salicortin and Neoplasms

Willow (Salix spp.) is well known as a source of medicinal compounds, the most famous being salicin, the progenitor of aspirin. Here we describe the isolation, structure determination, and anti-cancer activity of a cyclodimeric salicinoid (miyabeacin) from S. miyabeana and S. dasyclados. We also show that the capability to produce such dimers is a heritable trait and how variation in structures of natural miyabeacin analogues is derived via cross-over Diels-Alder reactions from pools of ortho-quinol precursors. These transient ortho-quinols have a role in the, as yet uncharacterised, biosynthetic pathways around salicortin, the major salicinoid of many willow genotypes.

Topics: Antineoplastic Agents, Phytogenic; Benzyl Alcohols; Biosynthetic Pathways; Cell Line, Tumor; Drug Screening Assays, Antitumor; Glucosides; Humans; Inhibitory Concentration 50; Neoplasms; Plant Bark; Salix