Of lycopene

A molecule of lycopene can absorb blue light because the electrons are not orbiting a single atom, they are sloshing around orbiting many atoms, and the energy needed to move them is a lot less than in a smaller molecule, or one without conjugated bonds. 

In addition, Montenegro et al., (2007) determined that the photosensitized RF-mediated degradation of vitamins A, D3, and RF itself in skimmed milk was strongly reduced by the addition of small amounts of lycopene-gum arabic-sucrose microcapsules, prepared by spray-drying. Under these conditions, the bulk properties of the skimmed milk were unmodified. The main photoprotection mechanism of the milk vitamins was the efficient quenching of the 3Rf by the protein moiety of GA. Small contributions (<5%) to the total photoprotection percentage was due to both inner filter effect and 1O2 quenching by the microencapsulated lycopene. 

The range (p,g/100 fresh weight) of lycopene and P-carotene in selected tomato cultivars can be 20-62000 and 35-2200 respectively, and of P-carotene and a-carotene in selected carrot cultivars 1100-64000 and 530-36000 respectively. Some of the carotenoids may be present as fatty acid esters (Breithaupt and Bamedi, 2001). More extensive listings can be found (O Neill et al, 2001 van den Berg et al, 2000 Hart and Scott 1995). 

An evaluation of the Health Professionals Follow-Up Study (Giovannucci et al., 1995) has detected a lower prostate cancer risk associated with the greater consumption of tomatoes and related food products. Tomatoes are the primary dietary source of lycopene and lycopene concentrations are highest in testis and adrenal tissue (Clinton, 1998). In paired benign and malignant prostate tissue from 25 American men, 53-74 yrs, undergoing... 

Fig. 7.4 Distribution of lycopene in hiunan tissnes. After Kaplan et al., 1990.

STAHL w, SCHWARZ w, SUNDQUIST A R and SIES H (1992) Cis-trans isomers of lycopene and beta-carotene in human serum and tissues. Arch Biochem Biophys 294(1) 173-7. 

Carotenoid accumulation during fruit ripening in tomato has been studied extensively and is a good model system to elucidate the regulation of the process. During ripening the concentration of carotenoids increases between 10 and 15-fold due mainly to a 500-fold increase in the concentration of lycopene (Fraser et al, 1994 Table 13.5). Accumulation of lycopene begins... 

The carotenoid pathway may also be regulated by feedback inhibition from the end products. Inhibition of lycopene cyclisation in leaves of tomato causes increase in the expression of Pds and Psy-1 (Giuliano et al, 1993 Corona et al, 1996). This hypothesis is supported by other studies using carotenoid biosynthesis inhibitors where treated photosynthetic tissues accumulated higher concentrations of carotenoids than untreated tissues (reviewed by Bramley, 1993). The mechanism of this regulation is unknown. A contrary view, however, comes from studies on the phytoene-accumulating immutans mutant of Arabidopsis, where there is no feedback inhibition of phytoene desaturase gene expression (Wetzel and Rodermel, 1998). 

Lycopene is a bright red pigment that colors several ripe fruits, vegetables, and flowers. Tomato and tomato products are the main dietary sources of this carotenoid, although it is also found in watermelons, guavas, pink grapefruits, and in small quantities in at least 40 plants. - The absorption of lycopene in the human gut is increased by heat treatment, probably because the breakdown of the plant cells makes the pigment more accessible. ... 

Carrots were also the main sonrces of a-carotene, whereas tomatoes and tomato prodncts were the major sources of lycopene. Lutein was mainly provided by peas in the Republic of Ireland and United Kingdom. Spinach was found to serve as the major source in other countries. Lutein and zeaxanthin xanthophylls are found in a wide variety of fruits and vegetables, particularly green leafy vegetables, but also in some animal products such as egg yolks. In all countries, P-cryptoxanthin was obtained primarily from citrus fruits. 

Carotenoids and prostate cancer — Numerous epidemiological studies including prospective cohort and case-control studies have demonstrated the protective roles of lycopene, tomatoes, and tomato-derived products on prostate cancer risk other carotenoids showed no effects. " In two studies based on correlations between plasma levels or dietary intake of various carotenoids and prostate cancer risk, lycopene appeared inversely associated with prostate cancer but no association was reported for a-carotene, P-carotene, lutein, zeaxanthin, or p-cryptoxanthin. - Nevertheless, a protective role of all these carotenoids (provided by tomatoes, pumpkin, spinach, watermelon, and citrus fruits) against prostate cancer was recently reported by Jian et al. ... 

Intervention trials confirmed this protective role of lycopene on prostate cancer risk. Three primary intervention studies evaluated the effect of lycopene supplementation on prostate cancer risk or on certain risk markers such as prostate-specific antigen (PSA) plasma concentration or oxidative alterations of leucocyte DNA. - All showed increases of plasma and prostate lycopene levels after diet supplementation with lycopene and inverse correlations between tumor incidence and risk biomarkers. 

The second major difficulty is that cells and tissues in the body are exposed to numerous metabolites displaying different structures compared to the parent molecules present in plant foods. For example, it has been suggested that the metabolites of lycopene may be responsible for reducing the risk of developing prostate cancer. These metabolites may interact with nuclear receptors such as PPARs, LXR, and others. " Future research is needed to produce metabolites (enzymatically or chemically) in order to elucidate their cellular mechanisms and thus clarify their effects on human health. 

Kucuk, O. et al.. Effects of lycopene supplementation in patients with localized prostate cancer, Exp. Biol. Med. (Maywood), 227, 881, 2002. van Breemen, R.B. et al.. Liquid chromatography-mass spectrometry of cis- and all-trans-lycopene in human serum and prostate tissue after dietary supplementation with tomato sauce, J. Agric. Food Chem., 50, 2214, 2002. 

