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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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NOESY experiment of compound 2.
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f2-ijms-14-19484: NOESY experiment of compound 2.

Mentions: Compound 2, obtained through acylation [19] of 1 in the presence of triethylamine (Et3N) and catalytic dimethylaminopyridine (DMAP) in dry dichloromethane (DCM), showed an accurate [M + Na]+ ion at m/z 615.2219 in the HR-ESI-MS, corresponding to the molecular formula C33H36O10. In the 1H-NMR spectrum of 2, the signal of H-8 for 1 at 4.45 ppm had moved to 5.39 ppm. Further assignments were made based on DEPT, HSQC, and HMBC experiments spectra. Structure, numbering and key NOESY correlations of 2 are shown in Figure 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)

NOESY experiment of compound 2.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f2-ijms-14-19484: NOESY experiment of compound 2.
Mentions: Compound 2, obtained through acylation [19] of 1 in the presence of triethylamine (Et3N) and catalytic dimethylaminopyridine (DMAP) in dry dichloromethane (DCM), showed an accurate [M + Na]+ ion at m/z 615.2219 in the HR-ESI-MS, corresponding to the molecular formula C33H36O10. In the 1H-NMR spectrum of 2, the signal of H-8 for 1 at 4.45 ppm had moved to 5.39 ppm. Further assignments were made based on DEPT, HSQC, and HMBC experiments spectra. Structure, numbering and key NOESY correlations of 2 are shown in Figure 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