32179-17-2Relevant academic research and scientific papers
Germacrone derivatives as new insecticidal and acaricidal compounds: A structure-activity relationship
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
, (2019/08/20)
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.
Structural diversity from the transannular cyclizations of natural germacrone and epoxy derivatives: A theoretical-experimental study
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.
supporting information, p. 6598 - 6612 (2013/06/27)
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
Biotransformation of germacrane epoxides by Cichorium intybus
Piet, Dennis P.,Schrijvers, Robert,Franssen, Maurice C. R.,De Groot, Aede
, p. 6303 - 6314 (2007/10/02)
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
BIOTRANSFORMATION OF GERMACRONE BY SUSPENSION CULTURED CELLS
Sakamoto, Shiho,Tsuchiya, Naoko,Kuroyanagi, Masanori,Ueno, Akira
, p. 1215 - 1220 (2007/10/02)
The transformation of germacrone, a 10-membered ring sesquiterpene, by suspension cultured cells of Lonicera japonica, Bupleurum falcatum, Polygonum tinctorium and Solidago altissima, was investigated.Germacrone was converted into several types of sesquiterpenes, such as guaiane, eudesman and seco-guaiane and their structures were determined from spectral and chemical evidence.The configurations of some of the products were determined by CD spectroscopy.The differences of the kinds of products among the four suspension cultured cells is discussed.
BIOTRANSFORMATION OF SESQUITERPENES BY CULTURED CELLS OF CURCUMA ZEDOARIA
Sakui, Norihiro,Kuroyanagi, Masanori,Ishitobi, Yoko,Sato, Makoto,Ueno, Akira
, p. 143 - 148 (2007/10/02)
The transformation of a 10-membered ring sesquiterpene, germacrone, into guaiane-type sesquiterpenes by suspension cultured cells of Curcuma zedoaria was investigated.Germacrone was converted into several sesquiterpenes, some of which were isolated from the Curcuma spp. plants through the key intermediate, (4R,5R)-germacrone 4,5-epoxide, and their structures were determined by spectral and chemical evidence.The configurations of some of the derivatives were opposite to those of the sesquiterpenes isolated from the Curcuma sp plants, C. aromatica, C. longa and C. zedoaria.An eudesmane-type product was also isolated and its structur e was determined.From the structure, the transformation of germacrone through the intermediate, (1S,10S)-germacrone 1,10-epoxide, was supposed and further confirmed by the transformation of germacrone 1,10-epoxide into the same product by acid treatment.The structures of two new products were also determined and their transformation mechanism through curcumenone and dihydrocurcumenone was deduced. Key Word Index - Curcuma zedoaria; Zingiberaceae; cell suspension culture; biotransformation; sesquiterpene; germacrone; guaiane; eudesmane.
THE STEREOSTRUCTURE OF WENJINE AND RELATED (1S,10S),(4S,5S)-GERMACRONE-1(10),4-DIEPOXIDE ISOLATED FROM CURCUMA WENYUJIN
Gao, Ji-Fu,Xie, Ji-Hong,Iitaka, Yoichi,Inayama, Seiichi
, p. 233 - 236 (2007/10/02)
A novel superoxidized sesquiterpenoid named wenjine (1) and germacrone diepoxide (2) with the germacrone epoxide (3) were isolated from the essential oil of the air-dried rhizoma of Curcuma wenyujin.The stereostructure of 1 was determined on the basis of its spectral data and X-ray diffraction.The absolute structure of 2 was also elucidated based on the spectral data and the transformation from 3. KEYWORDS - Curcuma wenyujin; wenjine; (1S,10S),(4S,5S)-germacrone-1(10),4-diepoxide; (4S,5S)-germacrone-4,5-epoxide; X-ray diffraction; peroxy hemiacetal; 1,2-dioxalane
