lignans and isoeugenol

Topics: Acetylcholine; Acetylcholinesterase; Alcohol Oxidoreductases; Ascorbic Acid; Biosensing Techniques; Biphenyl Compounds; Electrochemical Techniques; Eugenol; Lignans; Microscopy, Electron, Scanning; Phenols; Phenylenediamines; Polymerization; Polymers; Reproducibility of Results

A series of naturally occurring 8.0.4'-neolignans (1a-d, 1g, 2g, 2h) and their analogues (le-f, lh, 1i, 2a-f, 2i) have been synthesized in racemic form starting from commercially available phenols, such as eugenol, isoeugenol and 4-allyl-2,6-dimethoxyphenol and from aromatic aldehydes, such as piperonal, veratraldehyde and 3,4,5-trimethoxybenzaldehyde. The inhibitory activity of these compounds on superoxide anion (O2.-) release by human polymorphonuclear leukocytes (PMNLs) was tested and the structure-activity relationship was also studied.

Topics: Aldehydes; Antioxidants; Benzaldehydes; Benzodioxoles; Cells, Cultured; Eugenol; Humans; Lignans; Neutrophils; Phenols; Quantitative Structure-Activity Relationship; Superoxides

The total synthesis of four neolignans-fragnasols A (1), B (2), and C (3) and dehydrodiisoeugenol (4)-starting from the readily available phenol derivative isoeugenol (5) was accomplished. The key step of the synthesis of these natural products is a novel type of dimerization of 5 into 4 with iodobenzene diacetate.

Topics: Benzofurans; Dimerization; Eugenol; Lignans; Models, Chemical; Plant Extracts; Seeds; Spices