**1. Historical aspects of carotenoids**

It is often stated that without carotenoids, life in an oxygenic atmosphere would not be possible, and we would not exist. Thereby, over millions of years, the living organism chloroplasts maintained collections of carotenoids to protect the intricate and delicate photosynthetic apparatus against destruction by photooxidation [1, 2].

> © 2016 The Author(s). Licensee InTech. This chapter is distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. © 2018 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

According to Britton et al. [1], it can be considered that the study of carotenoids exceeds 200years of history. Was Braconnot in 1817 carried out the first investigation in paprika? The following year, Aschoff isolated from the saffron, the "crocin," apocarotenoid which we now know as bixin. In 1823, Goebel's research on crab (*Brachyura*) suggested for the first time the presence of these isoprenoids in animals. Later, after investigations with carrots (*Daucus carota* L.), from which the term carotenoids derives, Wackenroder in 1831 isolated and described for the first time carotene with structure C40, now β-carotene. Shortly thereafter in 1837, Berzelius introduced the term xanthophyll due to its presence in autumn leaves. After, Kraus and Millardet in 1843 made the first investigation of carotenoids into cyanobacteria. Only 30 years later, lycopene was isolated for the first time from fruits of *Tamus communis* by Hartsen.

is also considered an example of apocarotenoid, because it is the product of the symmetrical

Carotenoids: A Brief Overview on Its Structure, Biosynthesis, Synthesis, and Applications

http://dx.doi.org/10.5772/intechopen.79542

3

The formation of these carotenoid derivatives occurs via enzymatic and nonenzymatic oxidative cleavage of carotenoids [11, 12]. Carotenoid cleavage dioxygenases (CCDs) catalyze carotenoid cleavage at specific double bonds, typical act by incorporating oxygen atoms into adjacent carbon atoms along the conjugated carotenoid backbone. Some CCD cleavage reactions require isomerization to form substrate isomers favorable for cleavage [13]. On the other hand, nonenzymatic apocarotenoid formation can occur via singlet oxygen attack, primarily on β-carotene [14]. In addition, peroxidases and lipoxygenases are also reported to form

Regardless of metabolic origin, apocarotenoids present important biological functions, such as plant-environment interactions such as the attraction of pollinators and the defense against pathogens and herbivores. Also, include volatile aromatic compounds that act as repellents, chemoattractants, growth stimulators, and inhibitors, as well as the phytohormones abscisic acid and strigolactones [16]. Moreover, these isoprenoids are associated with other processes positively affecting human health were identified as responsible for inhibiting the lipid per-

Nonapocarotenoid carotenoid cleavage products include norcarotenoids, which lack one, two or three carbon atoms in the central hydrocarbons skeleton (C40) [3]. The primary determinant is the number of carbon atoms formally lost from the C40 carotenoid skeleton [5]. An example is the peridinin, is one of the most complex carotenoids, a C37-norcarotenoid possessing (Z)-γ-ylidenebutenolide and allene functions. In addition, it has five chiral centers,

Another subclass is that of secocarotenoids, in which a bond between two adjacent carbon atoms except between C(I) and C(6) in a ring has been broken [3, 5]. The semi-β-carotenone

In addition, isoprenoid structures with more than 40 carbon atoms are also reported. The rare C50 carotenoids are synthesized by the addition of two dimethylallyl pyrophosphate (DMAPP) molecules to C(2) and C(2′) of the respective C40 carotenoid [21]. These compounds have been mainly isolated from *Halobacteria, Halococcus*, and *Pseudomonas strain* and *Actinomycetales* [22]. The first C50 carotenoid discovered, decaprenoxanthin, was isolated

As shown in **Figure 1**, structurally, carotenoids have different terminal groups, of which there are seven: ψ, β, γ, ε, φ, χ, and κ, which may constitute the ends of the principal polyene chain of the structure of these molecules. In general terms, the terminal rings β, γ, and ε rings are

Lycopene is the common precursor structure for the synthesis of cyclic and bicyclic carotenoids. Cyclization of this molecule is a branching point in carotenoid biosynthesis, where β-, γ- and ε-end groups are formed by proton loss from alternative positions in the

formed from ψ ends, whereas φ, χ, and κ rings are formed from β end groups [6, 24].

) is an example identified as the product of β-carotene (C40H56) oxidation in perman-

oxidation and prevention of cancer and other degenerative diseases [14, 17, 18].

oxidative cleavage of β-carotene [7].

apocarotenoids [15].

including an epoxide ring [19].

from *Flavobacterium dehydrogenans* [23].

(C40H56O6

ganate solutions [20].

However, it was in the early twentieth century that a milestone occurred in the history of carotenoids. The Russian botanist Tswett in 1906 took the first step in the chromatographic technique of separation of these pigments, which together with the introduction of mass spectrometry (MS) in 1965 and high-performance liquid chromatography (HPLC) in 1971 provided a great advance in research [1, 3]. From this and with the advent of chromatographic methods and refinements in spectroscopy, the isolation and identification of carotenoids expanded greatly.

According to the last compilation, approximately 1178 naturally occurring carotenoids have been reported with 700 source organisms [4].
