- Chemoenzymatic Synthesis of all-trans-Isomers of Lutein and Zeaxanthin
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Abstract: A method for the synthesis of all-trans-isomers of lutein and zeaxanthin has been proposed, which includes the stage of esterification of lutein and zeaxanthin with benzoic acid in the presence of enantioselective lipase Novozyme 435. Further hydrolysis of lutein and zeaxanthin dibenzoates has led to the formation of the initial xanthophylls in the all-trans configuration.
- Kuregyan, A. G.,Oganesyan, E. T.,Pechinsky, S. V.
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p. 1674 - 1679
(2021/11/01)
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- Bidirectional Hiyama–Denmark Cross-Coupling Reactions of Bissilyldeca-1,3,5,7,9-pentaenes for the Synthesis of Symmetrical and Non-Symmetrical Carotenoids
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The construction of the carotenoid skeleton by Pd-catalyzed Csp2?Csp2 cross-coupling reactions of symmetrical and non-symmetrical 1,10-bissilyldeca-1,3,5,7,9-pentaenes and the corresponding complementary alkenyl iodides has been developed. Reaction conditions for these bidirectional and orthogonal Hiyama–Denmark cross-coupling reactions of bisfunctionalized pentaenes are mild and the carotenoid products preserve the stereochemical information of the corresponding oligoene partners. The carotenoids synthesized in this manner include β,β-carotene and (3R,3′R)-zeaxanthin (symmetrical) as well as 9-cis-β,β-carotene, 7,8-dihydro-β,β-carotene and β-cryptoxanthin (non-symmetrical).
- Rivas, Aurea,Pérez-Revenga, Víctor,Alvarez, Rosana,de Lera, Angel R.
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p. 14399 - 14407
(2019/11/03)
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- A simple and efficient method for the partial synthesis of pure (3R,3’s)-astaxanthin from (3R,3’r,6’r)-lutein and lutein esters via (3R,3’s)-zeaxanthin and theoretical study of their formation mechanisms
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Carotenoids are natural compounds that have important roles in promoting and maintaining human health. Synthetic astaxanthin is a highly requested product by the aquaculture industry, but natural astaxanthin is not. Various strategies have been developed
- Rodríguez-DeLeón, Eloy,Jiménez-Halla, Oscar J.C.,Báez, José E.,Moustapha Bah
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supporting information
(2019/04/30)
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- RPE65 has an additional function as the lutein to meso-zeaxanthin isomerase in the vertebrate eye
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Carotenoids are plant-derived pigment molecules that vertebrates cannot synthesize de novo that protect the fovea of the primate retina from oxidative stress and light damage. meso-Zeaxanthin is an ocular-specific carotenoid for which there are no common
- Shyam, Rajalekshmy,Gorusupudi, Aruna,Nelson, Kelly,Horvath, Martin P.,Bernstein, Paul S.
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p. 10882 - 10887
(2017/10/13)
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- Synthesis of (3 R,3 R)-zeaxanthin and its meso -stereoisomer from (3 R,3 R,6 R)-lutein via (3 R)-3,4-anhydrolutein
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A process has been developed for the partial synthesis of (3R,3R)-zeaxanthin and (3R,3S; meso)-zeaxanthin from commercially available (3R,3R,6R)-lutein. This involves the regioselective hydroboration of a dehydration product of lutein, namely (3R)-3,4-didehydro-,-caroten-3-ol [(3R)-3,4-anhydrolutein], to yield a mixture of (3R,3R)-zeaxanthin and (3R,3S; meso)-zeaxanthin followed by separation of these carotenoids by enzyme-mediated acylation. (3R,3R,6R)-Lutein, (3R,3R)-zeaxanthin and its meso-isomer accumulate in human ocular tissues and have been implicated in the prevention of age-related macular degeneration (AMD). Georg Thieme Verlag Stuttgart New York.
