Dihydrofurochromones from Prionosciadium thapsoides

Area of Science:

• Natural Product Chemistry
• Phytochemistry
• Organic Chemistry

Background:

• Prionosciadum thapsoides is a plant species with potential medicinal properties.
• The chemical constituents of this plant are not fully explored.
• Coumarins and furochromones are classes of compounds with diverse biological activities.

Purpose of the Study:

• To isolate and characterize new chemical compounds from Prionosciadum thapsoides roots.
• To elucidate the structures and absolute configurations of isolated compounds.
• To contribute to the understanding of the phytochemical profile of Prionosciadum thapsoides.

Main Methods:

• Isolation of compounds using chromatographic techniques.
• Structure elucidation of new compounds using 1D and 2D NMR spectroscopy.
• Determination of absolute configuration via chemical correlation, single-crystal X-ray diffraction, and vibrational circular dichroism (VCD) spectroscopy with DFT calculations.

Main Results:

• Isolation of two new dihydrofurochromones, (S)-(+)-4'-O-angeloyl-5-O-methylvisamminol (1) and (S)-(+)-4'-O-senecioyl-5-O-methylvisamminol (2).
• Identification of known coumarins: jatamansin, buchtormin, isopteryxin, isosamidin, psoralen, and bergapten.
• Confirmation of the absolute configuration of compounds 1 and 2 as (S) through chemical correlation with (+)-5-O-methylvisamminol (3).

Conclusions:

• The phytochemical investigation of Prionosciadum thapsoides roots yielded novel dihydrofurochromone derivatives.
• The structural and stereochemical assignments were rigorously confirmed using a combination of modern analytical techniques.
• This study expands the knowledge of Prionosciadum thapsoides constituents and provides valuable chemical entities for further biological evaluation.