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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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Astaxanthin from (3R,3’R,6’R)-Lutein and Lutein Esters Via (3R,3’S)-Zeaxanthin and Theoretical Study of Their Formation Mechanisms molecules Article 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 Eloy Rodríguez-deLeón 1, J. Oscar. C. Jiménez-Halla 2,* , José E. Báez 2 and M. Moustapha Bah 1,* 1 Posgrado en Ciencias Químico Biológicas, Faculty of Chemistry, Autonomous University of Querétaro, Querétaro 76010, Mexico; [email protected] 2 Department of Chemistry, Division of Natural and Exact Sciences, University of Guanajuato, Guanajuato 36050, Mexico; [email protected] * Correspondence: [email protected] (J.O.C.J.-H.); [email protected] (M.M.B.); Tel.: +52-473-732-0006 (ext. 1433) (J.O.C.J.-H.); +52-442-192-1200 (ext. 5536) (M.M.B.) Academic Editor: Vincenzo Piccialli Received: 26 March 2019; Accepted: 7 April 2019; Published: 9 April 2019 Abstract: 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 to synthesize this carotenoid. Nonetheless, these approaches have not only provided limited global yields, but its main commercial source also carries several health risks for humans. In this contribution, the one-pot base-catalyzed reaction of (3R,3’R,6’R)-lutein (1) esters has resulted in a successful isomerization process to easily obtain up to 95% meso-zeaxanthin (2), which in turn is oxidized to (3R,3’S)-astaxanthin (3) with a global yield of 68%. The same oxidation performed with UV irradiation (365 nm) for 5 min provided the highest global yield (76%). These chemical transformations have also been achieved with a significant reduction of the health risks associated with its potential human consumption. Furthermore, this is the first time only one of the configurational isomers has been obtained semisynthetically. The poorly understood formation mechanisms of these two compounds were also investigated using Density-Functional Theory (DFT) calculations. These theoretical studies revealed that the isomerization involves a base-catalyzed deprotonation at C-6’, followed by C-4’ protonation, while the oxidation occurs via free radical mechanisms. Keywords: carotenoids; meso-zeaxanthin; (3R,3’S)-astaxanthin; partial synthesis; DFT calculation; reaction mechanism 1. Introduction Carotenoids are natural compounds synthesized by plants and some other photosynthetic organisms such as algae, some types of bacteria, and a small number of aquatic organisms, whereby they have diverse and crucial functions [1]. More than 750 natural carotenoids have been identified in nature [2]. Lutein (1), (3R,3’R)-zeaxanthin, (3R)-β-cryptoxanthin (4), and β-carotene (5) (Figure1) are among the most abundant [3]. Molecules 2019, 24, 1386; doi:10.3390/molecules24071386 www.mdpi.com/journal/molecules Molecules 2019, 24, 1386 2 of 13 Molecules 2019, 24, x 2 of 13 Figure 1. Structures of some common carotenoids. Figure 1. Structures of some common carotenoids. These tetraterpenes first gained notability due to their colors. Currently, carotenoids and These tetraterpenes first gained notability due to their colors. Currently, carotenoids and some some apocarotenoids, which are sub-products resulting from the oxidative cleavage of a natural apocarotenoids, which are sub-products resulting from the oxidative cleavage of a natural carotenoid,carotenoid, have have important important commercial commercial applicationsapplications in in industry industry as as nutraceutical nutraceutical additives, additives, vitamin vitamin supplements,supplements, and and cosmetic cosmetic ingredients, ingredients, and and some some have have applications applications in in the the pharmaceutical pharmaceutical industryindustry [4]. For[4]. commercial For commercial purposes, purposes, carotenoids carotenoids are are mainly mainly produced produced by by chemical chemical synthesis synthesis oror lessless often by extractionby extraction from from their their natural natural sources sources [5,6 ],[5,6], as is as the is the case case for for astaxanthin astaxanthin (3 (),3), which which is is extracted extracted fromfrom the microalgathe microalgaHaematoccocus Haematoccocus pluvialis pluvialis. Commercial. Commercial synthetic synthetic astaxanthin astaxanthin is actuallyis actually a mixturea mixture of of the the two enantiomerstwo enantiomers (3R,3’R and(3R,3’ 3SR,3’ andS) and 3S,3’ theS) meso and compoundthe meso compound (3R,3’S) in the(3R ratio,3’S) ofin 1:1:2,the ratio respectively of 1:1:2, [7 ,8]. However,respectively astaxanthin [7,8]. However, obtained astaxanthin from H. pluvialis obtainedis mainly from H. obtained pluvialis inis itsmainly mono obtained and diesterified in its mono forms, andand