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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

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Transient Expression in Nicotiana Benthamiana Leaves for Triterpene Production at a Preparative Scale
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[Triterpene compounds from Cirsium setosum].

Lingling Li1, Zheng Sun, Xiaoya Shang

  • 1Beijing Key Laboratory of Bioactive Substances and Functional Foods, Beijing Union University, Beijing 100191, China.

Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica
|July 17, 2012
PubMed
Summary

Researchers identified twelve chemical compounds from Cirsium setosum, including six novel compounds from this plant genus. These findings contribute to understanding the phytochemical profile of Cirsium species.

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Area of Science:

  • Phytochemistry
  • Natural Products Chemistry
  • Pharmacognosy

Background:

  • Cirsium setosum is a plant species with potential medicinal properties.
  • Previous research suggests cytotoxic activity in extracts of Cirsium species.
  • Understanding the chemical constituents is crucial for further investigation.

Purpose of the Study:

  • To isolate and identify chemical constituents from the cytotoxic petroleum ether extractive fractions of Cirsium setosum.
  • To characterize novel compounds within this plant genus.

Main Methods:

  • Extraction of Cirsium setosum using ethanol and petroleum ether.
  • Purification using silica gel, Sephadex LH-20, and preparative High-Performance Liquid Chromatography (HPLC).
  • Structure elucidation via 1D, 2D Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS), supported by literature data.

Main Results:

  • Twelve compounds were isolated and identified: lupenyl acetate (1), lupeol (2), lupenone (3), beta-amyrin (4), psi-taraxasterol (5), psi-taraxasteryl acetate (6), taraxasteryl acetate (7), marsformoxide B (8), alpha-amyrenone (9), beta-amyrenone (10), taraxasterone (11), and psi-taraxasterone (12).
  • Compounds 3, 5, and 7-12 represent the first reported isolation from the Cirsium genus.
  • The study focused on triterpenoids.

Conclusions:

  • The petroleum ether fraction of Cirsium setosum ethanol extract contains a variety of triterpenoids.
  • Six of the identified compounds are reported for the first time in this genus, expanding the known phytochemical diversity of Cirsium.
  • Further research can explore the biological activities of these isolated compounds.