New Indole Alkaloids from Amsonia sinensis
1Institute of Materia Medica, Chinese Academy of Medical Sciences, 1 Xian Nong Tan Street, Beijing 100050, People's Republic of China.
Planta Medica
|December 1, 1991
Summary
Researchers isolated fourteen indole alkaloids from Amsonia sinensis, including two novel compounds, Delta(14)-isoeburnamine and amsosinine. Their structures were confirmed using spectral, chemical, and X-ray diffraction methods.
Area of Science:
- Natural Product Chemistry
- Phytochemistry
- Organic Chemistry
Background:
- Amsonia sinensis is a plant species known to produce various indole alkaloids.
- Indole alkaloids represent a significant class of secondary metabolites with diverse biological activities.
- Previous research has identified several alkaloids from Amsonia species, but a comprehensive analysis of Amsonia sinensis is warranted.
Purpose of the Study:
- To isolate and characterize indole alkaloids from Amsonia sinensis.
- To identify and elucidate the structures of novel compounds from this plant source.
- To contribute to the understanding of the chemical diversity of Amsonia alkaloids.
Main Methods:
- Extraction and isolation of secondary metabolites from Amsonia sinensis using chromatographic techniques.
- Structure elucidation of isolated compounds employing spectroscopic methods (NMR, MS) and chemical derivatization.
- Confirmation of the structures of new compounds through X-ray diffraction analysis of single crystals.
Main Results:
- Fourteen indole alkaloids were isolated, including Delta(14)-isoeburnamine (1) and amsosinine (2) as new compounds.
- The structures of Delta(14)-isoeburnamine (1) and amsosinine (2) were established using spectral and chemical analyses.
- A known sterol glycoside, daucosterol, was also obtained. The structures of compounds 1 and 2 were definitively confirmed by X-ray diffraction.
Conclusions:
- Amsonia sinensis is a rich source of diverse indole alkaloids.
- The discovery of Delta(14)-isoeburnamine and amsosinine expands the known chemical profile of this plant.
- The structural confirmation provides valuable data for further pharmacological investigations and chemotaxonomic studies.
More Related Videos
Related Concept Videos
Amines to Sulfonamides: The Hinsberg Test
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
Amines: Introduction
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
Physical Properties of Amines
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
Preparation of 1° Amines: Azide Synthesis
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...


