retention times were approximately 17, 28, 31 and 76 min for R-Rog, S-Rog, R-Nox and S-Nox, respectively. S-aminoglutethimide (S-Ag) served as the internal standard (retention time 70 min). An extraction procedure from plasma samples was developed on Bond Elut RP8 500-mg cartridges; conditioning was performed with 5 ml methanol and 5 ml water, after which 1 ml plasma that had previously been spiked with 5 microM S-Ag was applied. Washing was done with 6 ml water and elution, with 4 ml methanol. After evaporation to dryness, residues were dissolved in 400 microliters anhydrous ethanol and 12-48 microliters was injected onto the HPLC system. Blank plasma from healthy donors showed the random presence of a small interference eluting at the retention time of R-Rog, precluding the accurate quantification of R-Rog concentrations below 2.5 microM. Reproducibility assays demonstrated the need to use an internal standard. Taking into account the internal standard, at 2.5 microM the intra- and inter-assay coefficients of variation were 10.5% and 21.0% for R-Rog 5.5% and 8.7% for S-Rog, 7.6% and 20.8% for R-Nox and 11.7% and 6.4% for S-Nox, respectively. The detection limit was 2.5 microM for R-Rog, 0.5 microM for S-Rog, 0.25 microM for R-Nox and 0.5 microM for S-Nox. Linearity was satisfactory at concentrations ranging from 2.5 to 10 microM for R-Rog, from 0.5 to 10 microM for S-Rog, from 0.25 to 2.5 microM for R-Nox and from 0.50 to 2

  16. Prediction of ROA and ECD Related to Conformational Changes of Astaxanthin Enantiomers.

    PubMed

    Zajac, Grzegorz; Kaczor, Agnieszka; Buda, Szymon; Młynarski, Jacek; Frelek, Jadwiga; Dobrowolski, Jan Cz; Baranska, Małgorzata

    2015-09-17

    ECD, ROA, and VCD were used to characterize astaxanthin conformers that differ in their arrangements of the β-ionone ring in respect to the chain. We obtained ECD spectra experimentally, and the ECD, ROA, and VCD spectra of both individual conformers and conformation-averaged mixtures were predicted using quantum-chemical calculations at the CAM-B3LYP level of theory using the PCM solvation model. The chiroptical methods employed (particularly ECD and ROA) were considerably more sensitive to conformational changes of astaxanthin compared to "mono-signed" conventional Raman spectroscopy. Strikingly, conformers that are the same optical isomers (e.g., of 3S,3'S-astxanthin), while geometrically nearly mirror images, exhibited sign-inversed ECD and ROA spectra. The conformational sensitivity of these chiroptical methods makes them a promising tool in the study of carotenoids in the natural environment (for instance, in de novo algal or yeast astaxanthin sources). PMID:26305416

  17. 21 CFR 73.35 - Astaxanthin.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 1 2011-04-01 2011-04-01 false Astaxanthin. 73.35 Section 73.35 Food and Drugs... ADDITIVES EXEMPT FROM CERTIFICATION Foods § 73.35 Astaxanthin. (a) Identity. (1) The color additive astaxanthin is 3, 3′-dihydroxy-β, β-carotene-4, 4′-dione. (2) Astaxanthin may be added to the fish feed...

  18. 21 CFR 73.35 - Astaxanthin.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 1 2012-04-01 2012-04-01 false Astaxanthin. 73.35 Section 73.35 Food and Drugs... ADDITIVES EXEMPT FROM CERTIFICATION Foods § 73.35 Astaxanthin. (a) Identity. (1) The color additive astaxanthin is 3, 3′-dihydroxy-β, β-carotene-4, 4′-dione. (2) Astaxanthin may be added to the fish feed...

  19. 21 CFR 73.35 - Astaxanthin.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 1 2014-04-01 2014-04-01 false Astaxanthin. 73.35 Section 73.35 Food and Drugs... ADDITIVES EXEMPT FROM CERTIFICATION Foods § 73.35 Astaxanthin. (a) Identity. (1) The color additive astaxanthin is 3, 3′-dihydroxy-β, β-carotene-4, 4′-dione. (2) Astaxanthin may be added to the fish feed...

  20. 21 CFR 73.35 - Astaxanthin.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 1 2010-04-01 2010-04-01 false Astaxanthin. 73.35 Section 73.35 Food and Drugs... ADDITIVES EXEMPT FROM CERTIFICATION Foods § 73.35 Astaxanthin. (a) Identity. (1) The color additive astaxanthin is 3, 3′-dihydroxy-β, β-carotene-4, 4′-dione. (2) Astaxanthin may be added to the fish feed...

  1. 21 CFR 73.35 - Astaxanthin.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 1 2013-04-01 2013-04-01 false Astaxanthin. 73.35 Section 73.35 Food and Drugs... ADDITIVES EXEMPT FROM CERTIFICATION Foods § 73.35 Astaxanthin. (a) Identity. (1) The color additive astaxanthin is 3, 3′-dihydroxy-β, β-carotene-4, 4′-dione. (2) Astaxanthin may be added to the fish feed...

  2. Fatty acids attached to all-trans-astaxanthin alter its cis-trans equilibrium, and consequently its stability, upon light-accelerated autoxidation.

    PubMed

    de Bruijn, Wouter J C; Weesepoel, Yannick; Vincken, Jean-Paul; Gruppen, Harry

    2016-03-01

    Fatty acid esterification, common in naturally occurring astaxanthin, has been suggested to influence both colour stability and degradation of all-trans-astaxanthin. Therefore, astaxanthin stability was studied as influenced by monoesterification and diesterification with palmitate. Increased esterification decelerated degradation of all-trans-astaxanthin (RP-UHPLC-PDA), whereas, it had no influence on colour loss over time (spectrophotometry). This difference might be explained by the observation that palmitate esterification influenced the cis-trans equilibrium. Free astaxanthin produced larger amounts of 9-cis isomer whereas monopalmitate esterification resulted in increased 13-cis isomerization. The molar ratios of 9-cis:13-cis after 60min were 1:1.7 (free), 1:4.8 (monopalmitate) and 1:2.6 (dipalmitate). The formation of 9-cis astaxanthin, with its higher molar extinction coefficient than that of all-trans-astaxanthin, might compensate for colour loss induced by conjugated double bond cleavage. As such, it was concluded that spectrophotometry is not an accurate measure of the degradation of the all-trans-astaxanthin molecule. PMID:26471660

  3. Chiral Drugs: An Overview

    PubMed Central

    Nguyen, Lien Ai; He, Hua; Pham-Huy, Chuong

    2006-01-01

    About more than half of the drugs currently in use are chiral compounds and near 90% of the last ones are marketed as racemates consisting of an equimolar mixture of two enantiomers. Although they have the same chemical structure, most isomers of chiral drugs exhibit marked differences in biological activities such as pharmacology, toxicology, pharmacokinetics, metabolism etc. Some mechanisms of these properties are also explained. Therefore, it is important to promote the chiral separation and analysis of racemic drugs in pharmaceutical industry as well as in clinic in order to eliminate the unwanted isomer from the preparation and to find an optimal treatment and a right therapeutic control for the patient. In this article, we review the nomenclature, pharmacology, toxicology, pharmacokinetics, metabolism etc of some usual chiral drugs as well as their mechanisms. Different techniques used for the chiral separation in pharmaceutical industry as well as in clinical analyses are also examined. PMID:23674971

  4. Potential Anti-Atherosclerotic Properties of Astaxanthin.

    PubMed

    Kishimoto, Yoshimi; Yoshida, Hiroshi; Kondo, Kazuo

    2016-02-01

    Astaxanthin is a naturally occurring red carotenoid pigment classified as a xanthophyll, found in microalgae and seafood such as salmon, trout, and shrimp. This review focuses on astaxanthin as a bioactive compound and outlines the evidence associated with its potential role in the prevention of atherosclerosis. Astaxanthin has a unique molecular structure that is responsible for its powerful antioxidant activities by quenching singlet oxygen and scavenging free radicals. Astaxanthin has been reported to inhibit low-density lipoprotein (LDL) oxidation and to increase high-density lipoprotein (HDL)-cholesterol and adiponectin levels in clinical studies. Accumulating evidence suggests that astaxanthin could exert preventive actions against atherosclerotic cardiovascular disease (CVD) via its potential to improve oxidative stress, inflammation, lipid metabolism, and glucose metabolism. In addition to identifying mechanisms of astaxanthin bioactivity by basic research, much more epidemiological and clinical evidence linking reduced CVD risk with dietary astaxanthin intake is needed. PMID:26861359

  5. Potential Anti-Atherosclerotic Properties of Astaxanthin

    PubMed Central

    Kishimoto, Yoshimi; Yoshida, Hiroshi; Kondo, Kazuo

    2016-01-01

    Astaxanthin is a naturally occurring red carotenoid pigment classified as a xanthophyll, found in microalgae and seafood such as salmon, trout, and shrimp. This review focuses on astaxanthin as a bioactive compound and outlines the evidence associated with its potential role in the prevention of atherosclerosis. Astaxanthin has a unique molecular structure that is responsible for its powerful antioxidant activities by quenching singlet oxygen and scavenging free radicals. Astaxanthin has been reported to inhibit low-density lipoprotein (LDL) oxidation and to increase high-density lipoprotein (HDL)-cholesterol and adiponectin levels in clinical studies. Accumulating evidence suggests that astaxanthin could exert preventive actions against atherosclerotic cardiovascular disease (CVD) via its potential to improve oxidative stress, inflammation, lipid metabolism, and glucose metabolism. In addition to identifying mechanisms of astaxanthin bioactivity by basic research, much more epidemiological and clinical evidence linking reduced CVD risk with dietary astaxanthin intake is needed. PMID:26861359

  6. A novel radio-tolerant astaxanthin-producing bacterium reveals a new astaxanthin derivative: astaxanthin dirhamnoside.

    PubMed

    Asker, Dalal; Awad, Tarek S; Beppu, Teruhiko; Ueda, Kenji

    2012-01-01

    Astaxanthin is a red ketocarotenoid that exhibits extraordinary health-promoting activities such as antioxidant, anti-inflammatory, antitumor, and immune booster. The recent discovery of the beneficial roles of astaxanthin against many degenerative diseases such as cancers, heart diseases, and exercise-induced fatigue has raised its market demand as a nutraceutical and medicinal ingredient in aquaculture, food, and pharmaceutical industries. To satisfy the growing demand for this high-value nutraceuticals ingredient and consumer interest in natural products, many research efforts are being made to discover novel microbial producers with effective biotechnological production of astaxanthin. Using a rapid screening method based on 16S rRNA gene, and effective HPLC-Diodearray-MS methods for carotenoids analysis, we succeeded to isolate a unique astaxanthin-producing bacterium (strain TDMA-17(T)) that belongs to the family Sphingomonadaceae (Asker et al., Appl Microbiol Biotechnol 77: 383-392, 2007). In this chapter, we provide a detailed description of effective HPLC-Diodearray-MS methods for rapid analysis and identification of the carotenoids produced by strain TDMA-17(T). We also describe the methods of isolation and identification for a novel bacterial carotenoid (astaxanthin derivative), a major carotenoid that is produced by strain TDMA-17(T). Finally, we describe the polyphasic taxonomic analysis of strain TDMA-17(T) and the description of a novel species belonging to genus Sphingomonas. PMID:22623297

  7. Interstellar isomers

    NASA Technical Reports Server (NTRS)

    Defrees, D.; Mclean, D.; Herbst, E.

    1986-01-01

    Both observational and theoretical studies of molecular clouds are hindered by many difficulties. One way to partially circumvent the difficulties of characterizing the chemistry within these objects is to study the relative abundances of isomers which are synthesized from a common set of precursors. Unfortunately, only one such system has been confirmed, the HCN/HNC pair of isomers. While the basic outlines of its chemistry have been known for some years, there are still many aspects of the chemistry which are unclear. Another potential pair of isomers is HCO+/HOC+; HCO+ is an abundant instellar molecule and a tentative identification of HOC+ has been made in Sgr B2. This identification is being challenged, however, based on theoretical and laboratory evidence that HOC+ reacts with H2. Another potential pair of interstellar isomers is methyl cyanide (CH3CN, acetonitrile) and methyl isocyanide (CH3NC). The cyanide is well known, however the isocyanide has yet to be observed despite theoretical predictions that appreciable quantities should be present.

  8. Characterization and storage stability of astaxanthin esters, fatty acid profile and α-tocopherol of lipid extract from shrimp (L. vannamei) waste with potential applications as food ingredient.

    PubMed

    Gómez-Estaca, J; Calvo, M M; Álvarez-Acero, I; Montero, P; Gómez-Guillén, M C

    2017-02-01

    In this work a lipid extract from shrimp waste was obtained and characterized. The most abundant fatty acids found were C16:0, C18:2n6c, C18:1n9c, C22:6n3, and C20:5n3. The extract contained all-trans-astaxanthin, two cis-astaxanthin isomers, 5 astaxanthin monoesters, and 10 astaxanthin diesters (7±1mg astaxanthin/g). C22:6n3 and C20:5n3 were the most frequent fatty acids in the esterified forms. Appreciable amounts of α-tocopherol and cholesterol were also found (126±11mg/g and 65±1mg/g, respectively). Little lipid oxidation was observed after 120days of storage at room temperature, revealed by a slight reduction of ω-3 fatty acids, but neither accumulation of TBARS nor formation of oxidized cholesterol forms was found. This is attributed to the antioxidant effect of astaxanthin and α-tocopherol, as their concentrations decreased as storage continued. The lipid extract obtained has interesting applications as food ingredient, owing to the coloring capacity and the presence of healthy components. PMID:27596389

  9. Astaxanthin dynamics in Baltic Sea mesozooplankton communities

    NASA Astrophysics Data System (ADS)

    Snoeijs, Pauline; Häubner, Norbert

    2014-01-01

    The red pigment astaxanthin is a powerful antioxidant, which occurs in eggs and body tissues of crustaceans and fish. It is produced by crustaceans from algal carotenoids. In a two-year field study we assessed natural concentrations and dynamics of astaxanthin in mesozooplankton communities in the brackish Baltic Sea area. Astaxanthin levels varied between 0.37 and 36 ng L- 1. They increased with salinity along the Baltic Sea gradient and were linked to zooplankton biomass and phytoplankton community composition. Astaxanthin concentrations showed typical seasonal patterns and varied from 0.2 to 5.1 ng ind- 1, 0.2 to 3.4 ng (μg C)- 1 and 6 to 100 ng mm- 3. These concentrations were inversely related to water temperature and strongly linked to zooplankton community composition. Communities dominated by the calanoid copepods Temora longicornis, Pseudocalanus acuspes and Eurytemora spp. generally held the highest concentrations. With increasing cladocerans:copepods biomass ratios community astaxanthin concentrations decreased and with higher relative biomass of Acartia spp. the proportion of astaxanthin diesters decreased. Diesters prevailed in the cold season and they are thought to improve the antioxidant protection of storage lipids during winter. Climate change causes higher temperature and lower salinity in the Baltic Sea proper. This modifies zooplankton community composition, but not necessarily into a community with lower concentrations of astaxanthin since T. longicornis (high concentrations) has been reported to increase with higher temperature. However, decreased astaxanthin production in the ecosystem is expected if a basin-wide increase in the cladocerans:copepods biomass ratios would occur with further climate change.

  10. Astaxanthin as a Potential Protector of Liver Function: A Review

    PubMed Central

    Chen, Jui-Tung; Kotani, Kazuhiko

    2016-01-01

    Protecting against liver damage, such as non-alcoholic fatty liver disease, is currently considered to be important for the prevention of adverse conditions, such as cardiovascular and cancerous diseases. Liver damage often occurs in relation to oxidative stress with metabolic disorders, including cellular lipid accumulation. Astaxanthin (3,3′-dihydroxy-β,β-carotene-4,4′dione), a xanthophyll carotenoid, is a candidate for liver protection. Here, we briefly review astaxanthin as a potential protector against liver damage. In particular, studies have reported antioxidative effects of astaxanthin in liver tissues. Astaxanthin treatment is also reported to improve hyperlipidemia, which indirectly induces the antioxidative effects of astaxanthin on liver pathologies. Furthermore, astaxanthin may alleviate liver damage independent of its antioxidative effects. Of note, there are still insufficient human data to observe the effect of astaxanthin treatment on liver function in clinical conditions. More studies investigating the relevance of astaxanthin on liver protection are necessary.

  11. Biotechnological production of astaxanthin with Phaffia rhodozyma/Xanthophyllomyces dendrorhous.

    PubMed

    Schmidt, Isabell; Schewe, Hendrik; Gassel, Sören; Jin, Chao; Buckingham, John; Hümbelin, Markus; Sandmann, Gerhard; Schrader, Jens

    2011-02-01

    The oxygenated β-carotene derivative astaxanthin exhibits outstanding colouring, antioxidative and health-promoting properties and is mainly found in the marine environment. To satisfy the growing demand for this ketocarotenoid in the feed, food and cosmetics industries, there are strong efforts to develop economically viable bioprocesses alternative to the current chemical synthesis. However, up to now, natural astaxanthin from Haematococcus pluvialis, Phaffia rhodozyma or Paracoccus carotinifaciens has not been cost competitive with chemically synthesized astaxanthin, thus only serving niche applications. This review illuminates recent advances made in elucidating astaxanthin biosynthesis in P. rhodozyma. It intensely focuses on strategies to increase astaxanthin titers in the heterobasidiomycetous yeast by genetic engineering of the astaxanthin pathway, random mutagenesis and optimization of fermentation processes. This review emphasizes the potential of P. rhodozyma for the biotechnological production of astaxanthin in comparison to other natural sources such as the microalga H. pluvialis, other fungi and transgenic plants and to chemical synthesis. PMID:21046372

  12. Excited-state dynamics of astaxanthin aggregates

    NASA Astrophysics Data System (ADS)

    Fuciman, Marcel; Durchan, Milan; Šlouf, Václav; Keşan, Gürkan; Polívka, Tomáš

    2013-05-01

    Astaxanthin forms three types of aggregates in hydrated dimethyl sulfoxide (DMSO). In DMSO/water ratio of 1:1, a red-shifted J-aggregate with maximum at 570 nm is generated, while a ratio of 1:9 produces blue-shifted H-aggregates with peaks at 386 nm (H1) and 460 nm (H2). Monomeric astaxanthin in DMSO has an S1 lifetime of 5.3 ps, but a long-lived (33 ps) S∗ signal was also identified. Aggregation changes the S1 lifetimes to 17 ps (H1), 30 ps (H2), and 14 ps (J). Triplet state of astaxanthin, most likely generated via singlet homofission, was observed in H1 and H2 aggregates.

  13. High-harmonic spectroscopy of molecular isomers

    SciTech Connect

    Wong, M. C. H.; Brichta, J.-P.; Bhardwaj, V. R.; Spanner, M.; Patchkovskii, S.

    2011-11-15

    We demonstrate that high-order-harmonic generation (HHG) spectroscopy can be used to probe stereoisomers of randomly oriented 1,2-dichloroethylene (C{sub 2}H{sub 2}Cl{sub 2}) and 2-butene (C{sub 4}H{sub 8}). The high-harmonic spectra of these isomers are distinguishable over a range of laser intensities and wavelengths. Time-dependent numerical calculations of angle-dependent ionization yields for 1,2-dichloroethylene suggest that the harmonic spectra of molecular isomers reflect differences in their strong-field ionization. The subcycle ionization yields for the cis isomer are an order of magnitude higher than those for the trans isomer. The sensitivity in discrimination of the harmonic spectra of cis- and trans- isomers is greater than 8 and 5 for 1,2-dichloroethylene and 2-butene, respectively. We show that HHG spectroscopy cannot differentiate the harmonic spectra of the two enantiomers of the chiral molecule propylene oxide (C{sub 3}H{sub 6}O).

  14. Recovery of astaxanthin from seafood wastewater utilizing fish scales waste.

    PubMed

    Stepnowski, P; Olafsson, G; Helgason, H; Jastorff, B

    2004-01-01

    The paper presents basic data on astaxanthin adsorption from fisheries wastewater to fish scales. This process has been proposed to be applicable in fisheries and shrimp waste management [Helgason, Recovery of compounds using a natural adsorbent, Patent WO 01/77230, 2001]. The innovative feature of the method is the application of a solid waste (fish scales) as a natural adsorbent for a carotenoid pigment (astaxanthin) from the seafood industry wastewater. The model investigations were performed with pure synthetic carotenoids to exclude the role of matrix in which astaxanthin is present in the wastewater. Under the experimental conditions used, the maximum loading capacity of astaxanthin onto the scales is 360 mg kg(-1) dry wt. Studies of the thus formed value added product indicated that drying causes significant loss of astaxanthin activity. Due to the effective filtration characteristics of the studied sorption material, we suggest the scale/astaxanthin sorption process to be suitable for treatment of wastewater from different industries. PMID:14575754

  15. Free Radical Scavenging and Cellular Antioxidant Properties of Astaxanthin.

    PubMed

    Dose, Janina; Matsugo, Seiichi; Yokokawa, Haruka; Koshida, Yutaro; Okazaki, Shigetoshi; Seidel, Ulrike; Eggersdorfer, Manfred; Rimbach, Gerald; Esatbeyoglu, Tuba

    2016-01-01

    Astaxanthin is a coloring agent which is used as a feed additive in aquaculture nutrition. Recently, potential health benefits of astaxanthin have been discussed which may be partly related to its free radical scavenging and antioxidant properties. Our electron spin resonance (ESR) and spin trapping data suggest that synthetic astaxanthin is a potent free radical scavenger in terms of diphenylpicryl-hydrazyl (DPPH) and galvinoxyl free radicals. Furthermore, astaxanthin dose-dependently quenched singlet oxygen as determined by photon counting. In addition to free radical scavenging and singlet oxygen quenching properties, astaxanthin induced the antioxidant enzyme paroxoanase-1, enhanced glutathione concentrations and prevented lipid peroxidation in cultured hepatocytes. Present results suggest that, beyond its coloring properties, synthetic astaxanthin exhibits free radical scavenging, singlet oxygen quenching, and antioxidant activities which could probably positively affect animal and human health. PMID:26784174

  16. Free Radical Scavenging and Cellular Antioxidant Properties of Astaxanthin

    PubMed Central

    Dose, Janina; Matsugo, Seiichi; Yokokawa, Haruka; Koshida, Yutaro; Okazaki, Shigetoshi; Seidel, Ulrike; Eggersdorfer, Manfred; Rimbach, Gerald; Esatbeyoglu, Tuba

    2016-01-01

    Astaxanthin is a coloring agent which is used as a feed additive in aquaculture nutrition. Recently, potential health benefits of astaxanthin have been discussed which may be partly related to its free radical scavenging and antioxidant properties. Our electron spin resonance (ESR) and spin trapping data suggest that synthetic astaxanthin is a potent free radical scavenger in terms of diphenylpicryl-hydrazyl (DPPH) and galvinoxyl free radicals. Furthermore, astaxanthin dose-dependently quenched singlet oxygen as determined by photon counting. In addition to free radical scavenging and singlet oxygen quenching properties, astaxanthin induced the antioxidant enzyme paroxoanase-1, enhanced glutathione concentrations and prevented lipid peroxidation in cultured hepatocytes. Present results suggest that, beyond its coloring properties, synthetic astaxanthin exhibits free radical scavenging, singlet oxygen quenching, and antioxidant activities which could probably positively affect animal and human health. PMID:26784174

  17. Astaxanthin binding protein in Atlantic salmon.

    PubMed

    Matthews, Sarah J; Ross, Neil W; Lall, Santosh P; Gill, Tom A

    2006-06-01

    The rubicund pigmentation in salmon and trout flesh is unique and is due to the deposition of dietary carotenoids, astaxanthin and canthaxanthin in the muscle. The present study was undertaken to determine which protein was responsible for pigment binding. Salmon muscle proteins were solubilized by sequential extractions with non-denaturing, low ionic strength aqueous solutions and segregated as such into six different fractions. Approximately 91% of the salmon myofibrillar proteins were solubilized under non-denaturing conditions using a protocol modified from a method described by Krishnamurthy et al. [Krishnamurthy, G., Chang, H.S., Hultin, H.O., Feng, Y., Srinivasan, S., Kelleher. S.D., 1996. Solubility of chicken breast muscle proteins in solutions of low ionic strength. J. Agric. Food Chem. 44: 408-415.] for the dissolution of avian muscle. To our knowledge, this is the first time this solubilization approach has been applied to the study of molecular interactions in myofibrillar proteins. Astaxanthin binding in each fraction was determined using an in vitro binding assay. In addition, SDS-PAGE and quantitative densitometry were used to separate and determine the relative amounts of each of the proteins in the six fractions. The results showed that alpha-actinin was the only myofibrillar protein correlating significantly (P<0.05) with astaxanthin binding. Alpha-actinin was positively identified using electrophoretic techniques and confirmed by tandem mass spectroscopy. Purified salmon alpha-actinin bound synthetic astaxanthin in a molar ratio of 1.11:1.00. The study was repeated using halibut alpha-actinin, which was found to have a molar binding ratio of astaxanthin to alpha-actinin of 0.893:1. These results suggest that the difference in pigmentation between white fish and Atlantic salmon is not due to binding capacity in the muscle, but rather differences in the metabolism or transport of pigment. PMID:16644255

  18. Xanthophyllomyces dendrorhous for the industrial production of astaxanthin.

    PubMed

    Rodríguez-Sáiz, Marta; de la Fuente, Juan Luis; Barredo, José Luis

    2010-10-01

    Astaxanthin is a red xanthophyll (oxygenated carotenoid) with large importance in the aquaculture, pharmaceutical, and food industries. The green alga Haematococcus pluvialis and the heterobasidiomycetous yeast Xanthophyllomyces dendrorhous are currently known as the main microorganisms useful for astaxanthin production at the industrial scale. The improvement of astaxanthin titer by microbial fermentation is a requirement to be competitive with the synthetic manufacture by chemical procedures, which at present is the major source in the market. In this review, we show how the isolation of new strains of X. dendrorhous from the environment, the selection of mutants by the classical methods of random mutation and screening, and the rational metabolic engineering, have provided improved strains with higher astaxanthin productivity. To reduce production costs and enhance competitiveness from an industrial point of view, low-cost raw materials from industrial and agricultural origin have been adopted to get the maximal astaxanthin productivity. Finally, fermentation parameters have been studied in depth, both at flask and fermenter scales, to get maximal astaxanthin titers of 4.7 mg/g dry cell matter (420 mg/l) when X. dendrorhous was fermented under continuous white light. The industrial scale-up of this biotechnological process will provide a cost-effective method, alternative to synthetic astaxanthin, for the commercial exploitation of the expensive astaxanthin (about $2,500 per kilogram of pure astaxanthin). PMID:20711573

  19. Chiral Graphene Quantum Dots.

    PubMed

    Suzuki, Nozomu; Wang, Yichun; Elvati, Paolo; Qu, Zhi-Bei; Kim, Kyoungwon; Jiang, Shuang; Baumeister, Elizabeth; Lee, Jaewook; Yeom, Bongjun; Bahng, Joong Hwan; Lee, Jaebeom; Violi, Angela; Kotov, Nicholas A

    2016-02-23

    Chiral nanostructures from metals and semiconductors attract wide interest as components for polarization-enabled optoelectronic devices. Similarly to other fields of nanotechnology, graphene-based materials can greatly enrich physical and chemical phenomena associated with optical and electronic properties of chiral nanostructures and facilitate their applications in biology as well as other areas. Here, we report that covalent attachment of l/d-cysteine moieties to the edges of graphene quantum dots (GQDs) leads to their helical buckling due to chiral interactions at the "crowded" edges. Circular dichroism (CD) spectra of the GQDs revealed bands at ca. 210-220 and 250-265 nm that changed their signs for different chirality of the cysteine edge ligands. The high-energy chiroptical peaks at 210-220 nm correspond to the hybridized molecular orbitals involving the chiral center of amino acids and atoms of graphene edges. Diverse experimental and modeling data, including density functional theory calculations of CD spectra with probabilistic distribution of GQD isomers, indicate that the band at 250-265 nm originates from the three-dimensional twisting of the graphene sheet and can be attributed to the chiral excitonic transitions. The positive and negative low-energy CD bands correspond to the left and right helicity of GQDs, respectively. Exposure of liver HepG2 cells to L/D-GQDs reveals their general biocompatibility and a noticeable difference in the toxicity of the stereoisomers. Molecular dynamics simulations demonstrated that d-GQDs have a stronger tendency to accumulate within the cellular membrane than L-GQDs. Emergence of nanoscale chirality in GQDs decorated with biomolecules is expected to be a general stereochemical phenomenon for flexible sheets of nanomaterials. PMID:26743467

  20. Atroposelective Synthesis of Axially Chiral Thiohydantoin Derivatives.

    PubMed

    Sarigul, Sevgi; Dogan, Ilknur

    2016-07-15

    Nonracemic axially chiral thiohydantoins were synthesized atroposelectively by the reaction of o-aryl isothiocyanates with amino acid ester salts in the presence of triethylamine (TEA). The synthesis of the nonaxially chiral derivatives, however, gave thiohydantoins racemized at C-5 of the heterocyclic ring. The micropreparatively resolved enantiomers of the nonaxially chiral derivatives from the racemic products were found to be optically stable under neutral conditions. On formation of the 5-methyl-3-arylthiohydantoin ring, bulky o-aryl substituents at N3 were found to suppress the C-5 racemization and in this way enabled the transfer of chirality from the α-amino acid to the products. The corresponding 5-isopropylthiohydantoins turned out to be more prone to racemization at C-5 during the ring formation. The isomer compositions of the synthesized axially chiral thiohydantoins have been determined through HPLC analyses with chiral stationary phases. In most cases a high prevalence of the P isomers over the M isomers has been obtained. The barriers to rotation determined around the Nsp(2)-Caryl chiral axis were found to be dependent upon the size of the o-halo aryl substituents. PMID:27322739

  1. Influence of astaxanthin, emulsifier and organic phase concentration on physicochemical properties of astaxanthin nanodispersions

    PubMed Central

    2013-01-01

    Background The emulsification-evaporation method was used to prepare astaxanthin nanodispersions using a three-component emulsifier system composed of Tween 20, sodium caseinate and gum Arabic. Using Response-surface methodology (RSM), we studied the main and interaction effects of the major emulsion components, namely, astaxanthin concentration (0.02–0.38 wt %, x1), emulsifier concentration (0.2–3.8 wt %, x2) and organic phase (dichloromethane) concentration (2–38 wt %, x3) on nanodispersion characteristics. The physicochemical properties considered as response variables were: average particle size (Y1), PDI (Y2) and astaxanthin loss (Y3). Results The results indicated that the response-surface models were significantly (p < 0.05) fitted for all studied response variables. The fitted polynomial regression models for the prediction of variations in the response variables showed high coefficients of determination (R2 > 0.930) for all responses. The overall optimum region resulted in a desirable astaxanthin nanodispersions obtained with the concentrations of 0.08 wt % astaxanthin, 2.5 wt % emulsifier and 11.5 wt % organic phase. Conclusion No significant differences were found between the experimental and predicted values, thus certifying the adequacy of the Response-surface models developed for describing the changes in physicochemical properties as a function of main emulsion component concentrations. PMID:23875816

  2. Nonlinear optics of astaxanthin thin films

    NASA Astrophysics Data System (ADS)

    Esser, A.; Fisch, Herbert; Haas, Karl-Heinz; Haedicke, E.; Paust, J.; Schrof, Wolfgang; Ticktin, Anton

    1993-02-01

    Carotinoids exhibit large nonlinear optical properties due to their extended (pi) -electron system. Compared to other polyenes which show a broad distribution of conjugation lengths, carotinoids exhibit a well defined molecular structure, i.e. a well defined conjugation length. Therefore the carotinoid molecules can serve as model compounds to study the relationship between structure and nonlinear optical properties. In this paper the synthesis of four astaxanthins with C-numbers ranging from 30 to 60, their preparation into thin films, wavelength dispersive Third Harmonic Generation (THG) measurements and some molecular modelling calculations will be presented. Resonant (chi) (3) values reach 1.2(DOT)10-10 esu for C60 astaxanthin. In the nonresonant regime a figure of merit (chi) (3)/(alpha) of several 10-13 esu-cm is demonstrated.

  3. Spectrally resolved femtosecond photon echo spectroscopy of astaxanthin

    NASA Astrophysics Data System (ADS)

    Kumar, Ajitesh; Karthick Kumar, S. K.; Gupta, Aditya; Goswami, Debabrata

    2010-12-01

    We have studied the coherence and population dynamics of Astaxanthin solution in methanol and acetonitrile by spectrally resolving their photon echo signals. Our experiments indicate that methanol has a much stronger interaction with the ultrafast dynamics of Astaxanthin in comparison to that of acetonitrile.

  4. Spectrally resolved femtosecond photon echo spectroscopy of astaxanthin

    NASA Astrophysics Data System (ADS)

    Kumar, Ajitesh; Karthick Kumar, S. K.; Gupta, Aditya; Goswami, Debabrata

    2011-08-01

    We have studied the coherence and population dynamics of Astaxanthin solution in methanol and acetonitrile by spectrally resolving their photon echo signals. Our experiments indicate that methanol has a much stronger interaction with the ultrafast dynamics of Astaxanthin in comparison to that of acetonitrile.

  5. Asymmetric Synthesis of Overcrowded Alkenes by Transfer of Axial Single Bond Chirality to Axial Double Bond Chirality.

    PubMed

    Geertsema; Meetsma; Feringa

    1999-09-01

    Optically active overcrowded alkenes were synthesized by employing bis-beta-naphthol as a chiral template during an intramolecular coupling reaction. The major isomer 2 has a unique helical structure with twisted and folded structural moieties. Removal of the chiral template afforded overcrowded thioxanthylidene 3 with 96 % ee, which indicates that no racemization or isomerization of the enantiomers took place. PMID:10508366

  6. Stability and changes in astaxanthin ester composition from Haematococcus pluvialis during storage

    NASA Astrophysics Data System (ADS)

    Miao, Fengping; Geng, Yahong; Lu, Dayan; Zuo, Jincheng; Li, Yeguang

    2013-11-01

    In this paper, we investigated the effects of temperature, oxygen, antioxidants, and corn germ oil on the stability of astaxanthin from Haematococcus pluvialis under different storage conditions, and changes in the composition of astaxanthin esters during storage using high performance liquid chromatography and spectrophotometry. Oxygen and high temperatures (22-25°C) significantly reduced the stability of astaxanthin esters. Corn germ oil and antioxidants (ascorbic acid and vitamin E) failed to protect astaxanthin from oxidation, and actually significantly increased the instability of astaxanthin. A change in the relative composition of astaxanthin esters was observed after 96 weeks of long-term storage. During storage, the relative amounts of free astaxanthin and astaxanthin monoesters declined, while the relative amount of astaxanthin diesters increased. Thus, the ratio of astaxanthin diester to monoester increased, and this ratio could be used to indicate if astaxanthin esters have been properly preserved. If the ratio is greater than 0.2, it suggests that the decrease in astaxanthin content could be higher than 20%. Our results show that storing algal powder from H. pluvialis or other natural astaxanthin products under vacuum and in the dark below 4°C is the most economical and applicable storage method for the large-scale production of astaxanthin from H. pluvialis. This storage method can produce an astaxanthin preservation rate of at least 80% after 96 weeks of storage.

  7. Astaxanthin blocks preeclampsia progression by suppressing oxidative stress and inflammation.

    PubMed

    Xuan, Rong-Rong; Niu, Ting-Ting; Chen, Hai-Min

    2016-09-01

    To investigate the antioxidative effect of astaxanthin on Nω-nitro-L-arginine methyl ester (L-NAME)-induced preeclamptic rats. Cell survival, the level of reactive oxygen species (ROS) and the changes in mitochondrial membrane potential (MMP) were examined in astaxanthin and H2O2-treated human umbilical vein endothelial cells (HUVECs). The preeclamptic Sprague-Dawley (SD) rat model was established by injection of L‑NAME and treatment with astaxanthin. The activities of malondialdehyde (MDA), superoxide dismutase (SOD) and nitric oxide synthase (NOS) in serum were analyzed. Pathological changes were examined by hematoxylin and eosin (H&E) staining. The expression of nuclear factor (NF)‑κB, Rho‑associated protein kinase II (ROCK II), heme oxygenase‑1 (HO‑1) and caspase 3 in preeclamptic placentas were examined by immunohistochemistry. Astaxanthin significantly reduced H2O2‑induced HUVEC cell death, decreased ROS and increased MMP. Astaxanthin significantly reduced blood pressure and the content of MDA, but significantly increased the activity of SOD in preeclamptic rats. The urinary protein and the level of NO and NOS were also decreased. H&E staining revealed that the thickness of the basilar membrane was increased, while the content of trophoblast cells and spiral arteries were reduced following astaxanthin treatment. Immunohistochemistry results showed that the expression of NF‑κB, ROCK II and caspase 3 in preeclamptic placentas was significantly decreased after astaxanthin treatment, while HO‑1 expression was increased. In conclusion, astaxanthin inhibited H2O2‑induced oxidative stress in HUVECs. Astaxanthin treatment significantly improved L‑NAME‑induced preeclamptic symptoms and reduced the oxidative stress and inflammatory damages in preeclamptic placentas. Astaxanthin treatment may effectively prevent and treat preeclampsia. PMID:27484589

  8. Power optimization in logic isomers

    NASA Technical Reports Server (NTRS)

    Panwar, Ramesh; Rennels, David; Alkalaj, Leon

    1993-01-01

    Logic isomers are labeled, 2-isomorphic graphs that implement the same logic function. Logic isomers may have significantly different power requirements even though they have the same number of transistors in the implementation. The power requirements of the isomers depend on the transition activity of the input signals. The power requirements of isomorphic graph isomers of n-input NAND and NOR gates are shown. Choosing the less power-consuming isomer instead of the others can yield significant power savings. Experimental results on a ripple-carry adder are presented to show that the implementation using the least power-consuming isomers requires approximately 10 percent less power than the implementation using the most power-consuming isomers. Simulations of other random logic designs also confirm that designs using less power-consuming isomers can reduce the logic power demand by approximately 10 percent as compared to designs using more power-consuming isomers.

