Monolignol
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Monolignol
Monolignols, also called lignols, are the source materials for biosynthesis of both lignans and lignin and consist mainly of paracoumaryl alcohol (H), coniferyl alcohol (G) and sinapyl alcohol (S). These monolignols differ in their degree of methoxilation of the aromatic ring. The monolignols are derived from the amino acid phenylalanine via the phenylpropanoid pathway involving various enzymes. Phenylalanine is first converted to paracoumaryl alcohol (H), which is subsequently elaborated to coniferyl alcohol (G) and sinapyl alcohol (S). This reaction happens in the cytosol, while the polymerization of the monolignols occurs in the apoplast to which the monolignols have to be transported to though the cell membrane. The monolignols have been found as monolignol-4-O-β-d-glucosides, which might be their major way of storage. Another theory for this conversion is that is improving the transportation of the monolignols. The polymerization consists of oxidative coupling reactions, ...
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Monolignols
Monolignols, also called lignols, are the source materials for biosynthesis of both lignans and lignin and consist mainly of paracoumaryl alcohol (H), coniferyl alcohol (G) and sinapyl alcohol (S). These monolignols differ in their degree of methoxilation of the aromatic ring. The monolignols are derived from the amino acid phenylalanine via the phenylpropanoid pathway involving various enzymes. Phenylalanine is first converted to paracoumaryl alcohol (H), which is subsequently elaborated to coniferyl alcohol (G) and sinapyl alcohol (S). This reaction happens in the cytosol, while the polymerization of the monolignols occurs in the apoplast to which the monolignols have to be transported to though the cell membrane. The monolignols have been found as monolignol-4-O-β-d-glucosides, which might be their major way of storage. Another theory for this conversion is that is improving the transportation of the monolignols. The polymerization consists of oxidative coupling reactions, whic ...
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Lignin
Lignin is a class of complex organic polymers that form key structural materials in the support tissues of most plants. Lignins are particularly important in the formation of cell walls, especially in wood and bark, because they lend rigidity and do not rot easily. Chemically, lignins are polymers made by cross-linking phenolic precursors. History Lignin was first mentioned in 1813 by the Swiss botanist A. P. de Candolle, who described it as a fibrous, tasteless material, insoluble in water and alcohol but soluble in weak alkaline solutions, and which can be precipitated from solution using acid. He named the substance “lignine”, which is derived from the Latin word '' lignum'', meaning wood. It is one of the most abundant organic polymers on Earth, exceeded only by cellulose. Lignin constitutes 30% of non-fossil organic carbon on Earth, and 20 to 35% of the dry mass of wood. Lignin is present in red algae, which suggest that the common ancestor of plants and red algae ...
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Phenylpropanoid
The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. 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 (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid. Phenylpropanoids are found throughout the plant kingdom, where they serve as essential components of a number of structural polymers, provide protection from ultraviolet light, defend against herbivores and pathogens, and also mediate plant-pollinator interactions as floral pigments and scent compounds. Hydroxycinnamic acids Phenylalanine is first converted to cinnamic aci ...
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Coniferyl Alcohol
Coniferyl alcohol is an organic compound with the formula HO(CH3O)C6H3CH=CHCH2OH. A colourless or white solid, it is one of the monolignols, produced via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. Coniferin is a glucoside of coniferyl alcohol. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin. Gum benzoin contains significant amount of coniferyl alcohol and its esters. It is found in both gymnosperm and angiosperm plants. Sinapyl alcohol and paracoumaryl alcohol, the other two lignin monomers, are found in angiosperm plants and grasses. Occurrence Coniferyl alcohol is produced from coniferyl aldehyde by the action of dehydrogenase enzymes. It is a queen retinue pheromone (QRP), a type of honey bee pheromone found in the mandibular glands. In ''Forsythia intermedia'' a dirigent protein was found to direct the stereoselective biosynthesis of (+ ...
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Lignans
The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a role as antifeedants in the defense of seeds and plants against herbivores. Biosynthesis and metabolism Lignans and lignin differ in their molecular weight, the former being small and soluble in water, the latter being high polymers that are undigestable. Both are polyphenolic substances derived by oxidative coupling of monolignols. Thus, most lignans feature a C18 cores, resulting from the dimerization of C9 precursors. The coupling of the lignols occurs at C8. Eight classes of lignans are: "furofuran, furan, dibenzylbutane, dibenzylbutyrolactone, aryltetralin, arylnaphthalene, dibenzocyclooctadiene, and dibenzylbutyrolactol." Many lignans are metabolized by mammalian gut microflora, producing so-called enterolignans. Food sources Flax se ...
