Isolation and spectral characterization of thermally generated multi-<i>Z</i>-isomers of lycopene and the theoretically preferred pathway to di-<i>Z</i>-isomers
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- Masaki Honda
- Innovation Division, Kagome Co., Ltd., Nasushiobara, Japan
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- Tatsuya Kudo
- Department of Materials Science, The University of Shiga Prefecture, Hikone, Japan
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- Takahiro Kuwa
- Department of Materials Science, The University of Shiga Prefecture, Hikone, Japan
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- Takuma Higashiura
- Innovation Division, Kagome Co., Ltd., Nasushiobara, Japan
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- Tetsuya Fukaya
- Innovation Division, Kagome Co., Ltd., Nasushiobara, Japan
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- Yoshinori Inoue
- Department of Materials Science, The University of Shiga Prefecture, Hikone, Japan
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- Chitoshi Kitamura
- Department of Materials Science, The University of Shiga Prefecture, Hikone, Japan
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- Munenori Takehara
- Department of Materials Science, The University of Shiga Prefecture, Hikone, Japan
書誌事項
- 公開日
- 2017-02-01
- 権利情報
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- https://academic.oup.com/journals/pages/open_access/funder_policies/chorus/standard_publication_model
- DOI
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- 10.1080/09168451.2016.1249454
- 10.6084/m9.figshare.4524695.v1
- 10.6084/m9.figshare.4524695
- 公開者
- Informa UK Limited
この論文をさがす
説明
<jats:title>Abstract</jats:title> <jats:p>Lycopene has a large number of geometric isomers caused by E/Z isomerization at arbitrary sites within the 11 conjugated double bonds, offering varying characteristics related to features such as antioxidant capacity and bioavailability. However, the geometric structures of only a few lycopene Z-isomers have been thoroughly identified from natural sources. In this study, seven multi-Z-isomers of lycopene, (9Z,13′Z)-, (5Z,13Z,9′Z)-, (9Z,9′Z)-, (5Z,13′Z)-, (5Z,9′Z)-, (5Z,9Z,5′Z)-, and (5Z,9Z)-lycopene, were obtained from tomato samples by thermal isomerization, and then isolated by elaborate chromatography, and fully assigned using proton nuclear magnetic resonance. Moreover, the theoretically preferred pathway from (all-E)-lycopene to di-Z-isomers was examined with a computational approach using a Gaussian program. Fine-tuning of the HPLC separation conditions led to the discovery of novel multi-Z-isomers, and whose formation was supported by advanced theoretical calculations.</jats:p>
収録刊行物
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- Bioscience, Biotechnology, and Biochemistry
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Bioscience, Biotechnology, and Biochemistry 81 (2), 365-371, 2017-02-01
Informa UK Limited
