Synthesis, biotransformation and biological activity of halolactones obtained from β-ionone

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• 作者：Małgorzata Grabarczyk^a ; ^{magrab@onet.pl" class="auth_mail" title="E-mail the corresponding author} ; Katarzyna Wińska^a ; Wanda Mączka^a ; Barbara Żarowska^b ; Gabriela Maciejewska^c ; Katarzyna Dancewicz^d ; Beata Gabryś^d ; Mirosław Anioł^a
• 关键词：β-ionone ; Lactones ; Hydrolytic dehalogenation ; Fusarium species ; Antimicrobial activity
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：4 February 2016
• 年：2016
• 卷：72
• 期：5
• 页码：637-644
• 全文大小：549 K

文摘

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.