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Related Concept Videos

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...
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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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A new labdane diterpene from Vitex negundo.

Cheng-Jian Zheng1, Xiao-Peng Lan, Yang Wang

  • 1Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai, PR China.

Pharmaceutical Biology
|April 11, 2012
PubMed
Summary
This summary is machine-generated.

A new labdane diterpenoid, negundol, was isolated from Vitex negundo seeds. This compound demonstrated significant antifungal activity, suggesting its potential as a novel antifungal agent.

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Area of Science:

  • Natural Product Chemistry
  • Pharmacognosy
  • Mycology

Background:

  • Vitex negundo Linn. seeds are traditionally used for pain relief and inflammation.
  • These seeds are also utilized as a culinary spice.
  • Folk medicine highlights their use in managing rheumatism and joint inflammation.

Purpose of the Study:

  • To isolate and identify bioactive compounds from Vitex negundo seeds.
  • To characterize the chemical structure of isolated constituents.
  • To evaluate the antifungal properties of the identified compounds.

Main Methods:

  • Extraction of Vitex negundo seeds using ethanol.
  • Purification of compounds via repeated column chromatography.
  • Structure elucidation using Nuclear Magnetic Resonance (NMR), Infrared (IR), and Mass Spectrometry (MS) data.
  • Antifungal activity assessment against pathogenic fungi isolates.

Main Results:

  • A novel labdane diterpenoid, negundol (1a + 1b), was isolated as a mixture of two diastereoisomers (5:4 ratio).
  • The structures were determined to be (rel 3S, 5S, 8R, 9R, 10S, 13S, 16S)-3-acetoxy-9, 13-epoxy-16-hydroxy-labda-15, 16-olide and its diastereomer.
  • Compound 1 exhibited notable antifungal activity with Minimum Inhibitory Concentration (MIC₈₀) values ranging from 16-64 μg/mL.

Conclusions:

  • The isolation of negundol confirms the chemotaxonomic significance of labdane diterpenoids in the Vitex genus.
  • Negundol displays promising antifungal potential.
  • This compound can serve as a lead for developing new antifungal agents.