  9. Astaxanthin: A Potential Therapeutic Agent in Cardiovascular Disease

    PubMed Central

    Fassett, Robert G.; Coombes, Jeff S.

    2011-01-01

    Astaxanthin is a xanthophyll carotenoid present in microalgae, fungi, complex plants, seafood, flamingos and quail. It is an antioxidant with anti-inflammatory properties and as such has potential as a therapeutic agent in atherosclerotic cardiovascular disease. Synthetic forms of astaxanthin have been manufactured. The safety, bioavailability and effects of astaxanthin on oxidative stress and inflammation that have relevance to the pathophysiology of atherosclerotic cardiovascular disease, have been assessed in a small number of clinical studies. No adverse events have been reported and there is evidence of a reduction in biomarkers of oxidative stress and inflammation with astaxanthin administration. Experimental studies in several species using an ischaemia-reperfusion myocardial model demonstrated that astaxanthin protects the myocardium when administered both orally or intravenously prior to the induction of the ischaemic event. At this stage we do not know whether astaxanthin is of benefit when administered after a cardiovascular event and no clinical cardiovascular studies in humans have been completed and/or reported. Cardiovascular clinical trials are warranted based on the physicochemical and antioxidant properties, the safety profile and preliminary experimental cardiovascular studies of astaxanthin. PMID:21556169

  10. Accurate quantification of astaxanthin from Haematococcus crude extract spectrophotometrically

    NASA Astrophysics Data System (ADS)

    Li, Yeguang; Miao, Fengping; Geng, Yahong; Lu, Dayan; Zhang, Chengwu; Zeng, Mingtao

    2012-07-01

    The influence of alkali on astaxanthin and the optimal working wave length for measurement of astaxanthin from Haematococcus crude extract were investigated, and a spectrophotometric method for precise quantification of the astaxanthin based on the method of Boussiba et al. was established. According to Boussiba's method, alkali treatment destroys chlorophyll. However, we found that: 1) carotenoid content declined for about 25% in Haematococcus fresh cysts and up to 30% in dry powder of Haematococcus broken cysts after alkali treatment; and 2) dimethyl sulfoxide (DMSO)-extracted chlorophyll of green Haematococcus bares little absorption at 520-550 nm. Interestingly, a good linear relationship existed between absorbance at 530 nm and astaxanthin content, while an unknown interference at 540-550 nm was detected in our study. Therefore, with 530 nm as working wavelength, the alkali treatment to destroy chlorophyll was not necessary and the influence of chlorophyll, other carotenoids, and the unknown interference could be avoided. The astaxanthin contents of two samples were measured at 492 nm and 530 nm; the measured values at 530 nm were 2.617 g/100 g and 1.811 g/100 g. When compared with the measured values at 492 nm, the measured values at 530 nm decreased by 6.93% and 11.96%, respectively. The measured values at 530 nm are closer to the true astaxanthin contents in the samples. The data show that 530 nm is the most suitable wave length for spectrophotometric determination to the astaxanthin in Haematococcus crude extract.

  11. Atlas of Nuclear Isomers

    NASA Astrophysics Data System (ADS)

    Jain, Ashok Kumar; Maheshwari, Bhoomika; Garg, Swati; Patial, Monika; Singh, Balraj

    2015-09-01

    We present an atlas of nuclear isomers containing the experimental data for the isomers with a half-life ≥ 10 ns together with their various properties such as excitation-energy, half-life, decay mode(s), spin-parity, energies and multipolarities of emitted gamma transitions, etc. The ENSDF database complemented by the XUNDL database has been extensively used in extracting the relevant data. Recent literature from primary nuclear physics journals, and the NSR bibliographic database have been searched to ensure that the compiled data Table is as complete and current as possible. The data from NUBASE-12 have also been checked for completeness, but as far as possible original references have been cited. Many interesting systematic features of nuclear isomers emerge, some of them new; these are discussed and presented in various graphs and figures. The cutoff date for the extraction of data from the literature is August 15, 2015.

  12. Atlas of Nuclear Isomers

    SciTech Connect

    Jain, Ashok Kumar; Maheshwari, Bhoomika; Garg, Swati; Patial, Monika; Singh, Balraj

    2015-09-15

    We present an atlas of nuclear isomers containing the experimental data for the isomers with a half-life ≥ 10 ns together with their various properties such as excitation-energy, half-life, decay mode(s), spin-parity, energies and multipolarities of emitted gamma transitions, etc. The ENSDF database complemented by the XUNDL database has been extensively used in extracting the relevant data. Recent literature from primary nuclear physics journals, and the NSR bibliographic database have been searched to ensure that the compiled data Table is as complete and current as possible. The data from NUBASE-12 have also been checked for completeness, but as far as possible original references have been cited. Many interesting systematic features of nuclear isomers emerge, some of them new; these are discussed and presented in various graphs and figures. The cutoff date for the extraction of data from the literature is August 15, 2015.

  13. Structure investigations on assembled astaxanthin molecules

    NASA Astrophysics Data System (ADS)

    Köpsel, Christian; Möltgen, Holger; Schuch, Horst; Auweter, Helmut; Kleinermanns, Karl; Martin, Hans-Dieter; Bettermann, Hans

    2005-08-01

    The carotenoid r,r-astaxanthin (3R,3‧R-dihydroxy-4,4‧-diketo-β-carotene) forms different types of aggregates in acetone-water mixtures. H-type aggregates were found in mixtures with a high part of water (e.g. 1:9 acetone-water mixture) whereas two different types of J-aggregates were identified in mixtures with a lower part of water (3:7 acetone-water mixture). These aggregates were characterized by recording UV/vis-absorption spectra, CD-spectra and fluorescence emissions. The sizes of the molecular assemblies were determined by dynamic light scattering experiments. The hydrodynamic diameter of the assemblies amounts 40 nm in 1:9 acetone-water mixtures and exceeds up to 1 μm in 3:7 acetone-water mixtures. Scanning tunneling microscopy monitored astaxanthin aggregates on graphite surfaces. The structure of the H-aggregate was obtained by molecular modeling calculations. The structure was confirmed by calculating the electronic absorption spectrum and the CD-spectrum where the molecular modeling structure was used as input.

  14. Multispectral Imaging for Determination of Astaxanthin Concentration in Salmonids

    PubMed Central

    Dissing, Bjørn S.; Nielsen, Michael E.; Ersbøll, Bjarne K.; Frosch, Stina

    2011-01-01

    Multispectral imaging has been evaluated for characterization of the concentration of a specific cartenoid pigment; astaxanthin. 59 fillets of rainbow trout, Oncorhynchus mykiss, were filleted and imaged using a rapid multispectral imaging device for quantitative analysis. The multispectral imaging device captures reflection properties in 19 distinct wavelength bands, prior to determination of the true concentration of astaxanthin. The samples ranged from 0.20 to 4.34 g per g fish. A PLSR model was calibrated to predict astaxanthin concentration from novel images, and showed good results with a RMSEP of 0.27. For comparison a similar model were built for normal color images, which yielded a RMSEP of 0.45. The acquisition speed of the multispectral imaging system and the accuracy of the PLSR model obtained suggest this method as a promising technique for rapid in-line estimation of astaxanthin concentration in rainbow trout fillets. PMID:21573000

  15. Astaxanthin as a Potential Neuroprotective Agent for Neurological Diseases.

    PubMed

    Wu, Haijian; Niu, Huanjiang; Shao, Anwen; Wu, Cheng; Dixon, Brandon J; Zhang, Jianmin; Yang, Shuxu; Wang, Yirong

    2015-09-01

    Neurological diseases, which consist of acute injuries and chronic neurodegeneration, are the leading causes of human death and disability. However, the pathophysiology of these diseases have not been fully elucidated, and effective treatments are still lacking. Astaxanthin, a member of the xanthophyll group, is a red-orange carotenoid with unique cell membrane actions and diverse biological activities. More importantly, there is evidence demonstrating that astaxanthin confers neuroprotective effects in experimental models of acute injuries, chronic neurodegenerative disorders, and neurological diseases. The beneficial effects of astaxanthin are linked to its oxidative, anti-inflammatory, and anti-apoptotic characteristics. In this review, we will focus on the neuroprotective properties of astaxanthin and explore the underlying mechanisms in the setting of neurological diseases. PMID:26378548

  16. Astaxanthin as a Potential Neuroprotective Agent for Neurological Diseases

    PubMed Central

    Wu, Haijian; Niu, Huanjiang; Shao, Anwen; Wu, Cheng; Dixon, Brandon J.; Zhang, Jianmin; Yang, Shuxu; Wang, Yirong

    2015-01-01

    Neurological diseases, which consist of acute injuries and chronic neurodegeneration, are the leading causes of human death and disability. However, the pathophysiology of these diseases have not been fully elucidated, and effective treatments are still lacking. Astaxanthin, a member of the xanthophyll group, is a red-orange carotenoid with unique cell membrane actions and diverse biological activities. More importantly, there is evidence demonstrating that astaxanthin confers neuroprotective effects in experimental models of acute injuries, chronic neurodegenerative disorders, and neurological diseases. The beneficial effects of astaxanthin are linked to its oxidative, anti-inflammatory, and anti-apoptotic characteristics. In this review, we will focus on the neuroprotective properties of astaxanthin and explore the underlying mechanisms in the setting of neurological diseases. PMID:26378548

  17. Evaluation of hepatoprotective and antioxidant activity of astaxanthin and astaxanthin esters from microalga-Haematococcus pluvialis.

    PubMed

    Rao, A Ranga; Sarada, R; Shylaja, M D; Ravishankar, G A

    2015-10-01

    Effect of isolated astaxanthin (ASX) and astaxanthin esters (ASXEs) from green microalga-Haematococcus pluvialis on hepatotoxicity and antioxidant activity against carbon tetrachloride (CCl4) induced toxicity in rats was compared with synthetic astaxanthin (SASX). ASX, ASXEs, and SASX, all dissolved in olive oil, fed to rats with 100 and 250 μg/kg b.w for 14 days. They were evaluated for their hepatoprotective and antioxidant activity by measuring appropriate enzymes. Among the treated groups, the SGPT, SGOT and ALP levels were decreased by 2, 2.4, and 1.5 fold in ASXEs treated group at 250 μg/Kg b.w. when compared to toxin group. Further, antioxidant enzymes catalase, glutathione, superoxide dismutase and lipid peroxidase levels were estimated in treated groups, their levels were reduced by 30-50 % in the toxin group, however these levels restored by 136.95 and 238.48 % in ASXEs treated group at 250 μg/kg. The lipid peroxidation was restored by 5.2 and 2.8 fold in ASXEs and ASX treated groups at 250 μg/kg. The total protein, albumin and bilirubin contents were decreased in toxin group, whereas normalized in ASXEs treated group. These results indicates that ASX and ASXEs have better hepatoprotection and antioxidant activity, therefore can be used in pharmaceutical and nutraceutical applications and also extended to use as food colorant. PMID:26396419

  18. Astaxanthin intake attenuates muscle atrophy caused by immobilization in rats.

    PubMed

    Shibaguchi, Tsubasa; Yamaguchi, Yusuke; Miyaji, Nobuyuki; Yoshihara, Toshinori; Naito, Hisashi; Goto, Katsumasa; Ohmori, Daijiro; Yoshioka, Toshitada; Sugiura, Takao

    2016-08-01

    Astaxanthin is a carotenoid pigment and has been shown to be an effective inhibitor of oxidative damage. We tested the hypothesis that astaxanthin intake would attenuate immobilization-induced muscle atrophy in rats. Male Wistar rats (14-week old) were fed for 24 days with either astaxanthin or placebo diet. After 14 days of each experimental diet intake, the hindlimb muscles of one leg were immobilized in plantar flexion position using a plaster cast. Following 10 days of immobilization, both the atrophic and the contralateral plantaris muscles were removed and analyzed to determine the level of muscle atrophy along with measurement of the protein levels of CuZn-superoxide dismutase (CuZn-SOD) and selected proteases. Compared with placebo diet animals, the degree of muscle atrophy in response to immobilization was significantly reduced in astaxanthin diet animals. Further, astaxanthin supplementation significantly prevented the immobilization-induced increase in the expression of CuZn-SOD, cathepsin L, calpain, and ubiquitin in the atrophied muscle. These results support the postulate that dietary astaxanthin intake attenuates the rate of disuse muscle atrophy by inhibiting oxidative stress and proteolysis via three major proteolytic pathways. PMID:27482075

  19. Chiral superconductors.

    PubMed

    Kallin, Catherine; Berlinsky, John

    2016-05-01

    Chiral superconductivity is a striking quantum phenomenon in which an unconventional superconductor spontaneously develops an angular momentum and lowers its free energy by eliminating nodes in the gap. It is a topologically non-trivial state and, as such, exhibits distinctive topological modes at surfaces and defects. In this paper we discuss the current theory and experimental results on chiral superconductors, focusing on two of the best-studied systems, Sr2RuO4, which is thought to be a chiral triplet p-wave superconductor, and UPt3, which has two low-temperature superconducting phases (in zero magnetic field), the lower of which is believed to be chiral triplet f-wave. Other systems that may exhibit chiral superconductivity are also discussed. Key signatures of chiral superconductivity are surface currents and chiral Majorana modes, Majorana states in vortex cores, and the possibility of half-flux quantum vortices in the case of triplet pairing. Experimental evidence for chiral superconductivity from μSR, NMR, strain, polar Kerr effect and Josephson tunneling experiments are discussed. PMID:27088452

  20. Chiral squaring

    NASA Astrophysics Data System (ADS)

    Nagy, S.

    2016-07-01

    We construct the states and symmetries of N = 4 super-Yang-Mills by tensoring two N = 1 chiral multiplets and introducing two extra SUSY generators. This allows us to write the maximal N = 8 supergravity as four copies of the chiral multiplet. We extend this to higher dimensions and discuss applications to scattering amplitudes.

  1. Chiral superconductors

    NASA Astrophysics Data System (ADS)

    Kallin, Catherine; Berlinsky, John

    2016-05-01

    Chiral superconductivity is a striking quantum phenomenon in which an unconventional superconductor spontaneously develops an angular momentum and lowers its free energy by eliminating nodes in the gap. It is a topologically non-trivial state and, as such, exhibits distinctive topological modes at surfaces and defects. In this paper we discuss the current theory and experimental results on chiral superconductors, focusing on two of the best-studied systems, Sr2RuO4, which is thought to be a chiral triplet p-wave superconductor, and UPt3, which has two low-temperature superconducting phases (in zero magnetic field), the lower of which is believed to be chiral triplet f-wave. Other systems that may exhibit chiral superconductivity are also discussed. Key signatures of chiral superconductivity are surface currents and chiral Majorana modes, Majorana states in vortex cores, and the possibility of half-flux quantum vortices in the case of triplet pairing. Experimental evidence for chiral superconductivity from μSR, NMR, strain, polar Kerr effect and Josephson tunneling experiments are discussed.

  2. Complete Hexose Isomer Identification with Mass Spectrometry

    NASA Astrophysics Data System (ADS)

    Nagy, Gabe; Pohl, Nicola L. B.

    2015-04-01

    The first analytical method is presented for the identification and absolute configuration determination of all 24 aldohexose and 2-ketohexose isomers, including the D and L enantiomers for allose, altrose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, and tagatose. Two unique fixed ligand kinetic method combinations were discovered to create significant enough energetic differences to achieve chiral discrimination among all 24 hexoses. Each of these 24 hexoses yields unique ratios of a specific pair of fragment ions that allows for simultaneous determination of identification and absolute configuration. This mass spectrometric-based methodology can be readily employed for accurate identification of any isolated monosaccharide from an unknown biological source. This work provides a key step towards the goal of complete de novo carbohydrate analysis.

  3. Chiral plasmonic nanostructures on achiral nanopillars.

    PubMed

    Yeom, Bongjun; Zhang, Huanan; Zhang, Hui; Park, Jai Il; Kim, Kyoungwon; Govorov, Alexander O; Kotov, Nicholas A

    2013-11-13

    Chirality of plasmonic films can be strongly enhanced by three-dimensional (3D) out-of-plane geometries. The complexity of lithographic methods currently used to produce such structures and other methods utilizing chiral templates impose limitations on spectral windows of chiroptical effects, the size of substrates, and hence, further research on chiral plasmonics. Here we demonstrate 3D chiral plasmonic nanostructures (CPNs) with high optical activity in the visible spectral range based on initially achiral nanopillars from ZnO. We made asymmetric gold nanoshells on the nanopillars by vacuum evaporation at different inclination and rotation angles to achieve controlled symmetry breaking and obtained both left- and right-rotating isomers. The attribution of chiral optical effects to monolithic enantiomers made in this process was confirmed by theoretical calculations based on their geometry established from scanning electron microscope (SEM) images. The chirality of the nanoshells is retained upon the release from the substrate into a stable dispersion. Deviation of the incident angle of light from normal results in increase of polarization rotation and chiral g-factor as high as -0.3. This general approach for preparation of abiological nanoscale chiral materials can be extended to other out-of plane 3D nanostructures. The large area films made on achiral nanopillars are convenient for sensors, optical devices, and catalysis. PMID:24111695

  4. Electronic circular dichroism behavior of chiral Phthiobuzone

    PubMed Central

    Li, Li; Wang, Lin; Si, Yikang

    2014-01-01

    Phthiobuzone is a bis(thiosemicarbazone) derivative with a single chiral center which has been used as a racemate in the clinical treatment of herpes and trachoma diseases. In this study, its two enantiomers were prepared from chiral amino acids and their absolute configurations were investigated by electronic circular dichroism (ECD) combined with modern quantum-chemical calculations using time-dependent density functional theory. It was found that solvation changed both the conformational distribution and the ECD spectrum of each conformer. The theoretical ECD spectra of the two enantiomers were in good agreement with the experimentally determined spectra of the corresponding isomers in dimethyl sulfoxide. The ECD behavior of the bis(thiosemicarbazone) chromophore in a chiral environment is also discussed. Our results indicate that ECD spectroscopy may be a useful tool for the stereochemical evaluation of chiral drugs. PMID:26579380

  5. H-bond-driven supramolecular architectures of the syn and anti isomers of the dioxime of bicyclo[3.3.1]nonane-3,7-dione.

    PubMed

    Toşa, Nicoleta; Bende, Attila; Varga, Richard Attila; Terec, Anamaria; Bratu, Ioan; Grosu, Ion

    2009-05-15

    The formation and high stability of the H-bond-driven supramolecular architectures of the syn and anti isomers of the dioxime of bicyclo[3.3.1]nonane-3,7-dione were investigated by single crystal X-ray diffraction, NMR, FTIR, and molecular modeling. Self-assembly of the achiral syn isomer into a cyclic trimer (supramolecular wheel) and of the chiral anti isomer into homochiral cyclic dimers was observed. PMID:19371097

  6. Preparation of astaxanthin nanodispersions using gelatin-based stabilizer systems.

    PubMed

    Anarjan, Navideh; Nehdi, Imededdine Arbi; Sbihi, Hassen Mohamed; Al-Resayes, Saud Ibrahim; Malmiri, Hoda Jafarizadeh; Tan, Chin Ping

    2014-01-01

    The incorporation of lipophilic nutrients, such as astaxanthin (a fat soluble carotenoid) in nanodispersion systems can either increase the water solubility, stability and bioavailability or widen their applications in aqueous food and pharmaceutical formulations. In this research, gelatin and its combinations with sucrose oleate as a small molecular emulsifier, sodium caseinate (SC) as a protein and gum Arabic as a polysaccharide were used as stabilizer systems in the formation of astaxanthin nanodispersions via an emulsification-evaporation process. The results indicated that the addition of SC to gelatin in the stabilizer system could increase the chemical stability of astaxanthin nanodispersions significantly, while using a mixture of gelatin and sucrose oleate as a stabilizer led to production of nanodispersions with the smallest particle size (121.4±8.6 nm). It was also shown that a combination of gelatin and gum Arabic could produce optimal astaxanthin nanodispersions in terms of physical stability (minimum polydispersity index (PDI) and maximum zeta-potential). This study demonstrated that the mixture of surface active compounds showed higher emulsifying and stabilizing functionality compared to using them individually in the preparation of astaxanthin nanodispersions. PMID:25211006

  7. Isotopic chirality

    SciTech Connect

    Floss, H.G.

    1994-12-01

    This paper deals with compounds that are chiral-at least in part, due to isotope substitution-and their use in tracing the steric course of enzyme reaction in vitro and in vivo. There are other applications of isotopically chiral compounds (for example, in analyzing the steric course of nonenzymatic reactions and in probing the conformation of biomolecules) that are important but they will not be discussed in this context.

  8. Screening factors influencing the production of astaxanthin from freshwater and marine microalgae.

    PubMed

    Binti Ibnu Rasid, Elda Nurafnie; Mohamad, Shaza Eva; Jamaluddin, Haryati; Salleh, Madihah Md

    2014-02-01

    Astaxanthin, a carotenoid pigment found in several aquatic organisms, is responsible for the red colour of salmon, trout and crustaceans. In this study, astaxanthin production from freshwater microalga Chlorella sorokiniana and marine microalga Tetraselmis sp. was investigated. Cell growth and astaxanthin production were determined spectrophotometrically at 620 and 480 nm, respectively. Astaxanthin was extracted using acetone and measured subsequent to biomass removal. Aerated conditions favoured astaxanthin production in C. sorokiniana, whereas Tetraselmis sp. was best cultured under unaerated conditions. C. sorokiniana produced more astaxanthin with the highest yield reached at 7.83 mg/l in 6.0 mM in nitrate containing medium compared to Tetraselmis sp. which recorded the highest yield of only 1.96 mg/l in 1.5 mM nitrate containing medium. Production in C. sorokiniana started at the early exponential phase, indicating that astaxanthin may be a growth-associated product in this microalga. Further optimization of astaxanthin production was performed using C. sorokiniana through a 2(3) full factorial experimental design, and a yield of 8.39 mg/l was achieved. Overall, the study has shown that both microalgae are capable of producing astaxanthin. Additionally, this research has highlighted C. sorokiniana as a potential astaxanthin producer that could serve as a natural astaxanthin source in the current market. PMID:24338298

  9. Molecular mechanisms of the coordination between astaxanthin and fatty acid biosynthesis in Haematococcus pluvialis (Chlorophyceae).

    PubMed

    Chen, Guanqun; Wang, Baobei; Han, Danxiang; Sommerfeld, Milton; Lu, Yinghua; Chen, Feng; Hu, Qiang

    2015-01-01

    Astaxanthin, a red ketocarotenoid with strong antioxidant activity and high commercial value, possesses important physiological functions in astaxanthin-producing microalgae. The green microalga Haematococcus pluvialis accumulates up to 4% fatty acid-esterified astaxanthin (by dry weight), and is used as a model species for exploring astaxanthin biosynthesis in unicellular photosynthetic organisms. Although coordination of astaxanthin and fatty acid biosynthesis in a stoichiometric fashion was observed in H. pluvialis, the interaction mechanism is unclear. Here we dissected the molecular mechanism underlying coordination between the two pathways in H. pluvialis. Our results eliminated possible coordination of this inter-dependence at the transcriptional level, and showed that this interaction was feedback-coordinated at the metabolite level. In vivo and in vitro experiments indicated that astaxanthin esterification drove the formation and accumulation of astaxanthin. We further showed that both free astaxanthin biosynthesis and esterification occurred in the endoplasmic reticulum, and that certain diacylglycerol acyltransferases may be the candidate enzymes catalyzing astaxanthin esterification. A model of astaxanthin biosynthesis in H. pluvialis was subsequently proposed. These findings provide further insights into astaxanthin biosynthesis in H. pluvialis. PMID:25353310

  10. Using One's Hands for Naming Optical Isomers and Other Stereochemical Positions.

    ERIC Educational Resources Information Center

    Mezl, Vasek A.

    1996-01-01

    Presents a method that allows students to use their hands to obtain the stereochemistry of chiral centers without redrawing the structure. Discusses the use of the model in: determining the configurations of amino acids, determining if sugars are D or L isomers, the sequence rule procedure, prochirality, naming the sides of trigonal carbons, and…

  11. Improving the Stability of Astaxanthin by Microencapsulation in Calcium Alginate Beads

    PubMed Central

    Lin, Shen-Fu; Chen, Ying-Chen; Chen, Ray-Neng; Chen, Ling-Chun; Ho, Hsiu-O; Tsung, Yu-Han; Sheu, Ming-Thau; Liu, Der-Zen

    2016-01-01

    There has been considerable interest in the biological functions of astaxanthin and its potential applications in the nutraceutical, cosmetics, food, and feed industries in recent years. However, the unstable structure of astaxanthin considerably limits its application. Therefore, this study reports the encapsulation of astaxanthin in calcium alginate beads using the extrusion method to improve its stability. This study also evaluates the stability of the encapsulated astaxanthin under different storage conditions. The evaluation of astaxanthin stability under various environmental factors reveals that temperature is the most influential environmental factor in astaxanthin degradation. Stability analysis shows that, regardless of the formulation used, the content of astaxanthin encapsulated in alginate beads remains above 90% of the original amount after 21 days of storage at 25°C. These results suggest that the proposed technique is a promising way to enhance the stability of other sensitive compounds. PMID:27093175

  12. The effective photoinduction of Haematococcus pluvialis for accumulating astaxanthin with attached cultivation.

    PubMed

    Wan, Minxi; Hou, Dongmei; Li, Yuanguang; Fan, Jianhua; Huang, Jianke; Liang, Songtao; Wang, Weiliang; Pan, Ronghua; Wang, Jun; Li, Shulan

    2014-07-01

    As the optimal source of astaxanthin, Haematococcus pluvialis was cultured for commercial production of astaxanthin through two continuous phases: cell growth and astaxanthin induction. In this study, the efficiency of an attached system for producing astaxanthin from H. pluvialis was investigated and compared to that of the suspended system (bubble column bioreactor) under various conditions. Results showed that this attached system is more suitable for photoinduction of H. pluvialis than the suspended bioreactor. Under the optimal conditions, the astaxanthin productivity of the attached system was 65.8 mg m(-2)d(-1) and 2.4-fold of that in the suspended system. This attached approach also offers other advantages over suspended systems, such as, producing astaxanthin under a wide range of light intensities and temperatures, saving water, ease to harvest cells, resisting contamination. Therefore, the attached approach can be considered an economical, environmentally friendly and highly-efficient technology for producing astaxanthin from H. pluvialis. PMID:24787315

  13. Enantiodivergent Atroposelective Synthesis of Chiral Biaryls by Asymmetric Transfer Hydrogenation: Chiral Phosphoric Acid Catalyzed Dynamic Kinetic Resolution.

    PubMed

    Mori, Keiji; Itakura, Tsubasa; Akiyama, Takahiko

    2016-09-12

    Reported herein is an enantiodivergent synthesis of chiral biaryls by a chiral phosphoric acid catalyzed asymmetric transfer hydrogenation reaction. Upon treatment of biaryl lactols with aromatic amines and a Hantzsch ester in the presence of chiral phosphoric acid, dynamic kinetic resolution (DKR) involving a reductive amination reaction proceeded smoothly to furnish both R and S isomers of chiral biaryls with excellent enantioselectivities by proper choice of hydroxyaniline derivative. This trend was observed in wide variety of substrates, and various chiral biphenyl and phenyl naphthyl adducts were synthesized with satisfactory enantioselectivities in enantiodivergent fashion. The enantiodivergent synthesis of synthetically challenging, chiral o-tetrasubstituted biaryls were also accomplished, and suggests high synthetic potential of the present method. PMID:27491630

  14. Metabolic engineering of astaxanthin production in tobacco flowers.

    PubMed

    Mann, V; Harker, M; Pecker, I; Hirschberg, J

    2000-08-01

    Using metabolic engineering, we have modified the carotenoid biosynthesis pathway in tobacco (Nicotiana tabacum) to produce astaxanthin, a red pigment of considerable economic value. To alter the carotenoid pathway in chromoplasts of higher plants, the cDNA of the gene CrtO from the alga Haematococcus pluvialis, encoding beta-carotene ketolase, was transferred to tobacco under the regulation of the tomato Pds (phytoene desaturase) promoter. The transit peptide of PDS from tomato was used to target the CRTO polypeptide to the plastids. Chromoplasts in the nectary tissue of transgenic plants accumulated (3S,3'S) astaxanthin and other ketocarotenoids, changing the color of the nectary from yellow to red. This accomplishment demonstrates that plants can be used as a source of novel carotenoid pigments such as astaxanthin. The procedures described in this work can serve as a platform technology for future genetic manipulations of pigmentation of fruits and flowers of horticultural and floricultural importance. PMID:10932161

  15. Attached cultivation of Haematococcus pluvialis for astaxanthin production.

    PubMed

    Zhang, Wenduo; Wang, Junfeng; Wang, Jialin; Liu, Tianzhong

    2014-04-01

    Haematococcus pluvialis, the best natural source for astaxanthin, was cultivated with an immobilized biofilm method, viz. "attached cultivation", which was high in photosynthetic efficiency. A practical operational protocol for this "attached cultivation" method was investigated by studying the effects of inoculum density, light intensity, nitrogen quantity as well as medium volume on growth and astaxanthin accumulation. Results indicated the optimized inoculum density and light intensity were 10 g m(-2) and 100 μmol m(-2)s(-1), respectively. The optimized nitrogen supply strategy was circulating ca. 30 L of BG-11 medium with initial sodium nitrate concentration of ca. 1.8mM for 1m(2) of cultivation surface. With this strategy, the maximum astaxanthin productivity reached ca. 160 mg m(-2)d(-1) which is much higher than many other indoor researches. Both of the red and green cells were found in the biofilm with red cells on the top. PMID:24632411

  16. Effect of Astaxanthin on Human Sperm Capacitation

    PubMed Central

    Donà, Gabriella; Kožuh, Ivana; Brunati, Anna Maria; Andrisani, Alessandra; Ambrosini, Guido; Bonanni, Guglielmo; Ragazzi, Eugenio; Armanini, Decio; Clari, Giulio; Bordin, Luciana

    2013-01-01

    In order to be able to fertilize oocytes, human sperm must undergo a series of morphological and structural alterations, known as capacitation. It has been shown that the production of endogenous sperm reactive oxygen species (ROS) plays a key role in causing cells to undergo a massive acrosome reaction (AR). Astaxanthin (Asta), a photo-protective red pigment belonging to the carotenoid family, is recognized as having anti-oxidant, anti-cancer, anti-diabetic and anti-inflammatory properties and is present in many dietary supplements. This study evaluates the effect of Asta in a capacitating buffer which induces low ROS production and low percentages of acrosome-reacted cells (ARC). Sperm cells were incubated in the presence or absence of increasing concentrations of Asta or diamide (Diam) and analyzed for their ROS production, Tyr-phosphorylation (Tyr-P) pattern and percentages of ARC and non-viable cells (NVC). Results show that Asta ameliorated both sperm head Tyr-P and ARC values without affecting the ROS generation curve, whereas Diam succeeded in enhancing the Tyr-P level but only of the flagellum without increasing ARC values. It is suggested that Asta can be inserted in the membrane and therefore create capacitation-like membrane alteration which allow Tyr-P of the head. Once this has occurred, AR can take place and involves a higher numbers of cells. PMID:23736766

  17. Effect of astaxanthin on human sperm capacitation.

    PubMed

    Donà, Gabriella; Kožuh, Ivana; Brunati, Anna Maria; Andrisani, Alessandra; Ambrosini, Guido; Bonanni, Guglielmo; Ragazzi, Eugenio; Armanini, Decio; Clari, Giulio; Bordin, Luciana

    2013-06-01

    In order to be able to fertilize oocytes, human sperm must undergo a series of morphological and structural alterations, known as capacitation. It has been shown that the production of endogenous sperm reactive oxygen species (ROS) plays a key role in causing cells to undergo a massive acrosome reaction (AR). Astaxanthin (Asta), a photo-protective red pigment belonging to the carotenoid family, is recognized as having anti-oxidant, anti-cancer, anti-diabetic and anti-inflammatory properties and is present in many dietary supplements. This study evaluates the effect of Asta in a capacitating buffer which induces low ROS production and low percentages of acrosome-reacted cells (ARC). Sperm cells were incubated in the presence or absence of increasing concentrations of Asta or diamide (Diam) and analyzed for their ROS production, Tyr-phosphorylation (Tyr-P) pattern and percentages of ARC and non-viable cells (NVC). Results show that Asta ameliorated both sperm head Tyr-P and ARC values without affecting the ROS generation curve, whereas Diam succeeded in enhancing the Tyr-P level but only of the flagellum without increasing ARC values. It is suggested that Asta can be inserted in the membrane and therefore create capacitation-like membrane alteration which allow Tyr-P of the head. Once this has occurred, AR can take place and involves a higher numbers of cells. PMID:23736766

  18. Enantioselective separation of defined endocrine-disrupting nonylphenol isomers.

    PubMed

    Acir, Ismail-Hakki; Wüst, Matthias; Guenther, Klaus

    2016-08-01

    Nonylphenol is in the focus of worldwide endocrine-disrupter research and accounted for as a priority hazardous substance of the Water Framework Directive of the European Union. Technical nonylphenol consists of a very complex mixture of isomers and enantiomers. As estrogenic effect and degradation behavior in environmental processes of single nonylphenols are heavily dependent on the structure of the nonyl side chain, it is absolutely necessary to consider the nonylphenol problem from an isomer and enantiomer-specific viewpoint. In this study, an enantiomer-specific separation of eight defined synthesized nonylphenol isomers by five different special chiral cyclodextrin columns was performed underivatized and after methylation, silylation, and acylation. This work demonstrates that three columns out of the investigated five show an excellent separation behavior for the studied different nonylphenol isomers and can be used for the enantiomer-specific determination of nonylphenols in food, other biological matrices, and environmental samples in the future. Graphical abstract Enantiomeric pair of 4-NP170 (4-[1-ethyl-1,3,3-trimethylbutyl]phenol). PMID:27236316

  19. Punctuated Chirality

    NASA Astrophysics Data System (ADS)

    Gleiser, Marcelo; Thorarinson, Joel; Walker, Sara Imari

    2008-12-01

    Most biomolecules occur in mirror, or chiral, images of each other. However, life is homochiral: proteins contain almost exclusively L-amino acids, while only D-sugars appear in RNA and DNA. The mechanism behind this fundamental asymmetry of life remains an open problem. Coupling the spatiotemporal evolution of a general autocatalytic polymerization reaction network to external environmental effects, we show through a detailed statistical analysis that high intensity and long duration events may drive achiral initial conditions towards chirality. We argue that life’s homochirality resulted from sequential chiral symmetry breaking triggered by environmental events, thus extending the theory of punctuated equilibrium to the prebiotic realm. Applying our arguments to other potentially life-bearing planetary platforms, we predict that a statistically representative sampling will be racemic on average.

