Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol
Abstract Background Plant diseases caused by viruses and bacteria cause huge economic losses due to the lack of effective control agents. New potential pesticides can be discovered through biomimetic synthesis and structural modification of natural products. A series of ferulic acid derivatives cont...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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BMC
2022-05-01
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| Series: | BMC Chemistry |
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| Online Access: | https://doi.org/10.1186/s13065-022-00828-8 |
| _version_ | 1811250945609170944 |
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| author | Ali Dai Yuanqin Huang Lijiao Yu Zhiguo Zheng Jian Wu |
| author_facet | Ali Dai Yuanqin Huang Lijiao Yu Zhiguo Zheng Jian Wu |
| author_sort | Ali Dai |
| collection | DOAJ |
| description | Abstract Background Plant diseases caused by viruses and bacteria cause huge economic losses due to the lack of effective control agents. New potential pesticides can be discovered through biomimetic synthesis and structural modification of natural products. A series of ferulic acid derivatives containing an β-amino alcohol were designed and synthesized, and their biological activities were evaluated. Result Bioassays results showed that the EC50 values of compound D24 against Xanthomonas oryzae pv. oryzae (Xoo) was 14.5 μg/mL, which was better than that of bismerthiazol (BT, EC50 = 16.2 μg/mL) and thiodiazole copper (TC, EC50 = 44.5 μg/mL). The in vivo curative and protective activities of compound D24 against Xoo were 50.5% and 50.1%, respectively. The inactivation activities of compounds D2, D3 and D4 against tobacco mosaic virus (TMV) at 500 μg/mL were 89.1, 93.7 and 89.5%, respectively, superior to ningnanmycin (93.2%) and ribavirin (73.5%). In particular, the EC50 value of compound D3 was 38.1 μg/mL, and its molecular docking results showed that compound D3 had a strong affinity for TMV-CP with a binding energy of − 7.54 kcal/mol, which was superior to that of ningnanmycin (− 6.88 kcal /mol). Conclusions The preliminary mechanism research results indicated that compound D3 may disrupt the three-dimensional structure of the TMV coat protein, making TMV particles unable to self-assemble, which may provide potential lead compounds for the discovery of novel plant antiviral agents. Graphical Abstract |
| first_indexed | 2024-04-12T16:12:20Z |
| format | Article |
| id | doaj.art-f6ced6147d984a68964b2876c82b405d |
| institution | Directory Open Access Journal |
| issn | 2661-801X |
| language | English |
| last_indexed | 2024-04-12T16:12:20Z |
| publishDate | 2022-05-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj.art-f6ced6147d984a68964b2876c82b405d2022-12-22T03:25:52ZengBMCBMC Chemistry2661-801X2022-05-0116111510.1186/s13065-022-00828-8Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcoholAli Dai0Yuanqin Huang1Lijiao Yu2Zhiguo Zheng3Jian Wu4State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou UniversityState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou UniversityState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou UniversityState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou UniversityState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou UniversityAbstract Background Plant diseases caused by viruses and bacteria cause huge economic losses due to the lack of effective control agents. New potential pesticides can be discovered through biomimetic synthesis and structural modification of natural products. A series of ferulic acid derivatives containing an β-amino alcohol were designed and synthesized, and their biological activities were evaluated. Result Bioassays results showed that the EC50 values of compound D24 against Xanthomonas oryzae pv. oryzae (Xoo) was 14.5 μg/mL, which was better than that of bismerthiazol (BT, EC50 = 16.2 μg/mL) and thiodiazole copper (TC, EC50 = 44.5 μg/mL). The in vivo curative and protective activities of compound D24 against Xoo were 50.5% and 50.1%, respectively. The inactivation activities of compounds D2, D3 and D4 against tobacco mosaic virus (TMV) at 500 μg/mL were 89.1, 93.7 and 89.5%, respectively, superior to ningnanmycin (93.2%) and ribavirin (73.5%). In particular, the EC50 value of compound D3 was 38.1 μg/mL, and its molecular docking results showed that compound D3 had a strong affinity for TMV-CP with a binding energy of − 7.54 kcal/mol, which was superior to that of ningnanmycin (− 6.88 kcal /mol). Conclusions The preliminary mechanism research results indicated that compound D3 may disrupt the three-dimensional structure of the TMV coat protein, making TMV particles unable to self-assemble, which may provide potential lead compounds for the discovery of novel plant antiviral agents. Graphical Abstracthttps://doi.org/10.1186/s13065-022-00828-8Ferulic acid derivativesβ-amino alcoholSynthesizedAntiviral activityAntibacterial activity |
| spellingShingle | Ali Dai Yuanqin Huang Lijiao Yu Zhiguo Zheng Jian Wu Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol BMC Chemistry Ferulic acid derivatives β-amino alcohol Synthesized Antiviral activity Antibacterial activity |
| title | Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol |
| title_full | Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol |
| title_fullStr | Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol |
| title_full_unstemmed | Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol |
| title_short | Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol |
| title_sort | design synthesis and bioactivity of ferulic acid derivatives containing an β amino alcohol |
| topic | Ferulic acid derivatives β-amino alcohol Synthesized Antiviral activity Antibacterial activity |
| url | https://doi.org/10.1186/s13065-022-00828-8 |
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