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Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana
Five new derivatives (2–6) were semi-synthesized using compound 1, a dihydro-β-agarofuran sesquiterpene with C-2 ketone obtained from Parnassia wightiana, as the starting material by acylation, oxidation, reduction, esterification, and amination, respectively. Structures of 2–6 were confirmed by 1D-...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Molecular Diversity Preservation International (MDPI)
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3821568/ https://www.ncbi.nlm.nih.gov/pubmed/24077121 http://dx.doi.org/10.3390/ijms141019484 |
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author | Tang, Jiang-Jiang Zhang, Fei-Yu Wang, Dong-Mei Tian, Jun-Mian Dong, Shuai Gao, Jin-Ming |
author_facet | Tang, Jiang-Jiang Zhang, Fei-Yu Wang, Dong-Mei Tian, Jun-Mian Dong, Shuai Gao, Jin-Ming |
author_sort | Tang, Jiang-Jiang |
collection | PubMed |
description | Five new derivatives (2–6) were semi-synthesized using compound 1, a dihydro-β-agarofuran sesquiterpene with C-2 ketone obtained from Parnassia wightiana, as the starting material by acylation, oxidation, reduction, esterification, and amination, respectively. Structures of 2–6 were confirmed by 1D- and 2D-NMR and HR-ESI-MS spectra. In addition, antifeedant activities of these compounds (1–6) were tested against the 3rd-instar larvae of Mythimna separata. Antifeedant effects of compounds 2 and 4 were greater than the parent compound 1 whereas other compounds exhibited low to no feeding deterrent effects against third instar M. separata larvae in lab bioassays. Therefore, our results suggest that acylated and reduced derivatives at C-8 and C-2, respectively, of 1 may improve the antifeeding effect. This preliminary information will be useful in designing new insect control agents against M. separata and other important pests. |
format | Online Article Text |
id | pubmed-3821568 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Molecular Diversity Preservation International (MDPI) |
record_format | MEDLINE/PubMed |
spelling | pubmed-38215682013-11-11 Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana Tang, Jiang-Jiang Zhang, Fei-Yu Wang, Dong-Mei Tian, Jun-Mian Dong, Shuai Gao, Jin-Ming Int J Mol Sci Article Five new derivatives (2–6) were semi-synthesized using compound 1, a dihydro-β-agarofuran sesquiterpene with C-2 ketone obtained from Parnassia wightiana, as the starting material by acylation, oxidation, reduction, esterification, and amination, respectively. Structures of 2–6 were confirmed by 1D- and 2D-NMR and HR-ESI-MS spectra. In addition, antifeedant activities of these compounds (1–6) were tested against the 3rd-instar larvae of Mythimna separata. Antifeedant effects of compounds 2 and 4 were greater than the parent compound 1 whereas other compounds exhibited low to no feeding deterrent effects against third instar M. separata larvae in lab bioassays. Therefore, our results suggest that acylated and reduced derivatives at C-8 and C-2, respectively, of 1 may improve the antifeeding effect. This preliminary information will be useful in designing new insect control agents against M. separata and other important pests. Molecular Diversity Preservation International (MDPI) 2013-09-26 /pmc/articles/PMC3821568/ /pubmed/24077121 http://dx.doi.org/10.3390/ijms141019484 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Tang, Jiang-Jiang Zhang, Fei-Yu Wang, Dong-Mei Tian, Jun-Mian Dong, Shuai Gao, Jin-Ming Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana |
title | Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana |
title_full | Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana |
title_fullStr | Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana |
title_full_unstemmed | Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana |
title_short | Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana |
title_sort | semisynthesis and antifeedant activity of new derivatives of a dihydro-β-agarofuran from parnassia wightiana |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3821568/ https://www.ncbi.nlm.nih.gov/pubmed/24077121 http://dx.doi.org/10.3390/ijms141019484 |
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