Biological Activities of Z-Lycopenes Contained in Food
Mono-(5Z)-, -(9Z)-, and -(13Z)-lycopenes are found in food containing processed tomato products, while tetra-Z-(7Z, 9Z, 7′Z, 9′Z)-lycopene (prolycopene) is found in tangerine-strain tomatoes. We prepared pure mono-Z-lycopenes from all-E-lycopene via chemical reaction (heating in CH2Cl2 at 80℃ for 1...
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| Published in | Journal of Oleo Science Vol. 69; no. 11; pp. 1509 - 1516 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
Japan Oil Chemists' Society
01.01.2020
Japan Science and Technology Agency |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1345-8957 1347-3352 1347-3352 |
| DOI | 10.5650/jos.ess20163 |
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| Abstract | Mono-(5Z)-, -(9Z)-, and -(13Z)-lycopenes are found in food containing processed tomato products, while tetra-Z-(7Z, 9Z, 7′Z, 9′Z)-lycopene (prolycopene) is found in tangerine-strain tomatoes. We prepared pure mono-Z-lycopenes from all-E-lycopene via chemical reaction (heating in CH2Cl2 at 80℃ for 1 h) followed by purification using preparative silica gel HPLC, while prolycopene was isolated from tangerine tomatoes by partitioning with n-hexane and 90% MeOH followed by silica gel column chromatography. A simple method of distinguishing the mono-Z-lycopenes using the 13C NMR chemical shifts of their Z-methyl carbons is proposed. Additionally, the 1O2 quenching and 3T3-L1 cell differentiation activities of the compounds were then compared with all-E-lycopene for the first time. All the evaluated Z-isomers showed 1O2 quenching activities that were equal to or slightly lower than that of all-E-lycopene, with the IC50 values for the 1O2 quenching activities of (all-E)-, (5Z)-, (9Z)-, (13Z)-, and (7Z, 9Z, 7′Z, 9′Z)-lycopene being 4.4±0.36, 4.0±1.44, 5.3±1.08, 6.9±1.67, and 8.7±0.34 µM, respectively. The mouse 3T3-L1 cell differentiation activities followed the order: (all-E) > (9Z) > (5Z) ≈ (9Z) ≈ (13Z) ≈ (7Z, 9Z, 7′Z, 9′Z). |
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| AbstractList | Mono-(5Z)-, -(9Z)-, and -(13Z)-lycopenes are found in food containing processed tomato products, while tetra-Z-(7Z, 9Z, 7′Z, 9′Z)-lycopene (prolycopene) is found in tangerine-strain tomatoes. We prepared pure mono-Z-lycopenes from all-E-lycopene via chemical reaction (heating in CH2Cl2 at 80℃ for 1 h) followed by purification using preparative silica gel HPLC, while prolycopene was isolated from tangerine tomatoes by partitioning with n-hexane and 90% MeOH followed by silica gel column chromatography. A simple method of distinguishing the mono-Z-lycopenes using the 13C NMR chemical shifts of their Z-methyl carbons is proposed. Additionally, the 1O2 quenching and 3T3-L1 cell differentiation activities of the compounds were then compared with all-E-lycopene for the first time. All the evaluated Z-isomers showed 1O2 quenching activities that were equal to or slightly lower than that of all-E-lycopene, with the IC50 values for the 1O2 quenching activities of (all-E)-, (5Z)-, (9Z)-, (13Z)-, and (7Z, 9Z, 7′Z, 9′Z)-lycopene being 4.4±0.36, 4.0±1.44, 5.3±1.08, 6.9±1.67, and 8.7±0.34 µM, respectively. The mouse 3T3-L1 cell differentiation activities followed the order: (all-E) > (9Z) > (5Z) ≈ (9Z) ≈ (13Z) ≈ (7Z, 9Z, 7′Z, 9′Z). graphical abstract Abstract: Mono-(5Z)-, -(9Z)-, and -(13Z)-lycopenes are found in food containing processed tomato products, while tetra-Z-(7Z, 9Z, 7'Z, 9'Z)-lycopene (prolycopene) is found in tangerine-strain tomatoes. We prepared pure mono-Z-lycopenes from all-E-lycopene via chemical reaction (heating in CH2C12 at 