Carotenoids () are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, archaea, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Over 1,100 identified carotenoids can be further categorized into two classes xanthophylls (which contain oxygen) and carotenes (which are purely hydrocarbons and contain no oxygen).
All are derivatives of tetraterpenes, meaning that they are produced from 8 isoprene units and contain 40 carbon atoms. In general, carotenoids absorb wavelengths ranging from 400 to 550 nanometers (violet to green light). This causes the compounds to be deeply colored yellow, orange, or red. Carotenoids are the dominant pigment in autumn leaf coloration of about 15-30% of tree species, but many plant colors, especially reds and purples, are due to polyphenols.
Carotenoids serve two key roles in plants and algae: they absorb light energy for use in photosynthesis, and they provide photoprotection via non-photochemical quenching. Carotenoids that contain unsubstituted beta-ionone rings (including β-carotene, α-carotene, β-cryptoxanthin, and γ-carotene) have vitamin A activity (meaning that they can be converted to retinol). In the eye, lutein, meso-zeaxanthin, and zeaxanthin are present as macular pigments whose importance in visual function, as of 2016, remains under clinical research.
Structure and function
Carotenoids are produced by all photosynthetic organisms and are primarily used as accessory pigments to chlorophyll in the light-harvesting part of photosynthesis.
They are highly unsaturated with conjugated double bonds, which enables carotenoids to absorb light of various wavelengths. At the same time, the terminal groups regulate the polarity and properties within lipid membranes.
Most carotenoids are tetraterpenoids, regular C40 isoprenoids. Several modifications to these structures exist: including cyclization, varying degrees of saturation or unsaturation, and other functional groups. Carotenes typically contain only carbon and hydrogen, i.e., they are hydrocarbons. Prominent members include α-carotene, β-carotene, and lycopene, are known as carotenes. Carotenoids containing oxygen include lutein and zeaxanthin. They are known as xanthophylls. Their color, ranging from pale yellow through bright orange to deep red, is directly related to their structure, especially the length of the conjugation. Xanthophylls are often yellow, giving their class name.
Carotenoids also participate in different types of cell signaling. They are able to signal the production of abscisic acid, which regulates plant growth, seed dormancy, embryo maturation and germination, cell division and elongation, floral growth, and stress responses.
Photophysics
The length of the multiple conjugated double bonds determines their color and photophysics. After absorbing a photon, the carotenoid transfers its excited electron to chlorophyll for use in photosynthesis. Upon absorption of light, carotenoids transfer excitation energy to and from chlorophyll. The singlet-singlet energy transfer is a lower energy state transfer and is used during photosynthesis. The triplet-triplet transfer is a higher energy state and is essential in photoprotection. Light produces damaging species during photosynthesis, with the most damaging being reactive oxygen species (ROS). As these high energy ROS are produced in the chlorophyll the energy is transferred to the carotenoid’s polyene tail and undergoes a series of reactions in which electrons are moved between the carotenoid bonds in order to find the most balanced (lowest energy) state for the carotenoid.
Carotenoids defend plants against singlet oxygen, by both energy transfer and by chemical reactions. They also protect plants by quenching triplet chlorophyll. By protecting lipids from free-radical damage, which generate charged lipid peroxides and other oxidised derivatives, carotenoids support crystalline architecture and hydrophobicity of lipoproteins and cellular lipid structures, hence oxygen solubility and its diffusion therein.
Structure-property relationships
Like some fatty acids, carotenoids are lipophilic due to the presence of long unsaturated aliphatic chains. As a consequence, carotenoids are typically present in plasma lipoproteins and cellular lipid structures.
Morphology
Carotenoids are located primarily outside the cell nucleus in different cytoplasm organelles, lipid droplets, cytosomes and granules. They have been visualised and quantified by raman spectroscopy in an algal cell.