Design, Synthesis, In Vitro Antifungal Activity and Mechanism Study of the Novel 4-Substituted Mandelic Acid Derivatives
Plant diseases caused by phytopathogenic fungi are a serious threat in the process of crop production and cause large economic losses to global agriculture. To obtain high-antifungal-activity compounds with novel action mechanisms, a series of 4-substituted mandelic acid derivatives containing a 1,3...
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| Veröffentlicht in: | International journal of molecular sciences 2023-05, Vol.24 (10), p.8898 |
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| creator | Chen, Biao Song, Dandan Shi, Huabin Chen, Kuai Wu, Zhibing Chai, Huifang |
| description | Plant diseases caused by phytopathogenic fungi are a serious threat in the process of crop production and cause large economic losses to global agriculture. To obtain high-antifungal-activity compounds with novel action mechanisms, a series of 4-substituted mandelic acid derivatives containing a 1,3,4-oxadiazole moiety were designed and synthesized. In vitro bioassay results revealed that some compounds exhibited excellent activity against the tested fungi. Among them, the EC
values of
against
(
),
against
(
), and
against
(
) were 20.4, 12.7, and 8.0 mg/L, respectively, which were highly superior to that of the commercialized fungicide mandipropamid. The morphological studies of
with a fluorescence microscope (FM) and scanning electron microscope (SEM) indicated that
broke the surface of the hyphae and destroyed cell membrane integrity with increased concentration, thereby inhibiting fungal reproduction. Further cytoplasmic content leakage determination results showed a dramatic increase of the nucleic acid and protein concentrations in mycelia with
treatment, which also indicated that the title compound
could destroy cell membrane integrity and affect the growth of fungi. These results provide important information for further study of the mechanism of action of mandelic acid derivatives and their structural derivatization. |
| doi_str_mv | 10.3390/ijms24108898 |
| format | Article |
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values of
against
(
),
against
(
), and
against
(
) were 20.4, 12.7, and 8.0 mg/L, respectively, which were highly superior to that of the commercialized fungicide mandipropamid. The morphological studies of
with a fluorescence microscope (FM) and scanning electron microscope (SEM) indicated that
broke the surface of the hyphae and destroyed cell membrane integrity with increased concentration, thereby inhibiting fungal reproduction. Further cytoplasmic content leakage determination results showed a dramatic increase of the nucleic acid and protein concentrations in mycelia with
treatment, which also indicated that the title compound
could destroy cell membrane integrity and affect the growth of fungi. These results provide important information for further study of the mechanism of action of mandelic acid derivatives and their structural derivatization.</description><identifier>ISSN: 1422-0067</identifier><identifier>ISSN: 1661-6596</identifier><identifier>EISSN: 1422-0067</identifier><identifier>DOI: 10.3390/ijms24108898</identifier><identifier>PMID: 37240243</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Acids ; Agricultural production ; Antifungal activity ; Antifungal agents ; Antifungal Agents - chemistry ; Cell membranes ; Commercialization ; Crop production ; Crystal structure ; Economic impact ; Fluorescence microscopy ; Fungi ; Fungicides ; Fungicides, Industrial - pharmacology ; Hyphae ; Mandelic Acids - pharmacology ; Morphology ; NMR ; Nuclear magnetic resonance ; Nucleic acids ; Oxadiazoles ; Pesticides ; Phytopathogenic fungi ; Plant diseases ; Scanning electron microscopy ; Structure-Activity Relationship ; Substitutes</subject><ispartof>International journal of molecular sciences, 2023-05, Vol.24 (10), p.8898</ispartof><rights>COPYRIGHT 2023 MDPI AG</rights><rights>2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2023 by the authors. 