80℃ for 1 h) followed by purification using preparative silica gel HPLC, while prolycopene was isolated from tangerine tomatoes by partitioning with n-hexane and 90% MeOH followed by silica gel column chromatography. A simple method of distinguishing the mono-Z-lycopenes using the 13C NMR chemical shifts of their Z-methyl carbons is proposed. Additionally, the 1O2 quenching and 3T3-L1 cell differentiation activities of the compounds were then compared with all-E-lycopene for the first time. All the evaluated Z-isomers showed 1O2 quenching activities that were equal to or slightly lower than that of all-E-lycopene, with the IC50 values for the 1O2 quenching activities of (all-E)-, (5Z)-, (9Z)-, (13Z)-, and (7Z, 9Z, 7'Z, 9'Z)-lycopene being 4.4+-0.36, 4.0+-1.44, 5.3+-1.08, 6.9+-1.67, and 8.7+-0.34 μM, respectively. The mouse 3T3-L1 cell differentiation activities followed the order: (all-E)>(9Z)>(5Z)=(9Z)=(13Z)=(7Z, 9Z, 7'Z, 9'Z). Mono-(5Z)-, -(9Z)-, and -(13Z)-lycopenes are found in food containing processed tomato products, while tetra-Z-(7Z, 9Z, 7′Z, 9′Z)-lycopene (prolycopene) is found in tangerine-strain tomatoes. We prepared pure mono-Z-lycopenes from all-E-lycopene via chemical reaction (heating in CH2Cl2 at 80℃ for 1 h) followed by purification using preparative silica gel HPLC, while prolycopene was isolated from tangerine tomatoes by partitioning with n-hexane and 90% MeOH followed by silica gel column chromatography. A simple method of distinguishing the mono-Z-lycopenes using the 13C NMR chemical shifts of their Z-methyl carbons is proposed. Additionally, the 1O2 quenching and 3T3-L1 cell differentiation activities of the compounds were then compared with all-E-lycopene for the first time. All the evaluated Z-isomers showed 1O2 quenching activities that were equal to or slightly lower than that of all-E-lycopene, with the IC50 values for the 1O2 quenching activities of (all-E)-, (5Z)-, (9Z)-, (13Z)-, and (7Z, 9Z, 7′Z, 9′Z)-lycopene being 4.4±0.36, 4.0±1.44, 5.3±1.08, 6.9±1.67, and 8.7±0.34 µM, respectively. The mouse 3T3-L1 cell differentiation activities followed the order: (all-E) > (9Z) > (5Z) ≈ (9Z) ≈ (13Z) ≈ (7Z, 9Z, 7′Z, 9′Z). |
| Author | Hara, Kurumi Honda, Masaki Shindo, Kazutoshi Sakemi, Yuka Sato, Kana |
| Author_xml | – sequence: 1 fullname: Sato, Kana organization: Department of Food and Nutrition, Japan Women’s University – sequence: 1 fullname: Shindo, Kazutoshi organization: Department of Food and Nutrition, Japan Women’s University – sequence: 1 fullname: Sakemi, Yuka organization: Department of Food and Nutrition, Japan Women’s University – sequence: 1 fullname: Honda, Masaki organization: Department of Chemistry, Faculty of Science & Technology, Meijo University – sequence: 1 fullname: Hara, Kurumi organization: Department of Food and Nutrition, Japan Women’s University |
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| Cites_doi | 10.1096/fasebj.8.12.8088462 10.3109/10715762.2011.564168 10.3390/molecules16021055 10.1016/j.jff.2008.09.015 10.1093/jn/130.6.1613 10.1039/C5FO00004A 10.3906/sag-1202-44 10.1080/09168451.2019.1677144 10.1093/jn/128.11.2009 10.1177/153537020222701012 10.1021/jf1045969 10.1105/tpc.010302 10.1093/jn/132.9.2700 10.1016/j.tet.2006.05.023 10.1016/S0308-8146(96)00177-X 10.1021/acs.jafc.7b04254 10.1016/j.tips.2005.03.003 10.1017/S0007114507685201 10.1016/j.foodchem.2014.09.004 10.3390/molecules200815359 10.1021/jf402654e 10.1021/jf010888q 10.1021/acs.jafc.9b02102 10.1093/jn/125.8.2128 |
