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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Labdane diterpenes from Marrubium thessalum.
Catherine Argyropoulou1, Anastasia Karioti, Helen Skaltsa
1Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, Panepistimiopolis, Zografou, GR-15771 Athens, Greece.
Phytochemistry
|April 14, 2009
Summary
Four new labdane diterpenes, including 13S-preperegrinine, were isolated from Marrubium thessalum aerial parts. This study details their structures and identifies key compounds like peregrinine and ladanein.
Area of Science:
- Natural Product Chemistry
- Phytochemistry
- Organic Chemistry
Background:
- Marrubium thessalum is a plant species with potential medicinal properties.
- Diterpenes and flavonoids are classes of natural compounds often found in plants and known for diverse bioactivities.
Purpose of the Study:
- To isolate and characterize chemical constituents from the aerial parts of Marrubium thessalum.
- To identify novel labdane diterpenes and other secondary metabolites.
- To provide complete NMR assignments for newly isolated compounds.
Main Methods:
- Extraction of compounds from the aerial parts of Marrubium thessalum.
- Structure elucidation using advanced spectroscopic techniques, including Nuclear Magnetic Resonance (NMR) (COSY, HSQC, HMBC, NOESY, ROESY) and Mass Spectrometry (MS).
- Comparison with known compounds and literature data.
Main Results:
- Isolation of four new labdane diterpenes: 13S-preperegrinine, 3alpha-hydroxymarrubiin, 9alpha,13R-15,16-bisepoxy-15beta-methoxy-3-oxo-labdan-6beta,19-olide, and 15-methoxyvelutine C.
- Identification of four known diterpenes and one known methoxylated flavone, ladanein.
- Complete Nuclear Magnetic Resonance (NMR) assignments were determined for 13R-preperegrinine.
- Peregrinine and ladanein were identified as characteristic compounds of the plant.
Conclusions:
- The chemical investigation of Marrubium thessalum yielded a diverse array of labdane diterpenes and a methoxylated flavone.
- The structural characterization was confirmed through comprehensive spectroscopic analyses.
- This study contributes to the understanding of the phytochemical profile of Marrubium thessalum, highlighting peregrinine and ladanein as key constituents.
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