- Khachik, Frederick
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p. 453 - 459
(2012/03/27)
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- Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin
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Disclosed is a process for the synthesis of (3R)-3-hydroxy-β-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-α-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-α-ionone ketal that was prepared from (rac)-α-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-α-ionone ketal followed by deprotection, lead to 3-hydroxy-α-ionone that was transformed into (rac)-3-hydrox-β-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-α-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-β-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(β-ionylideneethyl)triphenylphosphonium chloride [(3R)-C15-Wittig salt] and its (3S)-enantiomer [(3S)-C15-Wittig salt] according to known procedures. Double Wittig condensation of these Wittig salts with commercial available 2,5- dimethtylocta-2,4,6-triene-1,8-dial provided all 3 stereoisomers of zeaxanthin. Similarly, (3R)-C15-Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal.
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Page/Page column 28
(2012/07/27)
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- Synthesis of C40-symmetrical fully conjugated carotenoids by olefin metathesis
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In an effort to push olefin metathesis to the limits of conjugation in reactants and products, the C40-symmetrical carotenoids β,β-carotene (1), lycopene (2), (3R,3′R)-zeaxanthin (3), and rac-isozeaxanthin (4), which are conjugated undecaenes, have been synthesized from C21-terminal hexaenes by treatment with Grubbs' second-generation Ru catalyst in dichloromethane at 50 °C.
- Fontan, Noelia,Dominguez, Marta,Ulvarez, Rosana,De Lera, Ungel R.
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experimental part
p. 6704 - 6712
(2012/01/03)
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- Fast regeneration of carotenoids from radical cations by isoflavonoid dianions: Importance of the carotenoid keto group for electron transfer
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Electron transfer to radical cations of β-carotene, zeaxanthin, canthaxanthin, and astaxanthin from each of the three acid/base forms of the diphenolic isoflavonoid daidzein and its C-glycoside puerarin, as studied by laser flash photolysis in homogeneous methanol/chloroform (1/9) solution, was found to depend on carotenoid structures and more significantly on the deprotonation degree of the isoflavonoids. None of the carotenoid radical cations reacted with the neutral forms of the isoflavonoids while the monoanionic and dianionic forms of the isoflavonoids regenerated the oxidized carotenoid. Electron transfer to the β-carotene radical cation from the puerarin dianion followed second order kinetics with the rate constant at 25 °C k2 = 5.5 × 109 M-1 s-1, zeaxanthin 8.5 × 109 M-1 s-1, canthaxanthin 6.5 × 1010 M-1 s-1, and astaxanthin 11.1 × 1010 M-1 s-1 approaching the diffusion limit and establishing a linear free energy relationship between rate constants and driving force. Comparable results found for the daidzein dianion indicate that the steric hindrance from the glucoside is not important suggesting the more reducing but less acidic 4′-OH/4′-O- as electron donors. On the basis of the rate constants obtained from kinetic analyses, the keto group of carotenoids is concluded to facilitate electron transfer. The driving force was estimated from oxidation potentials, as determined by cyclic-voltametry for puerarin and daidzein in aqueous solutions at varying pH conditions, which led to the standard reduction potentials E° = 1.13 and 1.10 V versus NHE corresponding to the uncharged puerarin and daidzein. For pH > pka2, the apparent potentials of both puerarin and daidzein became constants and were E° = 0.69 and 0.65 V, respectively. Electron transfer from isoflavonoids to the carotenoid radical cation, as formed during oxidative stress, is faster for astaxanthin than for the other carotenoids, which may relate to astaxanthins more effective antioxidative properties and in agreement with the highest electron accepting index of astaxanthin.
- Han, Rui-Min,Chen, Chang-Hui,Tian, Yu-Xi,Zhang, Jian-Ping,Skibsted, Leif H.
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scheme or table
p. 126 - 132
(2010/05/11)
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- MICRONIZED CAROTENOID PREPARATION AS IMMUNOSTIMULANT FOR CRUSTACEANS
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The present invention refers to micronized carotenoids in an oily carrier; the composition acts as immunostimulant for crustaceans.
