Names | |
---|---|
IUPAC name 2-Hydroxynonadecane-1,2,3-tricarboxylic acid | |
Other names Agaricic acid; Agaricin; 2-Hydroxy-1,2,3-nonadecanetricarboxylic acid | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.010.516 |
EC Number |
|
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C22H40O7 | |
Molar mass | 416.555 g·mol−1 |
Appearance | Powder [1] |
Density | 1.115g/cm3 |
Melting point | 138 °C (280 °F; 411 K) |
Boiling point | 509 °C (948 °F; 782 K)at 760 mmHg |
Insoluble | |
Acidity (pKa) | 2.93 |
Structure | |
Microcrystalline | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Agaric acid, also known as agaricin or 2-hydroxynonadecane-1,2,3-tricarboxylic acid, is an organic tricarboxylic acid (fatty acid) found in fungi, e.g. Laricifomes officinalis . Its molecular formula is C22H40O7.
Agaric acid, as any other fatty acid, has an amphipathic character. It means that it has both polar (hydroxyl groups) and nonpolar (hydrocarbon chain) sections, and therefore, it is not completely water-soluble. It is a tribasic acid, and therefore, it can donate up to 3 hydrogen ions to other bases in an acid-base reaction. Other examples of tribasic acids are phosphoric acid or citric acid. It is an odorless and tasteless acid, and we can also distinguish it by its white color. Its melting point at atmospheric pressure is 140 °C.
Agaric acid is a type of fatty acid that is composed by a long hydrocarbon chain ("tail") and three carboxylic acid groups at one end ("head"). The hydrocarbon chain has sixteen carbons and thirty four hydrogens.
This acid has microcrystalline properties, and therefore, forms small crystals that can not be seen through the naked eye, but are only visible with an optical microscope.
Agaric acid is used as an inhibitor of metabolism in several animal experiments. It is shown that this acid prevents the formation of C2 units from citrate and reduces the availability of citrate for the activation of acetyl-CoA carboxylase. Moreover, it has an important role in the metabolism of lipids, because it influences sterol synthesis.[ citation needed ]
Agaric acid induces the mitochondrial permeability transition by collaborating with adenine nucleotide translocase. [2] It facilitates the efflux of accumulated Ca2+, disrupts the potential of the membrane and causes mitochondrial lumps. All of these effects bet on membrane fluidity. It's thought that agaric acid activates the opening of membrane pores due to the union of citrate to ADP transporters.
However, a later research showed that N-ethylmaleimide inhibits carboxyatractyloside and agaric acid effects. It was found that this amine restricts the pore opening action of agaric acid, but it does not affect the constraint of ADP exchange by agaric acid. [3]
This section needs more medical references for verification or relies too heavily on primary sources . (July 2017) |
Agaric acid is used in medicine as an anhidrotic agent in order to stop excessive perspiration as it paralyses the nerve terminations in the human body's sweat glands.[ medical citation needed ] For example, it helps to avoid tuberculosis patients' frequent night sweats. In addition, when taken in doses from 5 to 15 grams, agaric acid produces vomiting in humans. In the past, agaric acid was used as an irritant, an antidiarrhoeal and a bronchial secretions reducer. [1]
Physicians use agaric acid, but it also can be used in many other subjects such as veterinary and biochemistry. In lower animals, this substance depresses the nervous, respiratory and circulatory systems. It has been used as a metabolic inhibitor at the cellular and subcellular level in scientific animal experiments. [4] Agaric acid has also been used as an alpha-glycerophosphate dehydrogenase inhibitor in Crithidia fasciculata , which is a species of parasitic protist.
Adenosine triphosphate (ATP) is an organic compound and hydrotrope that provides energy to drive many processes in living cells, such as muscle contraction, nerve impulse propagation, condensate dissolution, and chemical synthesis. Found in all known forms of life, ATP is often referred to as the "molecular unit of currency" of intracellular energy transfer. When consumed in metabolic processes, it converts either to adenosine diphosphate (ADP) or to adenosine monophosphate (AMP). it is a product of Cellular respiration, Other processes regenerate ATP so that the human body recycles its own body weight equivalent in ATP each day. It is also a precursor to DNA and RNA, and is used as a coenzyme.
