![]() Chemical structure of amarogentin | |
![]() Chemical structure of amarogentin | |
Names | |
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IUPAC name (4aS,5R,6S)-5-Ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl β-D-glucopyranoside 2-(3,3′,5-trihydroxy[1,1′-biphenyl]-2-carboxylate) | |
Systematic IUPAC name (2S,3R,4S,5S,6R)-2-{[(4aS,5R,6S)-5-Ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,3′,5-trihydroxy[1,1′-biphenyl]-2-carboxylate | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.166.688 |
PubChem CID | |
UNII | |
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Properties | |
C29H30O13 | |
Molar mass | 586.546 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Amarogentin is a chemical compound found in gentian ( Gentiana lutea ) or in Swertia chirata . [1]
Gentian root has a long history of use as a herbal bitter in the treatment of digestive disorders and is an ingredient of many proprietary medicines. The bitter principles of gentian root are secoiridoid glycosides amarogentin and gentiopicrin. The former is one of the most bitter natural compounds known [2] and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter taste receptor TAS2R50. [3] The biphenylcarboxylic acid moiety is biosynthesized by a polyketide-type pathway, with three units of acetyl-CoA and one unit of 3-hydroxybenzoyl-CoA, this being formed from an early shikimate pathway intermediate and not via cinnamic or benzoic acid. [4]
It also shows an antileishmanial activity in animal models [5] being an inhibitor of topoisomerase I. [6]
Gentiana is a genus of flowering plants belonging to the gentian family (Gentianaceae), the tribe Gentianeae, and the monophyletic subtribe Gentianinae. With about 400 species, it is considered a large genus. Gentians are notable for their mostly large trumpet-shaped flowers, which are often of an intense blue hue.
Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable. In addition to sugars like sucrose, many other chemical compounds are sweet, including aldehydes, ketones, and sugar alcohols. Some are sweet at very low concentrations, allowing their use as non-caloric sugar substitutes. Such non-sugar sweeteners include saccharin and aspartame. Other compounds, such as miraculin, may alter perception of sweetness itself.
Aftertaste is the taste intensity of a food or beverage that is perceived immediately after that food or beverage is removed from the mouth. The aftertastes of different foods and beverages can vary by intensity and over time, but the unifying feature of aftertaste is that it is perceived after a food or beverage is either swallowed or spat out. The neurobiological mechanisms of taste signal transduction from the taste receptors in the mouth to the brain have not yet been fully understood. However, the primary taste processing area located in the insula has been observed to be involved in aftertaste perception.
Gentiana lutea, the great yellow gentian, is a species of gentian native to the mountains of central and southern Europe.
TAS2R16 is a bitter taste receptor and one of the 25 TAS2Rs. TAS2Rs are receptors that belong to the G-protein-coupled receptors (GPCRs) family. These receptors detect various bitter substances found in nature as agonists, and get stimulated. TAS2R16 receptor is mainly expressed within taste buds present on the surface of the tongue and palate epithelium. TAS2R16 is activated by bitter β-glucopyranosides
Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen.
Oenanthotoxin is a toxin extracted from hemlock water-dropwort and other plants of the genus Oenanthe. It is a central nervous system poison, and acts as a noncompetitive antagonist of the neurotransmitter gamma-aminobutyric acid. A case has been made for the presence of this toxin in local Oenanthe species playing a causative role in euthanasia in ancient Sardinia. It was crystallized in 1949 by Clarke and co-workers. It is structurally closely related to the toxins cicutoxin and carotatoxin. Oenanthotoxin is a C17 polyacetylene isomer of cicutoxin.
A taste receptor or tastant is a type of cellular receptor which facilitates the sensation of taste. When food or other substances enter the mouth, molecules interact with saliva and are bound to taste receptors in the oral cavity and other locations. Molecules which give a sensation of taste are considered "sapid".