  20. Punctuated chirality.

    PubMed

    Gleiser, Marcelo; Thorarinson, Joel; Walker, Sara Imari

    2008-12-01

    Most biomolecules occur in mirror, or chiral, images of each other. However, life is homochiral: proteins contain almost exclusively L-amino acids, while only D-sugars appear in RNA and DNA. The mechanism behind this fundamental asymmetry of life remains an open problem. Coupling the spatiotemporal evolution of a general autocatalytic polymerization reaction network to external environmental effects, we show through a detailed statistical analysis that high intensity and long duration events may drive achiral initial conditions towards chirality. We argue that life's homochirality resulted from sequential chiral symmetry breaking triggered by environmental events, thus extending the theory of punctuated equilibrium to the prebiotic realm. Applying our arguments to other potentially life-bearing planetary platforms, we predict that a statistically representative sampling will be racemic on average. PMID:18841492

  1. Astaxanthin: sources, extraction, stability, biological activities and its commercial applications--a review.

    PubMed

    Ambati, Ranga Rao; Phang, Siew Moi; Ravi, Sarada; Aswathanarayana, Ravishankar Gokare

    2014-01-01

    There is currently much interest in biological active compounds derived from natural resources, especially compounds that can efficiently act on molecular targets, which are involved in various diseases. Astaxanthin (3,3'-dihydroxy-β, β'-carotene-4,4'-dione) is a xanthophyll carotenoid, contained in Haematococcus pluvialis, Chlorella zofingiensis, Chlorococcum, and Phaffia rhodozyma. It accumulates up to 3.8% on the dry weight basis in H. pluvialis. Our recent published data on astaxanthin extraction, analysis, stability studies, and its biological activities results were added to this review paper. Based on our results and current literature, astaxanthin showed potential biological activity in in vitro and in vivo models. These studies emphasize the influence of astaxanthin and its beneficial effects on the metabolism in animals and humans. Bioavailability of astaxanthin in animals was enhanced after feeding Haematococcus biomass as a source of astaxanthin. Astaxanthin, used as a nutritional supplement, antioxidant and anticancer agent, prevents diabetes, cardiovascular diseases, and neurodegenerative disorders, and also stimulates immunization. Astaxanthin products are used for commercial applications in the dosage forms as tablets, capsules, syrups, oils, soft gels, creams, biomass and granulated powders. Astaxanthin patent applications are available in food, feed and nutraceutical applications. The current review provides up-to-date information on astaxanthin sources, extraction, analysis, stability, biological activities, health benefits and special attention paid to its commercial applications. PMID:24402174

  2. Astaxanthin: Sources, Extraction, Stability, Biological Activities and Its Commercial Applications—A Review

    PubMed Central

    Ambati, Ranga Rao; Siew Moi, Phang; Ravi, Sarada; Aswathanarayana, Ravishankar Gokare

    2014-01-01

    There is currently much interest in biological active compounds derived from natural resources, especially compounds that can efficiently act on molecular targets, which are involved in various diseases. Astaxanthin (3,3′-dihydroxy-β, β′-carotene-4,4′-dione) is a xanthophyll carotenoid, contained in Haematococcus pluvialis, Chlorella zofingiensis, Chlorococcum, and Phaffia rhodozyma. It accumulates up to 3.8% on the dry weight basis in H. pluvialis. Our recent published data on astaxanthin extraction, analysis, stability studies, and its biological activities results were added to this review paper. Based on our results and current literature, astaxanthin showed potential biological activity in in vitro and in vivo models. These studies emphasize the influence of astaxanthin and its beneficial effects on the metabolism in animals and humans. Bioavailability of astaxanthin in animals was enhanced after feeding Haematococcus biomass as a source of astaxanthin. Astaxanthin, used as a nutritional supplement, antioxidant and anticancer agent, prevents diabetes, cardiovascular diseases, and neurodegenerative disorders, and also stimulates immunization. Astaxanthin products are used for commercial applications in the dosage forms as tablets, capsules, syrups, oils, soft gels, creams, biomass and granulated powders. Astaxanthin patent applications are available in food, feed and nutraceutical applications. The current review provides up-to-date information on astaxanthin sources, extraction, analysis, stability, biological activities, health benefits and special attention paid to its commercial applications. PMID:24402174

  3. Chemical stability of astaxanthin nanodispersions in orange juice and skimmed milk as model food systems.

    PubMed

    Anarjan, Navideh; Tan, Chin Ping

    2013-08-15

    Solubilising astaxanthin in nanodispersion systems is a promising approach to incorporate astaxanthin into water-based food formulations. In this research, the chemical stabilities of astaxanthin nanodispersions diluted in orange juice and skimmed milk as model food systems and in deionised water as a control were evaluated. The nanodispersions displayed significantly (p<0.05) better stability in food systems compared to the control. The effects of stabilisers and dilution factor were also studied. In skimmed milk and deionised water, the type of stabiliser had a significant effect (p<0.05) on astaxanthin degradation during storage. In vitro cellular uptake of astaxanthin from diluted astaxanthin nanodispersions in selected food systems was also evaluated. The cellular uptake of astaxanthin nanodispersions in skimmed milk was significantly higher (p<0.05) than that of astaxanthin nanodispersions in orange juice and deionised water. High in vitro cellular uptake of astaxanthin from the prepared astaxanthin nanodispersions can be achieved via incorporation into protein-based foods such as milk. PMID:23561141

  4. The role of photorespiration during astaxanthin accumulation in Haematococcus pluvialis (Chlorophyceae).

    PubMed

    Zhang, Chunhui; Zhang, Litao; Liu, Jianguo

    2016-10-01

    Most previous studies on Haematococcus pluvialis have been focused on growth and astaxanthin accumulation. However, the relationships between photorespiration and astaxanthin accumulation have not been clarified. The purpose of this study was to examine the role of photorespiration during the process of astaxanthin accumulation in H. pluvialis. During astaxanthin accumulation, the astaxanthin content was reduced significantly when photorespiration was inhibited by its specific inhibitor, carboxymethoxylamine. The inhibition of photorespiration did not change the dry weight, chlorophyll content and OJIP transients during the incubation; however, the inhibition of photorespiration significantly decreased the photochemistry of photosystem II and total photosynthetic O2 evolution capacity. Moreover, the restriction in photorespiration was synchronized with a decrease of astaxanthin accumulation. These results suggest that the photorespiratory pathway in H. pluvialis can accelerate astaxanthin accumulation. We speculate that photorespiration can enhance astaxanthin accumulation in the following ways: (i) photorespiration directly affects the glycerate-3-phosphate (PGA) level, which is intrinsically related to the accumulation of astaxanthin in H. pluvialis; (ii) the photorespiratory pathway indirectly affects the PGA level by effecting the dark reactions of photosynthesis, which then results in the enhancement of astaxanthin accumulation in H. pluvialis. PMID:27258571

  5. Prebiotic chirality

    NASA Astrophysics Data System (ADS)

    Mekki-Berrada, Ali

    Bringing closer phospholipids each other on a bilayer of liposome, causes their rotation around their fatty acids axis, generating a force which brings closer the two sheets of the bilayer. In this theoretical study I show that for getting the greater cohesion of the liposome, by these forces, the serine in the hydrophilic head must have a L chirality. In the case where the hydrophilic head is absent amino acids with L chirality could contribute to this cohesion by taking the place of L-serine. Some coenzymes having a configuration similar to ethanolamine may also contribute. This is the case of pyridoxamine, thiamine and tetrahydrofolic acid. The grouping of amino acids of L chirality and pyridoxamine on the wall could initialize the prebiotic metabolism of these L amino acids only. This would explain the origin of the homo-chirality of amino acids in living world. Furthermore I show that in the hydrophilic head, the esterification of glycerol-phosphate by two fatty acids go through the positioning of dihydroxyacetone-phosphate and L-glyceraldehyde-3-phosphate, but not of D-glyceraldehyde-3-phosphate, prior their hydrogenation to glycerol-3- phosphate. The accumulation of D-glyceraldehyde-3-phosphate in the cytoplasm displace the thermodynamic equilibria towards the synthesis of D-dATP from D-glyceraldehyde-3-phosphate, acetaldehyde and prebiotic adenine, a reaction which does not require a coenzyme in the biotic metabolism. D-dATP and thiamine, more prebiotic metabolism of L-amino acids on the wall, would initialize D-pentoses phosphate and D-nucleotides pathways from the reaction of D-glyceraldehyde-3-phosphate + dihydroxyacetone-phosphate + prebiotic nucleic bases. The exhaustion of the prebiotic glyceraldehyde (racemic) and the nascent biotic metabolism dominated by D-glyceraldehyde-3-phosphate, would explain the origin of homo-chirality of sugars in living world. References: http://en.wikiversity.org/wiki/Prebiotic_chirality

  6. Electromagnetic propulsion and separation by chirality of nanoparticles in liquids

    NASA Astrophysics Data System (ADS)

    Kirkinis, E.; Andreev, A. V.; Spivak, B.

    2012-01-01

    We introduce a new mechanism for the propulsion and separation by chirality of small ferromagnetic particles suspended in a liquid. Under the action of a uniform dc magnetic field H and an ac electric field E isomers with opposite chirality move in opposite directions. Such a mechanism could have a significant impact on a wide range of emerging technologies. The component of the chiral velocity that is odd in H is found to be proportional to the intrinsic orbital and spin angular momentum of the magnetized electrons. This effect arises because a ferromagnetic particle responds to the applied torque as a small gyroscope.

  7. Electromagnetic propulsion and separation by chirality of nanoparticles in liquids.

    PubMed

    Kirkinis, E; Andreev, A V; Spivak, B

    2012-01-01

    We introduce a new mechanism for the propulsion and separation by chirality of small ferromagnetic particles suspended in a liquid. Under the action of a uniform dc magnetic field H and an ac electric field E isomers with opposite chirality move in opposite directions. Such a mechanism could have a significant impact on a wide range of emerging technologies. The component of the chiral velocity that is odd in H is found to be proportional to the intrinsic orbital and spin angular momentum of the magnetized electrons. This effect arises because a ferromagnetic particle responds to the applied torque as a small gyroscope. PMID:22400671

  8. Kinetic model for astaxanthin aggregation in water-methanol mixtures

    NASA Astrophysics Data System (ADS)

    Giovannetti, Rita; Alibabaei, Leila; Pucciarelli, Filippo

    2009-07-01

    The aggregation of astaxanthin in hydrated methanol was kinetically studied in the temperature range from 10 °C to 50 °C, at different astaxanthin concentrations and solvent composition. A kinetic model for the formation and transformation of astaxanthin aggregated has been proposed. Spectrophotometric studies showed that monomeric astaxanthin decayed to H-aggregates that after-wards formed J-aggregates when water content was 50% and the temperature lower than 20 °C; at higher temperatures, very stable J-aggregates were formed directly. Monomer formed very stable H-aggregates when the water content was greater than 60%; in these conditions H-aggregates decayed into J-aggregates only when the temperature was at least 50 °C. Through these findings it was possible to establish that the aggregation reactions took place through a two steps consecutive reaction with first order kinetic constants and that the values of these depended on the solvent composition and temperature.

  9. The astaxanthin dideoxyglycoside biosynthesis pathway in Sphingomonas sp. PB304.

    PubMed

    Kim, Se Hyeuk; Kim, Jin Ho; Lee, Bun Yeol; Lee, Pyung Cheon

    2014-12-01

    A major carotenoid in Sphingomonas sp. PB304, originally isolated from a river in Daejon City, South Korea, was identified as astaxanthin dideoxyglycoside. Gene clusters encoding the astaxanthin dideoxyglycoside biosynthetic enzymes were identified by screening Sphingomonas sp. PB304 fosmid libraries using degenerate probes that harbor highly conserved sequences from the Sphigomonas elodea-derived crtI and Nostoc sp. PCC 7120-dervied crtW genes. Selected positive gene clusters were fully sequenced and annotated, revealing genes encoding six putative carotenogenic enzymes: phytoene synthase (CrtB), phytoene desaturase (CrtI), lycopene cyclase (CrtY), carotene hydroxylase (CrtZ), carotene ketolase (CrtW), and glycosyltransferase (CrtX). All of the carotenogenic enzymes, except for CrtX, were functional in the recombinant host Escherichia coli expressing synthetic carotenogenic modules from Pantoea agglomerans. CrtX did not take up UDP-glucose or GDP-fucose as sugar substrates during the in vitro reaction. Although no direct experimental evidence was obtained for the function of Sphingomonas sp. PB304 CrtX, it can be categorized as a putative deoxyglycosyltransferase based on the presence of astaxanthin dideoxyglycoside in Sphingomonas sp. PB304, a putative corresponding gene in the carotenoid biosynthetic gene cluster, and high amino acid sequence homology to the existing glycosyltransferases. Therefore, we propose that astaxanthin dideoxyglycoside can be synthesized in Sphingomonas sp. PB304 via sequential reactions of six pathway enzymes, including CrtX on the phytoene intermediate. PMID:25193422

  10. A new paradigm for producing astaxanthin from the unicellular green alga Haematococcus pluvialis.

    PubMed

    Zhang, Zhen; Wang, Baobei; Hu, Qiang; Sommerfeld, Milton; Li, Yuanguang; Han, Danxiang

    2016-10-01

    The unicellular green alga Haematococcus pluvialis has been exploited as a cell factory to produce the high-value antioxidant astaxanthin for over two decades, due to its superior ability to synthesize astaxanthin under adverse culture conditions. However, slow vegetative growth under favorable culture conditions and cell deterioration or death under stress conditions (e.g., high light, nitrogen starvation) has limited the astaxanthin production. In this study, a new paradigm that integrated heterotrophic cultivation, acclimation of heterotrophically grown cells to specific light/nutrient regimes, followed by induction of astaxanthin accumulation under photoautotrophic conditions was developed. First, the environmental conditions such as pH, carbon source, nitrogen regime, and light intensity, were optimized to induce astaxanthin accumulation in the dark-grown cells. Although moderate astaxanthin content (e.g., 1% of dry weight) and astaxanthin productivity (2.5 mg L(-1)  day(-1) ) were obtained under the optimized conditions, a considerable number of cells died off when subjected to stress for astaxanthin induction. To minimize the susceptibility of dark-grown cells to light stress, the algal cells were acclimated, prior to light induction of astaxanthin biosynthesis, under moderate illumination in the presence of nitrogen. Introduction of this strategy significantly reduced the cell mortality rate under high-light and resulted in increased cellular astaxanthin content and astaxanthin productivity. The productivity of astaxanthin was further improved to 10.5 mg L(-1)  day(-1) by implementation of such a strategy in a bubbling column photobioreactor. Biochemical and physiological analyses suggested that rebuilding of photosynthetic apparatus including D1 protein and PsbO, and recovery of PSII activities, are essential for acclimation of dark-grown cells under photo-induction conditions. Biotechnol. Bioeng. 2016;113: 2088-2099. © 2016 The Authors

  11. Enhancement of astaxanthin production using Haematococcus pluvialis with novel LED wavelength shift strategy.

    PubMed

    Xi, Tianqi; Kim, Dae Geun; Roh, Seong Woon; Choi, Jong-Soon; Choi, Yoon-E

    2016-07-01

    Haematococcus pluvialis is a green microalga of particular interest, since it is considered the best potential natural source of astaxanthin, which is widely used as an additive for natural pigmentation. In addition, astaxanthin has recently garnered commercial interest as a nutraceutical, cosmetic, and pharmaceutical. However, producing astaxanthin from H. pluvialis necessitates separation with distinctive culture conditions, dividing between the microalgae growth and the astaxanthin production stages. Light-emitting diodes (LEDs) have emerged as a replacement for traditional light sources, and LED applications are now rapidly expanding to multiple areas in fields such as biotechnology. However, further detail application into microalgae biotechnology remains limited. In this study, we have attempted to establish new protocols based on the specific wavelength of LEDs for the cultivation and production of astaxanthin using H. pluvialis. Specifically, we applied red LEDs for microalgae cell growth and then switched to blue LEDs to induce astaxanthin biosynthesis. The result showed that astaxanthin productions based on a wavelength shift from red to blue were significantly increased, compared to those with continuous illumination using red LEDs. Furthermore, additional increase of astaxanthin production was achieved with simultaneous application of exogenous carbon with blue LED illumination. Our approach based on the proper manipulation of LED wavelengths upon H. pluvialis cell stages will enable the improvement of biomass and enhance astaxanthin production using H. pluvialis. PMID:26860938

  12. Chiral streamers

    SciTech Connect

    Zou, Dandan; Cao, Xin; Lu, Xinpei; Ostrikov, Kostya

    2015-10-15

    The interaction of time-varying electromagnetic fields and solid, liquid, and gaseous matter may lead to electrical breakdown phenomena through the excitation of ionization waves or streamers that control the dynamics of localized plasma propagation through the media. The streamers usually propagate along straight lines, either between random points in space or along a certain direction in a guided mode. Here, we report on a new type of plasma discharges with the regular helical propagation pattern driven by a pulsed dc voltage in nitrogen at sub-atmospheric-pressure conditions. The helical guided streamers, named chiral streamers or chi-streamers, are excited without any external magnetic fields, which commonly cause helical plasma motions. We also demonstrate a hybrid propagation mode involving the interchangeable chiral streamers and the straight-line propagating plasmas. High-speed, time-resolved optical imaging reveals that the chiral streamers and the hybrid patterns are made of spatially localized discrete plasma bullets, similar to the straight-line guided streamers. These results may enable effective control of propagation of confined plasmas and electromagnetic energy along pre-determined, potentially deterministic paths, which have important implications for the development of next-generation plasma-based radiation sources, communication devices, and medical treatments.

  13. Chiral streamers

    NASA Astrophysics Data System (ADS)

    Zou, Dandan; Cao, Xin; Lu, Xinpei; Ostrikov, Kostya Ken

    2015-10-01

    The interaction of time-varying electromagnetic fields and solid, liquid, and gaseous matter may lead to electrical breakdown phenomena through the excitation of ionization waves or streamers that control the dynamics of localized plasma propagation through the media. The streamers usually propagate along straight lines, either between random points in space or along a certain direction in a guided mode. Here, we report on a new type of plasma discharges with the regular helical propagation pattern driven by a pulsed dc voltage in nitrogen at sub-atmospheric-pressure conditions. The helical guided streamers, named chiral streamers or chi-streamers, are excited without any external magnetic fields, which commonly cause helical plasma motions. We also demonstrate a hybrid propagation mode involving the interchangeable chiral streamers and the straight-line propagating plasmas. High-speed, time-resolved optical imaging reveals that the chiral streamers and the hybrid patterns are made of spatially localized discrete plasma bullets, similar to the straight-line guided streamers. These results may enable effective control of propagation of confined plasmas and electromagnetic energy along pre-determined, potentially deterministic paths, which have important implications for the development of next-generation plasma-based radiation sources, communication devices, and medical treatments.

  14. Genome mining of astaxanthin biosynthetic genes from Sphingomonas sp. ATCC 55669 for heterologous overproduction in Escherichia coli.

    PubMed

    Ma, Tian; Zhou, Yuanjie; Li, Xiaowei; Zhu, Fayin; Cheng, Yongbo; Liu, Yi; Deng, Zixin; Liu, Tiangang

    2016-02-01

    As a highly valued keto-carotenoid, astaxanthin is widely used in nutritional supplements and pharmaceuticals. Therefore, the demand for biosynthetic astaxanthin and improved efficiency of astaxanthin biosynthesis has driven the investigation of metabolic engineering of native astaxanthin producers and heterologous hosts. However, microbial resources for astaxanthin are limited. In this study, we found that the α-Proteobacterium Sphingomonas sp. ATCC 55669 could produce astaxanthin naturally. We used whole-genome sequencing to identify the astaxanthin biosynthetic pathway using a combined PacBio-Illumina approach. The putative astaxanthin biosynthetic pathway in Sphingomonas sp. ATCC 55669 was predicted. For further confirmation, a high-efficiency targeted engineering carotenoid synthesis platform was constructed in E. coli for identifying the functional roles of candidate genes. All genes involved in astaxanthin biosynthesis showed discrete distributions on the chromosome. Moreover, the overexpression of exogenous E. coli idi in Sphingomonas sp. ATCC 55669 increased astaxanthin production by 5.4-fold. This study described a new astaxanthin producer and provided more biosynthesis components for bioengineering of astaxanthin in the future. PMID:26580858

  15. Quantification of astaxanthin in shrimp waste hydrolysate by HPLC.

    PubMed

    López-Cervantes, J; Sánchez-Machado, D I; Gutiérrez-Coronado, M A; Ríos-Vázquez, N J

    2006-10-01

    In the present study, a simple and rapid reversed-phase HPLC method for the determination of astaxanthin in shrimp waste hydrolysate has been developed and validated. The analytical procedure involves the direct extraction of astaxanthin from the lipid fraction with methanol. The analytical column, SS Exil ODS, was operated at 25C. The mobile phase consisted of a mixture of water:methanol:dichloromethane:acetonitrile (4.5:28:22:45.5 v/v/v/v) at a flow rate of 1.0 mL/min. Detection and identification were performed using a photodiode array detector (lambda(detection) = 476 nm). The proposed HPLC method showed adequate linearity, repeatability and accuracy. PMID:16802328

  16. Metabolic engineering of astaxanthin biosynthesis in maize endosperm and characterization of a prototype high oil hybrid.

    PubMed

    Farré, Gemma; Perez-Fons, Laura; Decourcelle, Mathilde; Breitenbach, Jürgen; Hem, Sonia; Zhu, Changfu; Capell, Teresa; Christou, Paul; Fraser, Paul D; Sandmann, Gerhard

    2016-08-01

    Maize was genetically engineered for the biosynthesis of the high value carotenoid astaxanthin in the kernel endosperm. Introduction of a β-carotene hydroxylase and a β-carotene ketolase into a white maize genetic background extended the carotenoid pathway to astaxanthin. Simultaneously, phytoene synthase, the controlling enzyme of carotenogenesis, was over-expressed for enhanced carotenoid production and lycopene ε-cyclase was knocked-down to direct more precursors into the β-branch of the extended ketocarotenoid pathway which ends with astaxanthin. This astaxanthin-accumulating transgenic line was crossed into a high oil- maize genotype in order to increase the storage capacity for lipophilic astaxanthin. The high oil astaxanthin hybrid was compared to its astaxanthin producing parent. We report an in depth metabolomic and proteomic analysis which revealed major up- or down- regulation of genes involved in primary metabolism. Specifically, amino acid biosynthesis and the citric acid cycle which compete with the synthesis or utilization of pyruvate and glyceraldehyde 3-phosphate, the precursors for carotenogenesis, were down-regulated. Nevertheless, principal component analysis demonstrated that this compositional change is within the range of the two wild type parents used to generate the high oil producing astaxanthin hybrid. PMID:26931320

  17. Astaxanthin Inhibits Proliferation of Human Gastric Cancer Cell Lines by Interrupting Cell Cycle Progression

    PubMed Central

    Kim, Jung Ha; Park, Jong-Jae; Lee, Beom Jae; Joo, Moon Kyung; Chun, Hoon Jai; Lee, Sang Woo; Bak, Young-Tae

    2016-01-01

    Background/Aims Astaxanthin is a carotenoid pigment that has antioxidant, antitumoral, and anti-inflammatory properties. In this in vitro study, we investigated the mechanism of anticancer effects of astaxanthin in gastric carcinoma cell lines. Methods The human gastric adenocarcinoma cell lines AGS, KATO-III, MKN-45, and SNU-1 were treated with various concentrations of astaxanthin. A cell viability test, cell cycle analysis, and immunoblotting were performed. Results The viability of each cancer cell line was suppressed by astaxanthin in a dose-dependent manner with significantly decreased proliferation in KATO-III and SNU-1 cells. Astaxanthin increased the number of cells in the G0/G1 phase but reduced the proportion of S phase KATO-III and SNU-1 cells. Phosphorylated extracellular signal-regulated kinase (ERK) was decreased in an inverse dose-dependent correlation with astaxanthin concentration, and the expression of p27kip-1 increased the KATO-III and SNU-1 cell lines in an astaxanthin dose-dependent manner. Conclusions Astaxanthin inhibits proliferation by interrupting cell cycle progression in KATO-III and SNU-1 gastric cancer cells. This may be caused by the inhibition of the phosphorylation of ERK and the enhanced expression of p27kip-1. PMID:26470770

  18. Astaxanthin stimulates cell-mediated and humoral immune responses in cats.

    PubMed

    Park, Jean Soon; Mathison, Bridget D; Hayek, Michael G; Massimino, Stefan; Reinhart, Gregory A; Chew, Boon P

    2011-12-15

    Astaxanthin is a potent antioxidant carotenoid and may play a role in modulating immune response in cats. Blood was taken from female domestic shorthair cats (8-9 mo old; 3.2 ± 0.04 kg body weight) fed 0, 1, 5 or 10mg astaxanthin daily for 12 wk to assess peripheral blood mononuclear cell (PBMC) proliferation response, leukocyte subpopulations, natural killer (NK) cell cytotoxic activity, and plasma IgG and IgM concentration. Cutaneous delayed-type hypersensitivity (DTH) response against concanavalin A and an attenuated polyvalent vaccine was assessed on wk 8 (prior to vaccination) and 12 (post-vaccination). There was a dose-related increase in plasma astaxanthin concentrations, with maximum concentrations observed on wk 12. Dietary astaxanthin enhanced DTH response to both the specific (vaccine) and nonspecific (concanavalin A) antigens. In addition, cats fed astaxanthin had heightened PBMC proliferation and NK cell cytotoxic activity. The population of CD3(+) total T and CD4(+) T helper cells were also higher in astaxanthin-fed cats; however, no treatment difference was found with the CD8(+) T cytotoxic and MHC II(+) activated lymphocyte cell populations. Dietary astaxanthin increased concentrations of plasma IgG and IgM. Therefore, dietary astaxanthin heightened cell-mediated and humoral immune responses in cats. PMID:21930306

  19. [Characterization and evaluation of an astaxanthin over-producing Phaffia rhodozyma].

    PubMed

    Ni, Hui; Hong, Qinglin; Xiao, Anfeng; Li, Lijun; Cai, Huinong; Su, Wenjin

    2011-07-01

    We evaluated an astaxanthin overproducing Phaffia rhodozyma JMU-MVP14, and developed astaxanthin high-yielding fermentation process. We analyzed several fermentation parameters, i.e., biomass, astaxanthin and total carotenoids content to compare the characteristics of P rhodozyma JMU-MVP14 and the original strain through flask fermentation experiments. We conducted batch and fed-batch fermentation experiments in 7 L fermentor to investigate the effects of pH controlling models and feeding medium compositions on the production of astaxanthin. We further evaluated the capability and practical value of P rhodozyma JMU-MVP14 by fed-batch cultivation in the 1 m3 fermentor. Flask fermentation experiments revealed that P. rhodozyma JMU-MVP14 produced high yield of astaxanthin and carotenoids with specific productivity of astaxanthin and specific productivity of total carotenoids of 6.01 mg/g and 10.38 mg/g. Results of batch culture experiments in the 7 L fermentor showed that controlling the pH by ammonia auto-feeding was better than discontinuously adjusting pH value at 6.0 with regard to the high productivities of biomasses and astaxanthin. This P. rhodozyma strain synthesized astaxanthin partially linked to the growth with the Ks and pmax of 0.20 h ' and 21.73 g/L, respectively. Results of batch-fed fermentations in 7 L fermentor indicated that the complex feeding medium consisted of 50% glucose, 0.5% yeast extract and 0.3% corn steep syrup had lower astaxanthin productivity than the simple feeding medium containing only 50% glucose, which produced biomass, volumetric productivity of astaxanthin, volumetric productivity of total carotenoids, specific productivity of astaxanthin and total carotenoids at 32.81 g/L, 155.99 mg/L, 4.94 mg/g, 399.99 mg/L and 12.19 mg/g, respectively. As fed-batch cultured in 1 m3 fermentor, P rhodozyma JMU-MVP14 yielded 85.11 g/L of biomass, 279.96 mg/L of volumetric productivity of astaxanthin, 618.01 mg/L of volumetric productivity of

  20. Nuclear isomers: stepping stones to the unknown

    SciTech Connect

    Walker, P. M.

    2006-03-13

    The utility of isomers for exploring the nuclear landscape is discussed, including their role in superheavy-element research, and the possibility of observing neutron radioactivity. Emphasis is given to K isomers in deformed nuclei. Transition rates are examined in the NpNn scheme for 2- and 3-quasiparticle K-isomer decays, and in connection with level densities for higher quasiparticle numbers.

  1. Aggregation-Induced Resonance Raman Optical Activity (AIRROA): A New Mechanism for Chirality Enhancement.

    PubMed

    Zajac, Grzegorz; Kaczor, Agnieszka; Pallares Zazo, Ana; Mlynarski, Jacek; Dudek, Monika; Baranska, Malgorzata

    2016-05-01

    Raman optical activity (ROA) spectroscopy is hampered by low sensitivity, with limited possibilities for enhancing the signal. In the present study, we report a new mechanism whereby chirality is enhanced using the resonance resulting from supramolecular aggregation. We have named this mechanism aggregation-induced resonance Raman optical activity (AIRROA). As an example, we study J-aggregates of astaxanthin (AXT), which show strong absorption of circularly polarized light in the range of ROA excitation. The implications of aggregation-induced signal enhancement for chiroptical spectroscopy are discussed. PMID:27057926

  2. Chiral mirrors

    SciTech Connect

    Plum, Eric; Zheludev, Nikolay I.

    2015-06-01

    Mirrors are used in telescopes, microscopes, photo cameras, lasers, satellite dishes, and everywhere else, where redirection of electromagnetic radiation is required making them arguably the most important optical component. While conventional isotropic mirrors will reflect linear polarizations without change, the handedness of circularly polarized waves is reversed upon reflection. Here, we demonstrate a type of mirror reflecting one circular polarization without changing its handedness, while absorbing the other. The polarization-preserving mirror consists of a planar metasurface with a subwavelength pattern that cannot be superimposed with its mirror image without being lifted out of its plane, and a conventional mirror spaced by a fraction of the wavelength from the metasurface. Such mirrors enable circularly polarized lasers and Fabry-Pérot cavities with enhanced tunability, gyroscopic applications, polarization-sensitive detectors of electromagnetic waves, and can be used to enhance spectroscopies of chiral media.

  3. Chiral Hexahalogenated 4,4'-Bipyridines.

    PubMed

    Mamane, V; Peluso, P; Aubert, E; Cossu, S; Pale, P

    2016-06-01

    The preparation of 27 isomers of chiral hexahalogeno-4,4'-bipyridines by means of two complementary methods is described. The first one is convergent and based on the LDA-induced 4,4'-dimerization of trihalopyridines, whereas the second method is divergent and achieved through regioselective halogenation reactions of 4,4'-bipyridine-2,2'-diones. Iodine in 2,2'-positions of the 4,4'-bipyridines was introduced by a copper-catalyzed Finkelstein reaction (Buchwald procedure) performed on 2,2'-dibromo derivatives. Selected compounds of this new family of atropisomeric 4,4'-bipyridines were enantioseparated by high performance liquid chromatography on chiral stationary phases, and the absolute configurations of the separated enantiomers were assigned by using X-ray diffraction analysis. The latter revealed that various halogen bond types are responsible for crystal cohesion. PMID:27149320

  4. Astaxanthin reduces isoflurane-induced neuroapoptosis via the PI3K/Akt pathway.

    PubMed

    Wang, Chun-Mei; Cai, Xiao-Lan; Wen, Qing-Ping

    2016-05-01

    Astaxanthin is an oxygen-containing derivative of carotenoids that effectively suppresses reactive oxygen and has nutritional and medicinal value. The mechanisms underlying the effects of astaxanthin on isoflurane‑induced neuroapoptosis remain to be fully understood. The present study was conducted to evaluate the protective effect of astaxanthin to reduce isoflurane‑induced neuroapoptosis and to investigate the underlying mechanisms. The results demonstrated that isoflurane induced brain damage, increased caspase‑3 activity and suppressed the phosphatidylinositol 3‑kinase (PI3K)/protein kinase B (Akt) signaling pathway in an in vivo model. However, treatment with astaxanthin significantly inhibited brain damage, suppressed caspase‑3 activity and upregulated the PI3K/Akt pathway in the isoflurane‑induced rats. Furthermore, isoflurane suppressed cell growth, induced cell apoptosis, enhanced caspase‑3 activity and downregulated the PI3K/Akt pathway in organotypic hippocampal slice culture. Administration of astaxanthin significantly promoted cell growth, reduced cell apoptosis and caspase‑3 activity, and upregulated the PI3K/Akt pathway and isoflurane‑induced neuroapoptosis. The present study demonstrated that downregulation of the PI3K/Akt pathway reduced the effect of astaxanthin to protect against isoflurane‑induced neuroapoptosis in the in vitro model. The results of the current study suggested that the protective effect of astaxanthin reduces the isoflurane-induced neuroapoptosis via activation of the PI3K/Akt signaling pathway. PMID:27035665

  5. Astaxanthin ameliorates aluminum chloride-induced spatial memory impairment and neuronal oxidative stress in mice.

    PubMed

    Al-Amin, Md Mamun; Reza, Hasan Mahmud; Saadi, Hasan Mahmud; Mahmud, Waich; Ibrahim, Abdirahman Adam; Alam, Musrura Mefta; Kabir, Nadia; Saifullah, A R M; Tropa, Sarjana Tarannum; Quddus, A H M Ruhul

    2016-04-15

    Aluminum chloride induces neurodegenerative disease in animal model. Evidence suggests that aluminum intake results in the activation of glial cells and generation of reactive oxygen species. By contrast, astaxanthin is an antioxidant having potential neuroprotective activity. In this study, we investigate the effect of astaxanthin on aluminum chloride-exposed behavioral brain function and neuronal oxidative stress (OS). Male Swiss albino mice (4 months old) were divided into 4 groups: (i) control (distilled water), (ii) aluminum chloride, (iii) astaxanthin+aluminum chloride, and (iv) astaxanthin. Two behavioral tests; radial arm maze and open field test were conducted, and OS markers were assayed from the brain and liver tissues following 42 days of treatment. Aluminum exposed group showed a significant reduction in spatial memory performance and anxiety-like behavior. Moreover, aluminum group exhibited a marked deterioration of oxidative markers; lipid peroxidation (MDA), nitric oxide (NO), glutathione (GSH) and advanced oxidation of protein products (AOPP) in the brain. To the contrary, co-administration of astaxanthin and aluminum has shown improved spatial memory, locomotor activity, and OS. These results indicate that astaxanthin improves aluminum-induced impaired memory performances presumably by the reduction of OS in the distinct brain regions. We suggest a future study to determine the underlying mechanism of astaxanthin in improving aluminum-exposed behavioral deficits. PMID:26927754

  6. Studies on the metabolism of astaxanthin in the rainbow trout (Salmo gairdneri)

    SciTech Connect

    Al-Khalifah, A.S.

    1986-01-01

    Racemic astaxanthin was fed to rainbow trout (Salmo gairdneri) for 2, 4, and 6 weeks. The fish showed a bright pink coloration of the skin and flesh; the highest amount of astaxanthin was found in the skin of fish fed the test diet for six weeks. Lutein, 3-epilutein, and zeaxanthin were also detected in the flesh and skin; it was concluded that astaxanthin was converted to zeaxanthin in the skin. The mean vitamin A content of the liver was determined; the ratio of vitamin A/sub 1/:vitamin A/sub 2/ was approximately 1:3. Retinol and 3,4-dehydroretinol were extracted from the intestine of rainbow trout low in vitamin A, after force feeding with astaxanthin using a feeding tube. Antibiotic-treated fish had no marked difference in vitamin A content compared with a control group that received no antibiotic. This proves that astaxanthin was converted to vitamin A in fish depleted of vitamin A, that microorganisms were not involved in the conversion, and that conversion occurred in the intestine. An in vitro study using /sup 3/H 3S, 3S'-astaxanthin incubated with duodenal and ileal segments of the intestine provided HLPC and radioisotope data, which showed that rainbow trout were able to bioconvert astaxanthin to vitamin A.

  7. Assessment and comparison of in vitro immunoregulatory activity of three astaxanthin stereoisomers

    NASA Astrophysics Data System (ADS)

    Sun, Weihong; Xing, Lihong; Lin, Hong; Leng, Kailiang; Zhai, Yuxiu; Liu, Xiaofang

    2016-04-01

    In recent years, the immune-modulatory role of all- trans astaxanthin from different pigment sources has been studied. It was reported that all- trans astaxanthin might exist as three stereoisomers, and the composition of all- trans stereoisomers in natural materials differs from that of synthetic products. However, the different biological effects of various all- trans stereoisomers still remain unclear. In the present study, we evaluated the bioactivity of three astaxanthin stereoisomers, ( 3S, 3'S)- trans-, ( 3R,3'R)- trans-and meso-trans-astaxanthin, in regulating cell-mediated immune response using mice lymphocytes and peritoneal exudates cells (PECs) systems. After the treatment with three astaxanthin stereoisomers (20 μmol L-1), the lymphocyte proliferation capacity, neutral red phagocytosis of PECs and natural killer (NK) cell cytotoxic activity were comparatively assessed. The results showed that all three astaxanthin stereoisomers significantly promoted lymphocyte proliferation, phagocytic capacity of PECs, and cytotoxic activity of NK cells. Moreover, the ( 3S,3'S)-trans-astaxanthin exhibited a much higher response than others.

