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Cytotoxic 20,24-epoxywithanolides from Physalis angulata
Emma Maldonado1, Norma E Hurtado1, Ana L Pérez-Castorena1
1Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, D.F., Mexico.
Steroids
|September 4, 2015
Summary
A new withanolide, physangulide B, was isolated from Physalis angulata. This compound and derivatives showed potent cytotoxic activity against human cancer cell lines.
Area of Science:
- Natural Product Chemistry
- Medicinal Chemistry
- Pharmacognosy
Background:
- Physalis angulata is a plant species known for its diverse phytochemical constituents.
- Withanolides are a class of steroidal lactones with a wide range of biological activities.
- Previous studies have identified various withanolides from Physalis species, but further investigation is warranted.
Purpose of the Study:
- To isolate and characterize new and known withanolides from Physalis angulata.
- To elucidate the structures of isolated compounds using spectroscopic methods.
- To evaluate the cytotoxic potential of the isolated compounds against human cancer cell lines.
Main Methods:
- Phytochemical investigation involving extraction and chromatographic separation of Physalis angulata calyxes and aerial parts.
- Structure elucidation using comprehensive spectroscopic analyses, including NMR and Mass Spectrometry.
- X-ray crystallographic analysis of acetyl derivatives for structural confirmation.
- In vitro cytotoxic activity assay against selected human cancer cell lines.
Main Results:
- Isolation and identification of a new withanolide, physangulide B (1), along with known compounds including physangulide (4) and 24,25-epoxywithanolide D (6).
- Spectroscopic data revealed a 20,24-epoxy group in both physangulides.
- X-ray analysis confirmed the structures of physangulide B (as acetyl derivative 2) and 24,25-epoxywithanolide D (as acetyl derivative 7).
- The structure and configuration of physangulide were revised to 4.
- Physangulide B (1) and its derivative 2 exhibited potent cytotoxic activity against tested cancer cell lines.
Conclusions:
- Physalis angulata is a valuable source of bioactive withanolides.
- Physangulide B represents a novel withanolide with significant cytotoxic potential.
- The revised structure of physangulide provides a clearer understanding of this compound class.
- Further research into physangulide B and its derivatives could lead to the development of new anticancer agents.
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