Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds
Twenty-two novel longifolene-derived diphenyl ether-carboxylic acid compounds <b>7a–7v</b> were synthesized from renewable biomass resources longifolene, and their structures were confirmed by FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. The preliminary...
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| Format: | Article |
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MDPI AG
2023-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/4/1911 |
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| author | Xiaocui Wu Guishan Lin Wengui Duan Baoyu Li Yucheng Cui Bo Cen Fuhou Lei |
| author_facet | Xiaocui Wu Guishan Lin Wengui Duan Baoyu Li Yucheng Cui Bo Cen Fuhou Lei |
| author_sort | Xiaocui Wu |
| collection | DOAJ |
| description | Twenty-two novel longifolene-derived diphenyl ether-carboxylic acid compounds <b>7a–7v</b> were synthesized from renewable biomass resources longifolene, and their structures were confirmed by FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. The preliminary evaluation of in vitro antifungal activity displayed that compound <b>7b</b> presented inhibition rates of 85.9%, 82.7%, 82.7%, and 81.4% against <i>Alternaria solani, Cercospora arachidicola</i>, <i>Rhizoctonia solani,</i> and <i>Physalospora piricola</i>, respectively, and compound <b>7l</b> possessed inhibition rates of 80.7%, 80.4%, and 80.3% against <i>R. solani</i>, <i>C. arachidicola</i>, <i>P. piricola</i>, respectively, exhibiting excellent and broad-spectrum antifungal activities. Besides, compounds <b>7f</b> and <b>7a</b> showed significant antifungal activities with inhibition rates of 81.2% and 80.7% against <i>A.solani</i>, respectively. Meanwhile, a reasonable and effective 3D-QSAR mode (<i>r</i><sup>2</sup> = 0.996, <i>q</i><sup>2</sup> = 0.572) has been established by the CoMFA method. Furthermore, the drug-loading complexes <b>7b/MgAl-LDH</b> were prepared and characterized. Their pH-responsive controlled-release behavior was investigated as well. As a result, complex <b>7b/MgAl-LDH-2</b> exhibited excellent controlled-releasing performance in the water/ethanol (10:1, v:v) and under a pH of 5.7. |
| first_indexed | 2024-03-11T08:21:07Z |
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| id | doaj.art-86ba33341b6943a79acd98d899f1a0e8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T08:21:07Z |
| publishDate | 2023-02-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-86ba33341b6943a79acd98d899f1a0e82023-11-16T22:24:55ZengMDPI AGMolecules1420-30492023-02-01284191110.3390/molecules28041911Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid CompoundsXiaocui Wu0Guishan Lin1Wengui Duan2Baoyu Li3Yucheng Cui4Bo Cen5Fuhou Lei6School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, ChinaSchool of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, ChinaSchool of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, ChinaSchool of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, ChinaSchool of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, ChinaSchool of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, ChinaGuangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, Guangxi Minzu University, Nanning 530006, ChinaTwenty-two novel longifolene-derived diphenyl ether-carboxylic acid compounds <b>7a–7v</b> were synthesized from renewable biomass resources longifolene, and their structures were confirmed by FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. The preliminary evaluation of in vitro antifungal activity displayed that compound <b>7b</b> presented inhibition rates of 85.9%, 82.7%, 82.7%, and 81.4% against <i>Alternaria solani, Cercospora arachidicola</i>, <i>Rhizoctonia solani,</i> and <i>Physalospora piricola</i>, respectively, and compound <b>7l</b> possessed inhibition rates of 80.7%, 80.4%, and 80.3% against <i>R. solani</i>, <i>C. arachidicola</i>, <i>P. piricola</i>, respectively, exhibiting excellent and broad-spectrum antifungal activities. Besides, compounds <b>7f</b> and <b>7a</b> showed significant antifungal activities with inhibition rates of 81.2% and 80.7% against <i>A.solani</i>, respectively. Meanwhile, a reasonable and effective 3D-QSAR mode (<i>r</i><sup>2</sup> = 0.996, <i>q</i><sup>2</sup> = 0.572) has been established by the CoMFA method. Furthermore, the drug-loading complexes <b>7b/MgAl-LDH</b> were prepared and characterized. Their pH-responsive controlled-release behavior was investigated as well. As a result, complex <b>7b/MgAl-LDH-2</b> exhibited excellent controlled-releasing performance in the water/ethanol (10:1, v:v) and under a pH of 5.7.https://www.mdpi.com/1420-3049/28/4/1911longifolenehydrotalciteantifungal activity3D-QSARcontrolled-releasing |
| spellingShingle | Xiaocui Wu Guishan Lin Wengui Duan Baoyu Li Yucheng Cui Bo Cen Fuhou Lei Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds Molecules longifolene hydrotalcite antifungal activity 3D-QSAR controlled-releasing |
| title | Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds |
| title_full | Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds |
| title_fullStr | Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds |
| title_full_unstemmed | Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds |
| title_short | Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds |
| title_sort | synthesis antifungal activity 3d qsar and controlled release on hydrotalcite study of longifolene derived diphenyl ether carboxylic acid compounds |
| topic | longifolene hydrotalcite antifungal activity 3D-QSAR controlled-releasing |
| url | https://www.mdpi.com/1420-3049/28/4/1911 |
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