  8. Chlorella zofingiensis as an Alternative Microalgal Producer of Astaxanthin: Biology and Industrial Potential

    PubMed Central

    Liu, Jin; Sun, Zheng; Gerken, Henri; Liu, Zheng; Jiang, Yue; Chen, Feng

    2014-01-01

    Astaxanthin (3,3′-dihydroxy-β,β-carotene-4,4′-dione), a high-value ketocarotenoid with a broad range of applications in food, feed, nutraceutical, and pharmaceutical industries, has been gaining great attention from science and the public in recent years. The green microalgae Haematococcus pluvialis and Chlorella zofingiensis represent the most promising producers of natural astaxanthin. Although H. pluvialis possesses the highest intracellular astaxanthin content and is now believed to be a good producer of astaxanthin, it has intrinsic shortcomings such as slow growth rate, low biomass yield, and a high light requirement. In contrast, C. zofingiensis grows fast phototrophically, heterotrophically and mixtrophically, is easy to be cultured and scaled up both indoors and outdoors, and can achieve ultrahigh cell densities. These robust biotechnological traits provide C. zofingiensis with high potential to be a better organism than H. pluvialis for mass astaxanthin production. This review aims to provide an overview of the biology and industrial potential of C. zofingiensis as an alternative astaxanthin producer. The path forward for further expansion of the astaxanthin production from C. zofingiensis with respect to both challenges and opportunities is also discussed. PMID:24918452

  9. Inhibition of inflammation by astaxanthin alleviates cognition deficits in diabetic mice.

    PubMed

    Zhou, Xiaoyan; Zhang, Fang; Hu, Xiaotong; Chen, Jing; Wen, Xiangru; Sun, Ying; Liu, Yonghai; Tang, Renxian; Zheng, Kuiyang; Song, Yuanjian

    2015-11-01

    Neurons in the hippocampal and cortical functional regions are more susceptible to damage induced by hyperglycemia, which can result in severe spatial learning and memory impairment. Neuroprotection ameliorates cognitive impairment induced by hyperglycemia in diabetic encephalopathy (DE). Astaxanthin has been widely studied in diabetes mellitus and diabetic complications due to its hypoglycemic, antioxidant and anti-apoptotic effects. However, whether astaxanthin can alleviate cognition deficits induced by DE and its precise mechanisms remain undetermined. In this study, DE was induced by streptozotocin (STZ, 150 mg/kg) in ICR mice. We observed the effect of astaxanthin on cognition and investigated its potential mechanisms in DE mice. Results showed that astaxanthin treatment significantly decreased the latency and enhanced the distance and time spent in the target quadrant in the Morris water maze test. Furthermore, neuronal survival was significantly increased in the hippocampal CA3 region and the frontal cortex following treatment with astaxanthin. Meanwhile, immunoblotting was used to observe the nuclear translocation of nuclear factor-kappaB (NF-κB) p65 and the expression of tumor necrosis factor-α (TNF-α) in the hippocampus and frontal cortex. The results indicated that astaxanthin could inhibit NF-κB nuclear translocation and downregulate TNF-α expression in the hippocampus and frontal cortex. Overall, the present study implied that astaxanthin could improve cognition by protecting neurons against inflammation injury potentially through inhibiting the nuclear translocation of NF-κB and down-regulating TNF-α. PMID:26272354

  10. Ethanol induced astaxanthin accumulation and transcriptional expression of carotenogenic genes in Haematococcus pluvialis.

    PubMed

    Wen, Zewen; Liu, Zhiyong; Hou, Yuyong; Liu, Chenfeng; Gao, Feng; Zheng, Yubin; Chen, Fangjian

    2015-10-01

    Haematococcus pluvialis is one of the most promising natural sources of astaxanthin. However, inducing the accumulation process has become one of the primary obstacles in astaxanthin production. In this study, the effect of ethanol on astaxanthin accumulation was investigated. The results demonstrated that astaxanthin accumulation occurred with ethanol addition even under low-light conditions. The astaxanthin productivity could reach 11.26 mg L(-1) d(-1) at 3% (v/v) ethanol, which was 2.03 times of that of the control. The transcriptional expression patterns of eight carotenogenic genes were evaluated using real-time PCR. The results showed that ethanol greatly enhanced transcription of the isopentenyl diphosphate (IPP) isomerase genes (ipi-1 and ipi-2), which were responsible for isomerization reaction of IPP and dimethylallyl diphosphate (DMAPP). This finding suggests that ethanol induced astaxanthin biosynthesis was up-regulated mainly by ipi-1 and ipi-2 at transcriptional level, promoting isoprenoid synthesis and substrate supply to carotenoid formation. Thus ethanol has the potential to be used as an effective reagent to induce astaxanthin accumulation in H. pluvialis. PMID:26215339

  11. Recent breakthroughs in the biology of astaxanthin accumulation by microalgal cell.

    PubMed

    Solovchenko, Alexei E

    2015-09-01

    Massive accumulation of the secondary ketokarotenoid astaxanthin is a characteristic stress response of certain microalgal species with Haematococcus pluvialis as an illustrious example. The carotenogenic response confers these organisms a remarkable ability to survive in extremely unfavorable environments and makes them the richest source of natural astaxanthin. Exerting a plethora of beneficial effects on human and animal health, astaxanthin is among the most important bioproducts from microalgae. Though our understanding of astaxanthin biosynthesis, induction, and regulation is far from complete, this gap is filling rapidly with new knowledge generated predominantly by application of advanced "omics" approaches. This review focuses on the most recent progress in the biology of astaxanthin accumulation in microalgae including the genomic, proteomic, and metabolomics insights into the induction and regulation of secondary carotenogenesis and its role in stress tolerance of the photosynthetic microorganisms. Special attention is paid to the coupling of the carotenoid and lipid biosynthesis as well as deposition of astaxanthin in the algal cell. The place of the carotenogenic response among the stress tolerance mechanisms is revisited, and possible implications of the new findings for biotechnological production of astaxanthin from microalgae are considered. The potential use of the carotenogenic microalgae as a source not only of value-added carotenoids, but also of biofuel precursors is discussed. PMID:25975708

  12. Astaxanthin from Haematococcus pluvialis Prevents Oxidative Stress on Human Endothelial Cells without Toxicity.

    PubMed

    Régnier, Philippe; Bastias, Jorge; Rodriguez-Ruiz, Violeta; Caballero-Casero, Noelia; Caballo, Carmen; Sicilia, Dolores; Fuentes, Axelle; Maire, Murielle; Crepin, Michel; Letourneur, Didier; Gueguen, Virginie; Rubio, Soledad; Pavon-Djavid, Graciela

    2015-05-01

    Astaxanthin, a powerful antioxidant, is a good candidate for the prevention of intracellular oxidative stress. The aim of the study was to compare the antioxidant activity of astaxanthin present in two natural extracts from Haematococcus pluvialis, a microalgae strain, with that of synthetic astaxanthin. Natural extracts were obtained either by solvent or supercritical extraction methods. UV, HPLC-DAD and (HPLC-(atmospheric pressure chemical ionization (APCI)+)/ion trap-MS) characterizations of both natural extracts showed similar compositions of carotenoids, but different percentages in free astaxanthin and its ester derivatives. The Trolox equivalent antioxidant capacity (TEAC) assay showed that natural extracts containing esters displayed stronger antioxidant activities than free astaxanthin. Their antioxidant capacities to inhibit intracellular oxidative stress were then evaluated on HUVEC cells. The intracellular antioxidant activity in natural extracts was approximately 90-times higher than synthetic astaxanthin (5 µM). No modification, neither in the morphology nor in the viability, of vascular human cells was observed by in vitro biocompatibility study up to 10 µM astaxanthin concentrations. Therefore, these results revealed the therapeutic potential of the natural extracts in vascular human cell protection against oxidative stress without toxicity, which could be exploited in prevention and/or treatment of cardiovascular diseases. PMID:25962124

  13. Chlorella zofingiensis as an alternative microalgal producer of astaxanthin: biology and industrial potential.

    PubMed

    Liu, Jin; Sun, Zheng; Gerken, Henri; Liu, Zheng; Jiang, Yue; Chen, Feng

    2014-06-01

    Astaxanthin (3,3'-dihydroxy-β,β-carotene-4,4'-dione), a high-value ketocarotenoid with a broad range of applications in food, feed, nutraceutical, and pharmaceutical industries, has been gaining great attention from science and the public in recent years. The green microalgae Haematococcus pluvialis and Chlorella zofingiensis represent the most promising producers of natural astaxanthin. Although H. pluvialis possesses the highest intracellular astaxanthin content and is now believed to be a good producer of astaxanthin, it has intrinsic shortcomings such as slow growth rate, low biomass yield, and a high light requirement. In contrast, C. zofingiensis grows fast phototrophically, heterotrophically and mixtrophically, is easy to be cultured and scaled up both indoors and outdoors, and can achieve ultrahigh cell densities. These robust biotechnological traits provide C. zofingiensis with high potential to be a better organism than H. pluvialis for mass astaxanthin production. This review aims to provide an overview of the biology and industrial potential of C. zofingiensis as an alternative astaxanthin producer. The path forward for further expansion of the astaxanthin production from C. zofingiensis with respect to both challenges and opportunities is also discussed. PMID:24918452

  14. Astaxanthin from Haematococcus pluvialis Prevents Oxidative Stress on Human Endothelial Cells without Toxicity

    PubMed Central

    Régnier, Philippe; Bastias, Jorge; Rodriguez-Ruiz, Violeta; Caballero-Casero, Noelia; Caballo, Carmen; Sicilia, Dolores; Fuentes, Axelle; Maire, Murielle; Crepin, Michel; Letourneur, Didier; Gueguen, Virginie; Rubio, Soledad; Pavon-Djavid, Graciela

    2015-01-01

    Astaxanthin, a powerful antioxidant, is a good candidate for the prevention of intracellular oxidative stress. The aim of the study was to compare the antioxidant activity of astaxanthin present in two natural extracts from Haematococcus pluvialis, a microalgae strain, with that of synthetic astaxanthin. Natural extracts were obtained either by solvent or supercritical extraction methods. UV, HPLC-DAD and (HPLC-(atmospheric pressure chemical ionization (APCI)+)/ion trap-MS) characterizations of both natural extracts showed similar compositions of carotenoids, but different percentages in free astaxanthin and its ester derivatives. The Trolox equivalent antioxidant capacity (TEAC) assay showed that natural extracts containing esters displayed stronger antioxidant activities than free astaxanthin. Their antioxidant capacities to inhibit intracellular oxidative stress were then evaluated on HUVEC cells. The intracellular antioxidant activity in natural extracts was approximately 90-times higher than synthetic astaxanthin (5 µM). No modification, neither in the morphology nor in the viability, of vascular human cells was observed by in vitro biocompatibility study up to 10 µM astaxanthin concentrations. Therefore, these results revealed the therapeutic potential of the natural extracts in vascular human cell protection against oxidative stress without toxicity, which could be exploited in prevention and/or treatment of cardiovascular diseases. PMID:25962124

  15. Astaxanthin production in marine pelagic copepods grazing on two different phytoplankton diets

    NASA Astrophysics Data System (ADS)

    Van Nieuwerburgh, Lies; Wänstrand, Ingrid; Liu, Jianguo; Snoeijs, Pauli

    2005-02-01

    The red carotenoid astaxanthin is a powerful natural antioxidant of great importance in aquatic food webs where it is abundant in eggs and body tissues of fish and crustaceans. Little is known about the impact of the phytoplankton diet on astaxanthin production in copepods, its major pelagic producers. We followed the transfer of carotenoids from phytoplankton to copepods in a mesocosm experiment on the northern Atlantic coast (Norway) and recorded the astaxanthin production in copepods. Wild copepods grazed on nutrient-manipulated phytoplankton blooms, which differed in community composition and nutrient status (nitrogen or silicate limitation). The copepod pigments consisted mainly of free astaxanthin and mono- and diesters of astaxanthin. We found no significant difference in astaxanthin production per copepod individual or per unit C depending on the phytoplankton community. However, in the mesocosms astaxanthin per unit C decreased compared with natural levels, probably through a lower demand for photoprotection by the copepods in the dense phytoplankton blooms. The total astaxanthin production per litre was higher in the silicate-limited mesocosms through increased copepod density. Pigment ratio comparisons suggested that the copepod diet here consisted more of diatoms than in the nitrogen-limited mesocosms. Silicate-saturated diatoms were less grazed, possibly because they could invest more in defence mechanisms against their predators. Our study suggests that the production of astaxanthin in aquatic systems can be affected by changes in nutrient dynamics mediated by phytoplankton community composition and copepod population growth. This bottom-up force may have implications for antioxidant protection at higher trophic levels in the food web.

  16. Astaxanthin-Producing Green Microalga Haematococcus pluvialis: From Single Cell to High Value Commercial Products

    PubMed Central

    Shah, Md. Mahfuzur R.; Liang, Yuanmei; Cheng, Jay J.; Daroch, Maurycy

    2016-01-01

    Many species of microalgae have been used as source of nutrient rich food, feed, and health promoting compounds. Among the commercially important microalgae, Haematococcus pluvialis is the richest source of natural astaxanthin which is considered as “super anti-oxidant.” Natural astaxanthin produced by H. pluvialis has significantly greater antioxidant capacity than the synthetic one. Astaxanthin has important applications in the nutraceuticals, cosmetics, food, and aquaculture industries. It is now evident that, astaxanthin can significantly reduce free radicals and oxidative stress and help human body maintain a healthy state. With extraordinary potency and increase in demand, astaxanthin is one of the high-value microalgal products of the future.This comprehensive review summarizes the most important aspects of the biology, biochemical composition, biosynthesis, and astaxanthin accumulation in the cells of H. pluvialis and its wide range of applications for humans and animals. In this paper, important and recent developments ranging from cultivation, harvest and postharvest bio-processing technologies to metabolic control and genetic engineering are reviewed in detail, focusing on biomass and astaxanthin production from this biotechnologically important microalga. Simultaneously, critical bottlenecks and major challenges in commercial scale production; current and prospective global market of H. pluvialis derived astaxanthin are also presented in a critical manner. A new biorefinery concept for H. pluvialis has been also suggested to guide toward economically sustainable approach for microalgae cultivation and processing. This report could serve as a useful guide to present current status of knowledge in the field and highlight key areas for future development of H. pluvialis astaxanthin technology and its large scale commercial implementation. PMID:27200009

  17. Astaxanthin-Producing Green Microalga Haematococcus pluvialis: From Single Cell to High Value Commercial Products.

    PubMed

    Shah, Md Mahfuzur R; Liang, Yuanmei; Cheng, Jay J; Daroch, Maurycy

    2016-01-01

    Many species of microalgae have been used as source of nutrient rich food, feed, and health promoting compounds. Among the commercially important microalgae, Haematococcus pluvialis is the richest source of natural astaxanthin which is considered as "super anti-oxidant." Natural astaxanthin produced by H. pluvialis has significantly greater antioxidant capacity than the synthetic one. Astaxanthin has important applications in the nutraceuticals, cosmetics, food, and aquaculture industries. It is now evident that, astaxanthin can significantly reduce free radicals and oxidative stress and help human body maintain a healthy state. With extraordinary potency and increase in demand, astaxanthin is one of the high-value microalgal products of the future.This comprehensive review summarizes the most important aspects of the biology, biochemical composition, biosynthesis, and astaxanthin accumulation in the cells of H. pluvialis and its wide range of applications for humans and animals. In this paper, important and recent developments ranging from cultivation, harvest and postharvest bio-processing technologies to metabolic control and genetic engineering are reviewed in detail, focusing on biomass and astaxanthin production from this biotechnologically important microalga. Simultaneously, critical bottlenecks and major challenges in commercial scale production; current and prospective global market of H. pluvialis derived astaxanthin are also presented in a critical manner. A new biorefinery concept for H. pluvialis has been also suggested to guide toward economically sustainable approach for microalgae cultivation and processing. This report could serve as a useful guide to present current status of knowledge in the field and highlight key areas for future development of H. pluvialis astaxanthin technology and its large scale commercial implementation. PMID:27200009

  18. Effect of Diets Supplemented with Different Sources of Astaxanthin on the Gonad of the Sea Urchin Anthocidaris crassispina

    PubMed Central

    Peng, Juan; Yuan, Jian-Ping; Wang, Jiang-Hai

    2012-01-01

    The effect of the microalgae Haematococcus pluvialis and Chorella zofingiensis, and synthetic astaxanthin on the gonad of the sea urchin Anthocidaris crassispina was studied. The basal diet was supplemented with H. pluvialis, C. zofingiensis, or synthetic astaxanthin, at two levels of astaxanthin (approximately 400 mg/kg and 100 mg/kg), to obtain the experimental diets HP1, HP2, CZ1, CZ2, AST1, and AST2, respectively, for two months of feeding experiment. The results showed that the concentrations of astaxanthin in the gonads of the sea urchins fed these experimental diets ranged from 0.15 to 3.01 mg/kg dry gonad weight. The higher astaxanthin levels (>2.90 mg/kg) were found in the gonads of the sea urchins fed the diets HP1 (containing 380 mg/kg of astaxanthins, mostly mono- and diesters) and AST1 (containing 385 mg/kg of synthetic astaxanthin). The lowest astaxanthin level (0.15 mg/kg) was detected in the gonads of the sea urchins fed the diet CZ2 (containing 98 mg/kg of astaxanthins, mostly diesters). Furthermore, the highest canthaxanthin level (7.48 mg/kg) was found in the gonads of the sea urchins fed the diet CZ1 (containing 387 mg/kg of astaxanthins and 142 mg/kg of canthaxanthin), suggesting that astaxanthins, especially astaxanthin esters, might not be assimilated as easily as canthaxanthin by the sea urchins. Our results show that sea urchins fed diets containing astaxanthin pigments show higher incorporation of these known antioxidant constituents, with the resultant seafood products therefore being of potential higher nutritive value. PMID:23016124

  19. Chirality of Viral Capsids

    NASA Astrophysics Data System (ADS)

    Dharmavaram, Sanjay; Xie, Fangming; Bruinsma, Robijn; Klug, William; Rudnick, Joseph

    Most icosahedral viruses are classified by their T-number which identifies their capsid in terms of the number of capsomers and their relative arrangement. Certain T-numbers (T = 7 for instance) are inherently chiral (with no reflection planes) while others (e.g. T = 1) are achiral. We present a Landau-Brazovskii (LB) theory for weak crystallization in which a scalar order parameter that measures density of capsid proteins successfully predicts the various observed T-numbers and their respective chiralities. We find that chiral capsids gain stability by spontaneously breaking symmetry from an unstable chiral state. The inherently achiral LB-free energy does not preferentially select a particular chiral state from its mirror reflection. Based on the physical observation that proteins are inherently chiral molecules with directional interactions, we propose a new chiral term to the LB energy as a possible selection mechanism for chirality.

  20. Introduction to chiral symmetry

    SciTech Connect

    Koch, V.

    1996-01-08

    These lectures are an attempt to a pedagogical introduction into the elementary concepts of chiral symmetry in nuclear physics. Effective chiral models such as the linear and nonlinear sigma model will be discussed as well as the essential ideas of chiral perturbation theory. Some applications to the physics of ultrarelativistic heavy ion collisions will be presented.

  1. Cloning and selection of carotenoid ketolase genes for the engineering of high-yield astaxanthin in plants.

    PubMed

    Huang, Junchao; Zhong, Yujuan; Sandmann, Gerhard; Liu, Jin; Chen, Feng

    2012-08-01

    β-Carotene ketolase (BKT) catalyzes the rate-limiting steps for the biosynthesis of astaxanthin. Several bkt genes have been isolated and explored to modify plant carotenoids to astaxanthin with limited success. In this study, five algal BKT cDNAs were isolated and characterized for the engineering of high-yield astaxanthin in plants. The products of the cDNAs showed high similarity in sequence and enzymatic activity of converting β-carotene into canthaxanthin. However, the enzymes exhibited extremely different activities in converting zeaxanthin into astaxanthin. Chlamydomonas reinhardtii BKT showed the highest conversion rate (ca 85%), whereas, Neochloris wimmeri BKT exhibited very poor activity of ketolating zeaxanthin. Expression of C. reinhardtii BKT in tobacco led to a twofold increase of total carotenoids in the leaves with astaxanthin being the predominant. The bkt genes described here provide a valuable resource for metabolic engineering of plants as cell factories for astaxanthin production. PMID:22526507

  2. The effect of temperature on cell growth and astaxanthin accumulation of Haematococcus pluvialis during a light-dark cyclic cultivation.

    PubMed

    Wan, Minxi; Zhang, Jingkui; Hou, Dongmei; Fan, Jianhua; Li, Yuanguang; Huang, Jianke; Wang, Jun

    2014-09-01

    Haematococcus pluvialis is the best source of natural astaxanthin known as "the king of antioxidants". The mass outdoor culture is the most workable strategy for astaxanthin production, but the effects of daytime and night temperatures on the biomass concentration and astaxanthin content of H. pluvialis have received little attention. This study indicated that, raising the daytime or night temperature could stimulate night accumulation of astaxanthin until temperature up to 28°C; the night biomass loss increased firstly and then decreased along with the daytime temperature reducing; decreasing the night temperature can lessen night biomass loss; the daytime temperature of 28°C and the night temperature below 28°C were optimal for achieving high biomass and astaxanthin content. Subsequently, the outdoor culture strategy has been improved and can increase the net biomass and astaxanthin productivities by 5 and 2.9-fold as compared to the former strategy. PMID:24995877

  3. Review of genotoxicity and rat carcinogenicity investigations with astaxanthin.

    PubMed

    Edwards, James A; Bellion, Phillip; Beilstein, Paul; Rümbeli, Robert; Schierle, Joseph

    2016-03-01

    Synthetic astaxanthin has been extensively tested for safety. Genotoxicity studies including Ames and in vitro Micronucleus Tests show absence of genotoxic potential. Although a long-term mouse study showed no carcinogenicity potential, the rat carcinogenicity study with dietary dosages of 0 (control), 0 (placebo beadlet), 40, 200 and 1000 mg astaxanthin/kg bw/day showed an increased incidence of benign, hepatocellular adenoma in females only, at 200 mg/kg bw/day and above. There was no clear evidence of toxicity during the in-life phase. Discoloration of feces was observed and a reduction in body weight gain in all groups receiving beadlets, probably reflecting a nutritional influence. Blood sampling confirmed systemic exposure and some minor clinical chemistry differences in females at 200 and 1000 mg/kg bw/day. There was no effect on adjusted liver weight. Histopathological examination showed hepatic changes indicative of slight hepatotoxicity and hepatocyte regeneration in females at 200 and 1000 mg/kg bw/day, in addition to the adenoma. Taking into account this pathological background in the female rat, and a wide variety of other supporting information, it is concluded that the hepatocellular adenoma in female rats was secondary to hepatotoxicity and regeneration, and is most probably a species-specific phenomenon of doubtful human relevance. PMID:26713891

  4. Excited state dynamics of the astaxanthin radical cation

    NASA Astrophysics Data System (ADS)

    Amarie, Sergiu; Förster, Ute; Gildenhoff, Nina; Dreuw, Andreas; Wachtveitl, Josef

    2010-07-01

    Femtosecond transient absorption spectroscopy in the visible and NIR and ultrafast fluorescence spectroscopy were used to examine the excited state dynamics of astaxanthin and its radical cation. For neutral astaxanthin, two kinetic components corresponding to time constants of 130 fs (decay of the S 2 excited state) and 5.2 ps (nonradiative decay of the S 1 excited state) were sufficient to describe the data. The dynamics of the radical cation proved to be more complex. The main absorption band was shifted to 880 nm (D 0 → D 3 transition), showing a weak additional band at 1320 nm (D 0 → D 1 transition). We found, that D 3 decays to the lower-lying D 2 within 100 fs, followed by a decay to D 1 with a time constant of 0.9 ps. The D 1 state itself exhibited a dual behavior, the majority of the population is transferred to the ground state in 4.9 ps, while a small population decays on a longer timescale of 40 ps. Both transitions from D 1 were found to be fluorescent.

  5. Interconversion of diborane(4) isomers

    NASA Technical Reports Server (NTRS)

    Stanton, John F.; Gauss, Juergen; Bartlett, Rodney J.; Helgaker, Trygve; Jorgensen, Poul; Jensen, Hans J. A.; Taylor, Peter R.

    1992-01-01

    Highly correlated electronic structure computations using many-body perturbation theory and coupled-cluster gradient techniques are used to study the reaction pathway that links the two forms (C2u and D2d) of diborane(4). The results obtained indicate that a low-energy pathway exists for interconversion of the two low-lying isomers of diborane(4). The proposed mechanism consists of a single concerted but nonsynchronous rotation of the BH2 groups. The pathway first follows an idealized reaction coordinate which preserves C2 symmetry, but then bifurcates at a branch point, leading to two equivalent transition states which lack nontrivial elements of symmetry.

  6. Enhancing Photon Utilization Efficiency for Astaxanthin Production from Haematococcus lacustris Using a Split-Column Photobioreactor.

    PubMed

    Kim, Z-Hun; Park, Hanwool; Lee, Ho-Sang; Lee, Choul-Gyun

    2016-07-28

    A split-column photobioreactor (SC-PBR), consisting of two bubble columns with different sizes, was developed to enhance the photon utilization efficiency in an astaxanthin production process from Haematococcus lacustris. Among the two columns, only the smaller column of SC-PBR was illuminated. Astaxanthin productivities and photon efficiencies of the SC-PBRs were compared with a standard bubble-column PBR (BC-PBR). Astaxanthin productivity of SC-PBR was improved by 28%, and the photon utilization efficiencies were 28-366% higher than the original BC-PBR. The results clearly show that the effective light regime of SC-PBR could enhance the production of astaxanthin. PMID:27056475

  7. Sequential Heterotrophy-Dilution-Photoinduction Cultivation of Haematococcus pluvialis for efficient production of astaxanthin.

    PubMed

    Wan, Minxi; Zhang, Zhen; Wang, Jun; Huang, Jianke; Fan, Jianhua; Yu, Anquan; Wang, Weiliang; Li, Yuanguang

    2015-12-01

    A novel cultivation strategy called "Sequential Heterotrophy-Dilution-Photoinduction" was successfully applied in the cultivation of Haematococcus pluvialis to produce astaxanthin effectively. Cells were first cultivated heterotrophically to achieve a high cell density, then were diluted to a suitable concentration and switched to a favorable environment for cells acclimation. Finally, the culture was transferred to high light environment for astaxanthin accumulation. By this strategy, the dry cell weight of 26 g/L and biomass productivity of 64.1mg/L/h were obtained in heterotrophy stage which surpassed ever before reported in literatures. Meanwhile, the cells could accumulate considerable astaxanthin up to 4.6% of dry cell weight after 10 days of photoinduction. Furthermore, the application prospects of the strategy were confirmed further by outdoor experiments. Therefore, this novel strategy provided a promising approach for high-efficient production of natural astaxanthin from H. pluvialis to meet the huge demand of this high value product. PMID:26433152

  8. High spin isomer beam line at RIKEN

    SciTech Connect

    Kishida, T.; Ideguchi, E.; Wu, H.Y.

    1996-12-31

    Nuclear high spin states have been the subject of extensive experimental and theoretical studies. For the production of high spin states, fusion reactions are usually used. The orbital angular momentum brought in the reaction is changed into the nuclear spin of the compound nucleus. However, the maximum induced angular momentum is limited in this mechanism by the maximum impact parameter of the fusion reaction and by the competition with fission reactions. It is, therefore, difficult to populate very high spin states, and as a result, large {gamma}-detector arrays have been developed in order to detect subtle signals from such very high spin states. The use of high spin isomers in the fusion reactions can break this limitation because the high spin isomers have their intrinsic angular momentum, which can bring the additional angular momentum without increasing the excitation energy. There are two methods to use the high spin isomers for secondary reactions: the use of the high spin isomers as a target and that as a beam. A high spin isomer target has already been developed and used for several experiments. But this method has an inevitable shortcoming that only {open_quotes}long-lived{close_quotes} isomers can be used for a target: {sup 178}Hf{sup m2} (16{sup +}) with a half-life of 31 years in the present case. By developing a high spin isomer beam, the authors can utilize various short-lived isomers with a short half-life around 1 {mu}s. The high spin isomer beam line of RIKEN Accelerator Facility is a unique apparatus in the world which provides a high spin isomer as a secondary beam. The combination of fusion-evaporation reaction and inverse kinematics are used to produce high spin isomer beams; in particular, the adoption of `inverse kinematics` is essential to use short-lived isomers as a beam.

  9. Friction-induced enhancement in the optical activity of interacting chiral molecules

    NASA Astrophysics Data System (ADS)

    Bargueño, Pedro; Peñate-Rodríguez, Helen C.; Gonzalo, Isabel; Sols, Fernando; Miret-Artés, Salvador

    2011-11-01

    The stability of chiral molecules described by a non-linear two-state system which accounts for mean-field interactions between different isomers, including any external chiral influence (in particular, the parity violating energy difference) is investigated. By introducing the population and phase difference of the chiral states as a pair of canonical variables, driving an analogy to a bosonic Josephson junction, our study to include dissipative effects in condensed phase described by a Caldeira-Leggett like Hamiltonian is extended using the Langevin formalism. Dissipative effects produce an enhancement in the population difference, not leading to racemization.

  10. Anti-inflammatory Effect of Astaxanthin on the Sickness Behavior Induced by Diabetes Mellitus.

    PubMed

    Ying, Chang-jiang; Zhang, Fang; Zhou, Xiao-yan; Hu, Xiao-tong; Chen, Jing; Wen, Xiang-ru; Sun, Ying; Zheng, Kui-yang; Tang, Ren-xian; Song, Yuan-jian

    2015-10-01

    Chronic inflammation appears to play a critical role in sickness behavior caused by diabetes mellitus. Astaxanthin has been used in treating diabetes mellitus and diabetic complications because of its neuroprotective and anti-inflammatory actions. However, whether astaxanthin can improve sickness behavior induced by diabetes and its potential mechanisms are still unknown. The aim of this study was to investigate the effects of astaxanthin on diabetes-elicited abnormal behavior in mice and its corresponding mechanisms. An experimental diabetic model was induced by streptozotocin (150 mg/kg) and astaxanthin (25 mg/kg/day) was provided orally for 10 weeks. Body weight and water consumption were measured, and the sickness behavior was evaluated by the open field test (OFT) and closed field test (CFT). The expression of glial fibrillary acidic protein (GFAP) was measured, and the frontal cortical cleaved caspase-3 positive cells, interleukin-6 (IL-6), and interleukin-1β (IL-1β) expression levels were also investigated. Furthermore, cystathionine β-synthase (CBS) in the frontal cortex was detected to determine whether the protective effect of astaxanthin on sickness behavior in diabetic mice is closely related to CBS. As expected, we observed that astaxanthin improved general symptoms and significantly increase horizontal distance and the number of crossings in the OFT and CFT. Furthermore, data showed that astaxanthin could decrease GFAP-positive cells in the brain and down-regulate the cleaved caspase-3, IL-6, and IL-1β, and up-regulate CBS in the frontal cortex. These results suggest that astaxanthin provides neuroprotection against diabetes-induced sickness behavior through inhibiting inflammation, and the protective effects may involve CBS expression in the brain. PMID:25971983

  11. Prediction of enantiomeric selectivity in chromatography. Application of conformation-dependent and conformation-independent descriptors of molecular chirality.

    PubMed

    Aires-de-Sousa, João; Gasteiger, Johann

    2002-03-01

    In order to process molecular chirality by computational methods and to obtain predictions for properties that are influenced by chirality, a fixed-length conformation-dependent chirality code is introduced. The code consists of a set of molecular descriptors representing the chirality of a 3D molecular structure. It includes information about molecular geometry and atomic properties, and can distinguish between enantiomers, even if chirality does not result from chiral centers. The new molecular transform was applied to two datasets of chiral compounds, each of them containing pairs of enantiomers that had been separated by chiral chromatography. The elution order within each pair of isomers was predicted by means of Kohonen neural networks (NN) using the chirality codes as input. A previously described conformation-independent chirality code was also applied and the results were compared. In both applications clustering of the two classes of enantiomers (first eluted and last eluted enantiomers) could be successfully achieved by NN and accurate predictions could be obtained for independent test sets. The chirality code described here has a potential for a broad range of applications from stereoselective reactions to analytical chemistry and to the study of biological activity of chiral compounds. PMID:11885960

  12. Astaxanthin prevents and reverses diet-induced insulin resistance and steatohepatitis in mice: A comparison with vitamin E

    PubMed Central

    Ni, Yinhua; Nagashimada, Mayumi; Zhuge, Fen; Zhan, Lili; Nagata, Naoto; Tsutsui, Akemi; Nakanuma, Yasuni; Kaneko, Shuichi; Ota, Tsuguhito

    2015-01-01

    Hepatic insulin resistance and nonalcoholic steatohepatitis (NASH) could be caused by excessive hepatic lipid accumulation and peroxidation. Vitamin E has become a standard treatment for NASH. However, astaxanthin, an antioxidant carotenoid, inhibits lipid peroxidation more potently than vitamin E. Here, we compared the effects of astaxanthin and vitamin E in NASH. We first demonstrated that astaxanthin ameliorated hepatic steatosis in both genetically (ob/ob) and high-fat-diet-induced obese mice. In a lipotoxic model of NASH: mice fed a high-cholesterol and high-fat diet, astaxanthin alleviated excessive hepatic lipid accumulation and peroxidation, increased the proportion of M1-type macrophages/Kupffer cells, and activated stellate cells to improve hepatic inflammation and fibrosis. Moreover, astaxanthin caused an M2-dominant shift in macrophages/Kupffer cells and a subsequent reduction in CD4+ and CD8+ T cell recruitment in the liver, which contributed to improved insulin resistance and hepatic inflammation. Importantly, astaxanthin reversed insulin resistance, as well as hepatic inflammation and fibrosis, in pre-existing NASH. Overall, astaxanthin was more effective at both preventing and treating NASH compared with vitamin E in mice. Furthermore, astaxanthin improved hepatic steatosis and tended to ameliorate the progression of NASH in biopsy-proven human subjects. These results suggest that astaxanthin might be a novel and promising treatment for NASH. PMID:26603489

  13. Chirality in nonlinear optics.

    PubMed

    Haupert, Levi M; Simpson, Garth J

    2009-01-01

    The past decade has witnessed the emergence of new measurement approaches and applications for chiral thin films and materials enabled by the observations of the high sensitivity of second-order nonlinear optical measurements to chirality. In thin films, the chiral response to second harmonic generation and sum frequency generation (SFG) from a single molecular monolayer is often comparable with the achiral response. The chiral specificity also allows for symmetry-allowed SFG in isotropic chiral media, confirming predictions made approximately 50 years ago. With these experimental demonstrations in hand, an important challenge is the construction of intuitive predictive models that allow the measured chiral response to be meaningfully related back to molecular and macromolecular structure. This review defines and considers three distinct mechanisms for chiral effects in uniaxially oriented assemblies: orientational chirality, intrinsic chirality, and isotropic chirality. The role of each is discussed in experimental and computational studies of bacteriorhodopsin films, binaphthol, and collagen. Collectively, these three model systems support a remarkably simple framework for quantitatively recovering the measured chiral-specific activity. PMID:19046125

  14. Chirality in Nonlinear Optics

    NASA Astrophysics Data System (ADS)

    Haupert, Levi M.; Simpson, Garth J.

    2009-05-01

    The past decade has witnessed the emergence of new measurement approaches and applications for chiral thin films and materials enabled by the observations of the high sensitivity of second-order nonlinear optical measurements to chirality. In thin films, the chiral response to second harmonic generation and sum frequency generation (SFG) from a single molecular monolayer is often comparable with the achiral response. The chiral specificity also allows for symmetry-allowed SFG in isotropic chiral media, confirming predictions made ˜50 years ago. With these experimental demonstrations in hand, an important challenge is the construction of intuitive predictive models that allow the measured chiral response to be meaningfully related back to molecular and macromolecular structure. This review defines and considers three distinct mechanisms for chiral effects in uniaxially oriented assemblies: orientational chirality, intrinsic chirality, and isotropic chirality. The role of each is discussed in experimental and computational studies of bacteriorhodopsin films, binaphthol, and collagen. Collectively, these three model systems support a remarkably simple framework for quantitatively recovering the measured chiral-specific activity.

