Isomerization of Commercially Important Carotenoids (Lycopene, β-Carotene, and Astaxanthin) by Natural Catalysts: Isothiocyanates and Polysulfides

Honda, Masaki; Kageyama, Hakuto; Hibino, Takashi; Ichihashi, Kohei; Takada, Wataru; Goto, Motonobu

doi:10.1021/acs.jafc.0c00316

Cited by 54 publications

(97 citation statements)

References 59 publications

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“…[ 23,24 ] Furthermore, these studies clearly indicated that the speed of E / Z ‐isomerization and the type of isomers generated during storage differed depending on the kind of carotenoid. [ 9,20–25 ] For example, when ethyl acetate solutions of all‐ E ‐isomers of lycopene, β‐carotene, and astaxanthin were heated at 60 °C for 1 h, the total Z ‐isomerization contents increased in the following order: β‐carotene (23.3%) > lycopene (20.5%) > astaxanthin (5.9%). [ 25 ] Moreover, Murakami et al.…”

Section: Introductionmentioning

confidence: 99%

“…[ 9,20–25 ] For example, when ethyl acetate solutions of all‐ E ‐isomers of lycopene, β‐carotene, and astaxanthin were heated at 60 °C for 1 h, the total Z ‐isomerization contents increased in the following order: β‐carotene (23.3%) > lycopene (20.5%) > astaxanthin (5.9%). [ 25 ] Moreover, Murakami et al. [ 22 ] reported that photo‐irradiation promoted all‐ E ‐isomerization of lycopene, whereas Zhao et al.…”

Section: Introductionmentioning

confidence: 99%

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Thermal‐ and Photo‐Induced Isomerization of All‐E‐ and Z‐Isomer‐Rich Xanthophylls: Astaxanthin and Its Structurally‐Related Xanthophylls, Adonirubin, and Adonixanthin

Honda

Sowa

Kawashima

2020

Euro J Lipid Sci & Tech

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The effects of heating and photo-irradiation on the stability of all-E-isomer-rich and Z-isomer-rich xanthophylls, astaxanthin and its structurally related xanthophylls, adonirubin, and adonixanthin, are investigated. The xanthophylls with high Z-isomer content are prepared from their high-purity all-E-isomers by thermal isomerization and filtering techniques, that is, total Z-isomer ratios of adonirubin, astaxanthin, and adonixanthin are 80.9%, 89.5%, and 72.5%, respectively. The all-E-and Z-isomer-rich xanthophylls dissolved in ethanol are stored at 4, 30, and 50°C in the dark and at 30°C under photo-irradiation using a fluorescent light for 21 days. In the all-E-isomer-rich xanthophylls, as the storage temperature increases, the total Z-isomer ratio becomes higher, whereas in the Z-isomer-rich xanthophylls, the all-E-isomer ratio becomes higher. Photo-irradiation slightly promotes Z-isomerization in (all-E)-xanthophylls, but highly promotes all-E-isomerization in Z-isomer-rich xanthophylls. In addition, photo-irradiation prevents thermal Z-isomerization of (all-E)-xanthophylls. Moreover, it is found that some xanthophyll Z-isomers such as (9Z)-astaxanthin are more stable than that of the other Z-isomers against heating and photo-irradiation. These findings can contribute not only to establishing suitable storage conditions for Z-isomer-rich xanthophylls, but also to developing control techniques for the E/Z-isomer ratio of the xanthophylls. Practical Applications: The fundamental data on the stability of xanthophyll isomers against heating and photo-irradiation and finding stable xanthophyll Z-isomers are very important to develop xanthophyll materials rich in the Z-isomers. Moreover, this study clearly shows that the heat treatment enhances the Z-isomerization of xanthophylls, whereas the photo-irradiation enhances the all-E-isomerization and prevents thermal Z-isomerization of them. This information can be utilized in technology for arbitrarily controlling E/Z-isomerization of xanthophylls.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thermal‐ and Photo‐Induced Isomerization of All‐E‐ and Z‐Isomer‐Rich Xanthophylls: Astaxanthin and Its Structurally‐Related Xanthophylls, Adonirubin, and Adonixanthin

Honda

Sowa

Kawashima

2020

Euro J Lipid Sci & Tech

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“…n.d., Not detected substantially. b Tentatively assigned in the literatures 9,25,26,[29][30][31][32][33][34][35] .…”

Section: Synergistic Effects Of Food Ingredients and Vegetable Oils Omentioning

confidence: 99%

“…Mustard oil contains a large quantity of isothiocyanates, especially allyl isothiocyanate 41 . Isothiocyanates have a strong carotenoid isomerization-promoting effect 29,42 , and thus the use of mustard oil would enhance the thermal Z-isomerization reaction. In fact, we analyzed the volatile components of olive, sesame, and mustard oils used in this study by gas chromatography/ electron ionization-mass spectrometry GC/EI-MS; Agilent-7890A GC instrument coupled with 5975 MSD; Agilent Technologies Inc., Palo Alto, CA, USA , and confirmed that olive oil contained no polysulfides and isothiocyanates but sesame and mustard oils contained dimethyl disulfide and allyl isothiocyanate, respectively 43 .…”

Section: Effect Of the Combined Use Of Food Ingredients And Vegetablementioning

confidence: 99%

“…In general, onions, garlic, broccoli, and cabbage are traditionally combined in tomato-containing dishes. Furthermore, our group recently revealed that polysulfides, isothiocyanates, and iodine are the causative food components that enhance lycopene Z-isomerization, i.e., it is considered that their powerful electrophilicity and/or radical-generating capacity would enhance the Z-isomerization reaction 29 , and their combined use in certain cases, such as allyl isothiocyanate and diallyl disulfide, more efficiently promoted carotenoid Z-isomerization than their separate use 25,29,30 . Hence, the combined use of food ingredients might improve Z-isomerization efficiency, and the good understanding of such an effect would be very important for daily home cooking.…”

