Selected cis/trans isomers of carotenoids formed by bulk electrolysis and iron(III) chloride oxidation

Wei, C. C.; Gao, Guoqiang; Kispert, Lowell D.

doi:10.1039/a605027a

Cited by 40 publications

(38 citation statements)

References 19 publications

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“…(All‐ E )‐β‐carotene has been reported to show a singlet oxygen absorption capacity equivalent to that of lycopene (Ouchi and others ). Then, we propose that the mechanism of E / Z isomerization of lycopene using iron(III) chloride could follow a similar process to that of (all‐ E )‐β‐carotene using iron(III) chloride (Wei and others ; Gao and Kispert ), Fe‐MCM‐41 (Gao and others ; Kispert and Polyakov ), or titanium tetrachloride (Rajendran and Chen ) as described below:

{(Lycopene)}_{italicE} {+ Fe}^{3 +} ⇄ {(Lycopene}^{• +})_{italicE} {+ Fe}^{2 +}

{(Lycopene}^{• +})_{italicE} {+ Fe}^{3 +} ⇄ {(Lycopene}^{2 +})_{italicE} {+ Fe}^{2 +}

{(Lycopene}^{• +})_{italicE} ⇄ {(Lycopene}^{• +})_{italicZ}

{(Lycopene}^{2 +} {)_{italicE} ⇄ {(Lycopene}^{2 +})}_{italicZ}

{(Lycopene}^{2 +} {)_{italicZ} {+ Fe}^{2 +} ⇄ {(Lycopene}^{• +})}_{italicZ} {+ Fe}^{3 +}

{(Lycopene}^{• +})_{italicZ} {+ Fe}^{2 +} ⇄ {(Lycopene)}_{italicZ} {+ Fe}^{3}

…”

Section: Resultsmentioning

confidence: 99%

“…However, there is still considerable room for the development of E / Z isomerization of lycopene. Although there have been some reports on the E / Z isomerization of carotenoids, except for lycopene, using a catalyst such as iron(III) chloride (Wei and others ; Gao and Kispert ), Fe‐MCM‐41 (Gao and others ; Kispert and Polyakov ), and titanium tetrachloride (Rajendran and Chen ), no observations from the perspective of both isomerization efficiency and recovery of the carotenoids have been published. In connection with our studies of E / Z isomerization, we report here on the first instance of catalytic E / Z isomerization of (all‐ E )‐lycopene using iron(III) chloride applicable to industrial manufacturing in the fields of food, drink, and dietary supplements.…”

Section: Introductionmentioning

confidence: 99%

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Enhanced E/Z Isomerization of (All‐E)‐lycopene by Employing Iron(III) Chloride as a Catalyst

Honda¹,

Kawana²,

Takehara

et al. 2015

Journal of Food Science

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The dietary intake of lycopene, a natural red pigment found in brightly colored vegetables and fruits such as tomatoes and watermelons, has been reported to lower the risk of some diseases, including cancer. Lycopene molecules occur naturally in a long and “straight” shape, but on the other hand lycopene molecules with “bent” forms are highly absorbed by living cells, and showed good antioxidant activity. This study has demonstrated the efficient production of the “bent” lycopene using ionic iron as an accelerator, which is often contained in nutritional supplements.

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{(Lycopene)}_{italicE} {+ Fe}^{3 +} ⇄ {(Lycopene}^{• +})_{italicE} {+ Fe}^{2 +}

{(Lycopene}^{• +})_{italicE} {+ Fe}^{3 +} ⇄ {(Lycopene}^{2 +})_{italicE} {+ Fe}^{2 +}

{(Lycopene}^{• +})_{italicE} ⇄ {(Lycopene}^{• +})_{italicZ}

{(Lycopene}^{2 +} {)_{italicE} ⇄ {(Lycopene}^{2 +})}_{italicZ}

{(Lycopene}^{2 +} {)_{italicZ} {+ Fe}^{2 +} ⇄ {(Lycopene}^{• +})}_{italicZ} {+ Fe}^{3 +}

{(Lycopene}^{• +})_{italicZ} {+ Fe}^{2 +} ⇄ {(Lycopene)}_{italicZ} {+ Fe}^{3}

…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enhanced E/Z Isomerization of (All‐E)‐lycopene by Employing Iron(III) Chloride as a Catalyst

Honda¹,

Kawana²,

Takehara

et al. 2015

Journal of Food Science

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“…For example, when purified (all- E )-lycopene dissolved in hexane in the presence of erythrosine was irradiated at 480–600 nm for 1 h, the proportion of lycopene Z -isomers reached over 80% [36]. A few studies have demonstrated that electrolysis treatment promoted Z -isomerization of (all- E )-carotenoids such as β-carotene and canthaxanthin [37,38]. This electrochemical method shows very high efficiency and can prevent thermal degradation of carotenoids, e.g., approximately 50% of (all- E )-canthaxanthin was converted to the Z -isomers during 4–6 min of bulk electrolysis at 4 °C [37].…”

