Bioactive diels-alder type adducts from the stem bark of Morus macroura.

Abstract

Five new compounds, named guangsangons A (1), B (5), C (6), D (7), and E (8), along with four known compounds, albafuran C (2), kuwanon X (3), kuwanon P (4), and kuwanon Y (9) were isolated from Morus macroura Miq.. Their structures were determined by means of spectroscopic analyses and chemical methods. These compounds were regarded biogenetically as Diels-Al-der type adducts, and 1H-NMR variable temperature experience suggested that they all existed as an equilibrium mixture of conformational isomers in solution. Compounds 1-3 and 5-9 showed good anti-oxidation activity, with the inhibitory rate of malondialdehyde being from 90.1% to 102.7% at a concentration of 10(-4) mol/L and from 70.9% to 88.1% at a concentration of 10(-5) mol/L. Compounds 1, 5, and 7 showed anti-inflammation activity, with the inhibitory rates of release of lysosome enzyme from polymorphonuclear leukocytes of rats being 19.0% (P > 0.05), 57.3% (P < 0.001) and 24.3% (P < 0.05) at concentrations of 10(-5) mol/L, respectively.