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Composition of tomatoes and tomato products in antioxidants (WG1) page 65<br />

__________________________________________________________________________________________<br />

Among a series of carotenoids tested, lycopene was shown to be the most efficient<br />

quencher of singlet oxygen (Table 24). The explanation for the somewhat enhanced reactivity<br />

of lycopene towards singlet oxygen is not established.<br />

Carotenoid<br />

Lycopene<br />

Kq (x 10 9 M -1 s -1 )<br />

17<br />

Source<br />

Tomato, watermelon<br />

All-trans β-carotene 13 Carrots<br />

Astaxanthin 14 Salmon<br />

Zeaxanthin 12 Maize<br />

Lutein 2.9 Green vegetable<br />

Violaxanthin 1 Green vegetable<br />

Bixin 9.2 Annatto seeds<br />

Table 24 : Singlet oxygen quenching constants, from Conn et al. (1991)<br />

7.1.4.2 Quenching of free radicals<br />

Radicals are present in vivo in various forms, they are activated species of oxygen like<br />

hydroxyl radical (HO . .- .<br />

), superoxide (O2 ) or peroxyl radical (ROO ). The unpaired electron,<br />

characterizing the radical, gives them their instability. As molecules rich in electrons,<br />

carotenoids can react with a radical in order to fill its gap of electron, thus acting as a radicalquencher.<br />

Two mechanisms of radical quenching can occur. It is either a transfer of electron<br />

from the carotenoid to the radical (1), or an addition reaction (2). In both cases, the radical<br />

formed is delocalised along the polyunsaturated chain of the carotenoid, making it more stable<br />

and then less reactive. It should be noted that upon physical quenching of 1 O2 the carotenoid<br />

molecule stays intact. It is destroyed by chemical quenching of 1 O2 and by radical interactions<br />

(figure 10).<br />

R +. + CAR ➔ R + CAR +.<br />

(1)<br />

R +. + CAR ➔ [ R – CAR ] +. (2)<br />

Figure 10 : mechanisms of radical quenching by a carotenoid

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