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
Crocetin glycosides such as crocin are noted as functional food materials since the preventive effects of crocin have been reported against chronic disease and cancer. However, it is unclear how these apocarotenoids are structurally changed through cooking for our intake. We examined such changes in crocetin glycosides (crocin, tricrocin, and crocin-3) contained in saffron (stigmas of Crocus sativus) through cooking models. These glycosides were almost kept stable in boiling for 20 min (a boiled cooking model), while hydrolysis of the ester linkage between glucose and the crocetin aglycone occurred in a grilled cooking model (180°C, 5 min), along with a 13-cis isomerization reaction in a part of crocetin subsequently generated. We further here revealed that the yellow petals of freesia (Freesia x hybrida) with yellow flowers accumulate two unique crocetin glycosides, which were identified to be crocetin (mono)neapolitanosyl ester and crocetin dineapolitanosyl ester. A similar result as above was obtained on their changes through the cooking models. Utility applications of the freesia flowers as edible flowers are also suggested in this study. Additionally, we evaluated singlet oxygen (1O2)-quenching activities of the crocetin glycosides contained in saffron and freesia, and crocetin and 13-cis crocetin contained in the grilled saffron, indicating that they possessed moderate 1O2-quenching activities (IC50 24–64 μM).
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