A biological membrane, biomembrane or cell membrane is a selectively permeable membrane that separates cell from the external environment or creates intracellular compartments. Biological membranes, in the form of eukaryotic cell membranes, consist of a phospholipid bilayer with embedded, integral and peripheral proteins used in communication and transportation of chemicals and ions. The bulk of lipid in a cell membrane provides a fluid matrix for proteins to rotate and laterally diffuse for physiological functioning. Proteins are adapted to high membrane fluidity environment of lipid bilayer with the presence of an annular lipid shell, consisting of lipid molecules bound tightly to surface of integral membrane proteins. The cell membranes are different from the isolating tissues formed by layers of cells, such as mucous membranes, basement membranes, and serous membranes.
The citric acid cycle (CAC) – also known as the TCA cycle or the Krebs cycle – is a series of chemical reactions used by all aerobic organisms to release stored energy through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins. In addition, the cycle provides precursors of certain amino acids, as well as the reducing agent NADH, that are used in numerous other reactions. Its central importance to many biochemical pathways suggests that it was one of the earliest components of metabolism and may have originated abiogenically. Even though it is branded as a 'cycle', it is not necessary for metabolites to follow only one specific route; at least three segments of the citric acid cycle have been recognized.
Cellular respiration is a set of metabolic reactions and processes that take place in the cells of organisms to convert chemical energy from oxygen molecules or nutrients into adenosine triphosphate (ATP), and then release waste products. The reactions involved in respiration are catabolic reactions, which break large molecules into smaller ones, releasing energy because weak high-energy bonds, in particular in molecular oxygen, are replaced by stronger bonds in the products. Respiration is one of the key ways a cell releases chemical energy to fuel cellular activity. The overall reaction occurs in a series of biochemical steps, some of which are redox reactions. Although cellular respiration is technically a combustion reaction, it clearly does not resemble one when it occurs in a living cell because of the slow, controlled release of energy from the series of reactions.
| C23H38N7O17P3S |- | Molar mass | 809.57 g·mol−1 |- | Section3 = | Section4 = | Section5 = | Section6 = }} Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle (Krebs cycle) to be oxidized for energy production. Coenzyme A (CoASH or CoA) consists of a β-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3'-phosphorylated ADP. The acetyl group (indicated in blue in the structural diagram on the right) of acetyl-CoA is linked to the sulfhydryl substituent of the β-mercaptoethylamine group. This thioester linkage is a "high energy" bond, which is particularly reactive. Hydrolysis of the thioester bond is exergonic (−31.5 kJ/mol).
In the mitochondrion, the matrix is the space within the inner membrane. The word "matrix" stems from the fact that this space is viscous, compared to the relatively aqueous cytoplasm. The mitochondrial matrix contains the mitochondria's DNA, ribosomes, soluble enzymes, small organic molecules, nucleotide cofactors, and inorganic ions.[1] The enzymes in the matrix facilitate reactions responsible for the production of ATP, such as the citric acid cycle, oxidative phosphorylation, oxidation of pyruvate, and the beta oxidation of fatty acids.
Lipid emulsion or fat emulsion refers to an emulsion of lipid for human intravenous use. It is often referred to by the brand name of the most commonly used version, Intralipid, which is an emulsion of soy bean oil, egg phospholipids and glycerin, and is available in 10%, 20% and 30% concentrations. The 30% concentration is not approved for direct intravenous infusion, but should be mixed with amino acids and dextrose as part of a total nutrient admixture.
Cyclophilins (CYPs) are a family of proteins named after their ability to bind to ciclosporin, an immunosuppressant which is usually used to suppress rejection after internal organ transplants. They are found in all domains of life. These proteins have peptidyl prolyl isomerase activity, which catalyzes the isomerization of peptide bonds from trans form to cis form at proline residues and facilitates protein folding.
