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Related Concept Videos

Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

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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...
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Defenses Against Pathogens and Herbivores02:26

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Plants present a rich source of nutrients for many organisms, making it a target for herbivores and infectious agents. Plants, though lacking a proper immune system, have developed an array of constitutive and inducible defenses to fend off these attacks.
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

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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).
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

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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.
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Related Experiment Video

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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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[Terpenoids isolated from Viburnum ternatum].

Jiang Hu1, Xia Mao1, Nian-Hua Jing1

  • 1Institute of Characteristic Medicinal Resource of Ethnic Minorities, Qujing Normal University, Qujing 655011, China.

Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica
|August 20, 2017
PubMed
Summary

This study isolated 12 compounds from Viburnum ternatum, including new iridoids and triterpenoids. These findings expand the known chemical diversity of this plant species.

Keywords:
CaprifoliaceaeViburnum ternatumiridoid glucosidesiridoidstriterpenoids

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Area of Science:

  • Natural Product Chemistry
  • Phytochemistry
  • Organic Chemistry

Background:

  • Viburnum ternatum is a plant species with potential medicinal properties.
  • Understanding its chemical constituents is crucial for exploring its pharmacological applications.

Purpose of the Study:

  • To isolate and elucidate the structures of compounds from the aerial parts of Viburnum ternatum.
  • To identify novel compounds and those reported for the first time in this plant.

Main Methods:

  • Extraction of aerial parts using 70% Me2CO and ethyl acetate.
  • Isolation using various column chromatography techniques (silica gel, ODS, Sephadex LH-20, MCI).
  • Structure elucidation using spectroscopic data and physicochemical methods.

Main Results:

  • Twelve compounds were isolated: four iridoids (1-4), five iridoid glucosides (5-9), and three triterpenoids (10-12).
  • Compound 1 (ternatumin A) is a new iridoid.
  • Compound 2 (2,9-dioxatricyclo[4.3.1.03，7]decanes) is a new natural product.
  • Compounds 3-12 were isolated from Viburnum ternatum for the first time.

Conclusions:

  • The study successfully identified known and novel compounds from Viburnum ternatum.
  • This research contributes to the phytochemical knowledge of the Viburnum genus.
  • The isolated compounds, particularly novel ones, warrant further investigation for potential biological activities.