Summary of the effects of
Abstract
Carotenoids, the most common fat-soluble plant pigments in nature, are beneficial to human health due to their strong antioxidant activities and abilities to prevent various diseases. Carotenoids have many geometrical isomers forms caused by E/Z-isomerization at arbitrary sites within the multiple conjugated double bonds. Several studies have addressed that the bioavailability as well as the antioxidant, anticancer, and antiatherosclerotic activities of carotenoids varies among the isomers. In addition, those variations differ among carotenoids: Z-isomerization resulted in “positive” or “negative” effect for carotenoids bioavailability and functionality, for example, Z-isomers of lycopene are more bioavailable than the all-E-isomer, whereas the opposite is observed for β-carotene. Thus, to efficiently promote the beneficial effects of carotenoids by ingestion, it is important to have a good understanding of the impact of E/Z-isomerization on the corresponding functional changes. The objective of this contribution is to review the effects of carotenoid Z-isomerization on bioavailability and functionality and describe their differences among carotenoids.
Keywords
- lycopene
- β-carotene
- astaxanthin
- E/Z-isomer
- bioavailability
- antioxidant activity
1. Introduction
Carotenoids are the most common lipid-soluble pigments responsible for the colors of plants, animals, and microorganisms, and over 1100 different types of carotenoids have been characterized so far [1, 2]. Carotenoids can be divided into the following two groups: (1) carotenes, which are nonoxygenated molecules such as lycopene and β-carotene; (2) xanthophylls, which are oxygen-containing molecules such as astaxanthin and fucoxanthin (Figure 1) [3]. The daily consumption of carotenoid-rich foods would be beneficial for human health because of their high antioxidant, anticancer, and antiatherosclerotic activities [4, 5, 6]. Because carotenoids contain numerous conjugated double bonds, many kinds of geometrical isomers are theoretically possible (Figure 1C, E and F). In general, carotenoids in plants occur predominantly in the (all-
2. Effect of Z -isomerization of carotenoids on their bioavailabilities and functionalities
The effects of
2.1. Lycopene
Lycopene is an acyclic carotene (C40H56) that is principally responsible for the bright-red color found abundantly in vegetables and fruits such as tomatoes, guava, and watermelons [3, 9]. Lycopene shows an especially strong antioxidant activity among carotenoids [6] and can significantly reduce the risks for arteriosclerosis, atherogenesis, and many types of cancer (such as prostate and esophageal cancer) [4, 5]. Therefore, in recent years, the use of lycopene in health foods and supplements, and as a natural functional pigment has attracted attention. It is well documented that the bioavailability and antioxidant activity of lycopene are changed by
Data from both
Several previous reports have shown that lycopene
Based on the above findings,
2.2. β-Carotene
β-carotene is a cyclic carotene (C40H56) that is found abundantly in vegetables and fruits, and provides vegetables such as carrots and pumpkins with a deep orange-yellow color [3, 4]. As with other carotenoids, β-carotene has a high antioxidant capacity [6] and preventive effect against various diseases such as cancer and atherogenesis [4, 17]. Furthermore, β-carotene is very important as a retinol precursor, with a high conversion rate [3, 4]. It is also well documented that the bioavailability and antioxidant activity of β-carotene as well as its antiatherogenic activity are changed by
Data from several
Several studies have been conducted to compare the antioxidant activities of (all-
Moreover, as additional “positive” effects of β-carotene
Regarding β-carotene, considering that “positive” and “negative” effects are associated with
2.3. Astaxanthin