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Page/Page column 7; 8
(2010/09/17)
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- Process for Synthesis of (3R,3'R)-Zeaxanthin and (3R,3'S;meso)-Zeaxanthin from (3R,3'R,6'R)-Lutein via (3R)-3',4'-Anhydrolutein
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(3R, 3′R, 6′R)-Lutein and (3R, 3′R)-zeaxanthin are two dietary carotenoids that are present in most fruits and vegetables commonly consumed in the US and accumulate in the human plasma, major organs, and ocular tissues. Another stereoisomer of (3R, 3′R)-zeaxanthin that is not of dietary origin but is found in the human ocular tissues is (3R, 3′S; meso)-zeaxanthin. There is growing evidence that these carotenoids play an important role in the prevention of age-related macular degeneration (AMD) that is the leading cause of blindness in the U.S. and the Western World. In view of the potential therapeutic application of dietary lutein, (3R, 3′R)-zeaxanthin, and (3R, 3′S; meso)-zeaxanthin, the industrial production of these carotenoids is of considerable importance. The present invention provides a process for the partial synthesis of (3R, 3′R)-zeaxanthin and (3R, 3′S; meso)-zeaxanthin from a readily accessible dehydration product of (3R, 3′R, 6′R)-lutein, namely, (3R)-3′,4′-didehydro-β,β-caroten-3-ol [(3R)-3′,4′-anhydrolutein]. The process involves regioselective hydroboration of (3R)-3′,4′-anhydrolutein to a mixture of (3R, 3′R)-zeaxanthin and (3R, 3′S; meso)-zeaxanthin followed by separation of these carotenoids by enzyme-mediated acylation.
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Page/Page column 10
(2009/10/01)
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- NOVEL XANTHOPHYLL COMPOSITION CONTANING (TRANS, MESO) - ZEAXANTHIN, AND A PROCESS FOR ITS PREPARATION
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The invention disclosed in this application relates to a novel xanthophylls composition containing trans-isomeric forms of meso-zeaxanthin, zeaxanthin and lutein useful for nutrition and health care and a process for its preparation are disclosed. The pro
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Page/Page column 20 - 23
(2009/04/25)
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- Preparation method for high-content food-grade zeaxanthin
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This invention has disclosed a method for preparation of food-grade zeaxanthin through chemical isomerizaton reaction from lutein. The technical issues to be solved in this invention are quite low product yield obtained with existing methods, need of purification treatment process, and inadaptability to industrialized production. The technical schemes of this invention are: a. Mix xanthophyll crystal or its fatty acid ester with food-grade glycol or propylene glycol, for full dissolution under 60-90°C temperature. Add organic alkali into the mixed liquor acquired from step 1, for isomerization reaction to take place under inertial environment. c. Dilute the reaction solution gained from step b with the mixed solution of deionized water and ethanol, and separate the obtained crystal with conventional separating method. d. Vacuum dry the acquired crystal from step c, to get the zeaxanthin crystal. Glycol or propylene glycol is used in this invention for isomerization reaction under inertial environment after it has fully dissolved raw material under proper temperature. The product yield is reachable to more than 60%, very adaptable to industrialized product, without the need for further purification treatment.
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Page/Page column 5-6
(2008/06/13)
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- Method for Preparing High-Content Food-Grade Zeaxanthin
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This invention has disclosed a method for preparation of food-grade zeaxanthin through chemical isomerizaton reaction from lutein. The technical issues to be solved in this invention are quite low product yield obtained with existing methods, need of purification treatment process, and inadaptability to industrialized production. The technical schemes of this invention are: a. Mix xanthophyll crystal or its fatty acid ester with food-grade glycol or propylene glycol, for full dissolution under 60-90° C. temperature. Add organic alkali into the mixed liquor acquired from step 1, for isomerization reaction to take place under inertial environment. c. Dilute the reaction solution gained from step b with the mixed solution of deionized water and ethanol, and separate the obtained crystal with conventional separating method. d. Vacuum dries the acquired crystal from step c, to get the zeaxanthin crystal. Glycol or propylene glycol is used in this invention for isomerization reaction under inertial environment after it has fully dissolved raw material under proper temperature. The product yield is reachable to more than 60%, very adaptable to industrialized product, without the need for further purification treatment.
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Page/Page column 3-4
(2008/06/13)
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- Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants
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A process for extracting and isolating carotenoid esters or carotenoids in high purity from plants without the use of harmful organic solvents. Zeaxanthin esters were isolated and purified from the berries of Lycium Chinese Mill (LCM berries). The esters isolated according to the invention contain substantially no isomerized double bonds. The purified carotenoid esters or carotenoids isolated by this process are free from impurities and serve as a safe source of nutritional supplement for human consumption as well as providing a suitable and effective color additive for human foods.