  15. Determination of astaxanthin in Haematococcus pluvialis by first-order derivative spectrophotometry.

    PubMed

    Liu, Xiao Juan; Juan, Liu Xiao; Wu, Ying Hua; Hua, Wu Ying; Zhao, Li Chao; Chao, Zhao Li; Xiao, Su Yao; Yao, Xiao Su; Zhou, Ai Mei; Mei, Zhou Ai; Liu, Xin; Xin, Liu

    2011-01-01

    A highly selective, convenient, and precise method, first-order derivative spectrophotometry, was applied for the determination of astaxanthin in Haematococcus pluvialis. Ethyl acetate and ethanol (1:1, v/v) were found to be the best extraction solvent tested due to their high efficiency and low toxicity compared with nine other organic solvents. Astaxanthin coexisting with chlorophyll and beta-carotene was analyzed by first-order derivative spectrophotometry in order to optimize the conditions for the determination of astaxanthin. The results show that when detected at 432 nm, the interfering substances could be eliminated. The dynamic linear range was 2.0-8.0 microg/mL, with a correlation coefficient of 0.9916. The detection threshold was 0.41 microg/mL. The RSD for the determination of astaxanthin was in the range of 0.01-0.06%; the results of recovery test were 98.1-108.0%. The statistical analysis between first-order derivative spectrophotometry and HPLC by T-testing did not exceed their critical values, revealing no significant differences between these two methods. It was proved that first-order derivative spectrophotometry is a rapid and convenient method for the determination of astaxanthin in H. pluvialis that can eliminate the negative effect resulting from the coexistence of astaxanthin with chlorophyll and beta-carotene. PMID:22320081

  16. Effects of selected polysorbate and sucrose ester emulsifiers on the physicochemical properties of astaxanthin nanodispersions.

    PubMed

    Anarjan, Navideh; Tan, Chin Ping

    2013-01-01

    The effects of selected nonionic emulsifiers on the physicochemical characteristics of astaxanthin nanodispersions produced by an emulsification/evaporation technique were studied. The emulsifiers used were polysorbates (Polysorbate 20, Polysorbate 40, Polysorbate 60 and Polysorbate 80) and sucrose esters of fatty acids (sucrose laurate, palmitate, stearate and oleate). The mean particle diameters of the nanodispersions ranged from 70 nm to 150 nm, depending on the emulsifier used. In the prepared nanodispersions, the astaxanthin particle diameter decreased with increasing emulsifier hydrophilicity and decreasing carbon number of the fatty acid in the emulsifier structure. Astaxanthin nanodispersions with the smallest particle diameters were produced with Polysorbate 20 and sucrose laurate among the polysorbates and the sucrose esters, respectively. We also found that the Polysorbate 80- and sucrose oleate-stabilized nanodispersions had the highest astaxanthin losses (i.e., the lowest astaxanthin contents in the final products) among the nanodispersions. This work demonstrated the importance of emulsifier type in determining the physicochemical characteristics of astaxanthin nano-dispersions. PMID:23303336

  17. Enumeration of chiral and achiral edge and face substitutions of buckminsterfullerene

    NASA Astrophysics Data System (ADS)

    Balasubramanian, K.

    1995-05-01

    The edge and face groups of the buckminsterfullerene cluster are formulated. The generalized character cycle indices of all the irreducible representations of both edge and face groups are obtained. The generating functions computed from these groups yield the chiral and achiral isomers, and mappings that transform according to the specified irreducible representation for edge and face colorings of buckminsterfullerene.

  18. Chiral symmetry and chiral-symmetry breaking

    SciTech Connect

    Peskin, M.E.

    1982-12-01

    These lectures concern the dynamics of fermions in strong interaction with gauge fields. Systems of fermions coupled by gauge forces have a very rich structure of global symmetries, which are called chiral symmetries. These lectures will focus on the realization of chiral symmetries and the causes and consequences of thier spontaneous breaking. A brief introduction to the basic formalism and concepts of chiral symmetry breaking is given, then some explicit calculations of chiral symmetry breaking in gauge theories are given, treating first parity-invariant and then chiral models. These calculations are meant to be illustrative rather than accurate; they make use of unjustified mathematical approximations which serve to make the physics more clear. Some formal constraints on chiral symmetry breaking are discussed which illuminate and extend the results of our more explicit analysis. Finally, a brief review of the phenomenological theory of chiral symmetry breaking is presented, and some applications of this theory to problems in weak-interaction physics are discussed. (WHK)

  19. Analytical chiral separation of the stereoisomers of a novel carbonic anhydrase inhibitor and its deethylated metabolite, and the assignment of absolute configuration of the human metabolite and chiral degradation products.

    PubMed

    Matuszewski, B K; Constanzer, M L; Kiganda, M

    1994-03-01

    Several approaches to the separation of four stereoisomers, 1-4, of a novel, topically active, carbonic anhydrase inhibitor, 1, with two chiral centers in the molecule and four isomers, 5-8, of its chiral metabolite, 5, were evaluated. These methods include nonchiral derivatization followed by separation on chiral stationary phases (CSPs) and chiral derivatization and separation on nonchiral columns and on CSPs. Baseline separation of stereoisomers 1-4 was achieved in less than 15 min after chiral derivatization with (S)-(+)-1-(1-naphthyl)ethyl isocyanate (NEIC) and chiral chromatography on a (R)-N-(3,5-dinitrobenzoyl)phenyl glycine (DNBPG) column under normal phase (NP) conditions. Similarly, isomers 5-8 were baseline separated in less than 20 min after derivatization with NEIC and chromatography on nonchiral (nitrophenyl) and chiral [(S)-(3,5-dinitrobenzoyl)leucine; DNBL] columns in series under the same NP chromatographic conditions. Only partial separation of the diastereomeric derivatives was observed on a variety of nonchiral columns. In addition, all other direct and indirect chiral separation approaches gave only partial separation of at least two stereoisomers within the group of 1-4 or 5-8. The details of chiral separations using various methods and separation (alpha) and capacity factors (k') of the derivatized isomers 1-8 on a series of chiral and nonchiral columns are presented. Using these methods, the absolute configuration of the human metabolite of 1 was established as S1S2 (5), and the heat (HD) and light (LD) degradation products of 1 as R1S2 (3) and S1S2 (5), respectively. PMID:8008715

  20. High-performance liquid chromatographic resolution of reverse isomers of 1,2-diacyl-rac-glycerols as 3,5-dinitrophenylurethanes.

    PubMed

    Itabashi, Y; Myher, J J; Kuksis, A

    2000-10-01

    The resolution of reverse isomers remains a major unsolved problem in glycerolipid chromatography. We have investigated the separation of the reverse isomers of 1,2-diacyl-rac-glycerols under a variety of high-performance liquid chromatography (HPLC) conditions. The reverse isomers of diacylglycerols having various pairs of acyl groups including short and highly unsaturated chains, which were prepared by partial Grignard degradation of the corresponding triacylglycerols, were chromatographed as 3,5-dinitrophenylurethanes. Excellent resolution was achieved for the reverse isomers of very different pairs of acyl groups, such as acetate-palmitate and docosahexaenoate-palmitate, by chiral-phase HPLC on columns containing (R)- and (S)-1-(1-naphthyl)ethylamine polymeric phases, reversed-phase HPLC on a highly efficient C18 column (4 microm particle size) and silver ion HPLC on a silver loaded cation-exchange column. The chiral-phase HPLC also permitted complete enantiomer resolution for all the reverse isomers examined. No satisfactory resolution by any of the HPLC methods, however, was obtained for the reverse isomers possessing minor differences in chain lengths and degree of unsaturation, such as laurate-palmitate and oleate-linoleate. The limitations of resolution and characteristics of elution are described. PMID:11073297

  1. Separation and identification of cis and trans isomers of 2-butene-1,4-diol and lafutidine by HPLC and LC-MS*

    PubMed Central

    Pan, Chun-xiu; Xu, Xiu-zhu; He, Hong-mei; Cai, Xiao-jun; Zhang, Xue-jun

    2005-01-01

    The cis and trans isomers separation of 2-butene-1,4-diol and lafutidine were studied by HPLC on two kinds of chiral columns: (S,S)-Whelk-O 1 and ChiraSpher. The isomers of 2-butene-1,4-diol can be separated on both chiral columns while the isomers of lafutidine can only be resolved on ChiraSpher column. The influence of different type and amount of mobile phase modifier on the isomers separation was extensively studied. The resolution of cis and trans isomers of 2-butene-1,4-diol was 2.61 on (S,S)-Whelk-O 1 column with hexane-ethanol (97:3, v/v) as the mobile phase. The resolution of lafutidine was 1.89 on ChiraSpher column with hexane-ethanol-THF-diethylamine (92:3:5:0.1, v/v/v/v) as the mobile phase. LC-MS methods were developed to identify the isomer peaks. PMID:15593397

  2. E/Z Isomers and Isomerization

    NASA Astrophysics Data System (ADS)

    Liaaen-Jensen, Synnøve; Lutnœes, Bjart Frode

    The natural occurrence of several carotenoid cis isomers and their biological significance were not anticipated in 1962, when the classical monograph on cis-trans isomeric carotenoids [1] was published. More recent research has demonstrated that various cis isomers occur naturally in bacteria plants, algae and invertebrate animals, and are present in human blood and tissues. The participation of cis isomers in the biosynthethic route to coloured carotenoids is well established (Volume 3, Chapter 2). Important biological functions of (15Z)-carotenoids in photosynthesis have been revealed [2]. In relation to health aspects of carotenoids, the bioavailability of cis isomers may be higher than that of the all-trans isomer [3], and accumulated evidence suggests that cis/trans isomerization may occur in biological tissues, particularly of lycopene (31) in human serum [4] (Volume 5, Chapter 7).

  3. Enantioselective and Synergetic Toxicity of Axial Chiral Herbicide Propisochlor to SP2/0 Myeloma Cells.

    PubMed

    Liu, Yao; Zhang, Xuan; Liu, Chunhong; Yang, Ruili; Xu, Zhenlin; Zhou, Lijun; Sun, Yuanming; Lei, Hongtao

    2015-09-16

    The axial chiral herbicide propisochlor is used to control weeds. Different enantiomers of a compound usually have different biological activities. It is unclear how the toxicities of the propisochlor enantiomers differ. Propisochlor enantiomers, separated by high-performance liquid chromatography, were tested on SP2/0 myeloma cells. Cytotoxicity and apoptosis were measured, and interactions between the enantiomers were evaluated. The rac-propisochlor, pure R-(+) isomer, and pure S-(-) isomer inhibited cell proliferation and induced apoptosis. The rac-propisochlor, R-(+) isomer, and S-(-) isomer half maximal effective concentration values after 24 h of incubation were 111 ± 0.15, 68 ± 0.09, and 99 ± 0.21 μM, respectively. R-(+) isomer induced the most apoptosis. R-(+) isomer was ∼1.63 times more cytotoxic than rac-propisochlor and ∼1.46 times more cytotoxic than S-(-) isomer. Antagonistic cytotoxic interactions were found between R-(+) and S-(-) isomers. This is the first time the toxicities of these enantiomers and antagonism between the enantiomers have been reported. The antagonism indicates that the ecotoxicological effects of the enantiomers should be investigated. PMID:26299567

  4. The effect of various antioxidants on the degradation of O/W microemulsions containing esterified astaxanthins from Haematococcus pluvialis.

    PubMed

    Zhou, Qingxin; Xu, Jie; Yang, Shu; Xue, Yong; Zhang, Ting; Wang, Jingfeng; Xue, Changhu

    2015-01-01

    Esterified astaxanthins are used as functional nutraceuticals and pigments in many food products. Unfortunately, the utilization is currently limited due to their chemical instability and poor water-solubility. In this study, esterified astaxanthins were quantified and purified from Haematococcus pluvialis using a novel and precise approach. By HPLC-(+)APCI-MS/MS, twenty esterified astaxanthin molecular species were identified, of which classified into eight monoester forms (approximately 85%, w/w) and twelve diester forms (approximately 15%, w/w), depending on the number of fatty acids that bind thereto. The MS data showed that the predominant fatty acids in astaxanthin esters of H. pluvialis are usually a long chain fatty acid with 16~18 carbon atoms, such as C18:1, C18:2, C18:3, C18:4, C16:0, C16:1. The purity of the esterified astaxanthins was determined to be 96.8±1.2% after purification. A well water-dispersible microemulsion was fabricated using high purity esterified astaxanthins, ethyl butyrate, Tween 80 and ethanol; and that emulsion exhibited a mean particle radius around 60 nm. The chemical degradation of esterified astaxanthins was monitored under accelerated stress storage conditions. After storage for 20 days, the results indicated that the degradation of esterified astaxanthins was effectively slowed by the addition of antioxidants to the microemulsions. By investigating the dependence of the chemical degradation of the esterified astaxanthins in O/W microemulsions on the concentration of the additives, it was concluded that the effectiveness of the additives at inhibiting the degradation of the esterified astaxanthins decreased in the following order: EDTA > ascorbic acid > vitamin E acetate. The utilization of antioxidants in combination was less effective than using them individually. These results provide information for designing effective delivery systems, thereby delaying the chemical degradation of esterified astaxanthins in foods

  5. Induction of molecular chirality by circularly polarized light in cyclic azobenzene with a photoswitchable benzene rotor.

    PubMed

    Hashim, P K; Thomas, Reji; Tamaoki, Nobuyuki

    2011-06-20

    New phototriggered molecular machines based on cyclic azobenzene were synthesized in which a 2,5-dimethoxy, 2,5-dimethyl, 2,5-difluorine or unsubstituted-1,4-dioxybenzene rotating unit and a photoisomerizable 3,3'-dioxyazobenzene moiety are bridged together by fixed bismethylene spacers. Depending upon substitution on the benzene moiety and on the E/Z conformation of the azobenzene unit, these molecules suffer various degrees of restriction on the free rotation of the benzene rotor. The rotation of the substituted benzene rotor within the cyclic azobenzene cavity imparts planar chirality to the molecules. Cyclic azobenzene 1, with methoxy groups at both the 2- and 5-positions of the benzene rotor, was so conformationally restricted that free rotation of the rotor was prevented in both the E and Z isomers and the respective planar chiral enantiomers were resolved. In contrast, compound 2, with 2,5-dimethylbenzene as the rotor, demonstrated the property of a light-controlled molecular brake, whereby rotation of the 2,5-dimethylbenzene moiety is completely stopped in the E isomer (brake ON, rotation OFF), while the rotation is allowed in the Z isomer (brake OFF, rotation ON). The cyclic azobenzene 3, with fluorine substitution on the benzene rotor, was in the brake OFF state regardless of E/Z photoisomerization of the azobenzene moiety. More interestingly, for the first time, we demonstrated the induction of molecular chirality in a simple monocyclic azobenzene by circular-polarized light. The key characteristics of cyclic azobenzene 2, that is, stability of the chiral structure in the E isomer, fast racemization in the Z isomer, and the circular dichroism of enantiomers of both E and Z isomers, resulted in a simple reversible enantio-differentiating photoisomerization directly between the E enantiomers. Upon exposure to r- or l-circularly polarized light at 488 nm, partial enrichment of the (S)- or (R)-enantiomers of 2 was observed. PMID:21567494

  6. Mechanically selflocked chiral gemini-catenanes

    PubMed Central

    Li, Sheng-Hua; Zhang, Heng-Yi; Xu, Xiufang; Liu, Yu

    2015-01-01

    Mechanically interlocked and entangled molecular architectures represent one of the elaborate topological superstructures engineered at a molecular resolution. Here we report a methodology for fabricating mechanically selflocked molecules (MSMs) through highly efficient one-step amidation of a pseudorotaxane derived from dual functionalized pillar[5]arene (P[5]A) threaded by α,ω-diaminoalkane (DA-n; n=3–12). The monomeric and dimeric pseudo[1]catenanes thus obtained, which are inherently chiral due to the topology of P[5]A used, were isolated and fully characterized by NMR and circular dichroism spectroscopy, X-ray crystallography and DFT calculations. Of particular interest, the dimeric pseudo[1]catenane, named ‘gemini-catenane', contained stereoisomeric meso-erythro and dl-threo isomers, in which two P[5]A moieties are threaded by two DA-n chains in topologically different patterns. This access to chiral pseudo[1]catenanes and gemini-catenanes will greatly promote the practical use of such sophisticated chiral architectures in supramolecular and materials science and technology. PMID:26126502

  7. Encapsulation of astaxanthin-rich Xanthophyllomyces dendrorhous for antioxidant delivery.

    PubMed

    Lee, Ji-Soo; Park, Sun-Ah; Chung, Donghwa; Lee, Hyeon Gyu

    2011-10-01

    Calcium alginate gel (CAG) beads were used to entrap the antioxidant astaxanthin-rich Xanthophyllomyces dendrorhous (ASX) by ionic gelation. ASX-CAG bead entrapment efficiency and release behavior, as influenced by alginate and CaCl(2) concentration and hardening time, were investigated. The optimized bead preparation conditions that gave rise to an efficient ASX release pattern were 1.5% alginate, 50mM CaCl(2), and a 5min hardening time. The antioxidant activity of non-encapsulated ASX was maintained for 4 days and then sharply decreased, whereas encapsulated ASX was maintained for 6 days. These results revealed that physical entrapment of ASX within CAG beads could be an effective technique for protecting the antioxidant activity of ASX from lipid peroxidation. PMID:21575657

  8. Astaxanthin reduces ischemic brain injury in adult rats

    PubMed Central

    Shen, Hui; Kuo, Chi-Chung; Chou, Jenny; Delvolve, Alice; Jackson, Shelley N.; Post, Jeremy; Woods, Amina S.; Hoffer, Barry J.; Wang, Yun; Harvey, Brandon K.

    2009-01-01

    Astaxanthin (ATX) is a dietary carotenoid of crustaceans and fish that contributes to their coloration. Dietary ATX is important for development and survival of salmonids and crustaceans and has been shown to reduce cardiac ischemic injury in rodents. The purpose of this study was to examine whether ATX can protect against ischemic injury in the mammalian brain. Adult rats were injected intracerebroventricularly with ATX or vehicle prior to a 60-min middle cerebral artery occlusion (MCAo). ATX was present in the infarction area at 70-75 min after onset of MCAo. Treatment with ATX, compared to vehicle, increased locomotor activity in stroke rats and reduced cerebral infarction at 2 d after MCAo. To evaluate the protective mechanisms of ATX against stroke, brain tissues were assayed for free radical damage, apoptosis, and excitoxicity. ATX antagonized ischemia-mediated loss of aconitase activity and reduced glutamate release, lipid peroxidation, translocation of cytochrome c, and TUNEL labeling in the ischemic cortex. ATX did not alter physiological parameters, such as body temperature, brain temperature, cerebral blood flow, blood gases, blood pressure, and pH. Collectively, our data suggest that ATX can reduce ischemia-related injury in brain tissue through the inhibition of oxidative stress, reduction of glutamate release, and antiapoptosis. ATX may be clinically useful for patients vulnerable or prone to ischemic events.—Shen, H., Kuo, C.-C., Chou, J., Delvolve, A., Jackson, S. N., Post, J., Woods, A. S., Hoffer, B. J., Wang, Y., Harvey, B. K. Astaxanthin reduces ischemic brain injury in adult rats. PMID:19218497

  9. Planar plasmonic chiral nanostructures.

    PubMed

    Zu, Shuai; Bao, Yanjun; Fang, Zheyu

    2016-02-21

    A strong chiral optical response induced at a plasmonic Fano resonance in a planar Au heptamer nanostructure was experimentally and theoretically demonstrated. The scattering spectra show the characteristic narrow-band feature of Fano resonances for both left and right circular polarized lights, with a chiral response reaching 30% at the Fano resonance. Specifically, we systematically investigate the chiral response of planar heptamers with gradually changing the inter-particle rotation angles and separation distance. The chiral spectral characteristics clearly depend on the strength of Fano resonances and the associated near-field optical distributions. Finite element method simulations together with a multipole expansion method demonstrate that the enhanced chirality is caused by the excitation of magnetic quadrupolar and electric toroidal dipolar modes. Our work provides an effective method for the design of 2D nanostructures with a strong chiral response. PMID:26818746

  10. Effects of iron electrovalence and species on growth and astaxanthin production of Haematococcus pluvialis

    NASA Astrophysics Data System (ADS)

    Cai, Minggang; Li, Zhe; Qi, Anxiang

    2009-05-01

    To increase the cell concentration and the accumulation of astaxanthin in the cultivation of Haematococcus pluvialis, effects of different iron electrovalencies (Fe2+-EDTA and Fe3+-EDTA) and species (Fe-EDTA, Fe(OH){x/32x} and FeC6H5O7) addition on cell growth and accumulation of astaxanthin were studied. Results show that different iron electrovalencies have various effects on cell growth and astaxanthin accumulation of H. pluvialis. Compared with Fe3+-EDTA, Fe2+-EDTA stimulate more effectively the formation of astaxanthin. The maximum astaxanthin content (30.70 mg/g biomass cell) was obtained under conditions of 18 μmol/L Fe2+-EDTA, despite the lower cell density (2.3×105 cell/ml) in such condition. Fe3+-EDTA is more effective than Fe2+-EDTA in improving the cell growth. Especially, the maximal steady-state cell density, 2.9×105 cell/ml was obtained at 18 μmol/L Fe3+-EDTA addition. On the other hand, all the various species of iron (EDTA-Fe, Fe(OH){x/32x}, FeC6H5O7) are capable to improve the growth of the algae and astaxanthin production. Among the three iron species, FeC6H5O7 performed the best. Under the condition of a higher concentration (36 μmol/L) of FeC6H5O7, the cell density and astaxanthin production is 2 and 7 times higher than those of iron-limited group, respectively. The present study demonstrates that the effects of the stimulation with different iron species increased in the order of FeC6H5O7, Fe(OH){x/32x} and EDTA-Fe.

  11. Axially chiral BODIPYs.

    PubMed

    Lerrick, Reinner I; Winstanley, Thomas P L; Haggerty, Karen; Wills, Corinne; Clegg, William; Harrington, Ross W; Bultinck, Patrick; Herrebout, Wouter; Benniston, Andrew C; Hall, Michael J

    2014-05-11

    The synthesis and resolution of a class of chiral organic fluorophores, axially chiral 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (Ax*-BODIPY), is described. Ax*-BODIPYs were prepared through a modular synthesis combined with a late stage Heck functionalisation. Resolution was achieved by preparative chiral HPLC. Absolute stereochemical assignment was performed by comparison of experimental ECD spectra with TD-DFT calculations. PMID:24676233

  12. Chiral atomically thin films

    NASA Astrophysics Data System (ADS)

    Kim, Cheol-Joo; Sánchez-Castillo, A.; Ziegler, Zack; Ogawa, Yui; Noguez, Cecilia; Park, Jiwoong

    2016-06-01

    Chiral materials possess left- and right-handed counterparts linked by mirror symmetry. These materials are useful for advanced applications in polarization optics, stereochemistry and spintronics. In particular, the realization of spatially uniform chiral films with atomic-scale control of their handedness could provide a powerful means for developing nanodevices with novel chiral properties. However, previous approaches based on natural or grown films, or arrays of fabricated building blocks, could not offer a direct means to program intrinsic chiral properties of the film on the atomic scale. Here, we report a chiral stacking approach, where two-dimensional materials are positioned layer-by-layer with precise control of the interlayer rotation (θ) and polarity, resulting in tunable chiral properties of the final stack. Using this method, we produce left- and right-handed bilayer graphene, that is, a two-atom-thick chiral film. The film displays one of the highest intrinsic ellipticity values (6.5 deg μm–1) ever reported, and a remarkably strong circular dichroism (CD) with the peak energy and sign tuned by θ and polarity. We show that these chiral properties originate from the large in-plane magnetic moment associated with the interlayer optical transition. Furthermore, we show that we can program the chiral properties of atomically thin films layer-by-layer by producing three-layer graphene films with structurally controlled CD spectra.

  13. Chiral atomically thin films.

    PubMed

    Kim, Cheol-Joo; Sánchez-Castillo, A; Ziegler, Zack; Ogawa, Yui; Noguez, Cecilia; Park, Jiwoong

    2016-06-01

    Chiral materials possess left- and right-handed counterparts linked by mirror symmetry. These materials are useful for advanced applications in polarization optics, stereochemistry and spintronics. In particular, the realization of spatially uniform chiral films with atomic-scale control of their handedness could provide a powerful means for developing nanodevices with novel chiral properties. However, previous approaches based on natural or grown films, or arrays of fabricated building blocks, could not offer a direct means to program intrinsic chiral properties of the film on the atomic scale. Here, we report a chiral stacking approach, where two-dimensional materials are positioned layer-by-layer with precise control of the interlayer rotation (θ) and polarity, resulting in tunable chiral properties of the final stack. Using this method, we produce left- and right-handed bilayer graphene, that is, a two-atom-thick chiral film. The film displays one of the highest intrinsic ellipticity values (6.5 deg μm(-1)) ever reported, and a remarkably strong circular dichroism (CD) with the peak energy and sign tuned by θ and polarity. We show that these chiral properties originate from the large in-plane magnetic moment associated with the interlayer optical transition. Furthermore, we show that we can program the chiral properties of atomically thin films layer-by-layer by producing three-layer graphene films with structurally controlled CD spectra. PMID:26900756

  14. Organization of Astaxanthin within Oil Bodies of Haematococcus pluvialis Studied with Polarization-Dependent Harmonic Generation Microscopy

    PubMed Central

    Tokarz, Danielle; Cisek, Richard; El-Ansari, Omar; Espie, George S.; Fekl, Ulrich; Barzda, Virginijus

    2014-01-01

    Nonlinear optical microscopy was used to image the localization of astaxanthin accumulation in the green alga, Haematococcus pluvialis. Polarization-in, polarization-out (PIPO) second harmonic generation (SHG) and third harmonic generation (THG) microscopy was applied to study the crystalline organization of astaxanthin molecules in light-stressed H. pluvialis in vivo. Since astaxanthin readily forms H- and J-aggregates in aqueous solutions, PIPO THG studies of astaxanthin aggregates contained in red aplanospores were compared to PIPO THG of in vitro self-assembled H- and J-aggregates of astaxanthin. The PIPO THG data clearly showed an isotropic organization of astaxanthin in red aplanospores of H. pluvialis. This is in contrast to the highly anisotropic organization of astaxanthin in synthetic H- and J-aggregates, which showed to be uniaxial. Since carotenoids in vitro preferentially form H- and J-aggregates, but in vivo form a randomly organized structure, this implies that astaxanthin undergoes a different way of packing in biological organisms, which is either due to the unique physical environment of the alga or is controlled enzymatically. PMID:25215522

  15. Highly efficient biosynthesis of astaxanthin in Saccharomyces cerevisiae by integration and tuning of algal crtZ and bkt.

    PubMed

    Zhou, Pingping; Ye, Lidan; Xie, Wenping; Lv, Xiaomei; Yu, Hongwei

    2015-10-01

    Astaxanthin is a highly valued carotenoid with strong antioxidant activity and has wide applications in aquaculture, food, cosmetic, and pharmaceutical industries. The market demand for natural astaxanthin promotes research in metabolic engineering of heterologous hosts for astaxanthin production. In this study, an astaxanthin-producing Saccharomyces cerevisiae strain was created by successively introducing the Haematococcus pluvialis β-carotenoid hydroxylase (crtZ) and ketolase (bkt) genes into a previously constructed β-carotene hyperproducer. Further integration of strategies including codon optimization, gene copy number adjustment, and iron cofactor supplementation led to significant increase in the astaxanthin production, reaching up to 4.7 mg/g DCW in the shake-flask cultures which is the highest astaxanthin content in S. cerevisiae reported to date. Besides, the substrate specificity of H. pluvialis CrtZ and BKT and the probable formation route of astaxanthin from β-carotene in S. cerevisiae were figured out by expressing the genes separately and in combination. The yeast strains engineered in this work provide a basis for further improving biotechnological production of astaxanthin and might offer a useful general approach to the construction of heterologous biosynthetic pathways for other natural products. PMID:26156241

  16. Organization of astaxanthin within oil bodies of Haematococcus pluvialis studied with polarization-dependent harmonic generation microscopy.

    PubMed

    Tokarz, Danielle; Cisek, Richard; El-Ansari, Omar; Espie, George S; Fekl, Ulrich; Barzda, Virginijus

    2014-01-01

    Nonlinear optical microscopy was used to image the localization of astaxanthin accumulation in the green alga, Haematococcus pluvialis. Polarization-in, polarization-out (PIPO) second harmonic generation (SHG) and third harmonic generation (THG) microscopy was applied to study the crystalline organization of astaxanthin molecules in light-stressed H. pluvialis in vivo. Since astaxanthin readily forms H- and J-aggregates in aqueous solutions, PIPO THG studies of astaxanthin aggregates contained in red aplanospores were compared to PIPO THG of in vitro self-assembled H- and J-aggregates of astaxanthin. The PIPO THG data clearly showed an isotropic organization of astaxanthin in red aplanospores of H. pluvialis. This is in contrast to the highly anisotropic organization of astaxanthin in synthetic H- and J-aggregates, which showed to be uniaxial. Since carotenoids in vitro preferentially form H- and J-aggregates, but in vivo form a randomly organized structure, this implies that astaxanthin undergoes a different way of packing in biological organisms, which is either due to the unique physical environment of the alga or is controlled enzymatically. PMID:25215522

  17. Metal-Organic Framework Isomers with Diamondoid Networks Constructed of a Semi-Rigid Tetrahedral Linker

    SciTech Connect

    Tian, Jian; Motkuri, Radha K.; Thallapally, Praveen K.; McGrail, B. Peter

    2010-10-19

    Solvothermal assembly of a semi-rigid tetrahedral carboxylate ligand tetrakis[4-(carboxyphenyl)oxamethyl]methane acid (H4X) with Cd(II) ion in different solvent systems yields three novel metal-organic framework isomers (1-3) based on different secondary building units (SBUs). Although all three frameworks have the same dia (diamondoid) topology, complex 1 and 3 are chiral and complex 2 is achiral. One of the networks, 3 shows cross-linked three-fold interpenetration of the single dia net and exhibits permanent porosities, as confirmed by BET and selective CO2 adsorption.

  18. Introduction of a single isomer beta agonist.

    PubMed

    Rau, J L

    2000-08-01

    The release of levalbuterol offers the first approved single-isomer beta agonist for oral inhalation. Data from in vitro studies support the concept that S albuterol is not inactive and may have properties antagonistic to bronchodilation. There is some variability in the results of clinical studies with the separate isomers of albuterol, which suggests the need for further study. The introduction of levalbuterol into general clinical use in managing asthma and chronic obstructive disease should begin to offer additional information on the effects of a single isomer beta agonist in comparison to previous racemic mixtures. PMID:10963321

  19. Improved Chiral Separation of Methamphetamine Enantiomers Using CSP-LC-MS-MS.

    PubMed

    Ward, Lauren F; Enders, Jeffrey R; Bell, David S; Cramer, Hugh M; Wallace, Frank N; McIntire, Gregory L

    2016-05-01

    To determine the true enantiomeric composition of methamphetamine urine drug testing results, chiral separation of dextro (d) and levo (l) enantiomers is necessary. While enantiomeric separation of methamphetamine has traditionally been accomplished using gas chromatography-mass spectrometry (GC-MS), chiral separation ofd- andl-methamphetamine by chiral stationary phase (CSP) liquid chromatography-mass spectrometry/mass spectrometry (LC-MS-MS) has proved more reliable. Chirally selective detection of methamphetamine by GC-MS is often performed usingl-N-trifluoroacetyl-prolyl chloride (TPC).l-TPC, a chiral compound, is known to have impurities that can affect the chiral composition percentages of the methamphetamine sample, potentially leading to inaccurate patient results. The comparative analysis of the samples run by GC and LC methods showed preferential bias of the GC method for producing error rates, consistent with previous research, of 8-19%. The CSP-LC-MS-MS method produces percent deviation errors of <2%. Additionally, the GC method failed to produce results that were 100%d- orl-isomer even for enantiomerically pure standards. A higher rate ofd- andl-methamphetamine isomer racemization is seen in samples when analyzed by GC-MS usingl-TPC-derivatizing agent. This racemization is not seen when these samples are tested with CSP-LC-MS-MS. Thus, a more accurate method of enantiomeric analysis is provided by CSP-LC-MS-MS. PMID:26869715

  20. Milks pigmentation with astaxanthin and determination of colour stability during short period cold storage.

    PubMed

    Mezquita, Pedro Cerezal; Huerta, Blanca E Barragán; Ramírez, Jenifer C Palma; Hinojosa, Claudia P Ortíz

    2015-03-01

    Astaxanthin has been used as a colorant and antioxidant with excellent results, its application and stability in food matrices to human consumption has been little studied. The aim of this work was the incorporation of astaxanthin oleoresin to milks with different fat content, simulating the red-orange color that can impart apricot fruit. For astaxanthin determination by HPLC, a methodology was implemented for its extraction from the food matrix, followed by saponification with KOH. Milk samples were stored (5 ± 2 °C) and stability of color and astaxanthin content were determined by colorimetry and high performance liquid chromatography each 24 h for a week. Pigment degradation followed first-order kinetic with a constant degradation of 0.259 day(-1) and 0.104 day(-1), in whole and semi-skimmed milk, respectively. Chromaticity coordinates L*, a*, b* for different types of milk showed a low dispersion of their values during the storage time, indicating high stability of astaxanthin within the matrix. PMID:25745234

  1. Extraction of astaxanthin from Euphausia pacific using subcritical 1, 1, 1, 2-tetrafluoroethane

    NASA Astrophysics Data System (ADS)

    Han, Yuqian; Ma, Qinchuan; Wang, Lan; Xue, Changhu

    2012-12-01

    Euphausia pacific is an important source of natural astaxanthin. Studies were carried out to assess the extractability of astaxanthin from E. pacific using subcritical 1, 1, 1, 2-tetrafluoroethane (R134a). To examine the effects of multiple process variables on the extraction yield, astaxanthin was extracted under various conditions of pressure (30-150 bar), temperature (303-343 K), time (10-50 min), flow rate (2-10 g min-1), moisture content (5.5%-63.61%), and particle size (0.25-0.109 mm). The results showed that the extraction yield increased with temperature, pressure, time and flow rate, but decreased with moisture content and particle size. A maximum yield of 87.74% was obtained under conditions of 100 bar, 333 K, and 30 min with a flow rate of 6 g min-1 and a moisture content of 5.5%. The substantial astaxanthin yield obtained under low-pressure conditions demonstrates that subcritical R134a is a good alternative to CO2 for extraction of astaxanthin from E. pacific.

