Novel butyrolactones with antifungal activity

C - Chemistry – Metallurgy – 07 – D

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C07D 307/58 (2006.01) A01N 43/08 (2006.01) A61K 31/365 (2006.01) C07D 307/33 (2006.01) C07D 307/60 (2006.01)

Patent

CA 2246203

The bacterium Pseudomonas aureofaciens 63-28 is antagonistic to several plant pathogenic fungi, including Pythium spp. The bacterium produced at least four antifungal metabolites active against Pythium ultimum and Phytophthora cryptogea when tested in culture for antifungal activity. Three of these compounds were identified as the novel butyrolactones: 3-(1-hexenyl)-5-hydroxymethyl-2,5(I-~furanone (alternate nomenclature: (Z)-4-hydroxymethyl-2-(1-hexenyl)-2-butenolide), 3-(1-hexenyl)-5-hydroxy-5- methyl- 2,5(H)furanone (alternate nomenclature: (Z)-4-hydroxy-4-methyl-2-(1-hexenyl)-2- butenolide) and 3-(1-hexenyl)-5-methyl-2,5(H)furanone, respectively, by using NMR and GC-MS. All compounds were different from other antibiotics produced by Pseudomonas spp., including pyoluteorin, pyrrolnitrin, and 2,4-diacetylphloroglucinol, as determined by HPLC. This is the first report of butyrolactones with antifixngal activity produced by a saprophytic Pseudomonas spp.

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