Novel Algicides against Bloom-Forming Cyanobacteria from Allelochemicals: Design, Synthesis, Bioassay, and 3D-QSAR Study

Cyanobacteria bloom caused by water eutrophication has threatened human health and become a global environmental problem. To develop green algicides with strong specificity and high efficiency, three series of ester and amide derivatives from parent allelochemicals of caffeic acid (CA), cinnamic aci...

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Autores principales:	Yin Luo, Yushun Yang, Wenguang Hou, Jie Fu
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	cyanobacteria allelochemicals algicide phenolic acid 3D-QSAR Biology (General) QH301-705.5
Acceso en línea:	https://doaj.org/article/f14903c4899a4d189ade5b4e1557ee77
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spelling	oai:doaj.org-article:f14903c4899a4d189ade5b4e1557ee772021-11-25T16:47:25ZNovel Algicides against Bloom-Forming Cyanobacteria from Allelochemicals: Design, Synthesis, Bioassay, and 3D-QSAR Study10.3390/biology101111452079-7737https://doaj.org/article/f14903c4899a4d189ade5b4e1557ee772021-11-01T00:00:00Zhttps://www.mdpi.com/2079-7737/10/11/1145https://doaj.org/toc/2079-7737Cyanobacteria bloom caused by water eutrophication has threatened human health and become a global environmental problem. To develop green algicides with strong specificity and high efficiency, three series of ester and amide derivatives from parent allelochemicals of caffeic acid (CA), cinnamic acid (CIA), and 3-hydroxyl-2-naphthoic acid (HNA) were designed and synthesized. Their inhibitory effects on the growth of five harmful cyanobacterial species, <i>Microcystis aeruginosa</i> (<i>M. aeruginosa</i>), <i>Microcystis wesenbergii</i> (<i>M. wesenbergii</i>), <i>Microcystis flos-aquae</i> (<i>M. flos-aquae</i>), <i>Aphanizomenon flos-aquae</i> (<i>Ap. flos-aquae</i>), and <i>Anabaena flos-aquae</i> (<i>An. flos-aquae</i>), were evaluated. The results revealed that CIA esters synthesized by cinnamic acid and fatty alcohols showed the best inhibition effect, with EC<sub>50</sub> values ranging from 0.63 to >100 µM. Moreover, some CIA esters exhibited a good selectivity in inhibiting cyanobacteria. For example, the inhibitory activity of naphthalen-2-yl cinnamate was much stronger on <i>Ap. flos-aquae</i> (EC<sub>50</sub> = 0.63 µM) than other species (EC<sub>50</sub> > 10 µM). Three-dimensional quantitative structure–activity relationship (3D-QSAR) analysis was performed and the results showed that the steric hindrance of the compounds influenced the algicidal activity. Further mechanism study found that the inhibition of CIA esters on the growth of <i>M. aeruginosa</i> might be related to the accumulation of malondialdehyde (MDA).Yin LuoYushun YangWenguang HouJie FuMDPI AGarticlecyanobacteriaallelochemicalsalgicidephenolic acid3D-QSARBiology (General)QH301-705.5ENBiology, Vol 10, Iss 1145, p 1145 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	cyanobacteria allelochemicals algicide phenolic acid 3D-QSAR Biology (General) QH301-705.5
spellingShingle	cyanobacteria allelochemicals algicide phenolic acid 3D-QSAR Biology (General) QH301-705.5 Yin Luo Yushun Yang Wenguang Hou Jie Fu Novel Algicides against Bloom-Forming Cyanobacteria from Allelochemicals: Design, Synthesis, Bioassay, and 3D-QSAR Study
description	Cyanobacteria bloom caused by water eutrophication has threatened human health and become a global environmental problem. To develop green algicides with strong specificity and high efficiency, three series of ester and amide derivatives from parent allelochemicals of caffeic acid (CA), cinnamic acid (CIA), and 3-hydroxyl-2-naphthoic acid (HNA) were designed and synthesized. Their inhibitory effects on the growth of five harmful cyanobacterial species, <i>Microcystis aeruginosa</i> (<i>M. aeruginosa</i>), <i>Microcystis wesenbergii</i> (<i>M. wesenbergii</i>), <i>Microcystis flos-aquae</i> (<i>M. flos-aquae</i>), <i>Aphanizomenon flos-aquae</i> (<i>Ap. flos-aquae</i>), and <i>Anabaena flos-aquae</i> (<i>An. flos-aquae</i>), were evaluated. The results revealed that CIA esters synthesized by cinnamic acid and fatty alcohols showed the best inhibition effect, with EC<sub>50</sub> values ranging from 0.63 to >100 µM. Moreover, some CIA esters exhibited a good selectivity in inhibiting cyanobacteria. For example, the inhibitory activity of naphthalen-2-yl cinnamate was much stronger on <i>Ap. flos-aquae</i> (EC<sub>50</sub> = 0.63 µM) than other species (EC<sub>50</sub> > 10 µM). Three-dimensional quantitative structure–activity relationship (3D-QSAR) analysis was performed and the results showed that the steric hindrance of the compounds influenced the algicidal activity. Further mechanism study found that the inhibition of CIA esters on the growth of <i>M. aeruginosa</i> might be related to the accumulation of malondialdehyde (MDA).
format	article
author	Yin Luo Yushun Yang Wenguang Hou Jie Fu
author_facet	Yin Luo Yushun Yang Wenguang Hou Jie Fu
author_sort	Yin Luo
title	Novel Algicides against Bloom-Forming Cyanobacteria from Allelochemicals: Design, Synthesis, Bioassay, and 3D-QSAR Study
title_short	Novel Algicides against Bloom-Forming Cyanobacteria from Allelochemicals: Design, Synthesis, Bioassay, and 3D-QSAR Study
title_full	Novel Algicides against Bloom-Forming Cyanobacteria from Allelochemicals: Design, Synthesis, Bioassay, and 3D-QSAR Study
title_fullStr	Novel Algicides against Bloom-Forming Cyanobacteria from Allelochemicals: Design, Synthesis, Bioassay, and 3D-QSAR Study
title_full_unstemmed	Novel Algicides against Bloom-Forming Cyanobacteria from Allelochemicals: Design, Synthesis, Bioassay, and 3D-QSAR Study
title_sort	novel algicides against bloom-forming cyanobacteria from allelochemicals: design, synthesis, bioassay, and 3d-qsar study
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/f14903c4899a4d189ade5b4e1557ee77
work_keys_str_mv	AT yinluo novelalgicidesagainstbloomformingcyanobacteriafromallelochemicalsdesignsynthesisbioassayand3dqsarstudy AT yushunyang novelalgicidesagainstbloomformingcyanobacteriafromallelochemicalsdesignsynthesisbioassayand3dqsarstudy AT wenguanghou novelalgicidesagainstbloomformingcyanobacteriafromallelochemicalsdesignsynthesisbioassayand3dqsarstudy AT jiefu novelalgicidesagainstbloomformingcyanobacteriafromallelochemicalsdesignsynthesisbioassayand3dqsarstudy
_version_	1718412992416055296

Novel Algicides against Bloom-Forming Cyanobacteria from Allelochemicals: Design, Synthesis, Bioassay, and 3D-QSAR Study

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