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Design, Synthesis, and Antifungal Activities of Hymexazol Glycosides Based on a Biomimetic Strategy
Gao, Kun1,2; Qin, Yukun1,2; Wang, Linsong1,2; Li, Xin1,2; Liu, Song1,2; Xing, Ronge1,2; Yu, HuaHua1,2; Chen, Xiaolin1,2; Li, Pengcheng1,2
2022-07-25
Source PublicationJOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN0021-8561
Pages16
Corresponding AuthorQin, Yukun(ykqin@qdio.ac.cn) ; Li, Pengcheng(pcli@qdio.ac.cn)
AbstractHymexazol (HYM) is irreplaceable for treating soil-borne diseases due to its high efficiency and low cost, as a broadspectrum fungicide. However, when HYM is absorbed by plants, it is rapidly converted into two glycoside metabolites, and the antifungal activities of these glycosides are inferior to that of HYM. Therefore, in this study, to maintain strong antifungal activity in vitro and in vivo, HYM was glycosylated with amino sugars that have diverse biological activities to simulate plant glycosylation. The antifungal experiment proved that glycoside 15 has the highest antifungal activity, and N-acetyl glucosamine and HYM had obvious synergistic effects. According to the structure-activity relationship studies, glycoside 15 had greater numbers of active electron-rich regions and front-line orbital electrons due to the introduction of N-acetyl glucosamine. Moreover, glycoside 15 can significantly promote plant growth and induce an increase in plant defense enzyme activity. Additionally, compared to HYM, the results of electron microscopy and proteomics revealed that glycoside 15 has a unique antifungal mechanism. The promising antifungal activity and interactions with plants mean that glycoside 15 is a potential green fungicide candidate. Furthermore, this research conducted an interesting exploration of the agricultural applications of amino sugars.
Keywordhymexazol glycosylation antifungal DFT proteomics
DOI10.1021/acs.jafc.2c02507
Indexed BySCI
Language英语
Funding ProjectNational Key R&D Program of China[2019YFD0900705] ; National Natural Science Foundation of China[42076126] ; Shandong Provincial Natural Science Foundation[ZR2020MD072] ; Shandong Provincial Natural Science Foundation[ZR2021QC006] ; Qingdao Applied Basic Research Project[19-6-2-34-cg] ; Qingdao Science and Technology Demonstration and Guidance Project[20-3-4-22-nsh] ; Science and Technology Plan Project of Shinan District, Qingdao[2020-2-013-QT]
WOS Research AreaAgriculture ; Chemistry ; Food Science & Technology
WOS SubjectAgriculture, Multidisciplinary ; Chemistry, Applied ; Food Science & Technology
WOS IDWOS:000834104900001
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:6[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.qdio.ac.cn/handle/337002/179849
Collection实验海洋生物学重点实验室
Corresponding AuthorQin, Yukun; Li, Pengcheng
Affiliation1.Chinese Acad Sci, Inst Oceanol, Ctr Ocean Mega Sci, CAS & Shandong Prov Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China
2.Pilot Natl Lab Marine Sci & Technol Qingdao, Lab Marine Drugs & Bioprod, Qingdao 266237, Peoples R China
First Author AffilicationInstitute of Oceanology, Chinese Academy of Sciences
Corresponding Author AffilicationInstitute of Oceanology, Chinese Academy of Sciences
Recommended Citation
GB/T 7714
Gao, Kun,Qin, Yukun,Wang, Linsong,et al. Design, Synthesis, and Antifungal Activities of Hymexazol Glycosides Based on a Biomimetic Strategy[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,2022:16.
APA Gao, Kun.,Qin, Yukun.,Wang, Linsong.,Li, Xin.,Liu, Song.,...&Li, Pengcheng.(2022).Design, Synthesis, and Antifungal Activities of Hymexazol Glycosides Based on a Biomimetic Strategy.JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,16.
MLA Gao, Kun,et al."Design, Synthesis, and Antifungal Activities of Hymexazol Glycosides Based on a Biomimetic Strategy".JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2022):16.
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