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Withanolides from Physalis coztomatl.

Huaping Zhang¹, Cong-Mei Cao¹, Robert J Gallagher¹

¹Department of Medicinal Chemistry, School of Pharmacy, University of Kansas, Lawrence, KS 66045, USA.

|December 3, 2014

Summary

This summary is machine-generated.

Researchers isolated six novel withanolides from Physalis coztomatl. Structural analysis, including X-ray crystallography, confirmed their identities and revised the stereochemistry of coagulansin A.

Keywords:

Coagulansin A Physacoztolide Physalis coztomatl Solanaceae Structure revision Withanolide

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Area of Science:

Natural Product Chemistry
Phytochemistry
Organic Chemistry

Background:

Physalis coztomatl, a plant from the Solanaceae family, is a potential source of bioactive compounds.
Withanolides are a class of sterically hindered, oxygenated triterpenoid lactones derived from C28 sterols.

Purpose of the Study:

To isolate and characterize withanolides from the aerial parts of Physalis coztomatl.
To elucidate the structures of new withanolides using advanced spectroscopic methods.
To revise the stereochemical assignment of coagulansin A based on detailed NMR analysis.

Main Methods:

Isolation of compounds using chromatographic techniques.
Structure elucidation of isolated compounds via 2D Nuclear Magnetic Resonance (NMR) spectroscopy and other spectroscopic methods.
Confirmation of the structure of a key compound through X-ray crystallographic analysis.
Stereochemical analysis using Carbon-13 Nuclear Magnetic Resonance (13C NMR) shifts.

Main Results:

Six new withanolides (1-6) were isolated from Physalis coztomatl.
Two known withanolides, physachenolide D (7) and withanoside VI (8), were also identified.
The structure of compound 1 was confirmed by X-ray crystallography.
Stereochemical analysis revealed that coagulansin A possesses a 17α-hydroxy group, revising the previously reported 17β-hydroxy configuration.

Conclusions:

The study successfully identified novel withanolides from Physalis coztomatl.
The findings contribute to the understanding of withanolide chemistry and stereochemistry.
The revised structure of coagulansin A provides a more accurate chemical profile for this compound.