Biological Activities of <i>Z</i>-Lycopenes Contained in Food

Abstract

Fig. 1 is a principal carotenoid contained in ripe tomato Lycopersicum esculentum . AE-L has been claimed to possess cardioprotective effects 1 due to its antioxidant activity 2 , as well as anti-diabetic effects 3, 4 due to its antioxidant 2 and PPARγ agonistic activities 5 . Some Z-isomers of AE-L have also been reported to be present in foods in previous studies; for example, mono-5Z -, -9Z -, and -13Z -lycopenes 5Z-L, 9Z-L, and 13Z-L, Fig. 1 have been reported to be produced during the cooking of ripe tomatoes, and are claimed to be present in tomato puree, ketchup, and soup at levels of 10-30 6, 7 . Tetra-Z-7Z, 9Z, 7 Z, 9 Z -lycopene prolycopene, Fig. 1 has also been reported to exist in tangerine-strain tomatoes due to the lack of carotenoid isomerase CRTISO 8 , which converts prolycopene into AE-L 6 . Unlike AE-L, few of these Z-lycopenes have been reported to show biological activities, with the exception of the radical-quenching activities of 5Z-L, 9Z-L, and 13Z-L 9 and the PPARγ agonistic activity of 5Z-L 5 . This is due to the difficulty of preparing enough of the pure compounds for bioactivity tests.Studies on the bioavailabilities and pharmacological activities of Z-isomers of β-carotene were carried out in the

Antiherpetic Activity of a Root Exudate from Solanum lycopersicum

“…Furthermore, natural antioxidants, such as bioactive carotenoids (lycopene, β-carotene, lutein, phytoene, phytofluene), phytosterols (β-sitosterol), and flavonoids (quercetin, kaempferol, myricetin,) have a beneficial role in human health and chronic diseases owing to their ability to modulate the activity of specific enzymes or inhibit the production of reactive oxygen species (ROS) acting as free radical scavengers [ 48 , 49 , 50 ]. Additionally, it is well known that the pharmacological profile of flavonoids, carotenoids, glycoalkaloids, and phytosterols includes anticancer, anti-inflammatory, anti-allergenic, antithrombotic, antimicrobial, antioxidant, vasodilator, and cardioprotective effects [ 51 , 52 , 53 , 54 , 55 ].…”

In Vitro Evaluation of Skin-Related Physicochemical Properties and Biological Activities of Astaxanthin Isomers

“…Namely, all- E -isomer-rich astaxanthin showed greater singlet oxygen scavenging activity than the Z -isomer-rich astaxanthin (Figure A), whereas the opposite results were obtained on DPPH radical and hydroxyl radical scavenging activities (Figure B,C). Sakemi et al reported that, in the other carotenoid, lycopene, the all- E -isomer showed higher singlet oxygen scavenging activity than the Z -isomers, indicating that carotenoids commonly have decreased singlet oxygen scavenging activity upon isomerization from the all- E - to the Z -isomers. Carotenoids quench singlet oxygen through a physical mechanism involving the transfer of excitation energy, followed by thermal deactivation .…”

Application of <i>E/Z</i>-Isomerization Technology for Enhancing Processing Efficiency, Health-Promoting Effects, and Usability of Carotenoids: A Review and Future Perspectives

“…In addition, it has been reported that the strength (order) of antioxidant activity among the isomers present in other carotenoids (e.g., lutein, canthaxanthin, and fucoxanthin) differs depending on the assay method, wherein Z-isomers have an activity equal to or greater than that of the all-Eisomers 71−74) . Conversely, several studies indicated that (all-E) -carotenoids exhibit higher (or equal) antioxidant activity than the Z-isomers in certain assay methods, such as lycopene in singlet oxygen quenching activity assay and zeaxanthin in Trolox equivalent antioxidant capacity (TEAC) assay 71,76) (note that lycopene Z-isomers possess higher antioxidant activity than the all-E-isomer in TEAC and MbFe III lipid peroxidation assays 71,77) ) . Moreover, it has been observed that (9Z) -astaxanthin has higher anti-inflammatory and antiaging activities 23,75) , (9Z) -canthaxanthin exhibits higher pro-apoptotic activity 78) , and fucoxanthin Z-isomers have greater anticancer activity 24) than their all-E-isomers.…”