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Related Concept Videos

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.
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...
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction.
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends on...
Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
[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.
Biosynthesis of Lipids01:29

Biosynthesis of Lipids

Microbial membranes exhibit remarkable diversity in lipid composition, reflecting evolutionary adaptations to various environmental conditions. The three domains of life—Bacteria, Archaea, and Eukarya—synthesize membrane lipids through distinct biosynthetic pathways, leading to fundamental structural differences that impact membrane stability, function, and adaptability.Fatty Acid-Based Lipids in Bacteria and EukaryaBacteria and eukaryotes share a common fatty acid biosynthesis pathway, which...

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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

Highly functionalized daphnane diterpenoids from Trigonostemon thyrsoideum.

Ling Zhang1, Rong-Hua Luo, Fei Wang

  • 1State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China.

Organic Letters
|December 9, 2009
PubMed
Summary

New daphnane diterpenoids, Trigonothyrins A-C, were isolated from Trigonostemon thyrsoideum. One compound showed significant potential in inhibiting HIV-1, offering a promising therapeutic index.

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Area of Science:

  • Natural Products Chemistry
  • Organic Chemistry
  • Pharmacology

Background:

  • Daphnane diterpenoids are a class of complex natural products known for diverse biological activities.
  • Trigonostemon thyrsoideum is a plant source that may yield novel chemical entities.
  • Understanding the chemical diversity and bioactivity of plant-derived compounds is crucial for drug discovery.

Purpose of the Study:

  • To isolate and characterize new daphnane diterpenoids from Trigonostemon thyrsoideum.
  • To investigate the structural novelty of the isolated compounds.
  • To evaluate the potential of these compounds in inhibiting HIV-1 cytopathic effects.

Main Methods:

  • Phytochemical investigation of Trigonostemon thyrsoideum stems.
  • Isolation and purification of compounds using chromatographic techniques.
  • Structure elucidation of isolated compounds through spectroscopic methods (NMR, MS).
  • In vitro anti-HIV-1 activity assay to determine EC50 and therapeutic index.

Main Results:

  • Three new highly functionalized daphnane diterpenoids, Trigonothyrins A-C (1-3), were successfully isolated.
  • Compounds 1-3 possess unique structural features, including an oxygen-bridged four-membered ring and a 12,13,14-orthoester linkage, representing novel daphnane skeletons.
  • Trigonothyrin C (3) demonstrated significant inhibition of HIV-1 induced cytopathic effects with an EC50 of 2.19 microg/mL and a therapeutic index exceeding 90.

Conclusions:

  • Trigonothyrins A-C represent a new structural class of daphnane diterpenoids.
  • The novel structural motifs highlight the chemical diversity within this compound class.
  • Trigonothyrin C shows promising anti-HIV-1 activity, warranting further investigation as a potential therapeutic agent.