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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
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Absolute configuration of cembrane diterpenoids from Bursera multijuga
Natural Product Communications
|April 29, 2015
Summary
Researchers isolated novel cembrane derivatives from Bursera multijuga stems. These compounds
Area of Science:
- Natural Products Chemistry
- Organic Chemistry
- Phytochemistry
Background:
- The genus Bursera is known for its diverse chemical constituents, including terpenes.
- However, cembrane derivatives have not been previously reported from this genus.
Purpose of the Study:
- To investigate the chemical constituents of Bursera multijuga, specifically focusing on the isolation and structural elucidation of cembrane derivatives.
- To determine the absolute configuration of the isolated compounds using computational methods.
Main Methods:
- Phytochemical investigation of Bursera multijuga stems using chromatographic techniques.
- Structural elucidation of isolated compounds using spectroscopic methods (1D and 2D NMR, HRESIMS).
- Determination of absolute configuration using X-ray diffraction and vibrational circular dichroism (VCD) analysis supported by density functional theory (DFT) calculations.
Main Results:
- Isolation and characterization of (-)-(1S,3E,7R,8R,11E)-7,8-epoxycembra-3,11-dien-1-ol (1) and its acetate (2).
- Identification of known cembrane derivatives: cembrene A (3), nephthenol (4), and cembrenol (5).
- Confirmation of the absolute configuration of compound 1 through a combination of experimental and computational VCD data.
Conclusions:
- This study reports the first isolation of cembrane derivatives from the genus Bursera.
- The findings expand the known chemical diversity of Bursera species.
- The absolute configuration of a novel epoxycembranol was successfully established.
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