  2. Transcriptome Analysis in Haematococcus pluvialis: Astaxanthin Induction by Salicylic Acid (SA) and Jasmonic Acid (JA)

    PubMed Central

    Wu, Guanxun; Li, Guoqiang; Sun, Haifeng; Deng, Suzhen; Shen, Yicheng; Chen, Guoqiang; Zhang, Ruihao; Meng, Chunxiao; Zhang, Xiaowen

    2015-01-01

    Haematococcus pluvialis is an astaxanthin-rich microalga that can increase its astaxanthin production by salicylic acid (SA) or jasmonic acid (JA) induction. The genetic transcriptome details of astaxanthin biosynthesis were analyzed by exposing the algal cells to 25 mg/L of SA and JA for 1, 6 and 24 hours, plus to the control (no stress). Based on the RNA-seq analysis, 56,077 unigenes (51.7%) were identified with functions in response to the hormone stress. The top five identified subcategories were cell, cellular process, intracellular, catalytic activity and cytoplasm, which possessed 5600 (~9.99%), 5302 (~9.45%), 5242 (~9.35%), 4407 (~7.86%) and 4195 (~7.48%) unigenes, respectively. Furthermore, 59 unigenes were identified and assigned to 26 putative transcription factors (TFs), including 12 plant-specific TFs. They were likely associated with astaxanthin biosynthesis in Haematococcus upon SA and JA stress. In comparison, the up-regulation of differential expressed genes occurred much earlier, with higher transcript levels in the JA treatment (about 6 h later) than in the SA treatment (beyond 24 h). These results provide valuable information for directing metabolic engineering efforts to improve astaxanthin biosynthesis in H. pluvialis. PMID:26484871

  3. Production of the Marine Carotenoid Astaxanthin by Metabolically Engineered Corynebacterium glutamicum.

    PubMed

    Henke, Nadja A; Heider, Sabine A E; Peters-Wendisch, Petra; Wendisch, Volker F

    2016-01-01

    Astaxanthin, a red C40 carotenoid, is one of the most abundant marine carotenoids. It is currently used as a food and feed additive in a hundred-ton scale and is furthermore an attractive component for pharmaceutical and cosmetic applications with antioxidant activities. Corynebacterium glutamicum, which naturally synthesizes the yellow C50 carotenoid decaprenoxanthin, is an industrially relevant microorganism used in the million-ton amino acid production. In this work, engineering of a genome-reduced C. glutamicum with optimized precursor supply for astaxanthin production is described. This involved expression of heterologous genes encoding for lycopene cyclase CrtY, β-carotene ketolase CrtW, and hydroxylase CrtZ. For balanced expression of crtW and crtZ their translation initiation rates were varied in a systematic approach using different ribosome binding sites, spacing, and translational start codons. Furthermore, β-carotene ketolases and hydroxylases from different marine bacteria were tested with regard to efficient astaxanthin production in C. glutamicum. In shaking flasks, the C. glutamicum strains developed here overproduced astaxanthin with volumetric productivities up to 0.4 mg·L(-1)·h(-1) which are competitive with current algae-based production. Since C. glutamicum can grow to high cell densities of up to 100 g cell dry weight (CDW)·L(-1), the recombinant strains developed here are a starting point for astaxanthin production by C. glutamicum. PMID:27376307

  4. Separation of astaxanthin from cells of Phaffia rhodozyma using colloidal gas aphrons in a flotation column.

    PubMed

    Dermiki, Maria; Bourquin, Anne Lise; Jauregi, Paula

    2010-01-01

    The aim of this study is to investigate the separation of astaxanthin from the cells of Phaffia rhodozyma using colloidal gas aphrons (CGA), which are surfactant stabilized microbubbles, in a flotation column. It was reported in previous studies that optimum recoveries are achieved at conditions that favor electrostatic interactions. Therefore, in this study, CGA generated from the cationic surfactant hexadecyl trimethyl ammonium bromide (CTAB) were applied to suspensions of cells pretreated with NaOH. The different operation modes (batch or continuous) and the effect of volumetric ratio of CGA to feed, initial concentration of feed, operating height, and flow rate of CGA on the separation of astaxanthin were investigated. The volumetric ratio was found to have a significant effect on the separation of astaxanthin for both batch and continuous experiments. Additionally, the effect of homogenization of the cells on the purity of the recovered fractions was investigated, showing that the homogenization resulted in increased purity. Moreover, different concentrations of surfactant were used for the generation of CGA for the recovery of astaxanthin on batch mode; it was found that recoveries up to 98% could be achieved using CGA generated from a CTAB solution 0.8 mM, which is below the CTAB critical micellar concentration (CMC). These results offer important information for the scale-up of the separation of astaxanthin from the cells of P. rhodozyma using CGA. PMID:19941328

  5. Anti-inflammatory effects of astaxanthin in the human gingival keratinocyte line NDUSD-1

    PubMed Central

    Miyachi, Masashiro; Matsuno, Tomonori; Asano, Kazunari; Mataga, Izumi

    2015-01-01

    Oral lichen planus is a chronic inflammatory disease that affects the mucous membrane of the oral cavity and can contribute to the development of other diseases. Inflammation in oral lichen planus is a T-cell-mediated autoimmune disease that acts through cytotoxic CD8+ T cells to trigger apoptosis of keratinocytes. However, the specific cause of oral lichen planus remains unknown and no effective medical treatment has yet been established. Astaxanthin is a carotenoid pigment with capacity for anti-inflammatory and anti-oxidant activities. In this study, we evaluated whether astaxanthin could be used to improve the pathology of oral lichen planus by reducing inflammation. In particular, the anti-inflammatory effects of astaxanthin on the chronic inflammation caused by lipopolysaccharide derived from Escherichia coli O55 in human gingival keratinocytes (NDUSD-1) were evaluated. Following astaxanthin treatment, localization of nuclear factor κB/p65 and the level of inflammatory cytokines (interleukin-6, tumor necrosis factor-α) tended to decrease, and cell proliferation significantly increased in vitro. These results suggest that astaxanthin could be useful for improving chronic inflammation such as that associated with oral lichen planus. PMID:26060346

  6. Safety assessment of [3S, 3'S]-astaxanthin--Subchronic toxicity study in rats.

    PubMed

    Buesen, R; Schulte, S; Strauss, V; Treumann, S; Becker, M; Gröters, S; Carvalho, S; van Ravenzwaay, B

    2015-07-01

    Astaxanthin, a naturally occurring xanthophyll, is commercially used as a coloring agent in salmon feed, but also marketed as a dietary supplement. The objective of this study was to investigate the subchronic toxicity of synthetic [3S, 3'S]-Astaxanthin in rats. A powder formulation containing approximately 20% [3S, 3'S]-Astaxanthin was administered via the diet to groups of 10 male and 10 female Wistar rats at concentrations of 5000, 15,000 and 50,000 ppm for a period of 13 weeks. A formulation of comparable composition but without [3S, 3'S]-Astaxanthin served as a placebo control. There were no effects observed on survival, clinical examinations, clinical pathology, estrous cycle as well as on sperm parameters. At terminal necropsy, a macroscopically visible brown-blue discoloration of the gastrointestinal contents was noted which was considered to be secondary to the violet-brown color of the test material. No other significant or dose-related abnormalities were found in the tissues collected at termination. Our observations support that ingestion of [3S, 3'S]-Astaxanthin of up to 700-920 mg/kg bw/day in rats in a gelatin/carbohydrate formulation is without adverse effects. PMID:25910834

  7. Transcriptome Analysis in Haematococcus pluvialis: Astaxanthin Induction by Salicylic Acid (SA) and Jasmonic Acid (JA).

    PubMed

    Gao, Zhengquan; Li, Yan; Wu, Guanxun; Li, Guoqiang; Sun, Haifeng; Deng, Suzhen; Shen, Yicheng; Chen, Guoqiang; Zhang, Ruihao; Meng, Chunxiao; Zhang, Xiaowen

    2015-01-01

    Haematococcus pluvialis is an astaxanthin-rich microalga that can increase its astaxanthin production by salicylic acid (SA) or jasmonic acid (JA) induction. The genetic transcriptome details of astaxanthin biosynthesis were analyzed by exposing the algal cells to 25 mg/L of SA and JA for 1, 6 and 24 hours, plus to the control (no stress). Based on the RNA-seq analysis, 56,077 unigenes (51.7%) were identified with functions in response to the hormone stress. The top five identified subcategories were cell, cellular process, intracellular, catalytic activity and cytoplasm, which possessed 5600 (~9.99%), 5302 (~9.45%), 5242 (~9.35%), 4407 (~7.86%) and 4195 (~7.48%) unigenes, respectively. Furthermore, 59 unigenes were identified and assigned to 26 putative transcription factors (TFs), including 12 plant-specific TFs. They were likely associated with astaxanthin biosynthesis in Haematococcus upon SA and JA stress. In comparison, the up-regulation of differential expressed genes occurred much earlier, with higher transcript levels in the JA treatment (about 6 h later) than in the SA treatment (beyond 24 h). These results provide valuable information for directing metabolic engineering efforts to improve astaxanthin biosynthesis in H. pluvialis. PMID:26484871

  8. Four different methods comparison for extraction of astaxanthin from green alga Haematococcus pluvialis.

    PubMed

    Dong, Shengzhao; Huang, Yi; Zhang, Rui; Wang, Shihui; Liu, Yun

    2014-01-01

    Haematococcus pluvialis is one of the potent organisms for production of astaxanthin. Up to now, no efficient method has been achieved due to its thick cell wall hindering solvent extraction of astaxanthin. In this study, four different methods, hydrochloric acid pretreatment followed by acetone extraction (HCl-ACE), hexane/isopropanol (6:4, v/v) mixture solvents extraction (HEX-IPA), methanol extraction followed by acetone extraction (MET-ACE, 2-step extraction), and soy-oil extraction, were intensively evaluated for extraction of astaxanthin from H. pluvialis. Results showed that HCl-ACE method could obtain the highest oil yield (33.3±1.1%) and astaxanthin content (19.8±1.1%). Quantitative NMR analysis provided the fatty acid chain profiles of total lipid extracts. In all cases, oleyl chains were predominant, and high amounts of polyunsaturated fatty acid chains were observed and the major fatty acid components were oleic acid (13-35%), linoleic acid (37-43%), linolenic acid (20-31%), and total saturated acid (17-28%). DPPH radical scavenging activity of extract obtained by HCl-ACE was 73.2±1.0%, which is the highest amongst the four methods. The reducing power of extract obtained by four extraction methods was also examined. It was concluded that the proposed extraction method of HCl-ACE in this work allowed efficient astaxanthin extractability with high antioxidant properties. PMID:24574909

  9. Four Different Methods Comparison for Extraction of Astaxanthin from Green Alga Haematococcus pluvialis

    PubMed Central

    Dong, Shengzhao; Huang, Yi; Zhang, Rui; Wang, Shihui; Liu, Yun

    2014-01-01

    Haematococcus pluvialis is one of the potent organisms for production of astaxanthin. Up to now, no efficient method has been achieved due to its thick cell wall hindering solvent extraction of astaxanthin. In this study, four different methods, hydrochloric acid pretreatment followed by acetone extraction (HCl-ACE), hexane/isopropanol (6 : 4, v/v) mixture solvents extraction (HEX-IPA), methanol extraction followed by acetone extraction (MET-ACE, 2-step extraction), and soy-oil extraction, were intensively evaluated for extraction of astaxanthin from H. pluvialis. Results showed that HCl-ACE method could obtain the highest oil yield (33.3 ± 1.1%) and astaxanthin content (19.8 ± 1.1%). Quantitative NMR analysis provided the fatty acid chain profiles of total lipid extracts. In all cases, oleyl chains were predominant, and high amounts of polyunsaturated fatty acid chains were observed and the major fatty acid components were oleic acid (13–35%), linoleic acid (37–43%), linolenic acid (20–31%), and total saturated acid (17–28%). DPPH radical scavenging activity of extract obtained by HCl-ACE was 73.2 ± 1.0%, which is the highest amongst the four methods. The reducing power of extract obtained by four extraction methods was also examined. It was concluded that the proposed extraction method of HCl-ACE in this work allowed efficient astaxanthin extractability with high antioxidant properties. PMID:24574909

  10. Molasses-based growth and production of oil and astaxanthin by Chlorella zofingiensis.

    PubMed

    Liu, Jin; Huang, Junchao; Jiang, Yue; Chen, Feng

    2012-03-01

    The aim of this study is to evaluate the industrial waste cane molasses as a carbon source for cell growth, lipid and astaxanthin production of Chlorella zofingiensis. Pretreated with cation exchange resin to remove the metal ions, cane molasses provided better productivities of biomass, lipid, and astaxanthin (1.55, 0.71 g L(-1)day(-1) and 1.7 mg L(-1)day(-1), respectively) than glucose. Using a strategy of semi-continuous cultures coupled with feeding at a low concentration, molasses without pretreatment has the same effect as pretreated one on supporting the algal cell growth, lipid and astaxanthin production. The efficient metabolism of molasses triggered the up-regulation of genes involved in fatty acid and also astaxanthin biosynthesis, leading to the very high production of the two metabolites. This study highlights the possibility of using C. zofingiensis to deal with industrial wastes and to produce profitable biodiesel as well as the high-value astaxanthin. PMID:22221991

  11. Production of the Marine Carotenoid Astaxanthin by Metabolically Engineered Corynebacterium glutamicum

    PubMed Central

    Henke, Nadja A.; Heider, Sabine A. E.; Peters-Wendisch, Petra; Wendisch, Volker F.

    2016-01-01

    Astaxanthin, a red C40 carotenoid, is one of the most abundant marine carotenoids. It is currently used as a food and feed additive in a hundred-ton scale and is furthermore an attractive component for pharmaceutical and cosmetic applications with antioxidant activities. Corynebacterium glutamicum, which naturally synthesizes the yellow C50 carotenoid decaprenoxanthin, is an industrially relevant microorganism used in the million-ton amino acid production. In this work, engineering of a genome-reduced C. glutamicum with optimized precursor supply for astaxanthin production is described. This involved expression of heterologous genes encoding for lycopene cyclase CrtY, β-carotene ketolase CrtW, and hydroxylase CrtZ. For balanced expression of crtW and crtZ their translation initiation rates were varied in a systematic approach using different ribosome binding sites, spacing, and translational start codons. Furthermore, β-carotene ketolases and hydroxylases from different marine bacteria were tested with regard to efficient astaxanthin production in C. glutamicum. In shaking flasks, the C. glutamicum strains developed here overproduced astaxanthin with volumetric productivities up to 0.4 mg·L−1·h−1 which are competitive with current algae-based production. Since C. glutamicum can grow to high cell densities of up to 100 g cell dry weight (CDW)·L−1, the recombinant strains developed here are a starting point for astaxanthin production by C. glutamicum. PMID:27376307

  12. Chiral geometry in multiple chiral doublet bands

    NASA Astrophysics Data System (ADS)

    Zhang, Hao; Chen, Qibo

    2016-02-01

    The chiral geometry of multiple chiral doublet bands with identical configuration is discussed for different triaxial deformation parameters γ in the particle rotor model with . The energy spectra, electromagnetic transition probabilities B(M1) and B(E2), angular momenta, and K-distributions are studied. It is demonstrated that the chirality still remains not only in the yrast and yrare bands, but also in the two higher excited bands when γ deviates from 30°. The chiral geometry relies significantly on γ, and the chiral geometry of the two higher excited partner bands is not as good as that of the yrast and yrare doublet bands. Supported by Plan Project of Beijing College Students’ Scientific Research and Entrepreneurial Action, Major State 973 Program of China (2013CB834400), National Natural Science Foundation of China (11175002, 11335002, 11375015, 11461141002), National Fund for Fostering Talents of Basic Science (NFFTBS) (J1103206), Research Fund for Doctoral Program of Higher Education (20110001110087) and China Postdoctoral Science Foundation (2015M580007)

  13. Astaxanthin Normalizes Epigenetic Modifications of Bovine Somatic Cell Cloned Embryos and Decreases the Generation of Lipid Peroxidation.

    PubMed

    Li, R; Wu, H; Zhuo, W W; Mao, Q F; Lan, H; Zhang, Y; Hua, S

    2015-10-01

    Astaxanthin is an extremely common antioxidant scavenging reactive oxygen species (ROS) and blocking lipid peroxidation. This study was conducted to investigate the effects of astaxanthin supplementation on oocyte maturation, and development of bovine somatic cell nuclear transfer (SCNT) embryos. Cumulus-oocyte complexes were cultured in maturation medium with astaxanthin (0, 0.5, 1.0, or 1.5 mg/l), respectively. We found that 0.5 mg/l astaxanthin supplementation significantly increased the proportion of oocyte maturation. Oocytes cultured in 0.5 mg/l astaxanthin supplementation were used to construct SCNT embryos and further cultured with 0, 0.5, 1.0 or 1.5 mg/l astaxanthin. The results showed that the supplementation of 0.5 mg/l astaxanthin significantly improved the proportions of cleavage and blastulation, as well as the total cell number in blastocysts compared with the control group, yet this influence was not concentration dependent. Chromosomal analyses revealed that more blastomeres showed a normal chromosomal complement in 0.5 mg/l astaxanthin treatment group, which was similar to that in IVF embryos. The methylation levels located on the exon 1 of the imprinted gene H19 and IGF2, pluripotent gene OCT4 were normalized, and global DNA methylation, H3K9 and H4K12 acetylation were also improved significantly, which was comparable to that in vitro fertilization (IVF) embryos. Moreover, we also found that astaxanthin supplementation significantly decreased the level of lipid peroxidation. Our findings showed that the supplementation of 0.5 mg/l astaxanthin to oocyte maturation medium and embryo culture medium improved oocyte maturation, SCNT embryo development, increased chromosomal stability and normalized the epigenetic modifications, as well as inhibited overproduction of lipid peroxidation. PMID:26280670

  14. Astaxanthin enhances ATP-binding cassette transporter A1/G1 expressions and cholesterol efflux from macrophages.

    PubMed

    Iizuka, Maki; Ayaori, Makoto; Uto-Kondo, Harumi; Yakushiji, Emi; Takiguchi, Shunichi; Nakaya, Kazuhiro; Hisada, Tetsuya; Sasaki, Makoto; Komatsu, Tomohiro; Yogo, Makiko; Kishimoto, Yoshimi; Kondo, Kazuo; Ikewaki, Katsunori

    2012-01-01

    ATP-binding cassette transporters (ABC) A1 and G1 are key molecules in cholesterol efflux from macrophages, which is an initial step of reverse cholesterol transport (RCT), a major anti-atherogenic property of high-density lipoprotein (HDL). Astaxanthin is one of the naturally occurring carotenoids responsible for the pink-red pigmentation in a variety of living organisms. Although astaxanthin is known to be a strong antioxidant, it remains unclear through what mechanism of action it affects cholesterol homeostasis in macrophages. We therefore investigated the effects of astaxanthin on cholesterol efflux and ABCA1/G1 expressions in macrophages. Astaxanthin enhanced both apolipoprotein (apo) A-I- and HDL-mediated cholesterol efflux from RAW264.7 cells. In supporting these enhanced cholesterol efflux mechanisms, astaxanthin promoted ABCA1/G1 expression in various macrophages. In contrast, peroxisome proliferator-activated receptor γ, liver X receptor (LXR) α and LXRβ levels remained unchanged by astaxanthin. An experiment using actinomycin D demonstrated that astaxanthin transcriptionally induced ABCA1/G1 expression, and oxysterol depletion caused by overexpression of cholesterol sulfotransferase further revealed that these inductions in ABCA1/G1 were independent of LXR-mediated pathways. Finally, we performed luciferase assays using human ABCA1/G1 promoter-reporter constructs to reveal that astaxanthin activated both promoters irrespective of the presence or absence of LXR-responsive elements, indicating LXR-independence of these activations. In conclusion, astaxanthin increased ABCA1/G1 expression, thereby enhancing apoA-I/HDL-mediated cholesterol efflux from the macrophages in an LXR-independent manner. In addition to the anti-oxidative properties, the potential cardioprotective properties of astaxanthin might therefore be associated with an enhanced anti-atherogenic function of HDL. PMID:22790567

  15. On the nature of non-covalent interactions in isomers of 2,5-dichloro-1,4-benzoquinone dimers - ground- and excited-state properties.

    PubMed

    Vijaya Pandiyan, B; Deepa, P; Kolandaivel, P

    2014-10-01

    The competition between non-covalent interactions (NCIs), such as C-H∙∙∙O, C-H∙∙∙Cl, C-Cl∙∙∙O, C-Cl∙∙∙Cl-C, C-O∙∙∙C, C-Cl∙∙∙C and C-O∙∙∙π, in the isomers of the 2,5-dichloro-1,4-benzoquinone (DCBQ) dimer were investigated by quantum chemical calculations to study the properties of the ground and excited states. All the interactions were identified through bond critical points (BCP) with an atoms in molecule (AIM) study. Isomer 1 (IH) and isomer 6 (IP) were surprisingly very stable, and the largest stabilization energies of 4.16 and 5.39 kcal mol(-1), respectively, were observed for the ground state and 5.67 and 6.07 kcal mol(-1), respectively, were observed for the excited state at the MP2/6-31++G(d,p) level of theory. The orientations of the excited-state isomers were similar to those of the ground-state except for isomer 5 (IX) and isomer 9 (IM), which disturbed the relative energy stability order. The calculated absorption spectra have shown two absorption splits for isomers 5, 7, 8 and 9 through the acute angle between the transition dipole moment of the monomers. The circular dichroism (CD) couplet of the CD spectrum and the value of optical rotation (OR) have indicated that isomers 1, 3, 5, 7, 8 and 9 have chiral characteristics. The study of the absorption and CD spectra has revealed the impact of intermolecular NCIs on chirality. PMID:25119497

  16. Subthreshold kaons would reveal density isomers

    SciTech Connect

    Hartnack, C.; Aichelin, J.; Stoecker, H.; Greiner, W. Gesellschaft fuer Schwerionenforschung, D-64220 Darmstadt Institut fuer Theoretische Physik, Universitaet Frankfurt, D-60065 Frankfurt )

    1994-06-13

    If density isomers exist they can be detected by measuring the excitation function of subthreshold kaon production. When the system reaches the density where the density isomer has influence on the equation of state (which depends on the beam energy and on the optical potential), we observe a jump in the cross section of the kaons whereas other observables change little. Above threshold [bar [Lambda

  17. Energetic and Structural Study of Diphenylpyridine Isomers

    NASA Astrophysics Data System (ADS)

    Rocha, Marisa A. A.; Gomes, Lígia R.; Low, John N.; Santos, Luís M. N. B. F.

    2009-09-01

    The energetic and structural study of three diphenylpyridine isomers is presented in detail. The three isomers, 2,6-, 2,5-, and 3,5-diphenylpyridines, were synthesized via Suzuki-Miyaura methodology based on palladium catalysis, and the crystal structures of the isomers were obtained by X-ray diffraction. The relative energetic stabilities in the condensed and gaseous phases as well as volatilities and structures of the three studied isomers were evaluated, regarding the position of the phenyl groups relative to the nitrogen atom of the pyridine ring. The temperature, standard molar enthalpies, and entropies of fusion were measured and derived by differential scanning calorimetry. The vapor pressures of the considered isomers were determined by a static apparatus based on a MKS capacitance diaphragm manometer. The standard molar enthalpies, entropies, and Gibbs energies of sublimation, at T = 298.15 K, were derived, and the phase diagram near the triple point coordinates were determined for all isomers. The standard (p° = 0.1 MPa) molar enthalpies of combustion of all crystalline isomers were determined, at T = 298.15 K, by static bomb combustion calorimetry. The standard molar enthalpies of formation, in the crystalline and gaseous phases, at T = 298.15 K, were derived. The experimental results for the energetics in the gaseous phase of the three compounds were compared and assessed with the values obtained by ab initio calculations at different levels of theory (DFT and MP2) showing that, at this level of theory, the computational methods underestimate the energetic stability, in the gaseous phase, for these molecules. In order to understand the aromaticity in the central ring of each isomer, calculations of NICS (B3LYP/6-311G++(d,p) level of theory) values on the pyridine ring were also performed.

  18. Optimization of the IPP Precursor Supply for the Production of Lycopene, Decaprenoxanthin and Astaxanthin by Corynebacterium glutamicum

    PubMed Central

    Heider, Sabine A. E.; Wolf, Natalie; Hofemeier, Arne; Peters-Wendisch, Petra; Wendisch, Volker F.

    2014-01-01

    The biotechnologically relevant bacterium Corynebacterium glutamicum, currently used for the million ton-scale production of amino acids for the food and feed industries, is pigmented due to synthesis of the rare cyclic C50 carotenoid decaprenoxanthin and its glucosides. The precursors of carotenoid biosynthesis, isopenthenyl pyrophosphate (IPP) and its isomer dimethylallyl pyrophosphate, are synthesized in this organism via the methylerythritol phosphate (MEP) or non-mevalonate pathway. Terminal pathway engineering in recombinant C. glutamicum permitted the production of various non-native C50 and C40 carotenoids. Here, the role of engineering isoprenoid precursor supply for lycopene production by C. glutamicum was characterized. Overexpression of dxs encoding the enzyme that catalyzes the first committed step of the MEP-pathway by chromosomal promoter exchange in a prophage-cured, genome-reduced C. glutamicum strain improved lycopene formation. Similarly, an increased IPP supply was achieved by chromosomal integration of two artificial operons comprising MEP pathway genes under the control of a constitutive promoter. Combined overexpression of dxs and the other six MEP pathways genes in C. glutamicum strain LYC3-MEP was not synergistic with respect to improving lycopene accumulation. Based on C. glutamicum strain LYC3-MEP, astaxanthin could be produced in the milligrams per gram cell dry weight range when the endogenous genes crtE, crtB, and crtI for conversion of geranylgeranyl pyrophosphate to lycopene were coexpressed with the genes for lycopene cyclase and β-carotene hydroxylase from Pantoea ananatis and carotene C(4) oxygenase from Brevundimonas aurantiaca. PMID:25191655

  19. Effects of Astaxanthin from Litopenaeus Vannamei on Carrageenan-Induced Edema and Pain Behavior in Mice.

    PubMed

    Kuedo, Zulkiflee; Sangsuriyawong, Anantita; Klaypradit, Wanwimol; Tipmanee, Varomyalin; Chonpathompikunlert, Pennapa

    2016-01-01

    Carrageenan produces both inflammation and pain when injected in mouse paws via enhancement of reactive oxygen species formation. We have investigated an effect of astaxanthin extracted from Litopenaeus vannamei in carrageenan-induced mice paw edema and pain. The current study demonstrates interesting effects from astaxanthin treatment in mice: an inhibition of paw edema induced in hind paw, an increase in mechanical paw withdrawal threshold and thermal paw withdrawal latency, and a reduction in the amount of myeloperoxidase enzyme and lipid peroxidation products in the paw. Furthermore the effect was comparable to indomethacin, a standard treatment for inflammation symptoms. Due to adverse effects of indomethacin on cardiovascular and gastrointestinal systems, our study suggests promising prospect of astaxanthin extract as an anti-inflammatory alternative against carrageenan-induced paw edema and pain behavior. PMID:27007359

  20. Recovery of astaxanthin from discharged wastewater during the production of chitin

    NASA Astrophysics Data System (ADS)

    Chen, Xiaolin; Yang, Shengfeng; Xing, Ronge; Yu, Huahua; Liu, Song; Li, Pengcheng

    2012-06-01

    In this paper, studies were carried out to extract astaxanthin from discharged wastewater during the production of chitin and to reveal the scavenging effect of the obtained pigment on 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical. Different ratios of dichloromethane/methanol (V/V) were used to extract astaxanthin. When the ratio of dichloromethane/methanol was 2:8 and the ratio between the mixed organic solvent (dichloromethane/methanol, 2:8, V/V) and wastewater was 1:1, the highest yield of pigment was obtained (8.4 mg/50 mL). The concentration of free astaxanthin in the obtained pigment analyzed by HPLC was 30.02%. The obtained pigment possessed strong scavenging ability on DPPH radical and IC50 was 0.84mg/ml.

  1. Physico-chemical stability of astaxanthin nanodispersions prepared with polysaccharides as stabilizing agents.

    PubMed

    Anarjan, Navideh; Tan, Chin Ping

    2013-09-01

    The emulsification and stabilization ability of four selected polysaccharides, namely, gum Arabic, xanthan gum, pectin and methyl cellulose, in the preparation of water-dispersible astaxanthin nanoparticles using the emulsification-evaporation technique was investigated in this study. The chemical and molecular structure of polysaccharides had significant effects (p < 0.05) on the physicochemical properties of the prepared astaxanthin nanodispersions. Among all prepared nanodispersions, sample produced and stabilized using gum Arabic showed the smallest average particle size (295 nm) and highest physical stability. The observed considerable degradation of astaxanthin in the resulting nanodispersions during processing (24-70% w/w) and storage at 10 °C for 30 d (86-96% w/w) illustrated the limited chemical stability of polysaccharide-stabilized nanodispersions. PMID:23590613

  2. Cell-wall disruption and lipid/astaxanthin extraction from microalgae: Chlorella and Haematococcus.

    PubMed

    Kim, Dong-Yeon; Vijayan, Durairaj; Praveenkumar, Ramasamy; Han, Jong-In; Lee, Kyubock; Park, Ji-Yeon; Chang, Won-Seok; Lee, Jin-Suk; Oh, You-Kwan

    2016-01-01

    Recently, biofuels and nutraceuticals produced from microalgae have emerged as major interests, resulting in intensive research of the microalgal biorefinery process. In this paper, recent developments in cell-wall disruption and extraction methods are reviewed, focusing on lipid and astaxanthin production from the biotechnologically important microalgae Chlorella and Haematococcus, respectively. As a common, critical bottleneck for recovery of intracellular components such as lipid and astaxanthin from these microalgae, the composition and structure of rigid, thick cell-walls were analyzed. Various chemical, physical, physico-chemical, and biological methods applied for cell-wall breakage and lipid/astaxanthin extraction from Chlorella and Haematococcus are discussed in detail and compared based on efficiency, energy consumption, type and dosage of solvent, biomass concentration and status (wet/dried), toxicity, scalability, and synergistic combinations. This report could serve as a useful guide to the implementation of practical downstream processes for recovery of valuable products from microalgae including Chlorella and Haematococcus. PMID:26342788

  3. Specific light uptake rates can enhance astaxanthin productivity in Haematococcus lacustris.

    PubMed

    Lee, Ho-Sang; Kim, Z-Hun; Park, Hanwool; Lee, Choul-Gyun

    2016-05-01

    Lumostatic operation was applied for efficient astaxanthin production in autotrophic Haematococcus lacustris cultures using 0.4-L bubble column photobioreactors. The lumostatic operation in this study was performed with three different specific light uptake rates (q(e)) based on cell concentration, cell projection area, and fresh weight as one-, two- and three-dimensional characteristics values, respectively. The q(e) value from the cell concentration (q(e1D)) obtained was 13.5 × 10⁻⁸ μE cell⁻¹ s⁻¹, and the maximum astaxanthin concentration was increased to 150 % compared to that of a control with constant light intensity. The other optimum q e values by cell projection area (q(e2D)) and fresh weight (q( e3D)) were determined to be 195 μE m⁻² s⁻¹ and 10.5 μE g⁻¹ s⁻¹ for astaxanthin production, respectively. The maximum astaxanthin production from the lumostatic cultures using the parameters controlled by cell projection area (2D) and fresh weight (3D) also increased by 36 and 22% over that of the controls, respectively. When comparing the optimal q e values among the three different types, the lumostatic cultures using q(e) based on fresh weight showed the highest astaxanthin productivity (22.8 mg L⁻¹ day⁻¹), which was a higher level than previously reported. The lumostatic operations reported here demonstrated that more efficient and effective astaxanthin production was obtained by H. lacustris than providing a constant light intensity, regardless of which parameter is used to calculate the specific light uptake rate. PMID:26873706

  4. One-solvent extraction of astaxanthin from lactic acid fermented shrimp wastes.

    PubMed

    Gimeno, Miquel; Ramírez-Hernández, Jessica Yesemite; Mártinez-Ibarra, César; Pacheco, Neith; García-Arrazola, Roeb; Bárzana, Eduardo; Shirai, Keiko

    2007-12-12

    Free astaxanthin one-solvent extractions with ethanol, acetone, and liquid 1,1,1,2-tetrafluoroethane from raw and lactic acid fermented (ensilaged) shrimp residues were investigated. The total carotenoid recovery from ensilaged shrimp wastes was higher than that from non-ensilaged ones as assessed by HPLC analyses. Acetone gave the highest extraction yields of free astaxanthin with up to 115 microg/g of material. Moreover, liquid tetrafluoroethane is reported for the first time in a successful one-solvent extraction of carotenoids from shrimp. PMID:18020413

  5. Chiral Perturbation Theory

    NASA Astrophysics Data System (ADS)

    Tiburzi, Brian C.

    The era of high-precision lattice QCD has led to synergy between lattice computations and phenomenological input from chiral perturbation theory. We provide an introduction to chiral perturbation theory with a bent towards understanding properties of the nucleon and other low-lying baryons. Four main topics are the basis for this chapter. We begin with a discussion of broken symmetries and the procedure to construct the chiral Lagrangian. The second topic concerns specialized applications of chiral perturbation theory tailored to lattice QCD, such as partial quenching, lattice discretization, and finite-volume effects. We describe inclusion of the nucleon in chiral perturbation theory using a heavy-fermion Euclidean action. Issues of convergence are taken up as our final topic. We consider expansions in powers of the strange-quark mass, and the appearance of unphysical singularities in the heavy-particle formulation. Our aim is to guide lattice practitioners in understanding the predictions chiral perturbation theory makes for baryons, and show how the lattice will play a role in testing the rigor of the chiral expansion at physical values of the quark masses.

  6. Applications of chiral symmetry

    SciTech Connect

    Pisarski, R.D.

    1995-03-01

    The author discusses several topics in the applications of chiral symmetry at nonzero temperature. First, where does the rho go? The answer: up. The restoration of chiral symmetry at a temperature T{sub {chi}} implies that the {rho} and a{sub 1} vector mesons are degenerate in mass. In a gauged linear sigma model the {rho} mass increases with temperature, m{sub {rho}}(T{sub {chi}}) > m{sub {rho}}(0). The author conjectures that at T{sub {chi}} the thermal {rho} - a{sub 1}, peak is relatively high, at about {approximately}1 GeV, with a width approximately that at zero temperature (up to standard kinematic factors). The {omega} meson also increases in mass, nearly degenerate with the {rho}, but its width grows dramatically with temperature, increasing to at least {approximately}100 MeV by T{sub {chi}}. The author also stresses how utterly remarkable the principle of vector meson dominance is, when viewed from the modern perspective of the renormalization group. Secondly, he discusses the possible appearance of disoriented chiral condensates from {open_quotes}quenched{close_quotes} heavy ion collisions. It appears difficult to obtain large domains of disoriented chiral condensates in the standard two flavor model. This leads to the last topic, which is the phase diagram for QCD with three flavors, and its proximity to the chiral critical point. QCD may be very near this chiral critical point, and one might thereby generated large domains of disoriented chiral condensates.

  7. Chirality control in oligothiophene through chiral wrapping.

    PubMed

    Sanji, Takanobu; Kato, Nobu; Tanaka, Masato

    2006-01-19

    [structure: see text] Mixing oligothiophenes and polysaccharides, such as amylose and schizophyllan, affords novel inclusion complexes, in which oligothiophene guests adopt twisted conformation in the chiral channel created by left- or right-handed helical wrapping with the polysaccharide host polymers, leading to optical activity. PMID:16408883

  8. Astaxanthin reduces ischemic brain injury in adult rats.

    PubMed

    Shen, Hui; Kuo, Chi-Chung; Chou, Jenny; Delvolve, Alice; Jackson, Shelley N; Post, Jeremy; Woods, Amina S; Hoffer, Barry J; Wang, Yun; Harvey, Brandon K

    2009-06-01

    Astaxanthin (ATX) is a dietary carotenoid of crustaceans and fish that contributes to their coloration. Dietary ATX is important for development and survival of salmonids and crustaceans and has been shown to reduce cardiac ischemic injury in rodents. The purpose of this study was to examine whether ATX can protect against ischemic injury in the mammalian brain. Adult rats were injected intracerebroventricularly with ATX or vehicle prior to a 60-min middle cerebral artery occlusion (MCAo). ATX was present in the infarction area at 70-75 min after onset of MCAo. Treatment with ATX, compared to vehicle, increased locomotor activity in stroke rats and reduced cerebral infarction at 2 d after MCAo. To evaluate the protective mechanisms of ATX against stroke, brain tissues were assayed for free radical damage, apoptosis, and excitoxicity. ATX antagonized ischemia-mediated loss of aconitase activity and reduced glutamate release, lipid peroxidation, translocation of cytochrome c, and TUNEL labeling in the ischemic cortex. ATX did not alter physiological parameters, such as body temperature, brain temperature, cerebral blood flow, blood gases, blood pressure, and pH. Collectively, our data suggest that ATX can reduce ischemia-related injury in brain tissue through the inhibition of oxidative stress, reduction of glutamate release, and antiapoptosis. ATX may be clinically useful for patients vulnerable or prone to ischemic events. PMID:19218497

  9. Multiple Mechanisms of Anti-Cancer Effects Exerted by Astaxanthin

    PubMed Central

    Zhang, Li; Wang, Handong

    2015-01-01

    Astaxanthin (ATX) is a xanthophyll carotenoid which has been approved by the United States Food and Drug Administration (USFDA) as food colorant in animal and fish feed. It is widely found in algae and aquatic animals and has powerful anti-oxidative activity. Previous studies have revealed that ATX, with its anti-oxidative property, is beneficial as a therapeutic agent for various diseases without any side effects or toxicity. In addition, ATX also shows preclinical anti-tumor efficacy both in vivo and in vitro in various cancer models. Several researches have deciphered that ATX exerts its anti-proliferative, anti-apoptosis and anti-invasion influence via different molecules and pathways including signal transducer and activator of transcription 3 (STAT3), nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) and peroxisome proliferator-activated receptor gamma (PPARγ). Hence, ATX shows great promise as chemotherapeutic agents in cancer. Here, we review the rapidly advancing field of ATX in cancer therapy as well as some molecular targets of ATX. PMID:26184238

  10. Synthesis of Chiral Cyclopentenones.

    PubMed

    Simeonov, Svilen P; Nunes, João P M; Guerra, Krassimira; Kurteva, Vanya B; Afonso, Carlos A M

    2016-05-25

    The cyclopentenone unit is a very powerful synthon for the synthesis of a variety of bioactive target molecules. This is due to the broad diversity of chemical modifications available for the enone structural motif. In particular, chiral cyclopentenones are important precursors in the asymmetric synthesis of target chiral molecules. This Review provides an overview of reported methods for enantioselective and asymmetric syntheses of cyclopentenones, including chemical and enzymatic resolution, asymmetric synthesis via Pauson-Khand reaction, Nazarov cyclization and organocatalyzed reactions, asymmetric functionalization of the existing cyclopentenone unit, and functionalization of chiral building blocks. PMID:27101336

  11. The covariant chiral ring

    NASA Astrophysics Data System (ADS)

    Bourget, Antoine; Troost, Jan

    2016-03-01

    We construct a covariant generating function for the spectrum of chiral primaries of symmetric orbifold conformal field theories with N = (4 , 4) supersymmetry in two dimensions. For seed target spaces K3 and T 4, the generating functions capture the SO(21) and SO(5) representation theoretic content of the chiral ring respectively. Via string dualities, we relate the transformation properties of the chiral ring under these isometries of the moduli space to the Lorentz covariance of perturbative string partition functions in flat space.

