Photodynamic Action and Antimicrobial Activity of Some Excited Metabolites of Dalbergia Sissoides and Their Ability to Cleave DNA

Abstract

The photodynamic properties of two quinones, 4-methoxydalbergione (DS1) and sissoidenone (DS2), and a coumarin, dalbergin {6-hydroxy-7-methoxy-4-phenylcoumarin, (DS3)}, have been studied. Photogeneration of singlet oxygen (1O2) was monitored by both optical and EPR methods. Based on RNO bleaching, relative to Rose Bengal (RB), the singlet oxygen generating efficiencies of DS1, DS2, and DS3 were determined as 0.10, 0.051 and 0.041, respectively. Using the SOD inhibitable cytochrome c reduction assay, the photogeneration of superoxide anion (O2-•) was monitored. The formation of O2-• was enhanced in the presence of electron donors such as EDTA, DETAPAC and NADH. Photolysis of DS1 and DS3 in DMSO in the presence of 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) generated a twelve line EPR spectrum characteristic of an O2-• adduct. In the photosensitization of the DS series, both Type I and Type II paths were involved. The quantum mechanically calculated lowest unoccupied molecular orbital (LUMO) energies of DS1 and DS2 were correlated with the experimental redox potential. Photoinduced DNA scission by DS1, DS2, and DS3 confirms the generation of O2-• from these metabolites.