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Related Concept Videos

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Drugs that Stabilize Microtubules01:15

Drugs that Stabilize Microtubules

Microtubules are dynamic structures that undergo cycles of catastrophe and rescue. The microtubules play a central role in cell division by forming the spindle apparatus for segregating the chromosomes. This makes them ideal targets for regulating dividing cells in tumors and malignant cancer cells. Microtubule stabilizing drugs help stabilize the microtubule formation and promote its polymerization. Paclitaxel was the first microtubule stabilizing agent used as anticancer drug in chemotherapy...
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

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.
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.

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Updated: Jul 15, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
07:59

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

New dammarane triterpenes from Maytenus macrocarpa.

Virginia Torpocco1, Haydee Chávez, Ana Estévez-Braun

  • 1Instituto Universitario de Bio-Orgánica Antonio González, Avda, Astrofísico Francisco Sánchez No2, La Laguna, 38206 Tenerife, Spain.

Chemical & Pharmaceutical Bulletin
|May 3, 2007
PubMed
Summary

Two novel dammarane triterpenes were identified from Maytenus macrocarpa bark. These compounds were investigated for their potential antitumoral properties.

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Transient Expression in Nicotiana Benthamiana Leaves for Triterpene Production at a Preparative Scale
08:56

Transient Expression in Nicotiana Benthamiana Leaves for Triterpene Production at a Preparative Scale

Published on: August 16, 2018

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Last Updated: Jul 15, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
07:59

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

Transient Expression in Nicotiana Benthamiana Leaves for Triterpene Production at a Preparative Scale
08:56

Transient Expression in Nicotiana Benthamiana Leaves for Triterpene Production at a Preparative Scale

Published on: August 16, 2018

Area of Science:

  • Natural Products Chemistry
  • Phytochemistry
  • Medicinal Chemistry

Background:

  • Maytenus macrocarpa is a plant species known for its diverse chemical constituents.
  • Triterpenes are a class of organic compounds with a wide range of biological activities.
  • The isolation and characterization of new compounds from natural sources are crucial for drug discovery.

Purpose of the Study:

  • To isolate and elucidate the structures of new dammarane triterpenes from Maytenus macrocarpa stem bark exudates.
  • To evaluate the antitumoral activity of the isolated compounds.

Main Methods:

  • Isolation of compounds using chromatographic techniques.
  • Structure determination through comprehensive 1D and 2D Nuclear Magnetic Resonance (NMR) spectroscopic studies.
  • In vitro antitumoral activity assays.

Main Results:

  • Two new dammarane triterpenes, 24(Z)-3-oxodammara-20(21),24-dien-27-oic acid (1) and octa-nor-13-hydroxydammara-1-en-3,17-dione (2), were successfully isolated and characterized.
  • The structures were confirmed by detailed NMR analysis.

Conclusions:

  • The study successfully identified two novel dammarane triterpenes from Maytenus macrocarpa.
  • Further investigation into the antitumoral potential of these compounds is warranted.