Aglycone fragmentation accompanies β-glucosidase catalyzed hydrolysis of salicortin, a naturally-occurring phenol glycoside

Salicortin (1a), upon enzyme-mediated glycosidic hydrolysis, undergoes an unusual and rapid fragmentation-recombination reaction leading to 2 via postulated ortho-quinone methide (3) and enol (4) intermediates.