Section: Introductionmentioning

confidence: 99%

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Synergistic Effects of Food Ingredients and Vegetable Oils on Thermal Isomerization of Lycopene

et al. 2020

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such as tomato juice and puree 8, 9. However, lycopene Zisomers, such as the 5Z-and 9Z-isomers, are primarily found in animals and humans 8, 10, 11. A reason for the lycopene Z-isomer abundance in the body is thought to be the Z-isomerization during digestion and absorption 12 14. Re et al. reported that all-E-lycopene isomerized into the Zisomers in the human gastric juice and the 5Z-and 9Z-isomer ratios markedly increased 13. Recently, Huang and Hui found that the Z-isomerization site of all-E-lycopene was located in the small intestinal wall 14. Another possible reason for the high lycopene Z-isomer content in the body is that the Z-isomers are more bioavailable than the all-Eisomer. Several in vitro and in vivo comparative studies focusing on all-E-and Z-lycopene bioavailability have described greater lycopene Z-isomer bioavailability, and furthermore, human studies clearly showed that the ingestion of Z-isomer-rich diets resulted in higher Z-isomer ratio in the body compared to the ingestion of all-E-isomer-rich Abstract: Recent investigations have demonstrated that some food ingredients and vegetable oils, such as onion, garlic, and sesame oil, enhanced thermal Z-isomerization of (all-E)-lycopene in tomatoes. However, the synergistic effects of these ingredients and oils have not yet been investigated. This study aims at clarifying how the combined use of lycopene Z-isomerization-promoting food ingredients and vegetable oils impacts thermal Z-isomerization of (all-E)-lycopene in tomato puree. Apart from a few exceptions, when olive oil was used as a reaction medium, the combined use of garlic, cabbage, broccoli, shiitake mushroom, and makonbu improved the total Z-isomer ratio of lycopene after heating compared to the separate use of the tested ingredients. However, when onion was used together with the other ingredients, the Z-isomer ratio significantly decreased compared to its individual use. Moreover, when garlic, cabbage, broccoli, shiitake mushroom, and makonbu were used with sesame and mustard oils, that exhibit higher Z-isomerizationpromoting effect than that of olive oil, the lycopene Z-isomerization reaction was further enhanced. However, when onion was combined with these oils, the Z-isomer ratio decreased compared to that measured upon the combined use of onion with olive oil. Our results on these synergistic effects are not only important for the food and drink manufacturing industries but also for daily home cooking.

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Complex formation and stabilization of Z‐isomer‐enriched astaxanthin esters derived from Haematococcus lacustris with water‐soluble carriers via spray drying

Sakaguchi,

Ghosh,

Banik

et al. 2024

Euro J Lipid Sci & Tech

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To enhance the water solubility and bioavailability of astaxanthin esters, inclusion complexes of Z‐isomer‐enriched astaxanthin esters with water‐soluble carriers were prepared using a spray drying technique. A food‐grade Haematococcus alga extract was used as the source of astaxanthin esters, and the Z‐isomerization was performed via direct heating of the extract. Polyvinylpyrrolidone (PVP) and hydroxypropyl‐β‐cyclodextrin (HP‐β‐CD) were used as water‐soluble carriers. The effects of spray drying conditions on the encapsulation efficiency of astaxanthin esters in the carriers and the total Z‐isomer ratio of encapsulated astaxanthin esters were investigated, and the physical properties and storage stability of the resulting composites were evaluated. Under optimum spray drying conditions, efficient production of highly water‐soluble Z‐isomer‐rich astaxanthin esters was achieved in both carriers: >95% encapsulation efficiency and >55% total Z‐isomer ratio. The physical properties, such as surface morphology and particle size distributions, of the resulting particles differed significantly between PVP and HP‐β‐CD. Storage tests demonstrated that the formulated Z‐isomer‐rich astaxanthin esters were highly stable. Our findings will contribute to the practical applications of Z‐isomer‐rich astaxanthin materials.Practical Applications: The formulation technology developed in this study has the potential to address the industrial challenges of using astaxanthin, that is, low water solubility and low bioavailability. Furthermore, the low storage stability of astaxanthin Z‐isomers, which hinders their industrial use, can be solved simultaneously. The resulting Z‐isomer‐rich astaxanthin powders are expected to be used in a wide range of applications, including nutraceuticals, cosmetics, and animal feeds.

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Isomerization of Commercially Important Carotenoids (Lycopene, β-Carotene, and Astaxanthin) by Natural Catalysts: Isothiocyanates and Polysulfides

Cited by 54 publications

References 59 publications

Thermal‐ and Photo‐Induced Isomerization of All‐E‐ and Z‐Isomer‐Rich Xanthophylls: Astaxanthin and Its Structurally‐Related Xanthophylls, Adonirubin, and Adonixanthin

Thermal‐ and Photo‐Induced Isomerization of All‐E‐ and Z‐Isomer‐Rich Xanthophylls: Astaxanthin and Its Structurally‐Related Xanthophylls, Adonirubin, and Adonixanthin

Synergistic Effects of Food Ingredients and Vegetable Oils on Thermal Isomerization of Lycopene

Complex formation and stabilization of Z‐isomer‐enriched astaxanthin esters derived from Haematococcus lacustris with water‐soluble carriers via spray drying

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