A new prenylated aurone from Artocarpus altilis

Area of Science:

• Phytochemistry
• Natural Products Chemistry
• Organic Chemistry

Background:

• Artocarpus altilis (breadfruit) is a tropical plant with a history of traditional medicinal uses.
• The phytochemical investigation of plant extracts is crucial for discovering novel bioactive compounds.
• Prenylated flavonoids and triterpenes are classes of natural products known for diverse biological activities.

Purpose of the Study:

• To conduct a phytochemical analysis of the methanol extract of Artocarpus altilis.
• To isolate and characterize new and known compounds from the plant.
• To evaluate the antioxidant potential of the isolated compounds.

Main Methods:

• Extraction of Artocarpus altilis using methanol.
• Isolation of compounds using chromatographic techniques.
• Structure elucidation of isolated compounds utilizing spectroscopic methods (1D and 2D NMR, FT-ICR-MS).
• Assessment of radical scavenging activity using nitric oxide and DPPH assays.

Main Results:

• A new prenylated aurone, artocarpaurone (1), was isolated and its structure elucidated.
• Eight known compounds were identified: two prenylated chalcones (2, 3), three prenylated flavanones (4-6), and three triterpenes (7-9).
• Compound 1 demonstrated moderate nitric oxide radical scavenging activity.
• Compounds 2 and 3 exhibited moderate 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity.

Conclusions:

• The phytochemical study of Artocarpus altilis led to the discovery of a novel prenylated aurone, artocarpaurone.
• The isolated compounds, including artocarpaurone, prenylated chalcones, flavanones, and triterpenes, contribute to the known chemical diversity of the Artocarpus genus.
• The antioxidant properties of artocarpaurone and the prenylated chalcones highlight their potential therapeutic value.