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Aromatic Compounds: Overview

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...

NMR Spectroscopy of Aromatic Compounds

NMR Spectroscopy of Aromatic Compounds

Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range.

Nomenclature of Aromatic Compounds with a Single Substituent

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).

Five-Membered Heterocyclic Aromatic Compounds: Overview

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...

Nomenclature of Aromatic Compounds with Multiple Substituents

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

Mass Spectrometry: Aromatic Compound Fragmentation

Mass Spectrometry: Aromatic Compound Fragmentation

Upon ionization, aromatic compounds generate a molecular ion that is observed as a prominent peak in their mass spectra. For example, the molecular ion peak for benzene appears at a mass-to-charge ratio of 78, while toluene is observed at a mass-to-charge ratio of 92. The molecular ion benzene is highly stable and does not readily undergo further fragmentation due to the significant amount of energy required to disrupt the aromatic stability of the benzene ring. In contrast, the molecular ion...

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Bioorthogonal Chemical Imaging of Cell Metabolism Regulated by Aromatic Amino Acids

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Aromatic compounds from Endocomia macrocoma.

Fang Kuang¹, Ying Liu¹, Ye-Gao Chen¹

¹School of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, P. R. China.

Natural Product Research

|January 3, 2019

Summary

Researchers isolated 27 compounds from Endocomia macrocoma, including novel diarypropane and lignan molecules. These natural products showed no cytotoxic effects against five human tumor cell lines in preliminary evaluations.

Keywords:

Endocomia macrocoma flavonoids horsfielenidine lignans

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Area of Science:

Phytochemistry
Natural Product Chemistry
Pharmacology

Background:

Endocomia macrocoma is a plant species with potential for novel bioactive compound discovery.
Previous research may not have fully explored the chemical constituents of Endocomia macrocoma twigs and leaves.

Purpose of the Study:

To isolate and characterize chemical compounds from Endocomia macrocoma.
To evaluate the cytotoxic activity of the isolated novel compounds against human tumor cell lines.

Main Methods:

Phytochemical investigation involving extraction and isolation techniques.
Structure elucidation using spectroscopic methods (e.g., NMR, MS).
In vitro cytotoxicity assays against five human tumor cell lines.

Main Results:

Twenty-seven compounds were successfully isolated from Endocomia macrocoma.
A new diarypropane derivative and two new lignans were identified among the isolates.
None of the newly isolated compounds exhibited significant cytotoxic effects on the tested human tumor lines.

Conclusions:

The twigs and leaves of Endocomia macrocoma contain a diverse array of chemical compounds, including novel structures.
The investigated novel compounds from Endocomia macrocoma do not possess cytotoxic activity against the evaluated human tumor cell lines.
Further research may explore other biological activities or different plant parts.