Enzymatic and oxidative metabolites of lycopene.


Autoria(s): Ferreira, Ana Lúcia dos Anjos; Yeum, Kyung-Jin; Russell, Robert M; Krinsky, Norman I; Tang, Guangwen
Contribuinte(s)

Universidade Estadual Paulista (UNESP)

Data(s)

27/05/2014

27/05/2014

01/08/2004

Resumo

Using the post-mitochondrial fraction of rat intestinal mucosa, we have investigated lycopene metabolism. The incubation media was composed of NAD+, KCI, and DTT with or without added lipoxygenase. The addition of lipoxygenase into the incubation significantly increased the production of lycopene metabolites. The enzymatic incubation products of 2H10 lycopene were separated using high-performance liquid chromatography and analyzed by UV/Vis spectrophotometer and atmospheric pressure chemical ionization-mass spectroscopy. We have identified two types of products: cleavage products and oxidation products. The cleavage products are likely: (1) 3-keto-apo-13-lycopenone (C18H24O2 or 6,10,14-trimethyl-12-one-3,5,7,9,13-pentadecapentaen-2-one) with lambdamax = 365 nm and m/z =272 and (2) 3,4-dehydro-5,6-dihydro-15-apo-lycopenal (C20H28O or 3,7,11,15-tetramethyl-2,4,6,8,12,14-hexadecahexaen-l-al) with lambdamax= 380 nm and m/z = 284. The oxidative metabolites are likely: (3) 2-ene-5,8-lycopenal-furanoxide (C37H50O) with lambdamax = 415 nm, 435 nm, and 470 nm, and m/z = 510; (4) lycopene-5, 6, 5', 6'-diepoxide (C40H56O2) with lambdamax = 415 nm, 440 nm, and 470 nm, and m/z =568; (5) lycopene-5,8-furanoxide isomer (I) (C40H56O2) with lambdamax = 410 nm, 440 nm, and 470 nm, and m/z = 552; (6) lycopene-5,8-epoxide isomer (II) (C40H56O) with lambdamax = 410, 440, 470 nm, and m/z = 552; and (7) 3-keto-lycopene-5',8'-furanoxide (C40H54O2) with lambdamax = 400 nm, 420 nm, and 450 nm, and m/z = 566. These results demonstrate that both central and excentric cleavage of lycopene occurs in the rat intestinal mucosa in the presence of soy lipoxygenase.

Formato

493-502

Identificador

http://dx.doi.org/10.1016/S0955-2863(03)00107-4

The Journal of nutritional biochemistry, v. 15, n. 8, p. 493-502, 2004.

0955-2863

http://hdl.handle.net/11449/67810

10.1016/S0955-2863(03)00107-4

WOS:000185924900005

2-s2.0-16544366000

Idioma(s)

eng

Relação

The Journal of nutritional biochemistry

Direitos

closedAccess

Palavras-Chave #carotenoid #lipoxygenase #lycopene #animal #high performance liquid chromatography #intestine mucosa #male #mass spectrometry #metabolism #oxidation reduction reaction #rat #Animals #Carotenoids #Chromatography, High Pressure Liquid #Intestinal Mucosa #Lipoxygenase #Male #Mass Spectrometry #Oxidation-Reduction #Rats
Tipo

info:eu-repo/semantics/article