Simple indole alkaloids from the neotropical rutaceous tree Raputia simulans

Area of Science:

• Phytochemistry
• Natural Products Chemistry
• Organic Chemistry

Background:

• The genus Raputia Aubl. is part of the Rutaceae family, with 10 known neotropical species within the subtribe Cuspariinae.
• Indole alkaloids are a significant class of natural products with diverse biological activities.

Purpose of the Study:

• To isolate and characterize chemical constituents from the stem bark of Raputia simulans.
• To identify novel indole alkaloids and their structural features.

Main Methods:

• Dichloromethane extraction of Raputia simulans stem bark.
• Isolation of compounds using fast centrifugal partition chromatography (FCPC) and adsorption chromatography.
• Structural elucidation of isolated metabolites.

Main Results:

• Eleven indole alkaloids were isolated from the plant extract.
• Compounds 1-4 were identified as indole-5-carbaldehyde, 7-prenylindole, 5-prenylindole, and verticillatine B.
• Metabolites 5-11, including 5-(but-3'-en-2'-one)indole and various furan-substituted indoles, were isolated for the first time.

Conclusions:

• The study successfully identified eleven indole alkaloids from Raputia simulans.
• Metabolites 5-11 represent new chemical entities with unique substitutions at the indole 5-position.
• This research expands the known chemical diversity within the Raputia genus.