Herbicidal Characteristics and Structural Identification of the Potential Active Compounds from Streptomyces sp....

Weeds are notorious plant species exhibiting a harmful impact on crops. Biological weed control is an efficient and environmentally friendly technique, usually constitutes naturally derived compounds, including bioherbicidal metabolites produced by Streptomyces sp. The isolation and structural identification of phytotoxic compounds from Streptomyces have recently been proposed as an effective way to the discovery of novel bioherbicides. In the screening of bioherbicidal agents, isolated Streptomyces strain KRA17-580 demonstrated significant phytotoxic activity against Digitaria ciliaris. Phylogenetic analysis of the 16S rRNA sequence indicated that isolated KRA17-580 is similar to Streptomyces olivochromogenes. The bacterial culture conditions were optimized for temperature, agitation, and initial pH. Streptomyces strain KRA17-580 showed intense phytotoxic activity and high cell mass at an initial pH of 5.5-7.0, more than 150 rpm, and 25-30 °C. The herbicidal compounds isolated from the culture filtrate of strain KRA17-580 were purified by solvent partition, C₁₈, Sephadex LH20 column chromatography, and high-performance liquid chromatography. By 1D-NMR, 2D-NMR, and electrospray ionization mass spectrometry analysis, the 580-H1 and 580-H2 compounds were identified as a cinnoline-4-carboxamide (M_W, 173.0490; C₉H₇N₃O₂) and cinnoline-4-carboxylic acid (M_W, 174.0503; C₉H₆N₂O₂), respectively. Only these two herbicidal compounds showed strong phytotoxic activity against D. ciliaris in foliar applications. However, compound 580-H2 was more phytotoxic than 580-H1 and the toxicity was dose-dependent. The herbicidal metabolite KRA17-580 produced by Streptomyces sp. is a new bioherbicidal candidate that may provide a new lead molecule for more efficient phytotoxic compounds.