Cytotoxic non-aromatic B-ring flavanones from Piper carniconnectivum C. DC

Area of Science:

• Phytochemistry
• Natural Products Chemistry
• Medicinal Chemistry

Background:

• Piper carniconnectivum is a plant species with potential medicinal properties.
• Flavanones are a class of flavonoids with diverse biological activities.
• Leukemia remains a significant health concern, necessitating the search for new therapeutic agents.

Purpose of the Study:

• To isolate and characterize novel flavanone compounds from Piper carniconnectivum.
• To determine the absolute configurations of the isolated compounds.
• To evaluate the cytotoxic activity of the isolated compounds against human leukemia cell lines.

Main Methods:

• Chromatographic separation of EtOAc extract from Piper carniconnectivum leaves.
• Structure elucidation using electronic circular dichroism (ECD) spectroscopy and time-dependent density functional theory (TD-DFT) calculations.
• High-resolution nuclear magnetic resonance (NMR) experiments.
• Cytotoxicity assays on twelve human leukemia cell lines.

Main Results:

• Two non-aromatic B-ring flavanone compounds, (1) and (2), were isolated.
• The absolute configurations of (+)-1 and (+)-2 were determined as 2S,1'R using ECD and TD-DFT.
• Compound 1 exhibited significant cytotoxic activity (IC50 < 10 μM) against seven human leukemia cell lines.

Conclusions:

• Novel flavanone compounds with defined stereochemistry were identified from Piper carniconnectivum.
• Compound 1 displays promising cytotoxic effects against leukemia cells, warranting further investigation.
• The applied ECD and TD-DFT methodology is effective for absolute configuration determination of flavanones.