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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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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.
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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.
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Related Experiment Video

Updated: May 8, 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

Labdane diterpenes from Chloranthus serratus.

Mi Zhang1, Junsong Wang1, Jun Luo1

  • 1State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China.

Fitoterapia
|September 3, 2013
PubMed
Summary

Five new compounds, serralabdanes A-E, were isolated from Chloranthus serratus. These labdane diterpenes demonstrated inhibitory effects on nitric oxide production in cellular assays.

Keywords:
Anti-inflammatoryChloranthus serratusInduced circular dichroismLabdane diterpene

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Area of Science:

  • Natural Product Chemistry
  • Organic Chemistry
  • Pharmacology

Background:

  • Chloranthus serratus is a plant species with potential medicinal properties.
  • Diterpenes are a class of natural products with diverse biological activities.
  • Nitric oxide (NO) plays a key role in inflammatory processes.

Purpose of the Study:

  • To isolate and characterize new labdane diterpenes from Chloranthus serratus.
  • To investigate the potential anti-inflammatory effects of these isolated compounds.

Main Methods:

  • Phytochemical investigation of Chloranthus serratus whole plant extract.
  • Structure elucidation using various spectroscopic methods (NMR, MS).
  • Determination of absolute configuration using Induced Circular Dichroism (ICD).
  • In vitro assay for nitric oxide inhibition in RAW264.7 cells stimulated with lipopolysaccharide (LPS).

Main Results:

  • Five new labdane diterpenes, named serralabdanes A-E (1-5), were successfully isolated and identified.
  • The absolute configuration of serralabdane C (3) was determined.
  • All isolated compounds (serralabdanes A-E) exhibited inhibitory effects on lipopolysaccharide-induced nitric oxide production.

Conclusions:

  • The study successfully identified novel labdane diterpenes from Chloranthus serratus.
  • Serralabdanes A-E possess anti-inflammatory potential by inhibiting nitric oxide production.
  • These findings contribute to the understanding of the chemical constituents and bioactivity of Chloranthus serratus.