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Paracoumaryl Alcohol
Paracoumaryl alcohol is a phytochemical, one of the monolignols. It is a white solid. ''p''-Coumaryl alcohol is a major precursor to lignin or lignans. Biosynthesis and occurrence It is synthesized via the phenylpropanoid biochemical pathway. Esters of ''p''-coumaryl alcohol and fatty acids are the basis of epicuticular waxes covering the surfaces of apples. p-Coumaryl alcohol is an intermediate in biosynthesis of chavicol, stilbenoids, and coumarin Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain , forming a second six-membered h .... External links Molecule of the week: p-coumaryl alcohol References {{Monolignols Monolignols ...
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Sinapyl Alcohol
Sinapyl alcohol is an organic compound structurally related to cinnamic acid. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. This phytochemical is one of the monolignols, which are precursor to lignin or lignans. It is also a biosynthetic precursor to various stilbenoids and coumarins. See also *Sinapinic acid *Syringol *Syringaldehyde *Syringic acid *Acetosyringone *Sinapine *Canolol *Phenolic content in wine The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include ... References {{DEFAULTSORT:Sinapyl Alcohol Monolignols Ethers ...
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Amino Acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha amino acids appear in the genetic code. Amino acids can be classified according to the locations of the core structural functional groups, as Alpha and beta carbon, alpha- , beta- , gamma- or delta- amino acids; other categories relate to Chemical polarity, polarity, ionization, and side chain group type (aliphatic, Open-chain compound, acyclic, aromatic, containing hydroxyl or sulfur, etc.). In the form of proteins, amino acid '' residues'' form the second-largest component (water being the largest) of human muscles and other tissues. Beyond their role as residues in proteins, amino acids participate in a number of processes such as neurotransmitter transport and biosynthesis. It is thought that they played a key role in enabling life ...
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Phenylalanine
Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino acid is classified as neutral, and nonpolar because of the inert and hydrophobic nature of the benzyl side chain. The L-isomer is used to biochemically form proteins coded for by DNA. Phenylalanine is a precursor for tyrosine, the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), and the skin pigment melanin. It is encoded by the codons UUU and UUC. Phenylalanine is found naturally in the milk of mammals. It is used in the manufacture of food and drink products and sold as a nutritional supplement for its analgesic and antidepressant effects. It is a direct precursor to the neuromodulator phenethylamine, a commonly used dietary supplement. As an essential amino acid, phenylalanine is n ...
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Biosynthesis
Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. This process often consists of metabolic pathways. Some of these biosynthetic pathways are located within a single cellular organelle, while others involve enzymes that are located within multiple cellular organelles. Examples of these biosynthetic pathways include the production of lipid membrane components and nucleotides. Biosynthesis is usually synonymous with anabolism. The prerequisite elements for biosynthesis include: precursor compounds, chemical energy (e.g. ATP), and catalytic enzymes which may require coenzymes (e.g.NADH, NADPH). These elements create monomers, the building blocks for macromolecules. Some important biological macromolecules include: proteins, which are composed of amino acid monomers joined via peptide bon ...
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Cytosol
The cytosol, also known as cytoplasmic matrix or groundplasm, is one of the liquids found inside cells (intracellular fluid (ICF)). It is separated into compartments by membranes. For example, the mitochondrial matrix separates the mitochondrion into many compartments. In the eukaryotic cell, the cytosol is surrounded by the cell membrane and is part of the cytoplasm, which also comprises the mitochondria, plastids, and other organelles (but not their internal fluids and structures); the cell nucleus is separate. The cytosol is thus a liquid matrix around the organelles. In prokaryotes, most of the chemical reactions of metabolism take place in the cytosol, while a few take place in membranes or in the periplasmic space. In eukaryotes, while many metabolic pathways still occur in the cytosol, others take place within organelles. The cytosol is a complex mixture of substances dissolved in water. Although water forms the large majority of the cytosol, its structure and prope ...
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Apoplast
Inside a plant, the apoplast can mean the space outside of cell membranes, where material can diffuse freely; that is, the extracellular spaces. ''Apoplast '' can also refer especially to the continuum of cell walls of adjacent cells; fluid and material flows occurring there or in any extacellular space are called ''apoplastic'' flow or apoplastic transport. The apoplastic route is one way by which water and solutes are transported and distributed to different places through tissues and organs; another way is symplastic flow. To prevent uncontrolled leakage to unwanted places, in certain areas there are barriers to the apoplastic flow: in roots the Casparian strip has this function larification needed On the outside of the skin of certain plant parts is a protective waxy film called plant cuticle to achieve this (protection against e.g. drying out, but also waterproofing against soaking). Air bubbles occupying extracellular spaces can also hinder apoplastic transport. The a ...
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