Two acylated diarylheptanoid glycosides from red alder bark

Area of Science:

• Natural Product Chemistry
• Phytochemistry
• Organic Chemistry

Background:

• Red alder (Alnus rubra) bark is a source of various bioactive compounds.
• Diarylheptanoids are a class of natural products with diverse biological activities.
• Acylated glycosides represent a modification of natural products that can alter their properties.

Purpose of the Study:

• To isolate and characterize novel compounds from red alder bark.
• To elucidate the structures of newly discovered acylated diarylheptanoid glycosides.
• To contribute to the understanding of the chemical constituents of red alder.

Main Methods:

• Isolation of compounds using chromatographic techniques.
• Structure elucidation employing Nuclear Magnetic Resonance (NMR) spectroscopy.
• Mass spectrometry (MS) for molecular weight determination and fragmentation analysis.

Main Results:

• Two novel acylated diarylheptanoid glycosides, designated oregonosides A and B, were successfully isolated.
• The structures were determined to be (5S)-1,7-bis(3,4-dihydroxyphenyl)-5-O-(6-O-benzoyl-beta-D-glucopyranosyl)-heptan-3-one and (5S)-1,7-bis(3,4-dihydroxyphenyl)-5-O-(6-O-vanilloyl-beta-D-glucopyranosyl)-heptan-3-one.
• Spectrometric data confirmed the presence of benzoyl and vanilloyl acyl groups on the beta-D-glucopyranosyl moiety.

Conclusions:

• The study successfully identified two new acylated diarylheptanoid glycosides from red alder bark.
• Oregonosides A and B represent unique chemical structures within the diarylheptanoid class.
• Further research may explore the potential biological activities of these novel compounds.