2023</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c518t-aca8b463abfdb0c39487fc8fc90b29718ae31ccaefc6c700a6eaed2fcd9f4d3b3</citedby><cites>FETCH-LOGICAL-c518t-aca8b463abfdb0c39487fc8fc90b29718ae31ccaefc6c700a6eaed2fcd9f4d3b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10219514/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10219514/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37240243$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Biao</creatorcontrib><creatorcontrib>Song, Dandan</creatorcontrib><creatorcontrib>Shi, Huabin</creatorcontrib><creatorcontrib>Chen, Kuai</creatorcontrib><creatorcontrib>Wu, Zhibing</creatorcontrib><creatorcontrib>Chai, Huifang</creatorcontrib><title>Design, Synthesis, In Vitro Antifungal Activity and Mechanism Study of the Novel 4-Substituted Mandelic Acid Derivatives</title><title>International journal of molecular sciences</title><addtitle>Int J Mol Sci</addtitle><description>Plant diseases caused by phytopathogenic fungi are a serious threat in the process of crop production and cause large economic losses to global agriculture. To obtain high-antifungal-activity compounds with novel action mechanisms, a series of 4-substituted mandelic acid derivatives containing a 1,3,4-oxadiazole moiety were designed and synthesized. In vitro bioassay results revealed that some compounds exhibited excellent activity against the tested fungi. Among them, the EC
values of
against
(
),
against
(
), and
against
(
) were 20.4, 12.7, and 8.0 mg/L, respectively, which were highly superior to that of the commercialized fungicide mandipropamid. The morphological studies of
with a fluorescence microscope (FM) and scanning electron microscope (SEM) indicated that
broke the surface of the hyphae and destroyed cell membrane integrity with increased concentration, thereby inhibiting fungal reproduction. Further cytoplasmic content leakage determination results showed a dramatic increase of the nucleic acid and protein concentrations in mycelia with
treatment, which also indicated that the title compound
could destroy cell membrane integrity and affect the growth of fungi. These results provide important information for further study of the mechanism of action of mandelic acid derivatives and their structural derivatization.</description><subject>Acids</subject><subject>Agricultural production</subject><subject>Antifungal activity</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemistry</subject><subject>Cell membranes</subject><subject>Commercialization</subject><subject>Crop production</subject><subject>Crystal structure</subject><subject>Economic impact</subject><subject>Fluorescence microscopy</subject><subject>Fungi</subject><subject>Fungicides</subject><subject>Fungicides, Industrial - pharmacology</subject><subject>Hyphae</subject><subject>Mandelic Acids - pharmacology</subject><subject>Morphology</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Nucleic acids</subject><subject>Oxadiazoles</subject><subject>Pesticides</subject><subject>Phytopathogenic fungi</subject><subject>Plant diseases</subject><subject>Scanning electron microscopy</subject><subject>Structure-Activity Relationship</subject><subject>Substitutes</subject><issn>1422-0067</issn><issn>1661-6596</issn><issn>1422-0067</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>8G5</sourceid><sourceid>BENPR</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNpdkk1v1DAQhiMEoqVw44wsceGwKf5KYp_Qqi20UoHDAlfLsce7XiV2iZ1V999jtG21IB88sp_3Hc94quotweeMSfzRb8dEOcFCSPGsOiWc0hrjtnt-FJ9Ur1LaYkwZbeTL6oR1lGPK2Wl1fwnJr8MCrfYhb0qcFugmoF8-TxEtQ_ZuDms9oKXJfufzHulg0VcwGx18GtEqz3aPokNFi77FHQyI16u5T9nnOUNBCw-DN8XAW3QJk9_p4gTpdfXC6SHBm4f9rPr5-erHxXV9-_3LzcXytjYNEbnWRouet0z3zvbYMMlF54xwRuKeyo4IDYwYo8GZ1nQY6xY0WOqMlY5b1rOz6tPB927uR7AGQp70oO4mP-ppr6L26t-b4DdqHXeKYEpkQ3hx-PDgMMXfM6SsRp8MDIMOEOekqKCls7jFsqDv_0O3cZ5Cqa9QRPKmlUQU6vxAlcaC8sHFktiUZWH0JgZwvpwvu4Zy2hCKi2BxEJgppjSBe3o-wervEKjjISj4u-OSn-DHX2d_AN2tr7o</recordid><startdate>20230517</startdate><enddate>20230517</enddate><creator>Chen, Biao</creator><creator>Song, Dandan</creator><creator>Shi, Huabin</creator><creator>Chen, Kuai</creator><creator>Wu, Zhibing</creator><creator>Chai, Huifang</creator><general>MDPI AG</general><general>MDPI</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>MBDVC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20230517</creationdate><title>Design, Synthesis, In Vitro Antifungal Activity and Mechanism Study of the Novel 4-Substituted Mandelic Acid Derivatives</title><author>Chen, Biao ; Song, Dandan ; Shi, Huabin ; Chen, Kuai ; Wu, Zhibing ; Chai, Huifang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c518t-aca8b463abfdb0c39487fc8fc90b29718ae31ccaefc6c700a6eaed2fcd9f4d3b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acids</topic><topic>Agricultural production</topic><topic>Antifungal activity</topic><topic>Antifungal agents</topic><topic>Antifungal Agents - chemistry</topic><topic>Cell membranes</topic><topic>Commercialization</topic><topic>Crop production</topic><topic>Crystal structure</topic><topic>Economic impact</topic><topic>Fluorescence microscopy</topic><topic>Fungi</topic><topic>Fungicides</topic><topic>Fungicides, Industrial - pharmacology</topic><topic>Hyphae</topic><topic>Mandelic Acids - pharmacology</topic><topic>Morphology</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Nucleic acids</topic><topic>Oxadiazoles</topic><topic>Pesticides</topic><topic>Phytopathogenic fungi</topic><topic>Plant diseases</topic><topic>Scanning electron microscopy</topic><topic>Structure-Activity Relationship</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Biao</creatorcontrib><creatorcontrib>Song, Dandan</creatorcontrib><creatorcontrib>Shi, Huabin</creatorcontrib><creatorcontrib>Chen, Kuai</creatorcontrib><creatorcontrib>Wu, Zhibing</creatorcontrib><creatorcontrib>Chai, Huifang</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Research Library</collection><collection>Research Library (Corporate)</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>International journal of molecular sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Biao</au><au>Song, Dandan</au><au>Shi, Huabin</au><au>Chen, Kuai</au><au>Wu, Zhibing</au><au>Chai, Huifang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, Synthesis, In Vitro Antifungal Activity and Mechanism Study of the Novel 4-Substituted Mandelic Acid Derivatives</atitle><jtitle>International journal of molecular sciences</jtitle><addtitle>Int J Mol Sci</addtitle><date>2023-05-17</date><risdate>2023</risdate><volume>24</volume><issue>10</issue><spage>8898</spage><pages>8898-</pages><issn>1422-0067</issn><issn>1661-6596</issn><eissn>1422-0067</eissn><abstract>Plant diseases caused by phytopathogenic fungi are a serious threat in the process of crop production and cause large economic losses to global agriculture. To obtain high-antifungal-activity compounds with novel action mechanisms, a series of 4-substituted mandelic acid derivatives containing a 1,3,4-oxadiazole moiety were designed and synthesized. In vitro bioassay results revealed that some compounds exhibited excellent activity against the tested fungi. Among them, the EC
values of
against
(
),
against
(
), and
against
(
) were 20.4, 12.7, and 8.0 mg/L, respectively, which were highly superior to that of the commercialized fungicide mandipropamid. The morphological studies of
with a fluorescence microscope (FM) and scanning electron microscope (SEM) indicated that
broke the surface of the hyphae and destroyed cell membrane integrity with increased concentration, thereby inhibiting fungal reproduction. Further cytoplasmic content leakage determination results showed a dramatic increase of the nucleic acid and protein concentrations in mycelia with
treatment, which also indicated that the title compound
could destroy cell membrane integrity and affect the growth of fungi. These results provide important information for further study of the mechanism of action of mandelic acid derivatives and their structural derivatization.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>37240243</pmid><doi>10.3390/ijms24108898</doi><oa>free_for_read</oa></addata></record> |
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| source | MDPI - Multidisciplinary Digital Publishing Institute; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central |
| subjects | Acids Agricultural production Antifungal activity Antifungal agents Antifungal Agents - chemistry Cell membranes Commercialization Crop production Crystal structure Economic impact Fluorescence microscopy Fungi Fungicides Fungicides, Industrial - pharmacology Hyphae Mandelic Acids - pharmacology Morphology NMR Nuclear magnetic resonance Nucleic acids Oxadiazoles Pesticides Phytopathogenic fungi Plant diseases Scanning electron microscopy Structure-Activity Relationship Substitutes |
| title | Design, Synthesis, In Vitro Antifungal Activity and Mechanism Study of the Novel 4-Substituted Mandelic Acid Derivatives |
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