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Page/Page column 10
(2008/06/13)
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- Novel xanthophyll composition containing trans, meso-zeaxanthin, trans, R, R-zeaxanthin and trans, R, R-lutein useful for nutrition and health care and a process for its preparation
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The present invention relates to xanthophyll composition containing (trans, meso)-zeaxanthin), (trans, R,R)-zeaxanthin and (trans, R,R)-lutein useful for nutrition and health care and a process for its preparation. More particularly, the invention relates
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Page/Page column 8
(2008/06/13)
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- ISOLATION AND PURIFICATION OF CAROTENOIDS FROM MARIGOLD FLOWERS
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The present invention explains a realistic and effective process for isolating and purifying carotenoids containing higher concentrations of carotenoids such as trans-lutein, trans-zeaxanthin, Cis-lutein, ?-carotene and Cryptoxanthin from Marigold flower petals under controlled conditions leaving no traces of any organic hazardous solvents. The process involves ensilaging marigold flowers, dehydration, solvent extraction, alkali hydrolysis of carotenoid esters with absolute alcohol, crystallization/purification using water, absolute alcohol mixture followed by filteration and drying until the crystals are considerably free from moisture and absolutely free from residual hazardous solvents. These crystals are suitable for nutraceutical and food products as supplements.
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Page/Page column 10-12
(2008/06/13)
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- PROCESS FOR THE PREPARATION OF ALPHA- AND BETA-CRYPTOXANTHIN
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The present invention relates to a process for converting lutein and/or lutein esters to β-cryptoxanthin and α-cryptoxanthin, suitable for human consumption as dietary supplements, by employing safe and environmentally friendly reagents. In the first synthetic step, commercially available lutein and/or lutein esters are transformed into a mixture of dehydration products of lutein (anhydroluteins) in the presence of a catalytic amount of an acid. The resulting anhydroluteins are then converted to β-cryptoxanthin (major product) and α-cryptoxanthin (minor product) by heterogeneous catalytic hydrogenation employing transition elements of group VIII in a variety of organic solvents under atmospheric pressure of hydrogen. A novel feature of this invention is the regioselective hydrogenation of anhydroluteins while the highly conjugated polyene chain of these carotenoids remains intact.
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Page/Page column 14-20; 26-28
(2008/06/13)
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- Carotenoid analogs or derivatives for controlling C-reactive protein levels
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A method of controlling (e.g., influencing or affecting) C-reactive protein levels in a subject may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include an acyclic alkene including at least one substituent and/or a cyclic ring including at least one substituent. In some embodiments, a carotenoid analog or derivative may include at least one substituent.
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- Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease
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A method for inhibiting and/or ameliorating the occurrence of diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals in a subject whereby a subject is administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The analog or derivative is administered such that the subject's risk of experiencing diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals may be thereby reduced. The analog or analog combination may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include a pharmaceutical composition including a carotenoid analog or derivative. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ester functionality. In some embodiments, a pharmaceutical composition may include a biologically inactive carrier. The pharmaceutical composition may be adapted to be administered to a human subject.
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- Carotenoid analogs or derivatives for controlling connexin 43 expression
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A method of controlling (e.g., influencing or affecting) connexin 43 expression in a subject may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. In some embodiments, controlling connexin 43 expression in a subject may effectively treat cardiac arrhythmia and/or cancerous and pre-cancerous cells in a subject. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include an acyclic alkene including at least one substituent and/or a cyclic ring including at least one substituent. In some embodiments, a carotenoid analog or derivative may include at least one substituent.
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- Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
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A method for inhibiting and/or ameliorating the occurrence of diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals in a subject whereby a subject is administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The analog or derivative is administered such that the subject's risk of experiencing diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals may be thereby reduced. The analog or analog combination may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include a chemical compound including an at least partially water soluble carotenoid analog or derivative. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ether functionality.
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- Carotenoid analogs or derivatives for the inhibition and amelioration of liver disease
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A method of treating liver disease in a subject. The method may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include an acyclic alkene including at least one substituent and/or a cyclic ring including at least one substituent. In some embodiments, a carotenoid analog or derivative may include at least one substituent.
