Spectral characterisation of Z-isomers of lycopene formed during heat treatment and solvent effects on the E/Z isomerisation process

Honda, Masaki; Takahashi, Naoto; Kuwa, Takahiro; Takehara, Munenori; Inoue, Yasuhiro; Kumagai, Tsutomu

doi:10.1016/j.foodchem.2014.09.004

Cited by 79 publications

(148 citation statements)

References 36 publications

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“…The occurrence of (15Z)-lycopene from (all-E)-lycopene during a heating or irradiating process has been suggested by several studies, and this has mainly been based on analyses of UVevis spectra, in which the Z-peak ratio of the isomer, %D B /D II , was estimated to be 75e79% in a HPLC mobile phase [11,23,25]. However, the existence of the Z-isomer from a natural source has not yet been demonstrated.…”

Section: Resultsmentioning

confidence: 99%

“…In the first chromatographic purification step, three normalphase HPLC columns connected in tandem were applied to separate (15Z)-lycopene (retention time, 49.5e52.0 min; %D B /D II , 79%) [11] from the crude fraction ( Fig. 2A).…”

Section: Resultsmentioning

confidence: 99%

“…The NMR spectra of (15Z)-lycopene were recorded on a JMN-LA400 FT NMR spectrometer (JEOL, Tokyo) at 400 MHz for 1 H and 100 MHz for 13 C as previously described [10,11].…”

Section: Nmr Spectroscopymentioning

confidence: 99%

“…D.01) using the Becke-3eLeeeYangeParr (B3LYP) functional and 6-31G(d) basis set including a zero point vibrational energy correction. Prior to the calculation for (all-E)-lycopene, the structures of the conjugated all-E-polyenes, C n H nþ2 (n ¼ 4e22, even number) were optimized at the ground singlet states, and followed by the methylated undecaenes (2Z,4E 16,20,5,7,9,11,13,15,17,19,21,. The structure of HMHU was estimated using initial conformers at 30 intervals of the dihedral angles of the free rotation in a stepwise manner for two ethyl groups, and (all-E)-lycopene was then estimated in the same way.…”

Section: Computational Analysismentioning

confidence: 99%

“…For example, ultravioletevisible (UVevis) spectral studies examined lycopene in the 1950s [3,4], and the molar extinction coefficients of (all-E)-lycopene, the most abundant conformer in the organisms described above, obtained were subsequently used in numerous studies, regardless of measurements being carried out under different conditions, until recent findings were published [10]. The structural assignments and UVevis spectral features of (5Z)-, (9Z)-and (13Z)-lycopene, the predominant Z-isomers generated during heat [10,11] or photoirradiation treatment [12,13], were finally demonstrated through the acquisition of highly purified preparations of the isomers by using a series of chromatographies [11]. The other theoretically-possible mono-Zisomer by heating, (15Z)-lycopene ( Fig.…”

Section: Introductionmentioning

confidence: 99%

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Isolation and characterization of (15 Z )-lycopene thermally generated from a natural source

Takehara

Kuwa

Inoue

et al. 2015

Biochemical and Biophysical Research Communications

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…The NMR spectra of (15Z)-lycopene were recorded on a JMN-LA400 FT NMR spectrometer (JEOL, Tokyo) at 400 MHz for 1 H and 100 MHz for 13 C as previously described [10,11].…”

Section: Nmr Spectroscopymentioning

confidence: 99%

Section: Computational Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Isolation and characterization of (15 Z )-lycopene thermally generated from a natural source

Takehara

Kuwa

Inoue

et al. 2015

Biochemical and Biophysical Research Communications

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Rigidified Push–Pull Dyes: Using Chromophore Size, Donor, and Acceptor Units to Tune the Ground State between Neutral and the Cyanine Limit

et al. 2017

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Vegetable oil‐mediated thermal isomerization of (all‐E)‐lycopene: Facile and efficient production of Z‐isomers

Honda¹,

Horiuchi

Hiramatsu

et al. 2016

Euro J Lipid Sci & Tech

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Thermal isomerization of (all‐E)‐lycopene to the corresponding Z‐isomers was investigated in edible vegetable oils; perilla, linseed, grape seed, soybean, corn, sesame, rapeseed, rice bran, safflower seed, olive, and sunflower seed oil. Purified (all‐E)‐lycopene from tomato oleoresin was converted to Z‐isomers in the range of 44.8–58.8% content, and the remaining ratio of total amount of lycopene isomers without decomposition were ranged from 38.8 to 79.6% after heating at 100°C for 1 h in the vegetable oils. Both values were exceedingly high in sesame oil: 58.8% of total Z‐isomers content and 78.3% of remaining lycopene. In particular, (5Z)‐lycopene, which has higher bioavailability and antioxidant capacity as well as greater storage stability among the Z‐isomers, was notably increased in that oil; approximately threefold higher than the average of the other vegetable oils. Practical applications: Lycopene offers many health benefits such as decreased risk of cancer and arteriosclerosis. The Z‐isomers of lycopene, occurring in processed tomato products, are more bioavailable than the all‐E‐isomer which is a major configuration form in raw tomatoes. This study has developed an efficient production method for Z‐isomers of lycopene by heating (all‐E)‐lycopene in edible vegetable oils, in which neither organic solvents nor food additives are used. It would be practically feasible to utilize this procedure for the food, drink, and dietary supplement manufacturing, as well as for daily cooking at home. Thermal isomerization of (all‐E)‐lycopene to Z‐isomers was investigated in edible vegetable oils. In sesame oil, (5Z)‐lycopene, which has higher bioavailability, antioxidant capacity, and greater storage stability among the Z‐isomers, was increased significantly.

show abstract

Spectral characterisation of Z-isomers of lycopene formed during heat treatment and solvent effects on the E/Z isomerisation process

Cited by 79 publications

References 36 publications

Isolation and characterization of (15 Z )-lycopene thermally generated from a natural source

Isolation and characterization of (15 Z )-lycopene thermally generated from a natural source

Rigidified Push–Pull Dyes: Using Chromophore Size, Donor, and Acceptor Units to Tune the Ground State between Neutral and the Cyanine Limit

Vegetable oil‐mediated thermal isomerization of (all‐E)‐lycopene: Facile and efficient production of Z‐isomers

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