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Semisynthesis and antifeedant activity of new derivatives of a dihydro-β-agarofuran from Parnassia wightiana.

Tang JJ, Zhang FY, Wang DM, Tian JM, Dong S, Gao JM - Int J Mol Sci (2013)

Bottom Line: Structures of 2-6 were confirmed by 1D- and 2D-NMR and HR-ESI-MS spectra.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.

View Article: PubMed Central - PubMed

Affiliation: Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China. jinminggao@nwsuaf.edu.cn.

ABSTRACT
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.

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Semisynthesis of derivatives 2–6 from 1. 4-dimethylaminopyridine (DMAP), 1,1,1-tris(acetoxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (DMP), dichloromethane (DCM).
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f3-ijms-14-19484: Semisynthesis of derivatives 2–6 from 1. 4-dimethylaminopyridine (DMAP), 1,1,1-tris(acetoxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (DMP), dichloromethane (DCM).

Mentions: The synthetic pathways of derivatives 2–6 are shown in Scheme 1. All the structures of these derivatives were established on the basis of 1D- and 2D-NMR and HR-ESI-MS spectroscopic analysis (Figures S1–S19). NMR spectra are shown in Tables 1 and 2.


Semisynthesis and antifeedant activity of new derivatives of a dihydro-β-agarofuran from Parnassia wightiana.

Tang JJ, Zhang FY, Wang DM, Tian JM, Dong S, Gao JM - Int J Mol Sci (2013)

Semisynthesis of derivatives 2–6 from 1. 4-dimethylaminopyridine (DMAP), 1,1,1-tris(acetoxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (DMP), dichloromethane (DCM).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3821568&req=5

f3-ijms-14-19484: Semisynthesis of derivatives 2–6 from 1. 4-dimethylaminopyridine (DMAP), 1,1,1-tris(acetoxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (DMP), dichloromethane (DCM).
Mentions: The synthetic pathways of derivatives 2–6 are shown in Scheme 1. All the structures of these derivatives were established on the basis of 1D- and 2D-NMR and HR-ESI-MS spectroscopic analysis (Figures S1–S19). NMR spectra are shown in Tables 1 and 2.

Bottom Line: Structures of 2-6 were confirmed by 1D- and 2D-NMR and HR-ESI-MS spectra.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.

View Article: PubMed Central - PubMed

Affiliation: Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China. jinminggao@nwsuaf.edu.cn.

ABSTRACT
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.

Show MeSH
Related in: MedlinePlus