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-
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- Carotenoid ester analogs or derivatives for controlling connexin 43 expression
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A method of controlling (e.g., influencing or affecting) connexin 43 expression in a subject may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. In some embodiments, controlling connexin 43 expression in a subject may effectively treat cardiac arrhythmia and/or cancerous and pre-cancerous cells in a subject. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ester functionality.
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- Carotenoid ether analogs or derivatives for the inhibition and amelioration of liver disease
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A method of treating liver disease in a subject. The method may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ether functionality.
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- Carotenoid ether analogs or derivatives for controlling C-reactive protein levels
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A method of controlling (e.g., influencing or affecting) C-reactive protein levels in a subject may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one j e substituent. The substituent may be coupled to the cyclic ring with an ether functionality.
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-
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- Carotenoid ester analogs or derivatives for controlling C-reactive protein levels
-
A method of controlling (e.g., influencing or affecting) C-reactive protein levels in a subject may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ester functionality.
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-
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- Carotenoid ether analogs or derivatives for controlling connexin 43 expression
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A method of controlling (e.g., influencing or affecting) connexin 43 expression in a subject may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. In some embodiments, controlling connexin 43 expression in a subject may effectively treat cardiac arrhythmia and/or cancerous and pre-cancerous cells in a subject. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ether functionality.
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- METHOD FOR PRODUCING CAROTENOIDS
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The invention relates to a method for producing carotenoids. Said method is characterised in that a dialkoxy dialdehyde of general formula I, where R1 = C1-C6 alkyl, is reacted with a phosphonium salt of formula II in a double Wittig condensation, or with a phosphonate of formula III in a double Wittig-Horner condensation, whereby the substituents in formulas II and III independently of one another are defined as follows: R2 = IV; R3 represents aryl; R4 to R6 represent C1-C6 alkyl and X- represents an anion equivalent of an inorganic or organic acid.
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-
- Confirmation of the absolute (3R,3′S,6′R)-configuration of (all-E)-3′-epilutein
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Circular dichroism (CD) spectroscopy was used to distinguish between the isomeric (all-E)-configured 3′-epilutein (2) and 6′-epilutein (8) to establish the absolute configuration of epilutein samples of different (natural and semisynthetic) origin, including samples of 2 obtained from thermally processed sorrel. Thus, the CD data of lutein (1) and epilutein samples (2) were compared. Our results unambiguously confirmed the (3R,3′S,6′R)- configuration of all epilutein samples. Compound 2 was thoroughly characterized, and its 13C-NMR data are published herewith for the first time.
- Molnar, Peter,Deli, Jozsef,Osz, Erzsebet,Zsila, Ferenc,Simonyi, Miklos,Toth, Gyula
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p. 2159 - 2168
(2007/10/03)
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- Method for production of rare carotenoids from commercially available lutein
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Disclosed are processes for conversion of (3R,3′R,6′R)-lutein to (3R,6′R)-α-cryptoxanthin, (3R)-β-cryptoxanthin, anhydroluteins I, II, and III (dehydration products of lutein), and a method for separating and purifying the individual carotenoids including the unreacted (3R,3′R)-zeaxanthin. The invention also includes two methods that transform (3R,3′R,6′R)-lutein into (3R,6′R)-α-cryptoxanthin in excellent yields.
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Page/Page column 11-12
(2008/06/13)
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- Coenzyme Q10 formulation and process methodology for soft gel capsules manufacturing
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A formulation of Coenzyme Q10, beta-carotenes, Vitamin E, and medium chain triglycerides in rice bran oil and an optional thickener, such as bee's wax, is provided in a soft gel capsule so that a maximum of the Coenzyme Q10is absorbed by the human body. Generally, about 60 mg of Coenzyme Q10is the normal amount provided daily to a healthy sedentary adult.
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- Synthesis of symmetrical carotenoids by a two-fold Stille reaction
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β-Carotene 1 and (3R,3′R)-zeaxanthin 2 have been stereoselectively prepared in a highly convergent fashion by a 2-fold Stille cross-coupling reaction. The C12-pentaenylbis-stannane 8 is the central "lynchpin" that connects two units of the terminal C14-iodides 9 and 17 to afford 1 and 2, respectively.
- Vaz, Belen,Alvarez, Rosana,de Lera, Angel R.