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| References_xml | – reference: 8) Park, H.; Kreunen, S.S.; Cuttriss, A.J.; Della Penna, D.; Pogson, B.J. Identification of the carotenoid isomerase provides insight into carotenoid biosynthesis, prolamellar body formation, and photomorphogenesis. Plant Cell 14, 321-332 (2002). – reference: 24) Patenden, G.; Robson, D.C. Total synthesis of prolycopene, a novel 7,9,7′,9′-tetra-cis(Z)carotenoid and main pigment of the tangerine tomato Lycopersicon esculentum. Tetrahedron 62, 7477-7483 (2006). – reference: 21) Murakami, K.; Honda, M.; Takemura, R.; Fukaya, T.; Kubota, M.; Wahyudiono; Goto, M. The thermal Z-isomerization-induced change in solubility and physical properties of (all-E)-lycopene. Biochem. Biophys. Res. Commun. 491, 317-322 (2017). – reference: 10) Stahl, W.; Schwarz, W.; von Laar, J.; Sies, H. All-trans β-carotene preferentially accumulates in human chylomicrons and very low density lipoproteins compared with the 9-cis geometrical isomer. J. Nutr. 125, 2128-2133 (1995). – reference: 19) Yang, C.; Hassan, Y.I.; Liu, R.; Zhang, H.; Chen, Y.; Zhang, L.; Tsao, R. Anti-inflammatory effects of different astaxanthin isomers and the roles of lipid transporters in the cellular transport of astaxanthin isomers in Caco-2 cell monolayers. J. Agric. Food Chem. 67, 6222-6231 (2019). – reference: 11) Erdman Jr., J.W.; Thatcher, A.J.; Hofmann, N.E.; Lederman, J.D.; Block, S.S.; Lee, C.M.; Mokady, S. All-trans β-carotene is absorbed preferentially to 9-cis β-carotene, but the latter accumulates in the tissues of domestic ferrets (Mustela putorius puro). J. Nutr. 128, 2009-2013 (1998). – reference: 9) Müller, L.; Goupy, P.; Fröhlich, K.; Dangles, O.; Caris-Veyrat, C.; Böhm, V. Comparative study on antioxidant activity of lycopene(Z)-isomers in different assays. J. Agric. Food Chem. 59, 4504-4511 (2011). – reference: 28) Berger, J.P.; Akiyama, T.E.; Meinke, P.T. PPARs: Therapeutic targets for metabolic disease. Trends Pharmacol. Sci. 26, 244-251 (2005). – reference: 15) Nagao, A.; Olson, J.A. Enzymatic formation of 9-cis, 13-cis, and all-trans retinals from isomers of β-carotene. FASEB J. 8, 968-973 (1994). – reference: 5) Fenni, S.; Asier, J.; Bonnet, L.; Karkeni, E.; Gouranton, E.; Mounien, L.; Couturier, C.; Tourniaire, F.; Böhm, V.; Hammou, H.; Landrier, J. (All-E)- and (5Z)-Lycopene display similar biological effects on adipocytes. Mol. Nutr. Food Res. 63, 1800788 (2019). – reference: 13) Böhm, V.; Puspitasari-Nienaber, N.L.; Ferruzzi, M.G.; Schwartz, S.J. Trolox equivalent antioxidant capacity of different geometrical isomers of α-carotene, β-carotene, lycopene, and zeaxanthin. J. Agric. Food Chem. 50, 221-226 (2002). – reference: 1) Friedman, M. Anticarcinogenic, cardioprotective, and other health benefits of tomato compounds lycopene, α-tomatine, and tomatidine in pure form and in fresh and processed tomatoes. J. Agric. 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| Snippet | Mono-(5Z)-, -(9Z)-, and -(13Z)-lycopenes are found in food containing processed tomato products, while tetra-Z-(7Z, 9Z, 7′Z, 9′Z)-lycopene (prolycopene) is... Abstract: Mono-(5Z)-, -(9Z)-, and -(13Z)-lycopenes are found in food containing processed tomato products, while tetra-Z-(7Z, 9Z, 7'Z, 9'Z)-lycopene... |
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| SubjectTerms | 13C NMR chemical shift of Z-methyl signal 1O2 quenching activity Chemical reactions Column chromatography Dichloromethane Differentiation (biology) High-performance liquid chromatography Isomers mouse 3T3-L1 cells differentiation activity NMR Nuclear magnetic resonance Quenching Silica gel Silicon dioxide Tomatoes Z-lycopenes |
| Title | Biological Activities of Z-Lycopenes Contained in Food |
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