Section: Typical Methods For Z-isomerization Of Carotenoidsmentioning

confidence: 99%

“…A few studies have demonstrated that electrolysis treatment promoted Z -isomerization of (all- E )-carotenoids such as β-carotene and canthaxanthin [37,38]. This electrochemical method shows very high efficiency and can prevent thermal degradation of carotenoids, e.g., approximately 50% of (all- E )-canthaxanthin was converted to the Z -isomers during 4–6 min of bulk electrolysis at 4 °C [37]. Catalytic Z -isomerization of (all- E )-carotenoids have been traditionally conducted using iodine [39,40,41].…”

Section: Typical Methods For Z-isomerization Of Carotenoidsmentioning

confidence: 99%

Improved Carotenoid Processing with Sustainable Solvents Utilizing Z-Isomerization-Induced Alteration in Physicochemical Properties: A Review and Future Directions

et al. 2019

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Carotenoids—natural fat-soluble pigments—have attracted considerable attention because of their potential to prevent of various diseases, such as cancer and arteriosclerosis, and their strong antioxidant capacity. They have many geometric isomers due to the presence of numerous conjugated double bonds in the molecule. However, in plants, most carotenoids are present in the all-E-configuration. (all-E)-Carotenoids are characterized by high crystallinity as well as low solubility in safe and sustainable solvents, such as ethanol and supercritical CO2 (SC-CO2). Thus, these properties result in the decreased efficiency of carotenoid processing, such as extraction and emulsification, using such sustainable solvents. On the other hand, Z-isomerization of carotenoids induces alteration in physicochemical properties, i.e., the solubility of carotenoids dramatically improves and they change from a “crystalline state” to an “oily (amorphous) state”. For example, the solubility in ethanol of lycopene Z-isomers is more than 4000 times higher than the all-E-isomer. Recently, improvement of carotenoid processing efficiency utilizing these changes has attracted attention. Namely, it is possible to markedly improve carotenoid processing using safe and sustainable solvents, which had previously been difficult to put into practical use due to the low efficiency. The objective of this paper is to review the effect of Z-isomerization on the physicochemical properties of carotenoids and its application to carotenoid processing, such as extraction, micronization, and emulsification, using sustainable solvents. Moreover, aspects of Z-isomerization methods for carotenoids and functional difference, such as bioavailability and antioxidant capacity, between isomers are also included in this review.

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“…1). In this study, free iron [17,58,18] and heme iron, i.e., metmyoglobin, [54,55] were compared for their propensity to induce carotenoid autoxidation in a medium mimicking the environment in the human gastric compartment. As a prerequisite for intestinal absorption, dietary carotenoids must be incorporated into micelles mainly composed of phospholipids, cholesterol and triglyceride digestion products (fatty acids, monoglycerides) [5,57].…”

Section: Introductionmentioning

confidence: 99%

Stability of bacterial carotenoids in the presence of iron in a model of the gastric compartment – Comparison with dietary reference carotenoids

Sy¹,

Dangles

Borel

et al. 2015

Archives of Biochemistry and Biophysics

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Recently isolated spore-forming pigmented marine bacteria, Bacillus indicus HU36 and Bacillus firmus GB1 are sources of carotenoids (∼fifteen distinct yellow and orange pigments and ∼thirteen distinct pink pigments, respectively). They are glycosides of oxygenated lycopene derivatives (apo-lycopenoids) and are assumed to be more heat- and gastric-stable than common carotenoids. In this study, the oxidation by O2 of the bacterial carotenoids was initiated by free iron (Fe(II) and Fe(III)) or by heme iron (metmyoglobin) in a mildly acidic aqueous solution mimicking the gastro-intestinal compartment and compared to the oxidation of the common dietary carotenoids β-carotene, lycopene and astaxanthin. Under these conditions, all bacterial carotenoids appear more stable in the presence of heme iron vs. free iron. Carotenoid autoxidation initiated by Fe(II) is relatively fast and likely involves reactive oxygen-iron species derived from Fe(II) and O2. By contrast, the corresponding reaction with Fe(III) is kinetically blocked by the slow preliminary reduction of Fe(III) into Fe(II) by the carotenoids. The stability of carotenoids toward autoxidation increases as follows: β-carotene

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Selected cis/trans isomers of carotenoids formed by bulk electrolysis and iron(III) chloride oxidation

Cited by 40 publications

References 19 publications

Enhanced E/Z Isomerization of (All‐E)‐lycopene by Employing Iron(III) Chloride as a Catalyst

Enhanced E/Z Isomerization of (All‐E)‐lycopene by Employing Iron(III) Chloride as a Catalyst

Improved Carotenoid Processing with Sustainable Solvents Utilizing Z-Isomerization-Induced Alteration in Physicochemical Properties: A Review and Future Directions

Stability of bacterial carotenoids in the presence of iron in a model of the gastric compartment – Comparison with dietary reference carotenoids

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