Ceramides are a family of waxy lipid molecules. A ceramide is composed of sphingosine and a fatty acid. Ceramides are found in high concentrations within the cell membrane of eukaryotic cells, since they are component lipids that make up sphingomyelin, one of the major lipids in the lipid bilayer. Contrary to previous assumptions that ceramides and other sphingolipids found in cell membrane were purely supporting structural elements, ceramide can participate in a variety of cellular signaling: examples include regulating differentiation, proliferation, and programmed cell death (PCD) of cells.
The inner mitochondrial membrane (IMM) is the mitochondrial membrane which separates the mitochondrial matrix from the intermembrane space.
The mitochondrial permeability transition pore is a protein that is formed in the inner membrane of the mitochondria under certain pathological conditions such as traumatic brain injury and stroke. Opening allows increase in the permeability of the mitochondrial membranes to molecules of less than 1500 Daltons in molecular weight. Induction of the permeability transition pore, mitochondrial membrane permeability transition, can lead to mitochondrial swelling and cell death through apoptosis or necrosis depending on the particular biological setting.
Bongkrek acid is a respiratory toxin produced in fermented coconut or corn contaminated by the bacterium Burkholderia gladioli pathovar cocovenenans.
Adenine nucleotide translocator (ANT), also known as the ADP/ATP translocase (ANT), ADP/ATP carrier protein (AAC) or mitochondrial ADP/ATP carrier, exchanges free ATP with free ADP across the inner mitochondrial membrane. ANT is the most abundant protein in the inner mitochondrial membrane and belongs to mitochondrial carrier family.
Mitochondrial carriers are proteins from solute carrier family 25 which transfer molecules across the membranes of the mitochondria. Mitochondrial carriers are also classified in the Transporter Classification Database. The Mitochondrial Carrier (MC) Superfamily has been expanded to include both the original Mitochondrial Carrier (MC) family and the Mitochondrial Inner/Outer Membrane Fusion (MMF) family.
Translocase is a general term for a protein that assists in moving another molecule, usually across a cell membrane. These enzymes catalyze the movement of ions or molecules across membranes or their separation within membranes. The reaction is designated as a transfer from “side 1” to “side 2” because the designations “in” and “out”, which had previously been used, can be ambiguous. Translocases are the most common secretion system in Gram positive bacteria.
ADP/ATP translocase 1, or adenine nucleotide translocator 1 (ANT1), is an enzyme that in humans is encoded by the SLC25A4 gene.
ADP/ATP translocase 4 (ANT4) is an enzyme that in humans is encoded by the SLC25A31 gene on chromosome 4. This enzyme inhibits apoptosis by catalyzing ADP/ATP exchange across the mitochondrial membranes and regulating membrane potential. In particular, ANT4 is essential to spermatogenesis, as it imports ATP into sperm mitochondria to support their development and survival. Outside this role, the SLC25AC31 gene has not been implicated in any human disease.
ADP/ATP translocase 3, also known as solute carrier family 25 member 6, is a protein that in humans is encoded by the SLC25A6 gene.
The cell membrane is a biological membrane that separates the interior of all cells from the outside environment which protects the cell from its environment. The cell membrane consists of a lipid bilayer, including cholesterols that sit between phospholipids to maintain their fluidity at various temperatures. The membrane also contains membrane proteins, including integral proteins that go across the membrane serving as membrane transporters, and peripheral proteins that loosely attach to the outer (peripheral) side of the cell membrane, acting as enzymes shaping the cell. The cell membrane controls the movement of substances in and out of cells and organelles. In this way, it is selectively permeable to ions and organic molecules. In addition, cell membranes are involved in a variety of cellular processes such as cell adhesion, ion conductivity and cell signalling and serve as the attachment surface for several extracellular structures, including the cell wall, the carbohydrate layer called the glycocalyx, and the intracellular network of protein fibers called the cytoskeleton. In the field of synthetic biology, cell membranes can be artificially reassembled.
ADP/ATP translocase 2 is a protein that in humans is encoded by the SLC25A5 gene on the X chromosome.