Brevioxime:  A New Juvenile Hormone Biosynthesis Inhibitor Isolated from Penicillium brevicompactum

Isolation of N-(2-Methyl-3-oxodecanoyl)pyrrole and N-(2-Methyl-3-oxodec-8-enoyl)pyrrole, Two New Natural Products from Penicillium brevicompactum, and Synthesis of Analogues with Insecticidal and Fungicidal Activity

“…The procedure was similar to that previously reported for brevioxime (Moya et al, 1997 The strain was seeded in Petri dishes with PDA culture medium and incubated for 7 days at 28 °C. Then, sterile distilled water with Tween 80 (0.05 %) was used to obtain a suspension containing ca.…”

“…The radial mycelial growth was measured and the percentage of The fact that compounds 2 and 3 were isolated from a different fraction obtained from the same extract as the active brevioxime (1) (Moya et al, 1997), together with the 255 presence of a side chain of seven carbons (with or without a double bond) in the three natural products 1-3, prompted us to synthesize other related compounds in order to explore their biological activities.…”

“…Recently we have reported the isolation and identification of brevioxime (1), a new metabolite from P. brevicompactum, which exhibits a very high activity as JH biosynthesis 35 inhibitor (Moya et al, 1997). Its chemical structure contains an unusual heterobicyclic skeleton and an oxime functionality.…”

“…Their chemical structures are new: they were neither 40 described as fungal metabolites nor as synthetic compounds. The fact that compounds 2 and 3 were isolated from the same extract as the active brevioxime (1) (Moya et al, 1997), together with the structural analogies between the three natural products 1-3, prompted us to synthesize a series of related pyrroles and to determine their biological activities.…”

Synthesis and Biological Evaluation of New Analogues of the Active Fungal Metabolites N-(2-Methyl-3-oxodecanoyl)-2-pyrroline and N-(2-Methyl-3-oxodec-8-enoyl)-2-pyrroline

“…Thus, brevioxime (1), isolated from Penicillium brevicompactum, exhibits a very high activity as JH biosynthesis inhibitor 55 (Moya et al, 1997;Castillo et al, 1998). The related compounds, N-(2-methyl-3-oxodecanoyl)-2-pyrroline (2), N-(2-methyl-3-oxodec-6-enoyl)-2-pyrroline (3) and 2-hept-5-enyl-3-methyl-4-oxo-6,7,8,8a,-tetrahydro-4H-pyrrolo[2,1-b]-1,3-oxazine (4), isolated from the same source, show in vivo JH antagonistic and insecticidal activity Cantín et al, 1999).…”