Vomilenine

Last updated
Vomilenine
Vomilenine.svg
Names
IUPAC name
[(1R,10S,12R,13E,14R,16S,18R)-13-Ethylidene-14-hydroxy-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6,8-tetraen-18-yl] acetate
Other names
21α-Hydroxy-22-norajmala-1,19-dien-17α-yl acetate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • C/C=C/1\[C@@H]2C[C@H]3C4=NC5=CC=CC=C5[C@]46C[C@@H](C2[C@H]6OC(=O)C)N3[C@@H]1O
Properties
C21H22N2O3
Molar mass 350.418 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vomilenine is an alkaloid that is an intermediate chemical in the biosynthesis of ajmaline. [1]

Related Research Articles

Alkaloid Class of naturally occurring chemical compounds

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.

<i>Rauvolfia serpentina</i>

Rauvolfia serpentina, the Indian snakeroot, devil pepper, or serpentine wood, is a species of flower in the milkweed family Apocynaceae. It is native to the Indian subcontinent and East Asia.

Dihydrobenzophenanthridine oxidase is an enzyme. In the IUBMB Enzyme Nomenclature, dihydrobenzophenanthridine oxidase is EC 1.5.3.12.

Indole alkaloid

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

Ajmaline

Ajmaline is an alkaloid that is classified as a 1-A antiarrhythmic agent. It is often used to induce arrhythmic contraction in patients suspected of having Brugada syndrome. Individuals suffering from Brugada syndrome will be more susceptible to the arrhythmogenic effects of the drug, and this can be observed on an electrocardiogram as an ST elevation.

Lorajmine

Lorajmine (17-monochloroacetylajmaline) is a drug that is a potent sodium channel blocker that was used for treating arrhythmia. It is derived from ajmaline, an alkaloid from the roots of Rauvolfia serpentina, by synthetically adding a chloroacetate residue.

Sparteine

Sparteine is a class 1a antiarrhythmic agent; a sodium channel blocker. It is an alkaloid and can be extracted from scotch broom. It is the predominant alkaloid in Lupinus mutabilis, and is thought to chelate the bivalent cations calcium and magnesium. It is not FDA approved for human use as an antiarrhythmic agent, and it is not included in the Vaughan Williams classification of antiarrhythmic drugs.

In enzymology, a 1,2-dihydrovomilenine reductase (EC 1.3.1.73) is an enzyme that catalyzes the chemical reaction

In enzymology, a vinorine hydroxylase (EC 1.14.14.104, Formerly EC 1.14.13.75) is an enzyme that catalyzes the chemical reaction

In enzymology, a vomilenine reductase (EC 1.5.1.32) is an enzyme that catalyzes the chemical reaction

Strictosidine synthase (EC 4.3.3.2) is an enzyme in alkaloid biosynthesis that catalyses the condensation of tryptamine with secologanin to form strictosidine in a formal Pictet–Spengler reaction:

Polyneuridine-aldehyde esterase

The enzyme polyneuridine-aldehyde esterase (EC 3.1.1.78) catalyzes the following reaction:

In enzymology, a raucaffricine beta-glucosidase (EC 3.2.1.125) is an enzyme that catalyzes the chemical reaction

In enzymology, a vinorine synthase is an enzyme that catalyzes the chemical reaction

In enzymology, a vomilenine glucosyltransferase is an enzyme that catalyzes the chemical reaction

Tropane alkaloid Class of chemical compounds

Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.

Ajmalan

Ajmalan is a parent hydride used in the IUPAC nomenclature of natural products and also in CAS nomenclature. It is a 20-carbon alkaloid with six rings and seven chiral centres.

Benzylisoquinoline Chemical compound

Substitution of the heterocycle isoquinoline at the C1 position by a benzyl group provides 1‑benzylisoquinoline, the most widely examined of the numerous benzylisoquinoline structural isomers. The 1-benzylisoquinoline moiety can be identified within numerous compounds of pharmaceutical interest, such as moxaverine; but most notably it is found within the structures of a wide variety of plant natural products, collectively referred to as benzylisoquinoline alkaloids. This class is exemplified in part by the following compounds: papaverine, noscapine, codeine, morphine, apomorphine, berberine, tubocurarine.

Elymoclavine Chemical compound

Elymoclavine is an ergot alkaloid. It can be produced from C. fusiformis from Pennisetum typhoideum. It is a precursor in the biosynthesis of D-(+)-lysergic acid. Ergot alkaloids are natural products derived from L-tryptophan. They are often toxic for humans and animals. Despite that they are also well known for their pharmacological activities.

The enzyme acetylajmaline esterase (EC 3.1.1.80, AAE, 2β(R)-17-O-acetylajmalan:acetylesterase, acetylajmalan esterase; systematic name 17-O-acetylajmaline O-acetylhydrolase) catalyses the following reactions:

References

  1. von Schumann, Gerald; Gao, Shujuan; Stöckigt, Joachim (2002). "Vomilenine reductase--a novel enzyme catalyzing a crucial step in the biosynthesis of the therapeutically applied antiarrhythmic alkaloid ajmaline". Bioorg Med Chem. 10 (6): 1913–1918. doi:10.1016/s0968-0896(01)00435-7. PMID   11937349.