Literature DB >> 12381121

Feeding deterrence and contact toxicity of Stemona alkaloids-a source of potent natural insecticides.

Brigitte Brem1, Christoph Seger, Thomas Pacher, Otmar Hofer, Srunya Vajrodaya, Harald Greger.   

Abstract

On the basis of chronic feeding bioassays with neonate larvae of Spodoptera littoralis reared on an artificial diet, the methanolic leaf and root extracts from Stemona collinsae displayed very high insect toxicity compared to those of two Aglaia species, a commercial Pyrethrum extract, and azadirachtin, whereas S. tuberosa extracts demonstrated low activity in roots and no activity in leaves. Beyond that, in leaf disk choice tests against fifth instar larvae, S. collinsae showed strong antifeedant activity, whereas S. tuberosa was characterized by remarkable repellency. The anti-insect properties of both species were based on pyrrolo[1,2-a]azepine alkaloids, from which didehydrostemofoline (asparagamine A) was the major compound of the roots of S. collinsae, exhibiting the highest toxicity in feeding assays. Saturation and hydroxylation of the side chain in the co-occurring stemofoline and 2'-hydroxystemofoline, respectively, led to an increasing loss of activity. Contact toxicity tests with stemofoline and didehydrostemofoline exhibited even higher activities than those of Pyrethrum extract. Tuberostemonine was the dominating alkaloid in the roots of S. tuberosa, showing outstanding repellency but no toxic effects.

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Year:  2002        PMID: 12381121     DOI: 10.1021/jf0205615

Source DB:  PubMed          Journal:  J Agric Food Chem        ISSN: 0021-8561            Impact factor:   5.279


  12 in total

1.  Novel Entry to the Tricyclic Core of Stemofoline and Didehydrostemofoline.

Authors:  Jochen Dietz; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  Toward a total synthesis of the stemofoline alkaloids: Advancement of a 1,3-dipolar cycloaddition strategy.

Authors:  Charles S Shanahan; Nathan O Fuller; Bjoern Ludolph; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-08-10       Impact factor: 2.415

3.  Asymmetric Formal Total Synthesis of the Stemofoline Alkaloids: The Evolution, Development and Application of a Catalytic Dipolar Cycloaddition Cascade.

Authors:  Charles S Shanahan; Chao Fang; Daniel H Paull; Stephen F Martin
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

4.  Development of a pharmacodynamic screening model with Crithidia fasciculata.

Authors:  Oumaporn Tasanor; Doris Engelmeier; Brigitte Brem; Ursula Wiedermann-Schmidt; Harald Greger; Walther H Wernsdorfer
Journal:  Wien Klin Wochenschr       Date:  2006       Impact factor: 1.704

5.  Chemical analysis reveals the botanical origin of shatavari products and confirms the absence of alkaloid asparagamine A in Asparagus racemosus.

Authors:  Yukie Kumeta; Takuro Maruyama; Daigo Wakana; Hiroyuki Kamakura; Yukihiro Goda
Journal:  J Nat Med       Date:  2012-04-20       Impact factor: 2.343

6.  Application of an intramolecular dipolar cycloaddition to an asymmetric synthesis of the fully oxygenated tricyclic core of the stemofoline alkaloids.

Authors:  Ryan J Carra; Matthew T Epperson; David Y Gin
Journal:  Tetrahedron       Date:  2008-04-21       Impact factor: 2.457

7.  Enantioselective formal total syntheses of didehydrostemofoline and isodidehydrostemofoline through a catalytic dipolar cycloaddition cascade.

Authors:  Chao Fang; Charles S Shanahan; Daniel H Paull; Stephen F Martin
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-17       Impact factor: 15.336

8.  Simultaneous quantification of six alkaloid components from commercial stemonae radix by solid phase extraction-high-performance liquid chromatography coupled with evaporative light scattering detector.

Authors:  Rong-Rong Zhang; Dan-Yi Lu; Zhen-Ya Yang; Wen Zhao; Paul Pui-Hay But; Pang-Chui Shaw; Ren-Wang Jiang; Zhi-Guo Ma
Journal:  Pharmacogn Mag       Date:  2015 Apr-Jun       Impact factor: 1.085

9.  Development of a pharmacodynamic screening model with Entamoeba histolytica.

Authors:  Oumaporn Tasanor; Brigitte Brem; David Leitsch; Marina Binder; Michael Duchêne; Harald Greger; Walther H Wernsdorfer
Journal:  Wien Klin Wochenschr       Date:  2007       Impact factor: 2.275

10.  Impact of the Stem Extract of Thevetia neriifolia on the Feeding Potential and Histological Architecture of the Midgut Epithelial Tissue of Early Fourth Instars of Helicoverpa armigera Hübner.

Authors:  Monika Mishra; Kamal Kumar Gupta; Sarita Kumar
Journal:  Int J Insect Sci       Date:  2015-10-18
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