Murihexol, a linear acetogenin from Annona muricata

Area of Science:

• Natural Product Chemistry
• Phytochemistry
• Organic Chemistry

Background:

• Annona muricata seeds are a source of bioactive compounds.
• Acetogenins are a class of natural products with diverse biological activities.
• Previous research has identified various acetogenins from Annona species.

Purpose of the Study:

• To isolate and characterize novel and known acetogenins from Annona muricata seeds.
• To elucidate the chemical structure and stereochemistry of isolated compounds.
• To compare the structural features of newly identified acetogenins with known ones.

Main Methods:

• Extraction of compounds from Annona muricata seeds.
• Chromatographic techniques for isolation (e.g., HPLC, column chromatography).
• Spectroscopic methods for structural elucidation (e.g., NMR, Mass Spectrometry).

Main Results:

• Isolation of a novel C(35) acetogenin, murihexol (1).
• Isolation of three known acetogenins: donhexocin (2), annonacin A, and annonacin.
• Murihexol lacks THF rings and possesses six hydroxyl groups.
• Detailed stereochemical analysis of hydroxyl groups at C-4, C-10, C-15, C-16, C-19, and C-20 for compounds 1 and 2.
• Compound 1 exhibits threo configuration at C-15/C-16 and erythro at C-19/C-20.
• Compound 2 shows threo configuration at both C-15/C-16 and C-19/C-20.

Conclusions:

• Murihexol represents a new structural class of acetogenins.
• The stereochemical differences between murihexol and donhexocin highlight the structural diversity within Annona acetogenins.
• These findings contribute to the understanding of Annona muricata phytochemistry and acetogenin biosynthesis.