A novel alkaloid from Portulaca oleracea L

Area of Science:

• Natural Product Chemistry
• Phytochemistry
• Medicinal Chemistry

Background:

• Portulaca oleracea L. is a widely distributed plant with a history of traditional medicinal uses.
• The chemical constituents of Portulaca oleracea are diverse and have been explored for various biological activities.
• Isolation and characterization of novel compounds from medicinal plants contribute to drug discovery and development.

Purpose of the Study:

• To isolate and characterize novel and known compounds from Portulaca oleracea L.
• To elucidate the chemical structure of a newly discovered alkaloid, oleraciamide C.
• To evaluate the cytotoxicity of oleraciamide C against human adipose-derived stem cells (hADSCs).

Main Methods:

• Phytochemical investigation involving extraction and isolation techniques.
• Structure elucidation using advanced spectroscopic methods: High-Resolution Electrospray Ionization Time-of-Flight Mass Spectrometry (HR-ESI-TOF-MS) and Nuclear Magnetic Resonance (NMR) spectroscopy (1D and 2D).
• Cytotoxicity assay using the Cell Counting Kit-8 (CCK-8) method.

Main Results:

• A novel alkaloid, oleraciamide C (1), was isolated and characterized.
• Six known compounds, including hydroxydihydrobovolide (2), uracil (3), catechol (4), 4-aminophenol (5), vanillic acid (6), and 3-hydroxypyridine (7), were also identified.
• Hydroxydihydrobovolide (2), 4-aminophenol (5), and 3-hydroxypyridine (7) were reported from Portulaca oleracea for the first time.
• Oleraciamide C (1) exhibits an unusual structure with a bis-substituted eight-membered ring linked to a β-glucopyranose moiety.
• Preliminary evaluation of oleraciamide C's cytotoxicity against hADSCs was performed.

Conclusions:

• The study successfully identified a new alkaloid, oleraciamide C, from Portulaca oleracea, expanding the knowledge of its chemical profile.
• The structural novelty of oleraciamide C, particularly its eight-membered ring, presents an interesting scaffold for further chemical modification and biological investigation.
• The isolation of previously unreported compounds from this plant highlights its potential as a source of bioactive natural products.