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ARS Home » Northeast Area » Boston, Massachusetts » Jean Mayer Human Nutrition Research Center On Aging » Research » Publications at this Location » Publication #164170
Title: ENZYMATIC AND OXIDATIVE METABOLITES OF LYCOPENE

Author
item FERREIRA, ANA - UNIV ESTADUAL PAULISTA
item YEUM, KYUNG - TUFTS-HNRCA
item RUSSELL, ROBERT - TUFTS-HNRCA
item KRINSKY, NORMAN - TUFTS-HNRCA
item TANG, GUANGWEN - TUFTS-HNRCA

Submitted to: Journal of Nutritional Biochemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/1/2002
Publication Date: 9/1/2003
Citation: FERREIRA, A.L., YEUM, K.J., RUSSELL, R.M., KRINSKY, N.I., TANG, G. ENZYMATIC AND OXIDATIVE METABOLITES OF LYCOPENE. Journal of Nutritional Biochemistry. 2003;14:531-540.

Interpretive Summary: Lycopene (bright red compound found in tomato) has been reported as a potential anti cancer agent. Further, the inverse relation between lycopene intake and cancer risk might ascribe to 1) lycopene as an antioxidant, 2) increasing cell-cell communication, 3) reducing mutagenesis, 4) inhibiting tumor cell proliferation, and 5) improving antitumor immune responses. However, the mechanism(s) by which this carotenoid might exert its biological activities and thereby modulate disease processes is still unknown. Our laboratory has carried out extensive studies on understanding lycopene metabolism by intestinal enzyme with/without adding lipoxygenase. We have identified two types of products: cleavage products and oxidation products. Although the biological importance of these lycopene metabolites is still unknown, the health effect attributed to lycopene in humans may be due to the activity of some of these oxidation products.

Technical Abstract: Using the post-mitochondrial fraction of rat intestinal mucosa, we have investigated lycopene metabolism. The incubation media was composed of NAD(+), KCl, 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 (C(18)H(24)O(2) or 6,10,14-trimethyl-12-one-3,5,7,9,13-pentadecapentaen-2-one) with lambda-max = 365 nm and m/z = 272 and (2) 3,4-dehydro-5,6-dihydro-15,15'-apo-lycopenal (C(20)H(28)O or 3,7,11,15-tetramethyl-2,4,6,8,12,14-hexadecahexaen-1-al) with lambda-max = 380 nm and m/z = 284. The oxidative metabolites are likely: (3) 2-apo-5,8-lycopenal-furanoxide (C(37)H(50)O) with lambda-max = 415 nm, 435 nm, and 470 nm, and m/z = 510; (4) lycopene-5, 6, 5', 6'-diepoxide (C(40)H(56)O(2)) with lambda-max = 415 nm, 440 nm, and 470 nm, and m/z = 568; (5) lycopene-5,8-furanoxide isomer (I) (C(40)H(56)O) with lambda-max = 410 nm, 440nm, and 470 nm, and m/z = 552; (6) lycopene-5,8-epoxide isomer (II) (C(40)H(56)O) with lambda-max = 410, 440, 470 nm, and m/z = 552; and (7) 3-keto-lycopene-5',8'-furanoxide (C(40)H(54)O(2)) with lambda-max = 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.