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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

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, respectively.
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Aromatic Compounds: Overview01:25

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 benzene...
Pyruvate Oxidation01:15

Pyruvate Oxidation

After glycolysis, the charged pyruvate molecules enter the mitochondria via active transport and undergo three enzymatic reactions. These reactions ensure that pyruvate can enter the next metabolic pathway so that energy stored in the pyruvate molecules can be harnessed by the cells.
First, the enzyme pyruvate dehydrogenase removes the carboxyl group from pyruvate and releases it as carbon dioxide. The stripped molecule is then oxidized and releases electrons, which are then picked up by NAD+...

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A pyrrole derivative from Paeonia suffruticosa.

K Xiao1, Q-H Song, S-W Zhang

  • 1State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai, China.

Natural Product Research
|December 17, 2008
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Summary

A novel pyrrole derivative, paesuffrioside, was isolated from Paeonia suffruticosa root. This study details its structure and identifies two other compounds new to this plant species.

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Area of Science:

  • Phytochemistry
  • Natural Product Chemistry
  • Pharmacognosy

Background:

  • Paeonia suffruticosa (tree peony) is a valuable medicinal plant.
  • Its root cortex is a source of bioactive compounds.
  • Understanding its chemical constituents is crucial for its medicinal applications.

Purpose of the Study:

  • To isolate and characterize novel compounds from Paeonia suffruticosa root cortex.
  • To identify known compounds present in the water-soluble extract.
  • To elucidate the structures of isolated compounds using advanced analytical techniques.

Main Methods:

  • Water-soluble extraction of Paeonia suffruticosa root cortex.
  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation via spectroscopic analysis (NMR, MS) and chemical transformation.
  • Identification of known compounds through comparison with literature data.

Main Results:

  • A new pyrrole derivative, paesuffrioside (2-methyl-5-(2'-O-alpha-D-glucopyranosyl-1'-oxygen)-propylpyrrole) (1), was isolated and characterized.
  • Eleven known compounds were also isolated from the extract.
  • Two known compounds (2 and 3) were reported from this plant for the first time.

Conclusions:

  • The chemical investigation of Paeonia suffruticosa root cortex yielded a new pyrrole derivative, paesuffrioside.
  • The study expanded the known phytochemical profile of Paeonia suffruticosa.
  • This research contributes to the understanding of the chemical diversity of Paeonia species.