CyanoHABs 제어를 위한 1,4-naphthoquinone 유도체 합성 및 구조-활성 상관관계 분석

Abstract

Harmful Algal Blooms (HABs) are a phenomenon that occurs when certain types of algae become dominant, resulting in greenish water and the formation of "dead zones" due to the emission of a foul odor and a decrease in dissolved oxygen. HABs can cause damage to aquatic life and ecosystems, and also have economic and ecological impacts, affecting the availability of agricultural and drinking water. The causes of HABs are known to be rapid climate change caused by global warming, excessive organic matter inflow, and the construction of reservoirs and dams for water resources, which have led to annual range expansion and increased frequency. CyanoHABs occurring in eutrophic freshwater worldwide secrete a toxin, microcystin-LR, which inhibits PP1 protein (IC50 1.7 nM) and PP2A protein (IC50 40 pM) at low concentrations. This leads to toxic effects on the liver and nervous system, and may cause liver cancer and neurological diseases. The development of effective technologies to control HABs is needed, as the known technologies have limitations in terms of target range, efficiency, and economic feasibility. In this study, an organic algicide that can selectively control HABs using eco-friendly material, a derivative of vitamin K, was developed. 53 compounds were synthesized based on the core structure of vitamin K, 1,4-Naphthoquinone derivatives, and structure-activity relationships were analyzed. The algicidal activity and selectivity for two harmful cyanobacteria species (Microcystis aeruginosa, Anabaena Sp.) and two harmless green algae species (Selena Strum Gracile, Chlorella Vulgaris) were evaluated, resulting in the identification of lead compounds (compounds 11, 13, 31, 33, 37, 38, 47, 48) with LC50 values of 1M or less. For the highly active compounds, acute toxicity experiments were conducted using Daphnia magna and Zebrafish (Danio rerio), and low toxicity compounds 47 and 48 were finally selected. In addition, morphological analysis using an electron microscope was conducted to examine the interaction between the compounds and cyanobacteria. Although the mechanism could not be determined, based on the cellular condition, it was observed that the compounds were associated with cell membrane disruption.