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p. 5040 - 5043
(2007/10/03)
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- Agent for inhibiting carcinogenesis or tumor metastasis
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In order to provide a naturally derived agent for inhibiting carcinogenesis or tumor metastasis, having a low toxicity and excellent effectiveness in inhibiting carcinogenesis and tumor metastasis, zeaxanthin, and particularly zeaxanthin which is extracted from an alga, is used as an active ingredient.
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- Relative one-electron reduction potentials of carotenoid radical cations and the interactions of carotenoids with the vitamin E radical cation
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Pulse radiolysis studies have been used to determine the electron- transfer rate constants between various pairs of carotenoids, one of which is present as the radical cation. These dietary carotenoids include those of importance to vision, namely zeaxanthin and lutein. These results have suggested the order of relative ease of electron transfer between six carotenoids. Additional experiments, involving electron transfer between astaxanthin (ASTA), β-apo-8'-carotenal (APO), and vitamin E (TOH), lead to the following order in terms of relative ease of electron transfer for the seven carotenoid radical cations studied: astaxanthin > β-apo-8'-carotenal > canthaxanthin > lutein > zeaxanthin > β-carotene > lycopene, such that lycopene is the strongest reducing agent (the most easily oxidized) and astaxanthin is the weakest, and the radical cations of the visual carotenoids, lutein (LUT) and zeaxanthin (ZEA), are reduced by lycopene (LYC) but not by β-carotene (β-CAR). Work on 7,7'-dihydro-β-carotene (77DH) and vitamin E allows us to better understand the interaction of the vitamin E radicals with carotenoids.
- Edge, Ruth,Land, Edward J.,McGarvey, David,Mulroy, Louise,Truscott, T. George
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p. 4087 - 4090
(2007/10/03)
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- Kinetic Studies on the Thermal (Z/E)-Isomerization of C40-Carotenoids
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Rates of thermal (Z/E)-isomerization among all-E-, 9(9')Z-, 13Z-, 13'Z- and 15Z-isomers of zeaxanthin (1), natural violaxanthin (2), "semi-synthetic" violaxanthin (2a), capsorubin (3), capsanthin (4) and lutein epoxide (5) have been measured at temperatures over the range 333.4-368.4 K.From the specific rate constants calculated on the basis of four kinetic models, the Arrhenius and activation parameters have been derived.The effect of the different end groups and different solvents on the composition of the (Z/E)-equilibrium mixtures have been investigated as well.The rates of the isomerization reactions have been measured by HPLC, UV/VIS spectrophotometry and "classic" column chromatography.
- Molnar, Peter,Kortvelyesi, Tarnas,Matus, Zoltan,Szabolca, Jozsef
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p. 801 - 841
(2007/10/03)
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- Selective hydrogenation of carotenones II.? Reduction of rhodoxanthin to lutein and zeaxanthin, and of canthaxanthin to a dihydro-retro-carotenediol by tellurium hydride
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Racemic lutein and racemic zeaxanthin have been prepared from rhodoxanthin by reduction with tellurium hydride. Similarly, canthaxanthin was transformed into a retro-carotenediol. Acta Chemica Scandinivica 1996.
- Sliwka, Hans-Richard,Liaaen-Jensen, Synnove
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p. 637 - 639
(2007/10/03)
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- Interactions between carotenoids and the CCl3O2? radical
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The reactions of CCl3O2? (a model of alkyl peroxyl radicals which can be selectively generated in nanoseconds) with a range of carotenoids (β-carotene, septapreno-β-carotene, canthaxanthin, astaxanthin, zeaxanthin, and lutein) in the heterogeneous micellar environment, aqueous 2% Triton X-100, have been studied by pulse radiolysis. For all carotenoids investigated two reaction products, absorbing in the near-infrared region, are observed and assigned to the carotenoid radical cation and an addition radical. With the exception of astaxanthin, the carotenoid radical cation formation is biexponential and the slower component matches the first-order decay of the addition radical. In the case of astaxanthin, no radical cation is formed directly by reaction with CCl3O2?, it is formed exclusively from the decay of the addition radical. The results are discussed in terms of the antioxidant properties of carotenoid pigments.
