Gossypol has greater gastrointestinal toxicity than apogossypol. Balb/c mice were orally administered apogossypol (A), gossypol (G), or vehicle control (C) at a daily dose of 120 μmol/kg 5 times weekly for 3 weeks (6 mice per group). Representative H&E histology is presented of intestinal tissue (duodenum) of treated mice in cross-section (top) and longitudinal section (bottom). Note denuding of mucosal epithelium in gossypol-treated mice, with shortening and loss of villi. Size bars represent 100 μM.