1071-52-9Relevant articles and documents
Fractionation and Characterization of Lycopene-Oxidation Products by LC-MS/MS (ESI)+: Elucidation of the Chemopreventative Potency of Oxidized Lycopene in Breast-Cancer Cell Lines
Arathi, Bangalore Prabhashankar,Raghavendra-Rao Sowmya, Poorigali,Kuriakose, Gini Chempakathinal,Shilpa, Shivaprasad,Shwetha, Hulikere Jagdish,Kumar, Sharath,Raju, Marisiddaiah,Baskaran, Vallikannan,Lakshminarayana, Rangaswamy
, p. 11362 - 11371 (2018/11/21)
Lycopene (LYC) has been correlated with the reduction of certain cancers and chronic diseases. However, the existence and biofunctionality of degraded, oxidized, and biotransformed LYC products in vivo have not been revealed. Therefore, this study aimed t
Identification and quantification of apo-lycopenals in fruits, vegetables, and human plasma
Kopec, Rachel E.,Riedl, Ken M.,Harrison, Earl H.,Curley Jr, Robert W.,Hruszkewycz, Damian P.,Clinton, Steven K.,Schwartz, Steven J.
experimental part, p. 3290 - 3296 (2011/07/29)
Research has suggested that lycopene may be metabolized by eccentric cleavage, catalyzed by β-carotene oxygenase 2, resulting in the generation of apo-lycopenals. Apo-6′-lycopenal and apo8′-lycopenal have been reported previously in raw tomato. We now show that several other apolycopenals are also present in raw and processed foods, as well as in human plasma. Apo-lycopenal standards were prepared by in vitro oxidation of lycopene, and a high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method using atmospheric pressure chemical ionization in negative mode was developed to separate and detect the apo-6′-, apo-8′-, apo-10′-, apo-12′-, apo-14′-, and apo-15′-lycopenal products formed in the reaction. Hexane/acetone extracts of raw tomato, red grapefruit, watermelon, and processed tomato products were analyzed, as well as plasma of individuals who had consumed tomato juice for 8 weeks. Apo-6′-, apo-8′-, apo-10′-, apo-12′-, and apo-14′-lycopenals were detected and quantified in all food products tested, as well as plasma. The sum of apo-lycopenals was 6.5 μg/100 g Roma tomato, 73.4μg/100 g tomato paste, and 1.9 nmol/L plasma. We conclude that several apo-lycopenals, in addition to apo-6′- and -8′-lycopenal, are present in lycopene-containing foods. In addition, the presence of apo-lycopenals in plasma may derive from the absorption of apo-lycopenals directly from food and/or human metabolism.
Synthesis, Isolation, and NMR-Spectroscopic Characterization of Fourteen (Z)-Isomers of Lycopene and of Some Acetylenic Didehydro- and Tetradehydrolycopenes
Hengartner, Urs,Bernhard, Kurt,Meyer, Karl,Englert, Gerhard,Glinz, Ernst
, p. 1848 - 1865 (2007/10/02)
Eight (Z)-isomers of lycopene were prepared by stereocontrolled syntheses and fully characterized by 1H-NMR, 13C-NMR, mass, and UV/VIS-spectroscopy: (5Z)-, (7Z)-, (15Z)-, (5Z,5'Z)-, (7Z,7'Z)-, (7Z,9Z)-, (9Z,9'Z)-, and (7Z,9Z,7'Z,9'Z)-lycopene.Six additional (Z)-isomers, namely (9Z)-, (13Z)-, (5Z,9'Z)-, (9Z,13'Z)-, (5Z,9Z,5'Z)-, and (5Z,13Z,5'Z)-lycopene, were isolated in small quantities from isomer mixtures by semiprep.HPLC and were identified by 1H-NMR spectroscopy.
10'-Apolycopin-10'-ol und 10'-Apolycopin-10'-saeure aus Blueten der Rosenhybride "Marechal Niel"
Maerki-Fischer, Edith,Uebelhart, Peter,Eugster, Conrad Hans
, p. 1994 - 2002 (2007/10/02)
The novel 10'-apolycopen-10'-ol (1) and 10'-oic acid (4) were isolated from the yellow petals of the once world-renowned rose hybrid "Marechal Niel".The relative amount of either 1 or 4 produced by the plant depends upon the climatic conditions.Both 1 and
Synthesen von Carotinen mit ψ-Endgruppen und (Z)-Konfiguration an terminalen konjugierten Doppelbindungen
Zumbrunn, Albrecht,Uebelhart, Peter,Eugster, Conrad Hans
, p. 1519 - 1539 (2007/10/02)
Five carotenes bearing (5Z)-ψ-end groups were synthesized and carefully characterized: (5Z)-lycopene (6), (5Z,5'Z)-lycopene (7), (5'Z)-neurosporene (8), (5'Z)-β,ψ-carotene (12), and (5'Z)-εψ-carotene (14).