- Hill, Tessa J.,Land, Edward J.,McGarvey, David J.,Schalch, Wolfgang,Tinkler, Jane H.,Truscott, T. George
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p. 8322 - 8326
(2007/10/03)
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- 91. Synthesis, Isolation, and Full Spectroscopic Characterization of Eleven (Z)-Isomers of (3R,3'R)-Zeaxanthin
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Developmental efforts to improve the yield of the chemical synthesis of (3R,3'R)-zeaxanthin resulted in the isolation, partly by chromatography from reaction mixtures, and full spectroscopic characterization by 1H NMR, UV/VIS, and CD spectroscopy of eleven (Z/E)-isomers of zeaxanthin: (7Z)-, (9Z)-, (13Z)-, (15Z)-, (7Z,7'Z)-, (9Z,9'Z)-, (7Z,9Z,7'Z)-, (7Z,11Z,7'Z)-, (9Z,13Z,9'Z)-, (7Z,9Z,7'Z,9'Z)-, and (7Z,9Z,11Z,7'Z,9'Z)-zeaxanthin.Five of these isomers were obtained by specific synthesis, namely the (7Z)-, (7Z,7'Z)-, (9Z,9'Z)-, (7Z,9Z,7'Z)-, and (7Z,9Z,7'Z,9'Z)-isomers.
- Englert, Gerhard,Noack, Klaus,Broger, Emil A.,Glinz, Ernst,Vecchi, Max,Zell, Reinhard
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p. 969 - 982
(2007/10/02)
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- 87. Technical Procedures for the Syntheses of Carotenoids and Related Compounds from 6-Oxo-isophorone: Syntheses of (3R,3'R)-Zeaxanthin Part I
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Starting from the readily available, optically active (4R)-4-hydroxy-2,2,6-trimethylcyclohexanone (1), a new technical synthesis of (3R,3'R)-zeaxanthin is described.According to a 2(C9 + C6) + C10= C40 construction scheme, the ketone 1 was first transformed with (E)-3-methylpent-2-en-4-yn-1-ol (5) into a C15-intermediate which, by a three-step sequence, could be converted into the known olefinic C15-Wittig salt 4.Optimized conditions for the final Wittig reaction of 4 with the C10-dialdehyde 3 are discussed.Based on 1, the overall yield of the entire technical process is ca. 40percent.
- Widmer, Erich,Soukup, Milan,Zell, Reinhard,Broger, Emil,Wagner, Hans Peter,Imfeld, Marquard
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p. 861 - 867
(2007/10/02)
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- Sulfone polyene intermediates
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A process for producing carotenoids and carotenoid intermediates via reduction of sulfonyl polyenes with a dithionite in the presence of ammonia or an aliphatic amine, including novel intermediates in this process, which carotenoids are known coloring agents for foodstuffs, animal feeds, pharmaceuticals, etc.
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- Partial Syntheses of Diastereomeric Carotenols
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The application of the Mitsunobu reaction was successfully tested on (3R,3'R)-zeaxanthin, giving the (3S,3'S)-enantiomer and meso form.Applied to natural (3R,3'R,6'R)-lutein, this inversion reaction allowed the preparation of the three other 6'R diastereomers. (3S,3'S,6'R)-lutein with 3',6'-cis-configuration of the ε-ring has not been synthesized before.The observed Cotton effects of the eight lutein diastereomers are rationalized by application of the additivity hypothesis.New trivial names are suggested for the eight lutein isomers on the basis of structural relationships.
- Sliwka, Hans-Richard,Liaaen-Jensen, Synnoee
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p. 518 - 525
(2007/10/02)
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- ISOLATION AND STRUCTURAL ELUCIDATION OF CUCURBITAXANTHIN A AND B FROM PUMPKIN CUCURBITA MAXIMA
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Two new carotenoids, cucurbitaxanthin A and cucurbitaxanthin B have been isolated from the pumpkin Cucurbita maxima.Key Word Index-Cucurbita maxima; Cucurbitaceae; pumpkin; carotenoid; cucurbitaxanthin A; cucurbitaxanthin B.
