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Related Concept Videos

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Thermal Electrocyclic Reactions: Stereochemistry01:17

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

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Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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Naming Enantiomers02:21

Naming Enantiomers

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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system...
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Esters to β-Ketoesters: Claisen Condensation Overview01:24

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Regular Claisen condensation is a base-promoted reaction involving identical esters with two α hydrogens, condensing to produce β-ketoesters. It is a nucleophilic acyl substitution reaction wherein one of the ester molecules, upon deprotonation by the base, forms a nucleophilic enolate ion, while the other molecule serves as an electrophile.
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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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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Updated: Jun 5, 2025

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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Two new sesquiterpene eudesmanolides from the Croton cascarilloides Raeusch.

Tian-Yi Liu1, Hong-Li Liu1, Xi Jiang1

  • 1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, People's Republic of China.

Natural Product Research
|December 16, 2024
PubMed
Summary

Two new and six known sesquiterpene eudesmanolides were isolated from Croton cascarilloides. Some compounds exhibited cytotoxic activity against HL-60 leukaemia and SMMC-7721 hepatoma cells.

Keywords:
Croton LCroton cascarilloidescytotoxic activitysesquiterpenoids

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Area of Science:

  • Natural Products Chemistry
  • Medicinal Chemistry
  • Phytochemistry

Background:

  • Croton species are a rich source of bioactive natural products.
  • Sesquiterpene eudesmanolides are a class of compounds with diverse biological activities.

Purpose of the Study:

  • To isolate and characterize new and known sesquiterpene eudesmanolides from Croton cascarilloides.
  • To evaluate the cytotoxic activities of the isolated compounds against cancer cell lines.

Main Methods:

  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation using Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS).
  • Cytotoxicity assays using HL-60 leukaemia and SMMC-7721 hepatoma cell lines.

Main Results:

  • Two new sesquiterpene eudesmanolides, 5α-hydroxy-eudesman-7(11)-en-8α(12)-olide (1) and 5α-hydroxy-7(11)-en-8-oxo-eudesmane (2), were identified.
  • Six known sesquiterpene eudesmanolides were also isolated.
  • Compounds 6 and 8 showed inhibitory activity against HL-60 leukaemia cells.
  • Compound 2 exhibited inhibitory activity against both HL-60 and SMMC-7721 cells.

Conclusions:

  • The study successfully identified novel and known sesquiterpene eudesmanolides from Croton cascarilloides.
  • The isolated compounds, particularly compound 2, demonstrate potential as cytotoxic agents against leukaemia and hepatoma cells.