- Germacrone derivatives as new insecticidal and acaricidal compounds: A structure-activity relationship
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Currently, the use of synthetic pesticides is the main method of plant protection applied in agri- and horticulture. However, its excessive use leads to the development of pesticide resistance, a contamination of the environment, toxicity to non-target organisms, and risks for human health. With the ultimate aim of contributing to the develop of a more sustainable pest management, we used the natural product germacrone (compound 1), reported to possess significant insecticidal activity, as starting material for the generation of molecular diversity (2-24). Some of the generated derivatives are natural compounds, such as 1,10-epoxygermacrone (2), 4,5-epoxygermacrone (3), gajutsulactone A (7), germacrol (11), isogermacrone (14), 9-hydroxyeudesma-3,7(11)dien-6-one (19), eudesma-4,7(11),dien-8-one (20), eudesma-3,7(11)-dien-8-one (21) and eudesma-4(15),7(11)-dien-8-one (22). Compounds, 7,11-9,10-diepoxigermacr-4,5-en-8-ol (17), 7,11-epoxieudesma-4,7(11)-dien-8-one (23) and 7,11-epoxieudesma-3,7(11)-dien-8-one (24) are described for the first time. The biocidal activity of most of these compounds was assayed against the tick Hyalomma lusitanicum. The acaricidal effects of compound 24 were four times higher than that of germacrone (1). Compound 2 is an insect antifeedant a thousand times more potent than germacrone against Rhopalosiphum padi, which makes this substance a promising selective antifeedant against this cereal pest.
- Pretel, Alberto Galisteo,Del Pulgar, Helena Pérez,De León, Estela Guerrero,López-Pérez, José Luis,Olmeda, A. Sonia,Gonzalez-Coloma, Azucena,Barrero, Alejandro F.,Del Moral, José Francisco Quílez
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- Structural diversity from the transannular cyclizations of natural germacrone and epoxy derivatives: A theoretical-experimental study
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Treatment of germacrone (1) with different electrophiles, and of its epoxy derivatives germacrone-4,5-epoxide (2), germacrone-1,10-epoxide (3) and isogermacrone-4,5-epoxide (4) with Br?nsted/Lewis acids and Ti III, gives rise to a great structural diversity. Thus, by using a maximum of two steps, the production of more than 40 compounds corresponding to 14 skeletons is described. Computational calculations rationalizing the structural divergence produced are also described. Finally, since some of the compounds generated are bioactive natural sesquiterpenes, the mechanisms of formation of these substances will provide new insights in their biosynthesis. Copyright
- Pérez Morales, M. Carmen,Catalán, Julieta V.,Domingo, Victoriano,Jaraíz, Martín,Herrador, M. Mar,Quílez Del Moral, José F.,L?pez-Pérez, José-Luis,Barrero, Alejandro F.
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supporting information
p. 6598 - 6612
(2013/06/27)
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- Biotransformation of germacrane epoxides by Cichorium intybus
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The biotransformation of germacrone-4,5-epoxide (2), germacrone-1,10-epoxide (3), isogermacrone-4,5-epoxide (5), germacrene B-4,5-epoxide (6) and germacrene B-1,10-epoxide (7) by a suspension of fresh chicory root (Cichorium intybus) was investigated. Enz
- Piet, Dennis P.,Schrijvers, Robert,Franssen, Maurice C. R.,De Groot, Aede
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p. 6303 - 6314
(2007/10/02)
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