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Published on: November 30, 2022
Amides from the stem of Capsicum annuum
Chung-Yi Chen1, Yu-Ting Yeh, Woei-Ling Yang
1Department of Medical Laboratory Sciences and Biotechnology, School of Medical and Health Sciences, Fooyin University, Kaohsiung County, Taiwan, R.O.C. xx377@mail.fy.edu.tw
Natural Product Communications
|March 24, 2011
Summary
Researchers isolated 14 compounds from Capsicum annuum stems, including a new amide. Spectral analyses confirmed the structures of these natural products, expanding knowledge of chili pepper phytochemistry.
Area of Science:
- Phytochemistry
- Natural Products Chemistry
- Pharmacognosy
Background:
- Capsicum annuum (Solanaceae) is a widely cultivated plant with a rich history of traditional use.
- The chemical constituents of C. annuum stems are not fully elucidated, presenting an opportunity for novel compound discovery.
Purpose of the Study:
- To isolate and characterize chemical compounds from the stems of Capsicum annuum.
- To identify novel compounds and elucidate their structures using advanced analytical techniques.
Main Methods:
- Extraction of secondary metabolites from Capsicum annuum stems.
- Isolation of individual compounds using chromatographic techniques.
- Structure elucidation through comprehensive spectral analyses (NMR, MS, etc.).
Main Results:
- Fourteen compounds were successfully isolated and identified.
- Compound 1, 7'-(4'-hydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide, was identified as a new amide.
- Compounds 2-14 were identified as known natural products, including phenolic acids, lignans, and a pheophorbide.
Conclusions:
- The chemical investigation of Capsicum annuum stems yielded a diverse array of compounds.
- The discovery of a new amide compound contributes to the known phytochemistry of the Solanaceae family.
- This study provides valuable data for understanding the chemical basis of C. annuum's properties and potential applications.
Related Concept Videos
01:29Preparation of Amides
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
01:19Amines to Amides: Acylation of Amines
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
01:07Amines: 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.
01:26Physical 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.
01:202° Amines to N-Nitrosamines: Reaction with NaNO2
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
01:22Preparation 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...