has diesterified been reported forms, to accountand has for been up reported to 100% ofto (3accountS,3’S)[ 8for]. Various up to 100% strategies of (3S starting,3’S) [8]. from Various natural carotenoidsstrategies starting have been from developed natural carotenoids for obtaining have other been carotenoidsdeveloped for or obtaining their derivatives, other carotenoids as illustrated or intheir Scheme derivatives,1 for the as partial illustrated synthesis in Scheme of α -cryptoxanthins1 for the partial andsynthesisβ-cryptoxanthins, of α-cryptoxanthins anhydroluteins, and β- andcryptoxanthins, zeaxanthins, anhydroluteins, using compound and1 zeaxanthins,as the starting using material. compound For 1 example,as the starting in the material. presence For of a baseexample, and under in the heating, presence compound of a base and1 canunder isomerize heating, compound to meso-zeaxanthin 1 can isomerize (Scheme to meso-zeaxanthin1, route A) [ 9, 10]. (Scheme 1, route A) [9,10]. The mechanism by which this chemical transformation occurs has not yet The mechanism by which this chemical transformation occurs has not yet been unambiguously been unambiguously elucidated, since there is only one proposal, which was not sufficiently elucidated, since there is only one proposal, which was not sufficiently supported [11]. On the other supported [11]. On the other hand, the oxidation of the allylic hydroxyl group in 1 using MnO2 has hand, the oxidation of the allylic hydroxyl group in 1 using MnO has led to oxolutein (route B) [12], led to oxolutein (route B) [12], which is further reduced and then isomerized2 to the diastereoisomeric whichmixture is further composed reduced of 2 and and (3 thenR,3´R isomerized)-zeaxanthin. to Another the diastereoisomeric strategy for obtaining mixture (3R composed,3´R)-zeaxanthin of 2 and (3Rhas,3’R been)-zeaxanthin. the epimerization Another strategyof 1 to 3´-epilutein for obtaining in acid (3R,3’ mediaR)-zeaxanthin [13]. This hasepimer been in the turn epimerization undergoes of 1 toisomerization 3’-epilutein into acid(3R,3´ mediaR)-zeaxanthin [13]. This (route epimer C) in[14]. turn This undergoes epimerization isomerization process has to (3beenR,3’ reportedR)-zeaxanthin to (routeexperimentally C) [14]. This occur epimerization in green vegetables process has when been processing reported toin experimentallyan acid medium occur [15]. Also, in green Khachik vegetables et whenal. processinghave used in1 anas acidthe starting medium material [15]. Also, for Khachikthe partial etal. synthesis have used of 1α-cryptoxanthinsas the starting material and β- for thecrypthoxanthins. partial synthesis They of α -cryptoxanthinsdescribed an industrially and β-crypthoxanthins. viable process to Theytransform described 1 into anthe industriallyoptically active viable processcompound to transform 4 (Figure1 into 1) with the opticallya high yield active via compound allylic deoxygenation4 (Figure1) with in which a high a yield strong via acid allylic deoxygenation(Trifluoroacetic in whichacid: TFA) a strong and different acid (Trifluoroacetic hydride ion donors acid: TFA) are employed and different (route hydride D) [16].ion Finally, donors the are employedhigh-temperature (route D) and [16]. acid-catalyzed Finally, the high-temperature dehydration of 1 andprovided acid-catalyzed a mixture of dehydration anhydroluteins of 1 provided(route a mixtureE) with ofan anhydroluteinsoverall yield of 86% (route [17]. E) with an overall yield of 86% [17]. Molecules 2019, 24, 1386 3 of 13 Molecules 2019, 24, x 3 of 13 2 SchemeScheme 1. 1.Lutein Lutein as as the the starting starting materialmaterial for the the partial partial synthesis synthesis of of other other carotenoids. carotenoids. Also,Also, carotenoids carotenoids havehave gained attention attention for for their their beneficial beneficial effects effects on human on human health health[18–20]. [ 18For–20 ]. Forexample, example, (3 (3S,3S,3’S)-astaxanthinS)-astaxanthin is considered is considered one of one the of most the mostpowerful powerful antioxidants antioxidants in nature in [21], nature and [21 ], andhas has been been reported reported to topossess possess potential potential protective protective attributes attributes against against carcinogenesis carcinogenesis [22,23], [22 as,23 well], as as well ashave anti-inflammatoryanti-inflammatory [24], [24], antidiabetic antidiabetic [25,26], [25,26 ],and and antihypertensive antihypertensive effects effects [27]. [27 ].Synthetic Synthetic astaxanthinastaxanthin and and some some derivatives derivatives with the the same same skeleton skeleton as asthe the central central nucleus nucleus have have been beenshown shown to to contributecontribute
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