Astaxanthin is a xanthophyll (C40H52O4) that is principally responsible for the dark-red color in various microalgae and marine animals [1, 72]. Astaxanthin shows an especially strong antioxidant activity among carotenoids [6] and can significantly reduce the risk of cancer, eye disease, and cardiovascular disease [73, 74]. For instance, astaxanthin protected mice from carcinogenesis of the urinary bladder by reducing the incidence of chemically induced bladder carcinoma and further, astaxanthin supplementation in rats inhibited the stress-induced suppression of tumor-fighting natural killer cells [73]. In addition, astaxanthin is frequently used as an animal and fish feed additive to improve their body colors [75]. Data from several studies have demonstrated that the bioavailability and antioxidant activity of astaxanthin were changed by
In terms of the bioavailability, an
Although the antioxidant activity measured depends on the assay method employed, many studies have shown “positive” effects. Namely, assay that measure antioxidant enzyme activities, DPPH radical scavenging, oxygen radical-absorption capacity (ORAC), photochemiluminescence (PLC) and peroxidation have shown higher antioxidant activities of astaxanthin
Most investigators have concluded that “positive” effects on the bioavailability and antioxidant activity occurred following astaxanthin
2.4. Canthaxanthin
Canthaxanthin is a xanthophyll (C40H52O2) that is principally responsible for the orange-pink color found abundantly in egg yolk and various microbes such as
2.5. Fucoxanthin
Fucoxanthin is an allenic xanthophyll (C42H58O6) that is found abundantly in edible shellfish and brown seaweeds such as
2.6. Lutein
Lutein is a xanthophyll (C40H56O2) that is principally responsible for the yellow-orange color found abundantly in vegetables, for example, corn, carrots, kale, and peas, and in egg yolks [102]. Lutein has preventive effects against various diseases such as eye diseases and cardiovascular diseases [102, 103, 104]. In particular, several studies have addressed the role of lutein in reducing the risk of the two most common eye diseases in older people, that is, cataracts and macular degeneration [102, 103, 104]. Only a few reports have shown the effect of lutein
In terms of antioxidant activity, the
2.7. Other carotenoids
The effects of
To the best of our knowledge, the effect of
Carotenoid | Evaluation | Overview of results | Effect* | Reference |
---|---|---|---|---|
Lycopene | Bioavailability/bioaccessibility | + | [20] | |
+ | [21, 22] | |||
+ | [23] | |||
+ | [12, 24, 25, 26] | |||
Antioxidant activity | + | [10] | ||
+ | [11] | |||
All- | ± | [11] | ||
α-Carotene | Antioxidant activity | 13′ | ± | [10] |
β-Carotene | Bioavailability/bioaccessibility | All- | − | [14] |
All- | − | [41] | ||
All- | − | [42] | ||
All- | − | [43, 44, 45, 46, 47, 48] | ||
9 | + | [52] | ||
9 | + | [53] | ||
Antioxidant activity | 9 | + | [54] | |
9 | + | 18 | ||
9 | + | [55] | ||
All- | − | [17] | ||
All- | − | [10] | ||
All- | − | [56, 57] | ||
Atherogenesis activity | 9 | + | [58] | |
Atherosclerosis activity | 9 | + | [59, 60] | |
Astaxanthin | Bioavailability/bioaccessibility | + | [76] | |
13 | + | [77] | ||
+ | [16] | |||
All- | − | [78, 79] | ||
Antioxidant activity | + | [76] | ||
+ | [80] | |||
+ | [81] | |||
13 | ± | [81] | ||
Canthaxanthin | Antioxidant activity | 9 | + | [88] |
Pro-apoptotic activity | 9 | + | [90] | |
Fucoxanthin | Antioxidant activity | 13 | ± | [19] |
9′ | ± | [19] | ||
− | [100] | |||
Anticancer activity | + | [13] | ||
Lutein | Bioavailability/bioaccessibility | + | [15] | |
All- | − | [15] | ||
13 | + | [105] | ||
Antioxidant activity | + | [15] | ||
13′ | + | [15] | ||
All- | ± | [15] | ||
Zeaxanthin | Antioxidant activity | All- | − | [10] |
3. Changes in the physicochemical properties of carotenoids by Z -isomerization
Changes in the bioavailability and functionality of carotenoids after
4. Conclusions
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