Bioactive acetaminophen derivatives from Penicillum herquei JX4

Area of Science:

• Natural Product Chemistry
• Mycology
• Medicinal Chemistry

Background:

• Acetaminophen derivatives are a class of compounds with diverse biological activities.
• Fungal pathogens pose significant threats to agriculture and human health.
• The isolation of novel compounds from microbial sources is crucial for drug discovery.

Purpose of the Study:

• To isolate and characterize novel acetaminophen derivatives from Penicillium herquei.
• To determine the structures and absolute configurations of the isolated compounds.
• To evaluate the antifungal and α-glucosidase inhibitory activities of these novel derivatives.

Main Methods:

• Isolation of compounds using chromatographic techniques.
• Structure elucidation via comprehensive spectroscopic methods (NMR, MS).
• Determination of absolute configurations using modified Mosher's method and electronic circular dichroism (ECD) analysis.

Main Results:

• Two novel epimer pairs of acetaminophen derivatives, penicilquei A-D (1-4), were successfully isolated.
• The compounds possess an unprecedented carbon skeleton, marking a significant structural novelty.
• Penicilquei A-D (1-4) demonstrated strong inhibitory activity against at least eight out of nine tested phytopathogenic fungi.

Conclusions:

• Penicilquei A-D (1-4) represent the first reported acetaminophen derivatives with a unique carbon skeleton.
• These novel compounds exhibit broad-spectrum antifungal activity, suggesting potential applications in agriculture.
• Further investigation into their mechanism of action and potential therapeutic applications is warranted.