  12. Nonlinear chiral transport phenomena

    NASA Astrophysics Data System (ADS)

    Chen, Jiunn-Wei; Ishii, Takeaki; Pu, Shi; Yamamoto, Naoki

    2016-06-01

    We study the nonlinear responses of relativistic chiral matter to the external fields such as the electric field E , gradients of temperature and chemical potential, ∇T and ∇μ . Using the kinetic theory with Berry curvature corrections under the relaxation time approximation, we compute the transport coefficients of possible new electric currents that are forbidden in usual chirally symmetric matter but are allowed in chirally asymmetric matter by parity. In particular, we find a new type of electric current proportional to ∇μ ×E due to the interplay between the effects of the Berry curvature and collisions. We also derive an analog of the "Wiedemann-Franz" law specific for anomalous nonlinear transport in relativistic chiral matter.

  13. Spintronics: Chiral damping

    PubMed Central

    Kim, Kyoung-Whan; Lee, Hyun-Woo

    2016-01-01

    The analysis of the magnetic domain wall motion in a nanostructured magnetic system with strong spin-orbit coupling shows that the energy dissipation can be chiral when the inversion symmetry is broken. PMID:26906956

  14. Metolachlor stereoisomers: Enantioseparation, identification and chiral stability.

    PubMed

    Xie, Jingqian; Zhang, Lijuan; Zhao, Lu; Tang, Qiaozhi; Liu, Kai; Liu, Weiping

    2016-09-01

    Metolachlor is a chiral herbicide consisting of four stereoisomers, which is typically used as a racemic mixture or is enriched with the herbicidally active 1'S-isomers. Because studies on the enantioselective behavior of phyto-biochemical processes and the environmental fate of metolachlor have become significant, a practical method for analyzing and separating metolachlor stereoisomers must be developed. In the present study, the enantiomeric separation of metolachlor was achieved using OD-H, AS-H, OJ-H and AY-H chiral columns. The effects of different organic modifiers in an n-hexane-based mobile phase were investigated, and various temperatures and flow rates, which may influence metolachlor separation, were also explored. The optimal resolution was obtained using an AY-H column with n-hexane/EtOH (96/4) as the mobile phase at a rate and temperature of 0.6mLmin(-1) and 25°C, respectively. The absolute configuration of the four stereoisomers was identified as αSS, αRS, αSR, αRR using computed and experimentally measured ECD and VCD spectra. Thermal interconversion and solvent stability experiments were also performed. Pure metolachlor stereoisomers in different organic solvents and water at 4°C or 30°C were stable. These results were used to establish a sound method for analyzing, preparing, characterizing, and preserving individual metolachlor stereoisomers in most natural environments. PMID:27544750

  15. Chiral plasma instabilities.

    PubMed

    Akamatsu, Yukinao; Yamamoto, Naoki

    2013-08-01

    We study the collective modes in relativistic electromagnetic or quark-gluon plasmas with an asymmetry between left- and right-handed chiral fermions, based on the recently formulated kinetic theory with Berry curvature corrections. We find that there exists an unstable mode, signaling the presence of a plasma instability. We argue the fate of this "chiral plasma instability" including the effect of collisions, and briefly discuss its relevance in heavy ion collisions and compact stars. PMID:23952387

  16. Capillary electrochromatographic fast enantioseparation based on a chiral metal-organic framework.

    PubMed

    Fei, Zhi-Xin; Zhang, Mei; Xie, Sheng-Ming; Yuan, Li-Ming

    2014-12-01

    Metal-organic frameworks (MOFs) have received great attention because of their unusual properties and fascinating structures in separation sciences. However, to the best of our knowledge, there has been no attempt to utilize chiral MOFs as stationary phases in packed-CEC. Here, a chiral MOF [In3 O(obb)3 (HCO2 )(H2 O)]·solvent (4,4'-oxybisbenzoic acid) was explored as the chiral stationary phase in packed-CEC for separation of chiral compounds and isomers. The fabricated [In3 O(obb)3 (HCO2 )(H2 O)]·solvent packed capillary columns gave fast enantioseparation of (±)-hydrobenzoin, (±)-1-phenyl-1,2-ethanediol, and clenbuterol within 3 min in CEC. Besides, the baseline separations of nitrophenol isomers within 6 min were also achieved. The RSDs for the retention time of run-to-run, day-to-day, and column-to-column reproducibility were 1.51-3.63, 1.83-3.98, and 3.42-5.66%, respectively. These results demonstrate that chiral MOFs are promising for enantioseparation in CEC. PMID:25223618

  17. Nuclear isomer suitable for gamma ray laser

    NASA Technical Reports Server (NTRS)

    Jha, S.

    1979-01-01

    The operation of gamma ray lasers (gasers) are studied. It is assumed that the nuclear isomers mentioned in previously published papers have inherent limitations. It is further assumed that the judicious use of Bormann effect or the application of the total external reflection of low energy gamma radiation at grazing angle of incidence may permit the use of a gaser crystal sufficiently long to achieve observable stimulated emission. It is suggested that a long lived 0(+) isomer decaying by low energy gamma ray emission to a short lived 2(+) excited nuclear state would be an attractive gaser candidate. It is also suggested that the nuclear isomer be incorporated in a matrix of refractory material having an electrostatic field gradient whose principal axis lies along the length of the medium. This results in the preferential transmission of electric quadrupole radiation along the length of the medium.

  18. K isomers as probes of nuclear structure

    SciTech Connect

    Tandel, S. K.

    2014-08-14

    K isomers are studied in Pu and Cm isotopes, and also in Hf and W nuclei. Many high-K states, several of which are isomeric, are identified. Lifetime measurements spanning the ns-s range have been performed, and decay paths of isomers established. Rotational bands built on high-K states are also identified in many cases. Isomer decays are considerably hindered in many instances, both in the A≈180 and 250 regions indicating that K is an approximately conserved quantum number. High-K states become the favored excitation mode at high spins in the A≈180 region. The energies of the 2-quasiparticle high-K states in Cm isotopes suggest the presence of a deformed subshell gap at N=152.

  19. Separation of cis and trans geometric isomers by Coulomb explosion imaging

    NASA Astrophysics Data System (ADS)

    Ablikim, Utuq; Kaderiya, B.; Kumarapan, V.; Rudenko, A.; Rolles, D.; Bomme, C.; Savelyev, E.; Xiong, H.; Berrah, N.; Kilcoyne, D.

    2016-05-01

    Isomers, i.e. molecules with the same chemical formula but different chemical structure, play an important role in many biological processes. Recently, it was shown that it is possible to identify different isomers of a chiral molecule by Coulomb explosion imaging. Here, we show that by imaging the Coulomb explosion of C2 H2 Br2 molecules after inner-shell photoionization, we are able to separate a mixture of cis and trans structures using the momentum correlation between ionic fragments measured in coincidence. Furthermore, we used this capability to investigate the isomer-selective photoionization and fragmentation dynamics of C2 H2 Br2 after Br (3d) ionization. Coulomb explosion simulation results for momentum correlation as well as kinetic energies match closely the experimental results. This project is supported by the DOE, Office of Science, BES, Division of Chemical, Geological and Biological Sciences under Award Number DE-FG02-86ER13491 (U.A., B.K., V.K., A.R., D.R.) and Award Number DE-SC0012376 (H.X., N.B.).

  20. Origin of Kinetic Resolution of Hydroxy Esters through Catalytic Enantioselective Lactonization by Chiral Phosphoric Acids.

    PubMed

    Changotra, Avtar; Sunoj, Raghavan B

    2016-08-01

    Kinetic resolution is a widely used strategy for separation and enrichment of enantiomers. Using density functional theory computations, the origin of how a chiral BINOL-phosphoric acid catalyzes the selective lactonization of one of the enantiomers of α-methyl γ-hydroxy ester is identified. In a stepwise mechanism, the stereocontrolling transition state for the addition of the hydroxyl group to the si face of the ester carbonyl in the case of the S isomer exhibits a network of more effective noncovalent interactions between the substrate and the chiral catalyst. PMID:27463593

  1. A developmental toxicity study of 3S, 3'S-Astaxanthin in New Zealand white rabbits.

    PubMed

    Schneider, Steffen; Mellert, Werner; Schulte, Stefan; van Ravenzwaay, Bennard

    2016-04-01

    Astaxanthin, a naturally occurring pigment used to give the characteristic orange-pink colour to salmonid fish reared in aquaculture, is also marketed as a dietary supplement. Synthetic 3S, 3'S-Astaxanthin was tested for potential harmful effects on the in utero development of New Zealand white rabbits in a study according to international regulatory guidelines. There were two control groups, one being a placebo administration and three dose levels corresponding to 100, 200, and 400 mg of 3S, 3'S-Astaxanthin per kg body weight/day. The group sizes varied from 23 to 27 litters, providing approximately 200 fetuses per group for evaluation of developmental toxicity. There were no significant effects on the health of the does, nor on the size and viability of the litters. Malformations, both external and internal, were rare and occurred in all groups, including controls with no indication of a treatment relationship. Variations were much more common, being found in all litters. However, when examined by type and frequency, no pattern emerged indicating a relationship to administration of the test substance. It is concluded that administration of 3S, 3'S-Astaxanthin in a gelatin/carbohydrate powder formulation throughout pregnancy up to 400 mg/kg body weight/day is without harmful effects on reproduction or fetal development. PMID:26854919

  2. Response Surface Methodology for Ultrasound-Assisted Extraction of Astaxanthin from Haematococcus pluvialis

    PubMed Central

    Zou, Tang-Bin; Jia, Qing; Li, Hua-Wen; Wang, Chang-Xiu; Wu, Hong-Fu

    2013-01-01

    Astaxanthin is a novel carotenoid nutraceutical occurring in many crustaceans and red yeasts. It has exhibited various biological activities including prevention or amelioration of cardiovascular disease, gastric ulcer, hypertension, and diabetic nephropathy. In this study, ultrasound-assisted extraction was developed for the effective extraction of astaxanthin from Haematococcus pluvialis. Some parameters such as extraction solvent, liquid-to-solid ratio, extraction temperature, and extraction time were optimized by single-factor experiment and response surface methodology. The optimal extraction conditions were 48.0% ethanol in ethyl acetate, the liquid-to-solid ratio was 20:1 (mL/g), and extraction for 16.0 min at 41.1 °C under ultrasound irradiation of 200 W. Under optimal conditions, the yield of astaxanthin was 27.58 ± 0.40 mg/g. The results obtained are beneficial for the full utilization of Haematococcus pluvialis, which also indicated that ultrasound-assisted extraction is a very useful method for extracting astaxanthin from marine life. PMID:23697948

  3. Astaxanthin Protecting Membrane Integrity against Photosensitized Oxidation through Synergism with Other Carotenoids.

    PubMed

    Du, Hui-Hui; Liang, Ran; Han, Rui-Min; Zhang, Jian-Ping; Skibsted, Leif H

    2015-10-21

    Incorporation of astaxanthin or zeaxanthin in giant unilamellar vesicles (GUVs) of phosphatidylcholine resulted in a longer lag phase than incorporation of β-carotene or lycopene for the onset of budding induced by chlorophyll a photosensitization and quantified by a dimensionless entropy parameter using optical microscopy and digital image heterogeneity analysis. The lowest initial rate of GUV budding after the lag phase was seen for GUVs with astaxanthin as the least reducing carotenoid, while the lowest final level of entropy appeared for those with lycopene or β-carotene as a more reducing carotenoid. The combination of astaxanthin and lycopene gave optimal protection against budding with respect to both a longer lag phase and lower final level of entropy by combining good electron acceptance and good electron donation. Quenching of singlet oxygen by carotenoids close to chlorophyll a in the membrane interior in parallel with scavenging of superoxide radicals by astaxanthin anchored in the surface may explain the synergism between carotenoids involving both type I and type II photosensitization by chlorophyll a. PMID:26429551

  4. Gene expression profile analysis in astaxanthin-induced Haematococcus pluvialis using a cDNA microarray.

    PubMed

    Eom, Hyunsuk; Lee, Choul-Gyun; Jin, EonSeon

    2006-05-01

    The unicellular green alga Haematococcus pluvialis (Volvocales) is known for the ketocarotenoid astaxanthin (3, 3'-dihydroxy-beta, beta-carotene-4, 4'-dione) accumulation, which is induced under unfavorable culture conditions. In this work, we used cDNA microarray analysis to screen differentially expressed genes in H. pluvialis under astaxanthin-inductive culture conditions, such as combination of cell exposure to high irradiance and nutrient deprivation. Among the 965 genes in the cDNA array, there are 144 genes exhibiting differential expression (twofold changes) under these conditions. A significant decrease in the expression of photosynthesis-related genes was shown in astaxanthin-accumulating cells (red cells). Defense- or stress-related genes and signal transduction genes were also induced in the red cells. A comparison of microarray and real-time PCR analysis showed good correlation between the differentially expressed genes by the two methods. Our results indicate that the cDNA microarray approach, as employed in this work, can be relied upon and used to monitor gene expression profiles in H. pluvialis. In addition, the genes that were differentially expressed during astaxanthin induction are suitable candidates for further study and can be used as tools for dissecting the molecular mechanism of this unique pigment accumulation process in the green alga H. pluvialis. PMID:16320067

  5. Astaxanthin extraction from shrimp wastes and its stability in 2 model systems.

    PubMed

    Franco-Zavaleta, M E; Jiménez-Pichardo, R; Tomasini-Campocosio, A; Guerrero-Legarreta, I

    2010-06-01

    The objective of this work was to study the stability of astaxanthin, obtained from shrimp wastes, and incorporated to 2 model systems: egg albumin protein solution and sunflower oil. Shrimp wastes were ensiled by a treatment with formic/acetic acids (4%-4% v/w wastes) and stored at 4 degrees C for 24 h. The pigment was extracted with organic solvents (petroleum ether:acetone:water, 15 : 75 : 10) and concentrated. The storage parameters studied were: illumination (light/dark), temperature (4/20 degrees C), atmosphere (air/air-free), and storage time (0, 1, 2, 3, 4, 5 wk). Results showed that total xantophylls and astaxanthin were more stable in sunflower oil than in the protein system. Total xantophylls showed more stability than astaxanthin, possibly due to the presence of other, more stable carotenoids quantified together with xantophylls. Astaxanthin concentration was significantly affected by storage time; its degradation followed a first-order reaction rate under all the studied conditions. This pigment was stable only for 17 d, even when stored in air-free flasks, under refrigeration, and in the dark. PMID:20629858

  6. Astaxanthin induction in Microalga H. pluvialis with flat panel airlift photobioreactors under indoor and outdoor conditions.

    PubMed

    Poonkum, Woradej; Powtongsook, Sorawit; Pavasant, Prasert

    2015-01-01

    Astaxanthin was induced from Haematococcus pluvialis (NIES-144) under indoor and outdoor conditions using 17-, 50-, and 90-L flat-panel airlift photobioreactors (FP-APBRs). Preliminary experiments in 1.5-L bubble column photobioreactors (BC-PBRs) revealed that sterilized clean water with 3% CO2 aeration (1.47 cm(3) s(-1) CO2 loading) could best encourage astaxanthin accumulation at 18.21 g m(-3) (3.63% by weight). Operating 17-L FP-APBRs with these bubble column parameters under indoor conditions could further enhance astaxanthin to 26.63 g m(-3) (5.34% by weight). This was potentially due to the inherited up-lift force from the reactor that helped avoid cell precipitation by allowing the cells to be circulated within the reactor. In addition, the various sizes of FP-APBRs exhibited similar performance, implying a potential scale-up opportunity. However, similar operation under outdoor condition exhibited slightly poorer performance due to the light inhibition effect. The best outdoor performance was obtained with the FP-APBR covered with one layer of shading net, where 20.11 g m(-3) (4.47% by weight) of astaxanthin was resulted. PMID:25105532

  7. A Microreactor System for Cultivation of Haematococcus pluvialis and Astaxanthin Production.

    PubMed

    Kwak, Ho Seok; Kim, Jaoon Young Hwan; Sim, Sang Jun

    2015-02-01

    Development of efficient culture and monitoring system for cell growth and production of useful materials is required for practical utilization of microalgae. In the present study, we developed a PDMS-based microreactor system for efficient, rapid culture of microalgae and monitoring of cell growth, carotenoid content under diverse culture conditions. Due to advantages of PDMS, we optimized culture conditions (light intensity, pH, nitrate depletion, carbon dioxide concentration) for improving growth rate and astaxanthin productivity in considerably less time compared to conventional culture methods using flask or well plate. In addition, we found that there was a strong linear correlation between fluorescence intensity of astaxanthin stained by Nile red and the astaxanthin content, which can be utilized as a high-throughput screening tool in microfluidic systems. In this study, the growth rate of vegetative Haematococcus pluvialis was improved by 60% in microfluidic chamber than in flask and astaxanthin was produced up to 362 mg/L under the optimal conditions (300 µmol photon/m2/s of light, 7% CO2 (v/v), and pH 7.0) using designed microfluidic devices. This result shows that microfluidic system can provide effective means to address development of microalgal strains including H. pluvialis and bioprocess. PMID:26353702

  8. Elucidation of the pathway to astaxanthin in the flowers of Adonis aestivalis.

    PubMed

    Cunningham, Francis X; Gantt, Elisabeth

    2011-08-01

    A few species in the genus Adonis are the only land plants known to produce the valuable red ketocarotenoid astaxanthin in abundance. Here, we ascertain the pathway that leads from the β-rings of β-carotene, a carotenoid ubiquitous in plants, to the 3-hydroxy-4-keto-β-rings of astaxanthin (3,3'-dihydroxy-β,β-carotene-4,4'-dione) in the blood-red flowers of Adonis aestivalis, an ornamental and medicinal plant commonly known as summer pheasant's eye. Two gene products were found to catalyze three distinct reactions, with the first and third reactions of the pathway catalyzed by the same enzyme. The pathway commences with the activation of the number 4 carbon of a β-ring in a reaction catalyzed by a carotenoid β-ring 4-dehydrogenase (CBFD), continues with the further dehydrogenation of this carbon to yield a carbonyl in a reaction catalyzed by a carotenoid 4-hydroxy-β-ring 4-dehydrogenase, and concludes with the addition of an hydroxyl group at the number 3 carbon in a reaction catalyzed by the erstwhile CBFD enzyme. The A. aestivalis pathway is both portable and robust, functioning efficiently in a simple bacterial host. Our elucidation of the pathway to astaxanthin in A. aestivalis provides enabling technology for development of a biological production process and reveals the evolutionary origin of this unusual plant pathway, one unrelated to and distinctly different from those used by bacteria, green algae, and fungi to synthesize astaxanthin. PMID:21862704

  9. PCR-based method for the rapid identification of astaxanthin-accumulating yeasts (Phaffia spp.).

    PubMed

    Colabella, Fernando; Libkind, Diego

    2016-01-01

    It has been recently found that the natural distribution, habitat, and genetic diversity of astaxanthin-producing yeasts (i.e. Phaffia rhodozyma, synonym Xanthophyllomyces dendrorhous) is much greater than previously thought. P. rhodozyma is biotechnologically exploited due to its ability to produce the carotenoid pigment astaxanthin and thus, it is used as a natural source of this pigment for aquaculture. P. rhodozyma was also capable of synthesizing the potent UVB sunscreen mycosporine-glutaminol-glucoside (MGG). Therefore, further environmental studies are needed to elucidate its ecological aspects and detect new potential strains for the production of astaxanthin and MGG. However, obtaining new isolates of P. rhodozyma and related species is not always easy due to its low abundance and the presence of other sympatric and pigmented yeasts. In this work we report a successful development of a species-specific primer which has the ability to quickly and accurately detecting isolates representing all known lineages of the genus Phaffia (including novel species of the genus) and excluding closely related taxa. For this purpose, a primer of 20 nucleotides (called PhR) was designed to be used in combination with universal primers ITS3 and NL4 in a multiplex amplification. The proposed method has the sensitivity and specificity required for the precise detection of new isolates, and therefore represents an important tool for the environmental search for novel astaxanthin-producing yeasts. PMID:26922472

  10. Cholesterol oxidation and astaxanthin degradation in shrimp during sun drying and storage.

    PubMed

    Hernández Becerra, Josafat A; Ochoa Flores, Angélica A; Valerio-Alfaro, Gerardo; Soto-Rodriguez, Ida; Rodríguez-Estrada, María T; García, Hugo S

    2014-02-15

    Dried salted shrimps are made from raw shrimps, which are cooked and dried under direct sunlight. The preparation and storage include treatments and conditions that can promote oxidative changes in different components. The aim of this study was to monitor the formation of major cholesterol oxidation products and the changes in the astaxanthin content and fatty acid profile in dried salted shrimp during cooking, sun drying and storage. During sun drying, most of the astaxanthin (75%) was degraded in cooked shrimp, while cholesterol oxidation products (COPs) showed a dramatic increase (8.6-fold), reaching a total concentration of 372.9 ± 16.3 μg/g of lipids. Further storage favoured both astaxanthin degradation (83%) and COPs formation (886.6 ± 97.9 μg/g of lipids after 90 days of storage). The high degradation of astaxanthin and the elevated formation of COPs during sun drying and storage indicate the necessity to re-evaluate the processing and storage conditions of salted dried shrimp. PMID:24128553

  11. An Assessment of Nuclear Isomers as an Energy Storage Medium

    SciTech Connect

    Hartouni, Edward P.

    2009-03-16

    Nuclear Isomers have been suggested as a potential high energy density medium that might be used to store energy. This talk assesses the state of the science supporting key elements of using nuclear isomers in energy storage applications. The focus is on the nuclear isomer {sup 178m2}Hf which has been most widely suggested for energy storage applications. However, the science issues apply to all nuclear isomer. The assessment addresses the production of the nuclear isomer, and inducing the release of the isomer. Also discussed are novel speculations on photon and/or neutron chain reactions, both as a 'pure' material as well as mixed with other materials.

  12. An Assessment of Nuclear Isomers as an Energy Storage Medium

    SciTech Connect

    Hartouni, E P

    2008-12-08

    Nuclear Isomers have been suggested as a potential high energy density medium that might be used to store energy. This talk assesses the state of the science supporting key elements of using nuclear isomers in energy storage applications. The focus is on the nuclear isomer {sup 178m2}Hf which has been most widely suggested for energy storage applications. However, the science issues apply to all nuclear isomer. The assessment addresses the production of the nuclear isomer, and inducing the release of the isomer. Also discussed are novel speculations on photon and/or neutron chain reactions, both as a 'pure' material as well as mixed with other materials.

  13. New Millisecond Isomer Lifetime Measurements at LANSCE

    SciTech Connect

    Devlin, M. Nelson, R.O.; Fotiades, N.; O'Donnell, J.M.

    2014-06-15

    New half-life measurements have been made of the millisecond isomers {sup 71m}Ge, {sup 114m2}I, {sup 208m}Bi, {sup 88m1}Y, {sup 88m2}Y, and {sup 75m}As populated in neutron-induced reactions. These measurements were made using the unique time structure of the LANSCE/WNR neutron source, by observing the γ-ray decays of the isomers during the time between the LANSCE proton macropulses. Two different LANSCE proton beam time structures were used. The GEANIE array of HPGe detectors was used to detect the γ-ray decays.

  14. 'Melatonin isomer' in wine is not an isomer of the melatonin but tryptophan-ethylester.

    PubMed

    Gardana, Claudio; Iriti, Marcello; Stuknytė, Milda; De Noni, Ivano; Simonetti, Paolo

    2014-11-01

    Melatonin is a neurohormone, chronobiotic, and antioxidant compound found in wine and deriving directly from grapes and/or synthesized by yeast during alcoholic fermentation. In addition, a melatonin isomer has been detected in different foods, wine among them. The special interest for melatonin isomer related to the fact that it was found in greater quantities than melatonin and probably shares some of its biological properties. Despite this, its chemical structure has not yet been defined; although some researchers hypothesize, it could be melatonin with the ethylacetamide group shifted into position N1. Thus, the aim of our study was to identify the structures of the melatonin isomer. For this purpose, melatonin and melatonin isomer in Syrah wine were separated chromatographically by a sub-2 μm particle column and detected by tandem mass spectrometry. The sample was then purified and concentrated by solid-phase extraction, hydrolyzed with alkali or esterase, and substrates and products quantified by UPLC-MS/MS. Moreover, melatonin, melatonin isomer, and their product ions were evaluated by high-resolution mass spectrometry. The amount of melatonin isomer and melatonin in the wine was 84 ± 4 and 3 ± 0 ng/mL, respectively. In the solutions, containing diluted alkali or esterase, melatonin isomer was hydrolyzed in about 8 min. Correspondingly, tryptophan was detected, and its amount increased and reached the maximum concentration in about 8 min. Melatonin concentration was not affected by diluted alkali or esterase. The fragmentation pattern of melatonin isomer was different from that of melatonin but comparable to that of tryptophan-ethylester. Finally, the so-called melatonin isomer identity was verified by cochromatography with authentic standard of tryptophan-ethylester. PMID:25251161

  15. Chiral benzamidinate ligands in rare-earth-metal coordination chemistry.

    PubMed

    Benndorf, Paul; Kratsch, Jochen; Hartenstein, Larissa; Preuss, Corinna M; Roesky, Peter W

    2012-11-01

    The treatment of the recently reported potassium salt (S)-N,N'-bis-(1-phenylethyl)benzamidinate ((S)-KPEBA) and its racemic isomer (rac-KPEBA) with anhydrous lanthanide trichlorides (Ln = Sm, Er, Yb, Lu) afforded mostly chiral complexes. The tris(amidinate) complex [{(S)-PEBA}(3)Sm], bis(amidinate) complexes [{Ln(PEBA)(2)(μ-Cl)}(2)] (Ln = Sm, Er, Yb, Lu), and mono(amidinate) compounds [Ln(PEBA)(Cl)(2)(thf)(n)] (Ln = Sm, Yb, Lu) were isolated and structurally characterized. As a result of steric effects, the homoleptic 3:1 complexes of the smaller lanthanide atoms Yb and Lu were not accessible. Furthermore, chiral bis(amidinate)-amido complexes [{(S)-PEBA}(2)Ln{N(SiMe(3))(2)}] (Ln = Y, Lu) were synthesized by an amine-elimination reaction and salt metathesis. All of these chiral bis- and tris(amidinate) complexes had additional axial chirality and they all crystallized as diastereomerically pure compounds. By using rac-PEBA as a ligand, an achiral meso arrangement of the ligands was observed. The catalytic activities and enantioselectivities of [{(S)-PEBA}(2)Ln{N(SiMe(3))(2)}] (Ln = Y, Lu) were investigated in hydroamination/cyclization reactions. A clear dependence of the rate of reaction and enantioselectivity on the ionic radius was observed, which showed higher reaction rates but poorer enantioselectivities for the yttrium compound. PMID:23015310

  16. A sensitivity-enhanced field-effect chiral sensor

    NASA Astrophysics Data System (ADS)

    Torsi, Luisa; Farinola, Gianluca M.; Marinelli, Francesco; Tanese, M. Cristina; Omar, Omar Hassan; Valli, Ludovico; Babudri, Francesco; Palmisano, Francesco; Zambonin, P. Giorgio; Naso, Francesco

    2008-05-01

    Organic thin-film transistor sensors have been recently attracting the attention of the plastic electronics community for their potential exploitation in novel sensing platforms. Specificity and sensitivity are however still open issues: in this respect chiral discrimination-being a scientific and technological achievement in itself-is indeed one of the most challenging sensor bench-tests. So far, conducting-polymer solid-state chiral detection has been carried out at part-per-thousand concentration levels. Here, a novel chiral bilayer organic thin-film transistor gas sensor-comprising an outermost layer with built-in enantioselective properties-is demonstrated to show field-effect amplified sensitivity that enables differential detection of optical isomers in the tens-of-parts-per-million concentration range. The ad-hoc-designed organic semiconductor endowed with chiral side groups, the bilayer structure and the thin-film transistor transducer provide a significant step forward in the development of a high-performance and versatile sensing platform compatible with flexible organic electronic technologies.

  17. Astaxanthin down-regulates Rad51 expression via inactivation of AKT kinase to enhance mitomycin C-induced cytotoxicity in human non-small cell lung cancer cells.

    PubMed

    Ko, Jen-Chung; Chen, Jyh-Cheng; Wang, Tai-Jing; Zheng, Hao-Yu; Chen, Wen-Ching; Chang, Po-Yuan; Lin, Yun-Wei

    2016-04-01

    Astaxanthin has been demonstrated to exhibit a wide range of beneficial effects, including anti-inflammatory and anti-cancer properties. However, the molecular mechanism of astaxanthin-induced cytotoxicity in non-small cell lung cancer (NSCLC) cells has not been identified. Rad51 plays a central role in homologous recombination, and studies show that chemo-resistant carcinomas exhibit high levels of Rad51 expression. In this study, astaxanthin treatment inhibited cell viability and proliferation of two NSCLC cells, A549 and H1703. Astaxanthin treatment (2.5-20 μM) decreased Rad51 expression and phospho-AKT(Ser473) protein level in a time and dose-dependent manner. Furthermore, expression of constitutively active AKT (AKT-CA) vector rescued the decreased Rad51 mRNA and protein levels in astaxanthin-treated NSCLC cells. Combined treatment with phosphatidylinositol 3-kinase (PI3K) inhibitors (LY294002 or wortmannin) further decreased the Rad51 expression in astaxanthin-exposed A549 and H1703 cells. Knockdown of Rad51 expression by transfection with si-Rad51 RNA or cotreatment with LY294002 further enhanced the cytotoxicity and cell growth inhibition of astaxanthin. Additionally, mitomycin C (MMC) as an anti-tumor antibiotic is widely used in clinical NSCLC chemotherapy. Combination of MMC and astaxanthin synergistically resulted in cytotoxicity and cell growth inhibition in NSCLC cells, accompanied with reduced phospho-AKT(Ser473) level and Rad51 expression. Overexpression of AKT-CA or Flag-tagged Rad51 reversed the astaxanthin and MMC-induced synergistic cytotoxicity. In contrast, pretreatment with LY294002 further decreased the cell viability in astaxanthin and MMC co-treated cells. In conclusion, astaxanthin enhances MMC-induced cytotoxicity by decreasing Rad51 expression and AKT activation. These findings may provide rationale to combine astaxanthin with MMC for the treatment of NSCLC. PMID:26921637

  18. The effect of astaxanthin on vascular endothelial growth factor (VEGF) levels and peroxidation reactions in the aqueous humor

    PubMed Central

    Hashimoto, Hirotaka; Arai, Kiyomi; Hayashi, Shimmin; Okamoto, Hiroyuki; Takahashi, Jiro; Chikuda, Makoto

    2016-01-01

    We explored the effect of astaxanthin on vascular endothelial growth factor in the aqueous humor, by measuring vascular endothelial growth factor levels and oxidation-related parameters, including O2•− scavenging activity, H2O2 level, and total hydroperoxide level in the aqueous humor, obtained from 35 patients before and after astaxanthin administration. We evaluated the relationship between vascular endothelial growth factor and the oxidation-related parameters as well as the patient’s diabetic status, age, and sex. Vascular endothelial growth factor levels did not change significantly but O2•− scavenging activity and total hydroperoxide level significantly (p<0.05) increased and decreased, respectively. Both pre- and post- astaxanthin intake, vascular endothelial growth factor and total hydroperoxide levels were positively correlated (Pearson: r = 0.42, p<0.05; r = 0.55, p<0.01, respectively). Analysis of vascular endothelial growth factor levels and O2•− scavenging activities gave a negative correlation but only pre-astaxanthin intake (r = −0.37, p<0.05). Differences in levels pre- and post-astaxanthin only showed association between vascular endothelial growth factor and total hydroperoxide (r = 0.49, p<0.01) analyzed by multiple linear regression. Using multivariate analysis, pre-astaxanthin vascular endothelial growth factor level was associated with two factors of total hydroperoxide and O2•− scavenging activity (r = 0.49, p<0.05), and post-astaxanthin vascular endothelial growth factor level with two factors of total hydroperoxide and sex (r = 0.60, p<0.01). Astaxanthin intake may have affected vascular endothelial growth factor level through its antioxidant effects by increasing O2•− scavenging activity and suppressing peroxide production. PMID:27499573

  19. The effect of astaxanthin on vascular endothelial growth factor (VEGF) levels and peroxidation reactions in the aqueous humor.

    PubMed

    Hashimoto, Hirotaka; Arai, Kiyomi; Hayashi, Shimmin; Okamoto, Hiroyuki; Takahashi, Jiro; Chikuda, Makoto

    2016-07-01

    We explored the effect of astaxanthin on vascular endothelial growth factor in the aqueous humor, by measuring vascular endothelial growth factor levels and oxidation-related parameters, including O2 (•-) scavenging activity, H2O2 level, and total hydroperoxide level in the aqueous humor, obtained from 35 patients before and after astaxanthin administration. We evaluated the relationship between vascular endothelial growth factor and the oxidation-related parameters as well as the patient's diabetic status, age, and sex. Vascular endothelial growth factor levels did not change significantly but O2 (•-) scavenging activity and total hydroperoxide level significantly (p<0.05) increased and decreased, respectively. Both pre- and post- astaxanthin intake, vascular endothelial growth factor and total hydroperoxide levels were positively correlated (Pearson: r = 0.42, p<0.05; r = 0.55, p<0.01, respectively). Analysis of vascular endothelial growth factor levels and O2 (•-) scavenging activities gave a negative correlation but only pre-astaxanthin intake (r = -0.37, p<0.05). Differences in levels pre- and post-astaxanthin only showed association between vascular endothelial growth factor and total hydroperoxide (r = 0.49, p<0.01) analyzed by multiple linear regression. Using multivariate analysis, pre-astaxanthin vascular endothelial growth factor level was associated with two factors of total hydroperoxide and O2 (•-) scavenging activity (r = 0.49, p<0.05), and post-astaxanthin vascular endothelial growth factor level with two factors of total hydroperoxide and sex (r = 0.60, p<0.01). Astaxanthin intake may have affected vascular endothelial growth factor level through its antioxidant effects by increasing O2 (•-) scavenging activity and suppressing peroxide production. PMID:27499573

  20. Introduction of Branching Degrees of Octane Isomers.

    PubMed

    Perdih, Anton

    2016-01-01

    The concept of branching degrees is introduced. In the case of octane isomers it is derived from the values of a set of their physicochemical properties, calculating for each isomer the average of the normalized values and these averages are defined as branching degrees of octane isomers. The sequence of these branching degrees of octane isomers does not differ much from the »regular« one defined earlier. 2,2-Dimethylhexane appears to be less branched than 3,4-dimethylhexane and 3-ethyl, 2-methylpentane, whereas 2,3,4-trimethylpentane appears to be less branched than 3-ethyl, 3-methylpentane. While the increasing number of branches gives rise to increasing branching degrees, the peripheral position of branches and the separation between branches decreases the value of the branching degree. The central position of branches increases it. A bigger branch increases it more than a smaller one. The quantification of these structural features and their correlations with few indices is given as well. PMID:27333567

  1. Chiral quirkonium decays

    NASA Astrophysics Data System (ADS)

    Fok, R.; Kribs, Graham D.

    2011-08-01

    We calculate the two-body decay rates of quirkonium states formed from quirks that acquire mass solely through electroweak symmetry breaking. We consider SU(N)ic infracolor with two flavors of quirks transforming under the electroweak group (but not QCD) of the standard model. In one case, the quirks are in a chiral representation of the electroweak group, while in the other case, a vectorlike representation. The differences in the dominant decay channels between “chiral quirkonia” versus “vectorlike quirkonia” are striking. Several chiral quirkonia states can decay into the unique two-body resonance channels WH, ZH, tt¯, tb¯/bt¯, and γH, which never dominate for vectorlike quirkonia. Additionally, the channels WW, WZ, ZZ, and Wγ, are shared among both chiral and vectorlike quirkonia. Resonances of dileptons or light quarks (dijets) can dominate for some vectorlike quirkonia states throughout their mass range, while these modes never dominate for chiral quirkonia unless the decays into pairs of gauge or Higgs bosons are kinematically forbidden.

  2. Chiral Quirkonium Decays

    SciTech Connect

    Fok, R.; Kribs, Graham D.; /Fermilab

    2011-06-01

    We calculate the two-body decay rates of quirkonium states formed from quirks that acquire mass solely through electroweak symmetry breaking. We consider SU(N){sub ic} infracolor with two flavors of quirks transforming under the electroweak group (but not QCD) of the standard model. In one case, the quirks are in a chiral representation of the electroweak group, while in the other case, a vectorlike representation. The differences in the dominant decay channels between 'chiral quirkonia' versus 'vectorlike quirkonia' are striking. Several chiral quirkonia states can decay into the unique two-body resonance channels WH, ZH, t{bar t}, t{bar b}/b{bar t}, and {gamma}H, which never dominate for vectorlike quirkonia. Additionally, the channels WW, WZ, ZZ, and W{gamma}, are shared among both chiral and vectorlike quirkonia. Resonances of dileptons or light quarks (dijets) can dominate for some vectorlike quirkonia states throughout their mass range, while these modes never dominate for chiral quirkonia unless the decays into pairs of gauge or Higgs bosons are kinematically forbidden.