- Matsuno, Takao,Tani, Yasuko,Maoka, Takashi,Matsuo, Kenji,Komori, Tadaaki
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p. 2837 - 2840
(2007/10/02)
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- Carotenoid Sulfates. 4. Syntheses and Properties of Carotenoid Sulfates
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Carotenoid sulfates have been prepared from 14 selected carotenols for spectroscopic characterization, studies of their stability in solution and their water solubility.Carotenoids containing sec non-allylic hydroxy groups provided sulfates stable in methanol solution, exemplified by zeaxanthin mono- and disulfate, alloxathin mono- and disulfate, fucoxanthin monosulfate, peridinin monosufate, capsorubin mono- and disulfate and astaxanthin mono- and disulfate.Acid catalyzed methanolysis of zeaxanthin disulfate gave zeaxanthin with complete retention of configuration.Enzymatic hydrolysis of alloxanthin monosulfate is reported.Less stable sulfates were obtained from sec vic diol type-, phenolic and tert-carotenols; caloxanthin, nostoxanthin, 3-hydroxyisorenieratene, 3,3'-dihydroxyisorenieratene, rhodovibrin, di-OH-lycopene and OH-chlorobactene.Acid catalyzed methanolysis of the tert caratenols proceeded via carbocations, judged by the solvolysis products characterized.Characteristic spectroscopic properties of carotenoid sulfates are pointed out.Water solubilities were studied.
- Hertzberg, Sissel,Liaaen-Jensen, Synnoeve
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p. 629 - 638
(2007/10/02)
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- Further Synthesis of Zeaxanthin and Rhodoxanthin
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A modification of a previously reported synthesis of zeaxanthin (1), and routes to both zeaxanthin and rhodoxanthin (2) from α-ionone, are described.
- Ellis, Peter R.,Faruk, Erol A.,Moss, Gerald P.,Weedon, Basil C. L.
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p. 1092 - 1097
(2007/10/02)
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- 154. Synthese von optisch aktiven, natuerlichen Carotinoiden und strukturell verwandten Naturprodukten. V. Synthese von (3R,3'R)-, (3S,3'S)- und (3R,3'S; meso)-Zeaxanthin durch asymmetrische Hydroborierung. Ein neuer Zugang zu optisch aktiven Carotinoidba
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The synthesis of (3R,3'R)-, (3S,3'S)- and (3R,3'S; meso)-zeaxanthin (1), (19) and (21) is reported utilizing asymmetric hydroboration as the key reaction.Thus, safranol isopropenylmethylether (4) is hydroborated with (+)- and (-)-(IPC)2BH to give the opti
- Ruettimann, August,Mayer, Hans
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p. 1456 - 1462
(2007/10/02)
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- Mimulaxanthin, the Main Carotenoid in Lamium montanum, Determination of its Absolute Configuration. Absolute Configuration of Deepoxyneoxanthin by its Correlation with Neoxanthin
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The carotenoid mixture isolated from the yellow flowers of Lamium montanum PERS. (Labiatae) consists of more than 75percent of carotenoids with allenic end groups.Besides 32percent of neoxanthin/neochrome we isolated 44percent of mimulaxanthin (1a), a very rare carotenoid so far only found in Mimulus sp. (Scrophulariaceae).Its absolute configuration was determined by oxidative degradation to the known ketone 3 ("grasshopper ketone") and by spectroscopic and chiroptical comparisons with neoxanthin (6).Mimulaxanthin (1a) therefore is (3S,5R,6R,3'S,5'R,6'R)-6,7,6',7'-tetradehydro-5,6,5',6'-tetrahydro-β,β-carotene-3,5,3',5'-tetraol.Deepoxyneoxanthin, which was reisolated from Mimulus sp. is (3S,5R,6R,3'R)-6,7-didehydro-6,7-dihydro-β,β-carotene-3,5,3'-triol (2), as shown by spectroscopic and chemical correlation with neoxanthin (6; de-epoxydation by BuLi/FeCl3).
- Buchecker, Richard,Eugster, Conrad Hans
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p. 2531 - 2537
(2007/10/02)
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- Isomerizing cis-carotenoids to all-trans-carotenoids
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Cis-isomers of a carotenoid are isomerized to an all-trans-isomer of the carotenoid by heating the cis-isomers in water at above about 50° C.
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- Trimethyl-1,4-dioxaspiro[4,5]dec-7-en-8-methanol
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The compound 7,9,9-trimethyl-1,4-dioxoaspiro [4,5] dec-7-en-8-methanol an intermediate in the preparation of Zeaxanthin and Xanthophyll, known coloring agents for foodstuffs.
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