Gi protein alpha subunit is a family of heterotrimeric G protein alpha subunits. This family is also commonly called the Gi/o family or Gi/o/z/t family to include closely related family members. G alpha subunits may be referred to as Gi alpha, Gαi, or Giα.
Swertia is a genus in the gentian family containing plants sometimes referred to as the felworts. Some species bear very showy purple and blue flowers. Many members of this genus have medicinal and cultural purposes.
Transient receptor potential cation channel subfamily M member 5 (TRPM5), also known as long transient receptor potential channel 5 is a protein that in humans is encoded by the TRPM5 gene.
Free fatty acid receptor 1 (FFAR1), also known as G-protein coupled receptor 40 (GPR40), is a rhodopsin-like G-protein coupled receptor that is coded by the FFAR1 gene. This gene is located on the short arm of chromosome 19 at position 13.12. G protein-coupled receptors reside on their parent cells' surface membranes, bind any one of the specific set of ligands that they recognize, and thereby are activated to trigger certain responses in their parent cells. FFAR1 is a member of a small family of structurally and functionally related GPRs termed free fatty acid receptors (FFARs). This family includes at least three other FFARs viz., FFAR2, FFAR3, and FFAR4. FFARs bind and thereby are activated by certain fatty acids.
Taste receptor type 2 member 10 is a protein that in humans is encoded by the TAS2R10 gene. The protein is responsible for bitter taste recognition in mammals. It serves as a defense mechanism to prevent consumption of toxic substances which often have a characteristic bitter taste.
Taste receptor type 2 member 14 is a protein that in humans is encoded by the TAS2R14 gene.
T1R2 - Taste receptor type 1 member 2 is a protein that in humans is encoded by the TAS1R2 gene.
Taste receptor type 2 member 50 is a protein that in humans is encoded by the TAS2R50 gene.
The gustatory system or sense of taste is the sensory system that is partially responsible for the perception of taste (flavor). Taste is the perception stimulated when a substance in the mouth reacts chemically with taste receptor cells located on taste buds in the oral cavity, mostly on the tongue. Taste, along with the sense of smell and trigeminal nerve stimulation, determines flavors of food and other substances. Humans have taste receptors on taste buds and other areas, including the upper surface of the tongue and the epiglottis. The gustatory cortex is responsible for the perception of taste.
Aurintricarboxylic acid (ATA) is a chemical compound that readily polymerizes in aqueous solution, forming a stable free radical that inhibits protein-nucleic acid interactions. It is a potent inhibitor of ribonuclease and topoisomerase II by preventing the binding of the nucleic acid to the enzyme. It stimulates tyrosine phosphorylation processes including the Jak2/STAT5 pathway in NB2 lymphoma cells, ErbB4 in neuroblastoma cells, and MAP kinases, Shc proteins, phosphatidylinositide 3-kinase and phospholipase Cγ in PC12 cells. It also inhibits apoptosis. It prevents down-regulation of Ca2+-impermeable GluR2 receptors and inhibits calpain, a Ca2+-activated protease that is activated during apoptosis.
Deacetylasperulosidic acid is an iridoid compound found in a few medicinal plants, such as Morinda citrifolia. Some in vitro and in vivo bioactivities of deacetylasperulosidic acid include anti-inflammatory, analgesic, anti-cancer, antioxidant, anti-arthritic, anti-mutagenic, anti-clastogenic, and hepatoprotection.
Forsythoside B is a natural product from the phenylpropanoid glycoside group, which is found in a number of plant species such as Marrubium alysson, Phlomis armeniaca, Scutellaria salviifolia, Phlomoides tuberosa, Phlomoides rotata, Pedicularis longiflora and Teucrium chamaedrys, several of which are used in Chinese traditional medicine in preparations such as Shuanghuanglian (双黄连). It acts as an inhibitor of inflammatory mediators such as TNF-alpha, IL-6, IκB and NF-κB, as well as the temperature sensitive channel TRPV3, but also activates the RhoA/ROCK signaling pathway which can cause hypersensitivity reactions when it is injected intravenously.