Rao, A.V. and Agarwal, S., Bioavailability and in vivo antioxidant properties of lycopene from tomato products and their possible role in the prevention of cancer, Nutr. Cancer, 3, 199, 1998. 

Fuhrman, B. et al., Hypocholesterolemic effect of lycopene and beta-carotene is related to suppression of cholesterol synthesis and augmentation of LDL receptor activity in macrophages, Biochem. Biophys. Res. Commun., 233, 658, 1997. 

Stndies of the antoxidation of carotenoids in liposomal suspensions have also been performed since liposomes can mimic the environment of carotenoids in vivo. Kim et al. stndied the antoxidation of lycopene," P-carotene," and phytofluene" " in liposomal snspensions and identified oxidative cleavage compounds. Stabilities to oxidation at room temperature of various carotenoids incorporated in pig liver microsomes have also been studied." The model took into account membrane dynamics. After 3 hr of reactions, P-carotene and lycopene had completely degraded, whereas xanthophylls tested were shown to be more stable. 

There are few naturally occurring oxidation products that do not belong to the families of epoxides or apo-carotenoids. One of those is the metabolite of lycopene known as 2,6-cyclo-lycopene-1,5 diol found in human plasma and at lower levels in tomato products. ... 

FIGURE 3.3.2 Hypothesized mechanism of formation of lycopene oxidation products in an abiotic system. The compound numbers correspond to those cited in Britton, G. et ah, Carotenoids HandbookP... 

Gajic, M. et al., Apo-8-lycopenal and apo-12-lycopenal are metabolic products of lycopene in rat liver, J. Nutr. Biochem., 136, 1552, 2006. 

Caris-Veyrat, C. et al., Cleavage products of lycopene produced by in vitro oxidations characterization and mechanisms of formation, J. Agric. Food Chem., 51, 7318, 2003. Caris-Veyrat, C. et al., Mild oxidative cleavage of beta, beta-carotene by dioxygen induced by a ruthenium porphyrin catalyst characterization of products and of some possible intermediates, New J. Chem., 25, 203, 2001. 

Zhang, H. et al., A novel cleavage product formed by autoxidation of lycopene induces apoptosis in HL-60 cells.. Free Radic. Biol. Med., 35, 1653, 2003. 

Lycopene is well known as the predominant carotene in tomatoes, accounting for 65 to 98% of the total colored carotenoid content, depending on the cultivar (Table 4.2.3). The levels of lycopene in fresh tomatoes for salad varied from 21 to 79 g/g 34,35 jjj tomatoes for processing and deep-red tomatoes, the level of lycopene can be as high as 623 More than 80% of the tomatoes produced are... 

Freeze-dried tomato powders obtained from whole tomato fruits and from their pulp after centrifugation, containing 474 and 5399 pg/g dry weight, respectively, were developed for use as additives for food fortification. Cis isomers of lycopene were determined in only a few smdies. The 5-cis-, 9-cis-, and 13-d5 --El5-d5 -lycopene were the isomers found in commercial tomato products. The structures of lycopene cis isomers are shown in Figure 4.2.1 and the structure of the dll-trans isomer is displayed in Figure 6.2.1 in Chapter 6. 

Other common fruits are also good sources of lycopene that represents 87 to 95% of the total carotenoid content in several seeded and seedless watermelon cultivars," ° 56 to 66% in different papaya cultivars, and 24 to 58% in pink grapefruits (Table 4.2.3). 

Among tropical fruits, red guavas, containing 76 to 86% of lycopene in relation to total carotenoid, can be considered good sources of lycopene. An indigenous Southeast Asia fruit called gac in Vietnam and used as a rice colorant shows an intense red color in the seed membrane (seed pulp or aril) of the ripe fruit the mesocarp, characterized by its yellow color, is discarded. Although some discrepancies can be found in the literature regarding the lycopene content in gac fruits (Table 4.2.3), this fruit is an extraordinarily rich source of lycopene. ... 

Rich Food Sources of Lycopene and Its Cis Isomer Distribution... 

Isomerization of lycopene in tomato oleoresin increased at 75 and 100°C, reaching the formation of eight unidentified lycopene geometrical isomers in tomato oleoresin stored at 100°C. The k of 0.2597/min was higher, whereas the (11.7 kcal/mol) was lower than that observed for lycopene standard heated in safflower oil at 75°C. 

Only 6% of the iifitial total lycopene prepared as a thin film on the surface of each vial remained after 144 hr under fluorescent light (2000 to 3000 lux) at 25°C under N2. Lycopene degradation occurred as a first-order reaction at 2.93 x 10" /min, and the concentration of aU lycopene mono-c isomers already present in the sample, 5-cis-, 9-cis-, l3-cis- and 15-d5 -, showed an inconsistent change in this period. Nevertheless, formation of lycopene di-c isomers was observed after 32 hr of light exposure and when considering relative percentage, loss of 13% of all-trani-lycopene occurred while an increase of 11% for total cis isomers was found after 144 hr. ... 

Schierle, J. et al.. Content and isomeric ratio of lycopene in food and human blood plasma. Food Chem., 59, 459, 1997. 

Hackett, M.M. et al., Thermal stability and isomerization of lycopene in tomato oleoresins from different varieties, J. Food ScL, 69, C536, 2004. 

Lee, M.T. and Chen, B.H., Stability of lycopene during heating and illumination in a model system, Food Chem., 78, 425, 2002. 

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