  3. Chirality and Pinwheels

    ERIC Educational Resources Information Center

    Rodriguez-Fernandez, Emilio

    2013-01-01

    By using cardboard models that resemble propellers, the students of inorganic courses can easily visualizing the distinct rotation of optical isomers. These propellers rotate clockwise or counterclockwise when they are dropped from a certain height or in the presence of wind. (Contains 1 figure.)

  4. [Astaxanthin inhibits proliferation and promotes apoptosis of A549 lung cancer cells via blocking JAK1/STAT3 pathway].

    PubMed

    Wu, Chuntao; Zhang, Jinji; Liu, Tienan; Jiao, Guimei; Li, Changzai; Hu, Baoshan

    2016-06-01

    Objective To investigate the anti-tumor effects of astaxanthin on A549 lung cancer cells and the related mechanisms. Methods A549 cells were cultured with various concentrations of astaxanthin (20, 40, 60, 80, 100 μmol/L), and DMSO at the same concentrations served as vehicle controls. The viability of A549 cells was detected by CCK-8 assay; cell cycle and apoptosis were observed by flow cytometry; and the expressions of B-cell lymphoma-2 (Bcl-2), Bcl-2 associated X protein (Bax), signal transducers and activators of transcription 3 (STAT3), and Janus kinase 1 (JAK1) were evaluated by Western blotting. Results CCK-8 assay showed that astaxanthin decreased the proliferation of A549 cells in a dose-dependent manner. Flow cytometry showed that astaxanthin increased the number of cells in the G0/G1 phase and induced apoptosis in A549 cells. Western blotting showed that astaxanthin up-regulated the expression of Bax and down-regulated the expressions of Bcl-2, STAT3 and JAK1. Conclusion Astaxanthin functions as a potent inhibitor of A549 lung cancer cell growth by targeting JAK1/STAT3 signaling pathway. PMID:27371847

  5. Simultaneous production of triacylglycerol and high-value carotenoids by the astaxanthin-producing oleaginous green microalga Chlorella zofingiensis.

    PubMed

    Liu, Jin; Mao, Xuemei; Zhou, Wenguang; Guarnieri, Michael T

    2016-08-01

    The production of lipids and astaxanthin, a high-value carotenoid, by Chlorella zofingiensis was investigated under different culture conditions. Comparative analysis revealed a good correlation between triacylglycerol (TAG) and astaxanthin accumulation in C. zofingiensis. Stress conditions promoted cell size and weight and induced the accumulation of neutral lipids, especially TAG and astaxanthin, with a concomitant decrease in membrane lipids. The highest contents of TAG and astaxanthin achieved were 387 and 4.89mgg(-1) dry weight, respectively. A semi-continuous culture strategy was developed to optimize the TAG and astaxanthin productivities, which reached 297 and 3.3mgL(-1)day(-1), respectively. Additionally, astaxanthin accumulation was enhanced by inhibiting de novo fatty acid biosynthesis. In summary, our study represents a pioneering work of utilizing Chlorella for the integrated production of lipids and high-value products and C. zofingiensis has great potential to be a promising production strain and serve as an emerging oleaginous model alga. PMID:27152772

  6. The antioxidant effect of astaxanthin is higher in young mice than aged: a region specific study on brain.

    PubMed

    Al-Amin, Md Mamun; Akhter, Samiha; Hasan, Ahmed Tasdid; Alam, Tanzir; Nageeb Hasan, S M; Saifullah, A R M; Shohel, Mohammad

    2015-10-01

    Astaxanthin is a potential antioxidant which shows neuroprotective property. We aimed to investigate the age-dependent and region-specific antioxidant effects of astaxanthin in mice brain. Animals were divided into 4 groups; treatment young (3 months, n = 6) (AY), treatment old (16 months, n = 6) (AO), placebo young (3 months, n = 6) (PY) and placebo old (16 months, n = 6) (PO) groups. Treatment group was given astaxanthin (2 mg/kg/day, body weight), and placebo group was given 100 μl of 0.9% normal saline orally to the healthy Swiss albino mice for 4 weeks. The level of non-enzymatic oxidative markers namely malondialdehyde (MDA); nitric oxide (NO); advanced protein oxidation product (APOP); glutathione (GSH) and the activity of enzymatic antioxidants i.e.; catalase (CAT) and superoxide dismutase (SOD) were determined from the isolated brain regions. Treatment with astaxanthin significantly (p < 0.05) reduces the level of MDA, APOP, NO in the cortex, striatum, hypothalamus, hippocampus and cerebellum in both age groups. Astaxanthin markedly (p < 0.05) enhances the activity of CAT and SOD enzymes while improves the level of GSH in the brain. Overall, improvement of oxidative markers was significantly greater in the young group than the aged animal. In conclusion, we report that the activity of astaxanthin is age-dependent, higher in young in compared to the aged brain. PMID:26116165

  7. Astaxanthin present in the maturation medium reduces negative effects of heat shock on the developmental competence of porcine oocytes.

    PubMed

    Do, Lanh Thi Kim; Luu, Vien Viet; Morita, Yasuhiro; Taniguchi, Masayasu; Nii, Masahiro; Peter, Augustine T; Otoi, Takeshige

    2015-06-01

    Astaxanthin, one of the most common carotenoids, elicits antioxidant effects on cellular viability and embryonic development. This study was conducted to investigate the effects of astaxanthin on maturation, fertilization and development of porcine oocytes matured in vitro under heat stress conditions, and then fertilized and cultured under standard conditions. Porcine oocytes were cultured in maturation medium supplemented with different concentrations of astaxanthin (0, 0.25, 0.5 or 1 ppm) for 46 h at either 38.5 or 41 °C. In comparison to oocytes cultured at 38.5 °C, the exposure of porcine oocytes to 41.0 °C during in vitro maturation (IVM) significantly inhibited maturation and development of fertilized oocytes to the blastocyst stage. Supplementation of maturation medium with astaxanthin (0.5 ppm) significantly improved oocyte maturation, fertilization and development to the blastocysts stage in both oocyte groups. However, the total cell number and apoptosis index of blastocysts did not differ among groups. Moreover, astaxanthin (0.5 ppm) significantly increased the rate of oocytes that reached metaphase II and decreased proportion of apoptotic oocytes exposed to H2O2 (1.0mM) during IVM. In summary, we demonstrated that supplementation of maturation medium with astaxanthin (0.5 ppm) exerted antioxidative effects and improved the ability of maturation, fertilization, and development of porcine oocytes exposed to heat stress. PMID:26051456

  8. Effects of homogenization process parameters on physicochemical properties of astaxanthin nanodispersions prepared using a solvent-diffusion technique

    PubMed Central

    Anarjan, Navideh; Jafarizadeh-Malmiri, Hoda; Nehdi, Imededdine Arbi; Sbihi, Hassen Mohamed; Al-Resayes, Saud Ibrahim; Tan, Chin Ping

    2015-01-01

    Nanodispersion systems allow incorporation of lipophilic bioactives, such as astaxanthin (a fat soluble carotenoid) into aqueous systems, which can improve their solubility, bioavailability, and stability, and widen their uses in water-based pharmaceutical and food products. In this study, response surface methodology was used to investigate the influences of homogenization time (0.5–20 minutes) and speed (1,000–9,000 rpm) in the formation of astaxanthin nanodispersions via the solvent-diffusion process. The product was characterized for particle size and astaxanthin concentration using laser diffraction particle size analysis and high performance liquid chromatography, respectively. Relatively high determination coefficients (ranging from 0.896 to 0.969) were obtained for all suggested polynomial regression models. The overall optimal homogenization conditions were determined by multiple response optimization analysis to be 6,000 rpm for 7 minutes. In vitro cellular uptake of astaxanthin from the suggested individual and multiple optimized astaxanthin nanodispersions was also evaluated. The cellular uptake of astaxanthin was found to be considerably increased (by more than five times) as it became incorporated into optimum nanodispersion systems. The lack of a significant difference between predicted and experimental values confirms the suitability of the regression equations connecting the response variables studied to the independent parameters. PMID:25709435

  9. Construction of transplastomic lettuce (Lactuca sativa) dominantly producing astaxanthin fatty acid esters and detailed chemical analysis of generated carotenoids.

    PubMed

    Harada, Hisashi; Maoka, Takashi; Osawa, Ayako; Hattan, Jun-Ichiro; Kanamoto, Hirosuke; Shindo, Kazutoshi; Otomatsu, Toshihiko; Misawa, Norihiko

    2014-04-01

    The plastid genome of lettuce (Lactuca sativa L.) cv. Berkeley was site-specifically modified with the addition of three transgenes, which encoded β,β-carotenoid 3,3'-hydroxylase (CrtZ) and β,β-carotenoid 4,4'-ketolase (4,4'-oxygenase; CrtW) from a marine bacterium Brevundimonas sp. strain SD212, and isopentenyl diphosphate isomerase from a marine bacterium Paracoccus sp. strain N81106. Constructed transplastomic lettuce plants were able to grow on soil at a growth rate similar to that of non-transformed lettuce cv. Berkeley and generate flowers and seeds. The germination ratio of the lettuce transformants (T0) (98.8%) was higher than that of non-transformed lettuce (93.1 %). The transplastomic lettuce (T1) leaves produced the astaxanthin fatty acid (myristate or palmitate) diester (49.2% of total carotenoids), astaxanthin monoester (18.2%), and the free forms of astaxanthin (10.0%) and the other ketocarotenoids (17.5%), which indicated that artificial ketocarotenoids corresponded to 94.9% of total carotenoids (230 μg/g fresh weight). Native carotenoids were there lactucaxanthin (3.8%) and lutein (1.3 %) only. This is the first report to structurally identify the astaxanthin esters biosynthesized in transgenic or transplastomic plants producing astaxanthin. The singlet oxygen-quenching activity of the total carotenoids extracted from the transplastomic leaves was similar to that of astaxanthin (mostly esterified) from the green algae Haematococcus pluvialis. PMID:24287848

  10. Dietary Carotenoids Regulate Astaxanthin Content of Copepods and Modulate Their Susceptibility to UV Light and Copper Toxicity

    PubMed Central

    Caramujo, Maria-José; de Carvalho, Carla C. C. R.; Silva, Soraya J.; Carman, Kevin R.

    2012-01-01

    High irradiation and the presence of xenobiotics favor the formation of reactive oxygen species in marine environments. Organisms have developed antioxidant defenses, including the accumulation of carotenoids that must be obtained from the diet. Astaxanthin is the main carotenoid in marine crustaceans where, among other functions, it scavenges free radicals thus protecting cell compounds against oxidation. Four diets with different carotenoid composition were used to culture the meiobenthic copepod Amphiascoides atopus to assess how its astaxanthin content modulates the response to prooxidant stressors. A. atopus had the highest astaxanthin content when the carotenoid was supplied as astaxanthin esters (i.e., Haematococcus meal). Exposure to short wavelength UV light elicited a 77% to 92% decrease of the astaxanthin content of the copepod depending on the culture diet. The LC50 values of A. atopus exposed to copper were directly related to the initial astaxanthin content. The accumulation of carotenoids may ascribe competitive advantages to certain species in areas subjected to pollution events by attenuating the detrimental effects of metals on survival, and possibly development and fecundity. Conversely, the loss of certain dietary items rich in carotenoids may be responsible for the amplification of the effects of metal exposure in consumers. PMID:22822352

  11. Spontaneous chirality in simple systems

    PubMed

    Pickett; Gross; Okuyama

    2000-10-23

    Two simple examples of spontaneous chiral symmetry breaking are presented. The first is close-packed cylindrically confined spheres. As the cylinder diameter is varied, one obtains a variety of chiral phases. The second example involves unconfined dipolar particles with an isotropic attraction, which also exhibits chiral ground states. We speculate that a dilute magnetorheological fluid film, with the addition of smaller particles to provide an attractive entropic interaction, will exhibit a chiral columnar ground state. PMID:11030973

  12. Excitation of nuclear isomers by X rays from laser plasma

    SciTech Connect

    Andreev, Aleksandr A; Karpeshin, F; Trzhaskovskaya, M B; Platonov, Konstantin Yu; Rozhdestvenskii, Yu V

    2010-06-23

    The possibility of obtaining isomer nuclei is studied by the example of the molybdenum isomer {sup 93}Mo upon irradiation of a niobium {sup 93}Nb target by {approx}50-J, 100-fs laser pulses. It is shown that the modern laser technique allows production of isomer nuclei by accelerated protons and radiative de-excitation of isomer nuclear states by thermal or line X-rays from laser plasma. (interaction of laser radiation with matter. laser plasma)

  13. Uptake and incorporation of labeled tryptophan isomers into IAA in the jsR sub 1 mutant of Lemna gibba

    SciTech Connect

    Baldi, B.G.; Maher, B.R.; Cohen, J.D. )

    1989-04-01

    Analyses of the IAA-overproducing mutant of Lemna have been initiated in order to study in vivo biosynthesis of IAA. Using radiolabelled tryptophan isomers prepared from commercial sources of {sup 14}C-D,L tryptophan by chiral separation kinetics of uptake of L and D tryptophan were determined for sterile cultures of individual jsR{sub 1} four-frond colonies. Over a 24 h period, about 50% of the radioactivity from {sup 14}C-L-TRP in media, or about 25% from {sup 14}C-D-TRP, was found in the plant tissue. Maximal rates of uptake were seen in the first six hors for both isomers. Endogenous levels of tryptophan determined in jsR{sub 1} as measures of pool sizes in vivo show 5 to 10 ug/g FW total tryptophan with less than 1% in the D isomer form. Information on uptake and endogenous pool sizes of tryptophan isomers is being used for feeding of stable isotope labeled tryptophan ({sup 13}C, {sup 14}N) to jsR{sub 1} at physiological levels. Analyses of incorporation of label into IAA using GC-MS and high resolution mass spectrometry are currently underway.

  14. Chiral molecules in the ISM: the best candidates

    NASA Astrophysics Data System (ADS)

    Pilme, J.; Marloie, G.; Lattelais, M.; Pauzat, F.; Ellinger, Y.

    2011-05-01

    In this report we address the question of whether some chiral molecules have a probability of being detected in the interstellar medium (ISM). It is a crucial question since life on Earth, as we know it today, is inseparable from homochirality. Under these conditions, the identification of any chiral species in the interstellar medium (ISM) would be a considerable breakthrough in the pursuit of the origin of life. To this end we rely on the Minimum Energy Principle that states that the most abundant isomer of a given generic formula should be that of lowest energy (Lattelais et al. 2009). We present here computations of the relative stability of complex organic molecules (COMs) believed to be potentially able to exist in the ISM under a chiral isomeric form. Such a search is submitted to a number of constraints. The molecules we are looking for should present precise characteristics, namely: i) have no improper axis of rotation Sn; possess at least one asymmetric center ; ii) satisfy the Minimum Energy Principle; iii) be small with a large enough dipole moment to be possibly identified through their radio millimeter rotational spectra. The energies and dipole moments are calculated by means of quantum simulations based on density functional theory (DFT). The result is that no chiral isomer in the C3H6O (acetone), C2H5ON, C3H7ON (amides), C2H5O2N, C3H7O2N (amino acid) families is the most stable species. This is also true of the C2(H2O)2 and C3(H2O)3 species when restricted to the sugar families, but another chiral molecule of the same chemical formula, i.e. lactic acid HOCH(CH3)COOH is found to be the most stable of all structures. Two other molecules with an NH2 group, namely, NH2CH(CH3)CN, the precursor of α-alanine and NH2CH(CH3)OH, the simplest chiral molecule (beyond halogen or isotopically substituted methane curiosities) are also the most stable species in their respective families. These three molecules satisfy the conditions for being detected according

  15. Baryon chiral perturbation theory

    NASA Astrophysics Data System (ADS)

    Scherer, S.

    2012-03-01

    We provide a short introduction to the one-nucleon sector of chiral perturbation theory and address the issue of power counting and renormalization. We discuss the infrared regularization and the extended on-mass-shell scheme. Both allow for the inclusion of further degrees of freedom beyond pions and nucleons and the application to higher-loop calculations. As applications we consider the chiral expansion of the nucleon mass to order Script O(q6) and the inclusion of vector and axial-vector mesons in the calculation of nucleon form factors. Finally, we address the complex-mass scheme for describing unstable particles in effective field theory.

  16. Functional characterization of various algal carotenoid ketolases reveals that ketolating zeaxanthin efficiently is essential for high production of astaxanthin in transgenic Arabidopsis.

    PubMed

    Zhong, Yu-Juan; Huang, Jun-Chao; Liu, Jin; Li, Yin; Jiang, Yue; Xu, Zeng-Fu; Sandmann, Gerhard; Chen, Feng

    2011-06-01

    Extending the carotenoid pathway to astaxanthin in plants is of scientific and industrial interest. However, expression of a microbial β-carotene ketolase (BKT) that catalyses the formation of ketocarotenoids in transgenic plants typically results in low levels of astaxanthin. The low efficiency of BKTs in ketolating zeaxanthin to astaxanthin is proposed to be the major limitation for astaxanthin accumulation in engineered plants. To verify this hypothesis, several algal BKTs were functionally characterized using an Escherichia coli system and three BKTs were identified, with high (up to 85%), moderate (∼38%), and low (∼1%) conversion rate from zeaxanthin to astaxanthin from Chlamydomonas reinhardtii (CrBKT), Chlorella zofingiensis (CzBKT), and Haematococcus pluvialis (HpBKT3), respectively. Transgenic Arabidopsis thaliana expressing the CrBKT developed orange leaves which accumulated astaxanthin up to 2 mg g(-1) dry weight with a 1.8-fold increase in total carotenoids. In contrast, the expression of CzBKT resulted in much lower astaxanthin content (0.24 mg g(-1) dry weight), whereas HpBKT3 was unable to mediate synthesis of astaxanthin in A. thaliana. The none-native astaxanthin was found mostly in a free form integrated into the light-harvesting complexes of photosystem II in young leaves but in esterified forms in senescent leaves. The alteration of carotenoids did not affect chlorophyll content, plant growth, or development significantly. The astaxanthin-producing plants were more tolerant to high light as shown by reduced lipid peroxidation. This study advances a decisive step towards the utilization of plants for the production of high-value astaxanthin. PMID:21398427

  17. Contesting the paradigm of chirality

    NASA Astrophysics Data System (ADS)

    Efrati, Efi

    2012-02-01

    In 1893 Lord Kelvin coined the term chirality, and stated what is to become the elementary paradigm of chirality: 'I call any geometrical figure, or any group of points, chiral, and say it has chirality, if its image in a plane mirror , ideally realized cannot be brought to coincide with itself'. While the notion of chirality has greatly advanced our understanding of the structures of molecules and crystals, it has been shown to be inconsistent with every pseudo-scalar quantification. In this talk I will present a tabletop demonstration of a chiral structure which is constructed through the achiral summation of identical elementary units which are symmetric under reflection. The seeming contradiction to the definition of chirality is reconciled by proposing an alternative definition, relying on the physicist interpretation of the right hand rule.

  18. Enantiomeric separation of tapentadol by capillary electrophoresis--study of chiral selectivity manipulation by various types of cyclodextrins.

    PubMed

    Znaleziona, Joanna; Fejős, Ida; Ševčík, Juraj; Douša, Michal; Béni, Szabolcs; Maier, Vítězslav

    2015-02-01

    The chiral recognition of the centrally acting analgesic agent tapentadol and its isomers with various cyclodextrins (CDs) was studied by capillary electrophoresis, focusing on the migration order of four stereoisomers. In the case of non-charged hydroxypropylated CDs (2-hydroxypropyl-β-CD, 2-hydroxypropyl-γ-CD) the beta derivative was able to discriminate the S,R- and R,S-isomers in acidic background electrolyte, whereas the gamma allowed the separation of S,S- and R,R-tapentadol, respectively. Dual CD system containing both hosts was used to separate all of four isomers. Negatively charged sulfated-α-CD at 1.0% (w/v) concentration in 100mM sodium borate buffer (pH 9.5) was capable of separating the isomers with favorable enantiomer migration order and the optimized method was able to determine 0.15% of chiral impurities of tapentadol in the presence of the last migrating clinically important R,R-isomer. PMID:25527976

  19. Isomer Shifts in Solid State Chemistry

    NASA Astrophysics Data System (ADS)

    Wagner, F. E.; Stievano, L.

    The isomer shift of the Mössbauer resonance is a rather unique quantity that cannot be obtained by any of the other techniques used for measuring hyperfine interactions in solids, such as NMR or perturbed angular correlations (TDPAC). It shifts the resonance pattern as a whole without affecting the magnetic dipole and electric quadrupole hyperfine splittings. Methods that measure only these hyperfine splittings are insensitive to the isomer shift. The magnitude of the observed shift is proportional to the product of a nuclear parameter, the change Δ⟨r 2⟩ of the nuclear radius that goes along with the Mössbauer transition, and to an electronic property of the material, the electron density ρ(0) at the Mössbauer nucleus or, more precisely, to the difference Δρ(0) of the electron densities at the Mössbauer nuclei in the materials of which the source and the absorber are made. The electron density at the nucleus is due to s-electrons and, to a lesser extent and mainly in heavy nuclei, to relativistic p1 / 2-electrons. All the other electrons have a vanishing density inside the nucleus and do not contribute. Thus, to a very good accuracy, the Mössbauer isomer shift enables one to obtain information on the s-electron density at the Mössbauer nuclei in solids.

  20. Biodegradation of cresol isomers in anoxic aquifers.

    PubMed Central

    Smolenski, W J; Suflita, J M

    1987-01-01

    The biodegradation of o-, m-, and p-cresol was examined in material obtained from a shallow anaerobic alluvial sand aquifer. The cresol isomers were preferentially metabolized, with p-cresol being the most easily degraded. m-Cresol was more persistent than the para-isomer, and o-cresol persisted for over 90 days. Biodegradation of cresol isomers was favored under sulfate-reducing conditions (SRC) compared with that under methanogenic conditions (MC). Slurries that were acclimated to p-cresol metabolism transformed this substrate at 18 and 330 nmol/h per g (dry weight) for MC and SRC, respectively. Inhibition of electron flow to sulfate reduction with 2.0 mM molybdate reduced p-cresol metabolism in incubations containing sulfate. When methanogenesis was blocked with 5 mM bromoethanesulfonic acid in incubations lacking sulfate, p-cresol catabolism was retarded. Under SRC 3.4 mol of sulfate was consumed per mol of p-cresol metabolized. The addition of sulfate to methanogenic incubations stimulated p-cresol degradation. Simultaneous adaptation studies in combination with spectrophotometric and chromatographic analysis of metabolites indicated that p-cresol was oxidized under SRC to p-hydroxybenzoate via the corresponding alcohol and aldehyde. This series of reactions was inhibited under sulfate-limited or aerobic conditions. Therefore, the primary catabolic event for p-cresol decomposition under SRC appears to involve the hydroxylation of the aryl methyl group. PMID:3579279

  1. Photo-stimulated phase and anchoring transitions of chiral azo-dye doped nematic liquid crystals.

    PubMed

    Kundu, Sudarshan; Kang, Shin-Woong

    2013-12-16

    We report concurring phase and anchoring transitions of chiral azo-dye doped nematic liquid crystals. The transitions are induced by photo-stimulation and stable against light and thermal treatments. Photochromic trans- to cis-isomerization of azo-dye induces an augmented dipole moment and strong dipole-dipole interaction of the cis-isomers, resulting in the formation of nano-sized dye-aggregates. Consequent phase separation of the aggregates of a chiral azo-dye induces phase transition from a chiral to nonchiral nematic phase. In addition, the deposition of dye-aggregates at the surfaces brings about anchoring transition of LC molecules. The stability and irreversibility of the transition, together with no need of pretreatments for LC alignment, provide fascinating opportunity for liquid crystal device applications. PMID:24514707

  2. On the bathochromic shift of the absorption by astaxanthin in crustacyanin: a quantum chemical study

    NASA Astrophysics Data System (ADS)

    Durbeej, Bo; Eriksson, Leif A.

    2003-06-01

    The structural origin of the bathochromic shift assumed by the electronic absorption spectrum of protein-bound astaxanthin, the carotenoid that upon binding to crustacyanin is responsible for the blue colouration of lobster shell, is investigated by means of quantum chemical methods. The calculations suggest that the bathochromic shift is largely due to one of the astaxanthin C4 keto groups being hydrogen-bonded to a histidine residue of the surrounding protein, and that the effect of this histidine is directly dependent on its protonation state. Out of the different methodologies (CIS, TD-DFT, and ZINDO/S) employed to calculate wavelengths of maximum absorption, the best agreement with experimental data is obtained using the semiempirical ZINDO/S method.

  3. Enhanced production of fatty acids and astaxanthin in Aurantiochytrium sp. by the expression of Vitreoscilla hemoglobin.

    PubMed

    Suen, Yung Lee; Tang, Hongmei; Huang, Junchao; Chen, Feng

    2014-12-24

    Dissolved oxygen is a critical factor for heterotrophic cell growth and metabolite production. The aim of this study was to investigate the effects of an oxygen-involved protein on cell growth and fatty acid and astaxanthin production in the biologically important thraustochytrid Aurantiochytrium sp. The hemoglobin of the Vitreoscilla stercoraria (VHb) gene was fused upstream with a zeocin resistance gene (ble) and driven by the Aurantiochytrium tubulin promoter. The expression construct was introduced into two strains of Aurantiochytrium sp. by electroporation. Transgenic Aurantiochytrium sp. strains MP4 and SK4 expressing the heterologous VHb achieved significantly higher maximum biomass than their corresponding controls in microaerobic conditions. Furthermore, the transformants of Aurantiochytrium sp. SK4 produced 44% higher total fatty acid and 9-fold higher astaxanthin contents than the wild type control in aerobic conditions. The present study highlights the biotechnological application of VHb in high-cell density fermentation for enhanced biomass production as well as high-value metabolites. PMID:25420960

  4. Astaxanthin preparation by lipase-catalyzed hydrolysis of its esters from Haematococcus pluvialis algal extracts.

    PubMed

    Zhao, Yingying; Guan, Feifei; Wang, Guili; Miao, Lili; Ding, Jing; Guan, Guohua; Li, Ying; Hui, Bodi

    2011-05-01

    Five of 8 fungal lipases screened were found to effectively hydrolyze astaxanthin esters from Haematococcus pluvialis algal cell extracts. Among these, an alkaline lipase from Penicillium cyclopium, expressed in Pichia pastoris, had the highest enzymolysis efficiency. Tween80 was shown to be an effective emulsifier in this lipase hydrolysis system for the 1st time. A series of experiments were performed to find optimal conditions for hydrolysis (pH, temperature, reaction time, lipase dosage). In the optimal reaction system, Tween80 and H. pluvialis extracts (mass ratio 1:1) were emulsified and added to the above lipase at a dosage of 4.6 U/μg (relative to total carotenoids), in phosphate buffer (0.1 M, pH 7.0), and incubated at 28 °C for 7 h, with agitation at 180 rpm. The free astaxanthin recovery ratio under these conditions was 63.2%. PMID:22417348

  5. Effect of temperature on chitin and astaxanthin recoveries from shrimp waste using lactic acid bacteria.

    PubMed

    Pacheco, Neith; Garnica-González, Mónica; Ramírez-Hernández, Jessica Y; Flores-Albino, Belem; Gimeno, Miquel; Bárzana, Eduardo; Shirai, Keiko

    2009-06-01

    The chitin and astaxanthin recoveries by lactic acid fermentation of shrimp wastes (Litopenaeus sp) were conducted in bed-column reactors at 15, 20, 25, 30, 35, 40 and 45 degrees C. The response surface methodology showed that the fermentations carried out in the 27-36 degrees C temperature range with lactic acid above 0.319 mmol/g resulted in the highest demineralization. The maximal deproteinizations were attained from 30 to 40 degrees C. The extraction of free-astaxanthin did not present significant differences between 20 and 35 degrees C and the proportion of cis-stereoisomer forms increased with temperature. The growth rates of Lactobacillus plantarum were estimated in the 15-45 degrees C range and analyzed by Arrhenius and square root models. The cardinal values were 3.94 and 51.7 degrees C for minimum and maximum temperatures, respectively, with activation energy of 43.38 Jmol(-1). PMID:19230657

  6. Astaxanthin alleviates oxidative stress insults-related derangements in human vascular endothelial cells exposed to glucose fluctuations.

    PubMed

    Abdelzaher, Lobna A; Imaizumi, Takahiro; Suzuki, Tokiko; Tomita, Kengo; Takashina, Michinori; Hattori, Yuichi

    2016-04-01

    Glycemic fluctuations may play a critical role in the pathogenesis of diabetic complications, such as cardiovascular disease. We investigated whether the oxycarotenoid astaxanthin can reduce the detrimental effects of fluctuating glucose on vascular endothelial cells. Human umbilical venous endothelial cells were incubated for 3 days in media containing 5.5mM glucose, 22 mM glucose, or 5.5mM glucose alternating with 22 mM glucose in the absence or presence of astaxanthin or N-acetyl-L-cysteine (NAC). Constant high glucose increased reactive oxygen species (ROS) generation, but such an effect was more pronounced in fluctuating glucose. This was associated with up-regulated p22(phox) expression and down-regulated peroxisome proliferator activated receptor-γ coactivator (PGC-1α) expression. Astaxanthin inhibited ROS generation, p22(phox) up-regulation, and PGC-1α down-regulation by the stimuli of glucose fluctuation. Fluctuating glucose, but not constant high glucose, significantly decreased the endothelial nitric oxide synthase (eNOS) phosphorylation level at Ser-1177 without affecting total eNOS expression, which was prevented by astaxanthin as well as by the anti-oxidant NAC. Transferase-mediated dUTP nick end labeling (TUNEL) showed increased cell apoptosis in fluctuating glucose. Glucose fluctuation also resulted in up-regulating gene expression of pro-inflammatory mediators, interleukin-6 and intercellular adhesion molecule-1. These adverse changes were subdued by astaxanthin. The phosphorylation levels of c-Jun N-terminal kinase (JNK) and p38 were significantly increased by glucose fluctuations, and astaxanthin significantly inhibited the increase in JNK and p38 phosphorylation. Taken together, our results suggest that astaxanthin can protect vascular endothelial cells against glucose fluctuation by reducing ROS generation. PMID:26924495

  7. Elucidation of the Pathway to Astaxanthin in the Flowers of Adonis aestivalis[C][W

    PubMed Central

    Cunningham, Francis X.; Gantt, Elisabeth

    2011-01-01

    A few species in the genus Adonis are the only land plants known to produce the valuable red ketocarotenoid astaxanthin in abundance. Here, we ascertain the pathway that leads from the β-rings of β-carotene, a carotenoid ubiquitous in plants, to the 3-hydroxy-4-keto-β-rings of astaxanthin (3,3′-dihydroxy-β,β-carotene-4,4’-dione) in the blood-red flowers of Adonis aestivalis, an ornamental and medicinal plant commonly known as summer pheasant’s eye. Two gene products were found to catalyze three distinct reactions, with the first and third reactions of the pathway catalyzed by the same enzyme. The pathway commences with the activation of the number 4 carbon of a β-ring in a reaction catalyzed by a carotenoid β-ring 4-dehydrogenase (CBFD), continues with the further dehydrogenation of this carbon to yield a carbonyl in a reaction catalyzed by a carotenoid 4-hydroxy-β-ring 4-dehydrogenase, and concludes with the addition of an hydroxyl group at the number 3 carbon in a reaction catalyzed by the erstwhile CBFD enzyme. The A. aestivalis pathway is both portable and robust, functioning efficiently in a simple bacterial host. Our elucidation of the pathway to astaxanthin in A. aestivalis provides enabling technology for development of a biological production process and reveals the evolutionary origin of this unusual plant pathway, one unrelated to and distinctly different from those used by bacteria, green algae, and fungi to synthesize astaxanthin. PMID:21862704

  8. Stereochemical control of nonamphiphilic lyotropic liquid crystals: chiral nematic phase of assemblies separated by six nanometers of aqueous solvents.

    PubMed

    Yang, Sijie; Wang, Bing; Cui, Dawei; Kerwood, Deborah; Wilkens, Stephan; Han, Junjie; Luk, Yan-Yeung

    2013-06-13

    Unlike conventional thermotropic and lyotropic liquid crystals, nonamphiphilic lyotropic liquid crystals consist of hydrated assemblies of nonamphiphilic molecules that are aligned with a separation of about 6 nm between assemblies in an aqueous environment. This separation raises the question of how chirality, either from chiral mesogens or chiral dopants, would impact the phase as the assemblies that need to interact with each other are about 6 nm apart. Here, we report the synthesis of three stereoisomers of disodium chromonyl carboxylate, 5'DSCG-diviol, and the correlation between the molecular structure, bulk assembly, and liquid crystal formation. We observed that the chiral isomers (enantiomers 5'DSCG-(R,R)-diviol and 5'DSCG-(S,S)-diviol) formed liquid crystals while the achiral isomer 5'DSCG-meso-diviol did not. Circular dichroism indicated a chiral conformation with bisignate cotton effect. The nuclear Overhauser effect in proton NMR spectroscopy revealed conformations that are responsible for liquid crystal formation. Cryogenic transmission electron microscopy showed that chiral 5'DSCG-diviols form assemblies with crossings. Interestingly, only planar alignment of the chiral nematic phase was observed in liquid crystal cells with thin spacers. The homeotropic alignment that permitted a fingerprint texture was obtained only when the thickness of the liquid crystal cell was increase to above ~500 μm. These studies suggest that hydrated assemblies of chiral 5'DSCG-diviol can interact with each other across a 6 nm separation in an aqueous environment by having a twist angle of about 0.22° throughout the sample between the neighboring assemblies. PMID:23688325

  9. Influence of Oxygen and Glucose on Primary Metabolism and Astaxanthin Production by Phaffia rhodozyma in Batch and Fed-Batch Cultures: Kinetic and Stoichiometric Analysis

    PubMed Central

    Yamane, Y.; Higashida, K.; Nakashimada, Y.; Kakizono, T.; Nishio, N.

    1997-01-01

    The influence of the oxygen and glucose supply on primary metabolism (fermentation, respiration, and anabolism) and astaxanthin production in the yeast Phaffia rhodozyma was investigated. When P. rhodozyma grew under fermentative conditions with limited oxygen or high concentrations of glucose, the astaxanthin production rate decreased remarkably. On the other hand, when the yeast grew under aerobic conditions, the astaxanthin production rate increased with increasing oxygen uptake. A kinetic analysis showed that the respiration rate correlated positively with the astaxanthin production rate, whereas there was a negative correlation with the ethanol production rate. The influence of glucose concentration at a fixed nitrogen concentration with a high level of oxygen was then investigated. The results showed that astaxanthin production was enhanced by an initial high carbon/nitrogen ratio (C/N ratio) present in the medium, but cell growth was inhibited by a high glucose concentration. A stoichiometric analysis suggested that astaxanthin production was enhanced by decreasing the amount of NADPH required for anabolism, which could be achieved by the repression of protein biosynthesis with a high C/N ratio. Based on these results, we performed a two-stage fed-batch culture, in which cell growth was enhanced by a low C/N ratio in the first stage and astaxanthin production was enhanced by a high C/N ratio in the second stage. In this culture system, the highest astaxanthin production, 16.0 mg per liter, was obtained. PMID:16535733

  10. Genetic engineering of the complete carotenoid pathway towards enhanced astaxanthin formation in Xanthophyllomyces dendrorhous starting from a high-yield mutant.

    PubMed

    Gassel, Sören; Breitenbach, Jürgen; Sandmann, Gerhard

    2014-01-01

    The yeast Xanthophyllomyces dendrorhous is one of the rare organisms which can synthesize the commercially interesting carotenoid astaxanthin. However, astaxanthin yield in wild-type and also in classical mutants is still too low for an attractive bioprocess. Therefore, we combined classical mutagenesis with genetic engineering of the complete pathway covering improved precursor supply for carotenogenesis, enhanced metabolite flow into the pathway, and efficient conversion of intermediates into the desired end product astaxanthin. We also constructed new transformation plasmids for the stepwise expression of the genes of 3-hydroxymethyl-3-glutaryl coenzyme A reductase, geranylgeranyl pyrophosphate synthase, phytoene synthase/lycopene cyclase, and astaxanthin synthase. Starting from two mutants with a 15-fold higher astaxanthin, we obtained transformants with an additional 6-fold increase in the final step of pathway engineering. Thus, a maximum astaxanthin content of almost 9 mg per g dry weight was reached in shaking cultures. Under optimized fermenter conditions, astaxanthin production with these engineered transformants should be comparable to Haematococcus pluvialis, the leading commercial producer of natural astaxanthin. PMID:24241897