Synthesis, biotransformation and biological activity of halolactones obtained from β-ionone. Issue 5 (4th February 2016)

• Record Type: Journal Article
• Authors: Grabarczyk, Małgorzata; Wińska, Katarzyna; Mączka, Wanda; Żarowska, Barbara; Maciejewska, Gabriela; Dancewicz, Katarzyna; Gabryś, Beata; Anioł, Mirosław
• Is Part Of: Tetrahedron. Volume 72:Issue 5(2016)
• Page Start: 637
• Page End: 644
• Publication Date: 2016-02-04
• Subjects: β-ionone -- Lactones -- Hydrolytic dehalogenation -- Fusarium species -- Antimicrobial activity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.12.005
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Commercially available β-ionone was used as a starting material for a four-step chemical synthesis of three new γ-halolactones. During these processes one known (β-ionol) and some new compounds (γ, δ-unsaturated ester, γ, δ-unsaturated acid, chloro-, bromo- and iodo-lactone) were obtained. In the last step, halolactones were converted into a hydroxylactone by several fungal strains ( Fusarium species, Syncephalastrum racemosum, Botrytis cinerea ). Most of the selected microorganisms transformed these lactones by the hydrolytic dehalogenation. The synthetic halolactones and the hydroxylactone obtained during biotransformation inhibited growth of some bacteria, yeasts and fungi and showed deterrent activity against aphids Myzus persicae . Graphical abstract: