Kukoamines

Last updated
Kukoamine A [1]
Kukoamine A Structure.svg
Kukoamines structure 3d.png
Names
Preferred IUPAC name
3-(3,4-Dihydroxyphenyl)-N-[3-[4-[3-[3-(3,4-dihydroxyphenyl)propanoylamino]propylamino]butylamino]propyl]propanamide
Other names
N(1),N(12)-bis(dihydrocaffeoyl)spermine
AC1NSXD9
BDBM50240622
DNC013917
C17615
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C28H42N4O6/c33-23-9-5-21(19-25(23)35)7-11-27(37)31-17-3-15-29-13-1-2-14-30-16-4-18-32-28(38)12-8-22-6-10-24(34)26(36)20-22/h5-6,9-10,19-20,29-30,33-36H,1-4,7-8,11-18H2,(H,31,37)(H,32,38)
    Key: IOLDDENZPBFBHV-UHFFFAOYSA-N
  • C1=CC(=C(C=C1CCC(=O)NCCCNCCCCNCCCNC(=O)CCC2=CC(=C(C=C2)O)O)O)O
Properties
C28H42N4O6
Molar mass 530.666 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Kukoamines are chemicals that are present in some plants including Lycium chinense , potatoes, and tomatoes. [2] [3] [4] The most prevalent example is kukoamine A; others include kukoamine B, C, and D. [5] [6] [7]

Chemically, kukoamines are catechols and also dihydrocaffeic acid derivatives of polyamines. [4]

Related Research Articles

Salicylic acid Chemical compound used in medicines and industry

Salicylic acid is an organic compound with the formula HOC6H4CO2H. A colorless, bitter-tasting solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone, and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen. The name is from Latin salix for willow tree. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.

Salvinorin A Chemical compound

Salvinorin A is the main active psychotropic molecule in Salvia divinorum. Salvinorin A is considered a dissociative hallucinogen.

Pyrethrin Class of organic chemical compounds with insecticidal properties

The pyrethrins are a class of organic compounds normally derived from Chrysanthemum cinerariifolium that have potent insecticidal activity by targeting the nervous systems of insects. Pyrethrin naturally occurs in chrysanthemum flowers and is often considered an organic insecticide when it is not combined with piperonyl butoxide or other synthetic adjuvants. Their insecticidal and insect-repellent properties have been known and used for thousands of years.

Agmatine, also known as (4-aminobutyl)guanidine, is an aminoguanidine that was discovered in 1910 by Albrecht Kossel. Agmatine is a chemical substance which is naturally created from the amino acid arginine. Agmatine has been shown to exert modulatory action at multiple molecular targets, notably: neurotransmitter systems, ion channels, nitric oxide (NO) synthesis and polyamine metabolism and this provides bases for further research into potential applications.

Chemical space

Chemical space is a concept in cheminformatics referring to the property space spanned by all possible molecules and chemical compounds adhering to a given set of construction principles and boundary conditions. It contains millions of compounds which are readily accessible and available to researchers. It is a library used in the method of molecular docking.

Aldicarb Chemical compound (insecticide)

Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide. Aldicarb is a cholinesterase inhibitor which prevents the breakdown of acetylcholine in the synapse. In case of severe poisoning, the victim dies of respiratory failure.

Spermine is a polyamine involved in cellular metabolism that is found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. It is an essential growth factor in some bacteria as well. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, particularly in viruses.

A triazole is a heterocyclic compound featuring a five-membered ring of two carbon atoms and three nitrogen atoms with molecular formula C2H3N3. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within the ring.

Limonin Chemical compound

Limonin is a limonoid, and a bitter, white, crystalline substance found in citrus and other plants. It is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as furanolactones.

Adenosine A<sub>2B</sub> receptor Protein-coding gene in the species Homo sapiens

The adenosine A2B receptor, also known as ADORA2B, is a G-protein coupled adenosine receptor, and also denotes the human adenosine A2b receptor gene which encodes it.

PAOX

Peroxisomal N(1)-acetyl-spermine/spermidine oxidase is an enzyme that in humans is encoded by the PAOX gene.

7-OH-DPAT Chemical compound

7-OH-DPAT is a synthetic compound that acts as a dopamine receptor agonist with reasonable selectivity for the D3 receptor subtype, and low affinity for serotonin receptors, unlike its structural isomer 8-OH-DPAT. 7-OH-DPAT is self-administered in several animal models, and is used to study addiction to cocaine.

<i>Quercus infectoria</i> Species of oak tree

Quercus infectoria or the Aleppo oak is a species of oak well known for producing galls that have been traditionally used for centuries in Asia medicinally while also used in softening leather and in making black dye and ink.

Momordin is one of several saponins derived from oleanolic acid, a triterpenoid. These chemical compounds are found in some plants of the genus Momordica, which includes the bitter melon and the balsam apple, as well as in other Asian herbal medicine plants such as Kochia scoparia and Ampelopsis radix.

A polyamine is an organic compound having more than two amino groups. Alkyl polyamines occur naturally, but some are synthetic. Alkylpolyamines are colorless, hygroscopic, and water soluble. Near neutral pH, they exist as the ammonium derivatives. Most aromatic polyamines are crystalline solids at room temperature.

Sibiricine Chemical compound

Sibiricine is a bioactive isoquinoline alkaloid isolated from Corydalis crispa (Fumariaceae), which is a Bhutanese medicinal plant from the Himalayas.

Nyasol Chemical compound

Nyasol, also known as cis-hinokiresinol or as (Z)-hinokiresinol, is a lignan that is found in Anemarrhena asphodeloides. It has estrogenic activity, acting as a selective agonist of the ERβ, and hence is a phytoestrogen. In addition, (-)-nyasol has been found to inhibit the production of eicosanoids and nitric oxide in vitro and shows anti-inflammatory effects.

Apparicine Chemical compound

Apparicine is a monoterpenoid indole alkaloid. It is named after Apparicio Duarte, a Brazilian botanist who studied the Aspidosperma species from which apparicine was first isolated. It was the first member of the vallesamine group of alkaloids to be isolated and have its structure established, which was first published in 1965. It has also been known by the synonyms gomezine, pericalline, and tabernoschizine.

Cannabidiolic acid Chemical compound

Cannabidiolic acid (CBDA), is a cannabinoid found in cannabis plants. It is most abundant in the glandular trichomes on the female seedless flowers or more accurately infructescence often colloquially referred to as buds. CBDA is the chemical precursor to cannabidiol (CBD). Through the process of decarboxylation cannabidol is derived via a loss of a carbon and two oxygen atoms from the 1 position of the benzoic acid ring.

References

  1. CID 5318865 from PubChem
  2. Lim, T. K. (2016-02-11). Edible Medicinal and Non-Medicinal Plants: Volume 12 Modified Stems, Roots, Bulbs. Springer. ISBN   9783319260655.
  3. "Kukoamines Found in Potatoes". cabi.org. Retrieved 2017-04-07.
  4. 1 2 Parr, Adrian J.; Mellon, Fred A.; Colquhoun, Ian J.; Davies, Howard V. (2005). "Dihydrocaffeoyl Polyamines (Kukoamine and Allies) in Potato (Solanum tuberosum) Tubers Detected during Metabolite Profiling". Journal of Agricultural and Food Chemistry. 53 (13): 5461–6. doi:10.1021/jf050298i. PMID   15969534.
  5. CID 10346914 from PubChem , entry for kukoamine B
  6. CID 10052730 from PubChem , entry for kukoamine C
  7. CID 10075692 from PubChem , entry for kukoamine D