Cutin is one of two waxy polymers that are the main components of the plant cuticle, which covers all aerial surfaces of plants, the other being cutan. It is an insoluble substance with waterproof quality. Cutin also harbors cuticular waxes, which assist in cuticle structure. [1] Cutan, the other major cuticle polymer, is much more readily preserved in fossil records. [2] Cutin consists of omega hydroxy acids and their derivatives, which are interlinked via ester bonds, forming a polyester polymer of indeterminate size.
There are two major monomer families of cutin, the C16 and C18 families. The C16 family consists mainly of 16-hydroxy palmitic acid and 9,16- or 10,16-dihydroxypalmitic acid. The C18 family consists mainly of 18-hydroxy oleic acid, 9,10-epoxy-18-hydroxy stearic acid, and 9,10,18-trihydroxystearate. [3]
Biopolymers are natural polymers produced by the cells of living organisms. Like other polymers, biopolymers consist of monomeric units that are covalently bonded in chains to form larger molecules. There are three main classes of biopolymers, classified according to the monomers used and the structure of the biopolymer formed: polynucleotides, polypeptides, and polysaccharides. The Polynucleotides, RNA and DNA, are long polymers of nucleotides. Polypeptides include proteins and shorter polymers of amino acids; some major examples include collagen, actin, and fibrin. Polysaccharides are linear or branched chains of sugar carbohydrates; examples include starch, cellulose, and alginate. Other examples of biopolymers include natural rubbers, suberin and lignin, cutin and cutan, melanin, and polyhydroxyalkanoates (PHAs).
A cell wall is a structural layer that surrounds some cell types, found immediately outside the cell membrane. It can be tough, flexible, and sometimes rigid. Primarily, it provides the cell with structural support, shape, protection, and functions as a selective barrier. Another vital role of the cell wall is to help the cell withstand osmotic pressure and mechanical stress. While absent in many eukaryotes, including animals, cell walls are prevalent in other organisms such as fungi, algae and plants, and are commonly found in most prokaryotes, with the exception of mollicute bacteria.
Plant cells are the cells present in green plants, photosynthetic eukaryotes of the kingdom Plantae. Their distinctive features include primary cell walls containing cellulose, hemicelluloses and pectin, the presence of plastids with the capability to perform photosynthesis and store starch, a large vacuole that regulates turgor pressure, the absence of flagella or centrioles, except in the gametes, and a unique method of cell division involving the formation of a cell plate or phragmoplast that separates the new daughter cells.
Waxes are a diverse class of organic compounds that are lipophilic, malleable solids near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting to give low viscosity liquids. Waxes are insoluble in water but soluble in nonpolar organic solvents such as hexane, benzene and chloroform. Natural waxes of different types are produced by plants and animals and occur in petroleum.
Tallow is a rendered form of beef or mutton suet, primarily made up of triglycerides.
Suberin is a lipophilic, complex polyester biopolymer of plants, composed of long-chain fatty acids called suberin acids and glycerol. Suberin, interconnected with cutins and lignins, also complex macromolecules, form a protective barrier in the epidermal and peridermal cell walls of higher plants. Suberins and lignins are considered covalently linked to lipids and carbohydrates, respectively, and lignin is covalently linked to suberin, and to a lesser extent, to cutin. Suberin is a major constituent of cork, and is named after the cork oak, Quercus suber. Its main function is as a barrier to movement of water and solutes.
Fatty alcohols (or long-chain alcohols) are usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils. The precise chain length varies with the source. Some commercially important fatty alcohols are lauryl, stearyl, and oleyl alcohols. They are colourless oily liquids (for smaller carbon numbers) or waxy solids, although impure samples may appear yellow. Fatty alcohols usually have an even number of carbon atoms and a single alcohol group (–OH) attached to the terminal carbon. Some are unsaturated and some are branched. They are widely used in industry. As with fatty acids, they are often referred to generically by the number of carbon atoms in the molecule, such as "a C12 alcohol", that is an alcohol having 12 carbons, for example dodecanol.
Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes in eukaryotic cells. They are a type of lipid, of which its composition affects membrane structure and properties. Two major classes are known: those for bacteria and eukaryotes and a separate family for archaea.
In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups. The general molecular formula for dicarboxylic acids can be written as HO2C−R−CO2H, where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids.
Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.
Alpha hydroxy carboxylic acids, or α-hydroxy carboxylic acids (AHAs), are a group of carboxylic acids featuring a hydroxy group located one carbon atom away from the acid group. This structural aspect distinguishes them from beta hydroxy acids, where the functional groups are separated by two carbon atoms. Notable AHAs include glycolic acid, lactic acid, mandelic acid, and citric acid.
The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid.
Epicuticular wax is a waxy coating which covers the outer surface of the plant cuticle in land plants. It may form a whitish film or bloom on leaves, fruits and other plant organs. Chemically, it consists of hydrophobic organic compounds, mainly straight-chain aliphatic hydrocarbons with or without a variety of substituted functional groups. The main functions of the epicuticular wax are to decrease surface wetting and moisture loss. Other functions include reflection of ultraviolet light, assisting in the formation of an ultra-hydrophobic and self-cleaning surface and acting as an anti-climb surface.
A plant cuticle is a protecting film covering the outermost skin layer (epidermis) of leaves, young shoots and other aerial plant organs that have no periderm. The film consists of lipid and hydrocarbon polymers infused with wax, and is synthesized exclusively by the epidermal cells.
Cutan is one of two waxy biopolymers which occur in the cuticle of some plants. The other and better-known polymer is cutin. Cutan is believed to be a hydrocarbon polymer, whereas cutin is a polyester, but the structure and synthesis of cutan are not yet fully understood. Cutan is not present in as many plants as once thought; for instance it is absent in Ginkgo.
The enzyme cutinase is a member of the hydrolase family. It catalyzes the following reaction:
A cuticle, or cuticula, is any of a variety of tough but flexible, non-mineral outer coverings of an organism, or parts of an organism, that provide protection. Various types of "cuticle" are non-homologous, differing in their origin, structure, function, and chemical composition.
Omega hydroxy acids are a class of naturally occurring straight-chain aliphatic organic acids n carbon atoms long with a carboxyl group at position 1, and a hydroxyl at terminal position n where n > 3. They are a subclass of hydroxycarboxylic acids. The C16 and C18 omega hydroxy acids 16-hydroxy palmitic acid and 18-hydroxy stearic acid are key monomers of cutin in the plant cuticle. The polymer cutin is formed by interesterification of omega hydroxy acids and derivatives of them that are substituted in mid-chain, such as 10,16-dihydroxy palmitic acid. Only the epidermal cells of plants synthesize cutin.
Most fossils represent mineralized material such as bone or shells. However, biopolymers such as chitin and collagen can sometimes leave fossils – most famously in Burgess Shale type preservation and palynomorphs. The preservation of soft tissue is not as rare as sometimes thought.
Juniperic acid or 16-hydroxyhexadecanoic acid is an omega-hydroxy long-chain fatty acid that is palmitic acid which is substituted at position 16 by a hydroxy group. Palmitic acid is converted to juniperic acid by cytochrome P450 various enzymes, including CYP704B22.