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

Abstract

Two new natural products have been isolated from culture broth of Penicillium brevicompactum Dierckx. The structures have been assigned as N-(2-methyl-3-oxodecanoyl)pyrrole and N-(2-methyl-3-oxodec-8-enoyl)pyrrole on the basis of spectral data. Synthesis of analogues has been carried out by acylation of the pyrrole ring at C2 with different acylated Meldrum's acids. Two analogues (6b and 7b) have shown interesting insecticidal activities, and three other ones (6a, 6c, and 7a) have exhibited significant broad-spectrum fungicidal activities. These synthetic products might be considered as a starting point in the search for new pesticides. Keywords: Penicillium brevicompactum; fungal metabolites; Meldrum's acid; 2-(3-oxoacyl)pyrrole; insecticide; fungicide

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 (II)

“…One of the most interesting compounds, brevioxime (1), exhibits a very high activity as a juvenile hormone (JH) biosynthesis inhibitor (Moya et al, 1997;Castillo et al, 1998). Other metabolites possessing in vivo anti-JH activity, N-(2-methyl-3-oxodecanoyl)-2-pyrroline (2a) and N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline (2b), and insecticidal activity, 2-hept-5-enyl-3-methyl-4-oxo-6,7,8,8a,-tetrahydro-4H-pyrrolo[2,1-b]-1,3-oxazine (3), were synthesized following a common route, which diverged only in the last step; this confirmed the chemical and suggested the biosynthetic relationship between both natural products (1-3) Cantín et al, 1998).…”

Exploring the Extracellular Macromolecular Composition of Crude Extracts of Penicillium rubens Strain 212 for Elucidation Its Mode of Action as a Biocontrol Agent

“…Cantín et al [ 77 , 78 ] isolated and identified N -(2-methyl-3-oxodecanoyl)-2-pyrroline from the culture medium of Penicillium brevicompactum , which the authors relate to in vivo anti-juvenile hormone activity [ 79 ]. The antioomycete activity of several Metarhizium extracts was also associated with previously isolated aurovertins, fungerin, N -(methyl-3-oxodec-6-enoyl)-2-pyrroline, and N -(methyl-3-oxodecanoyl)-2-pyrroline [ 80 ].…”

“…There are a number of both naturally occurring and synthetic pyrroles which possess plant protection properties. In particular, most of these compounds are effective against fungi and insects [ 78 ]. Pyrogallol-type phenolic compounds have three adjacent hydroxyl groups on the same benzene ring, which enables their easy oxidation or autoxidation and also allows metal ion chelation, both characteristics contributing significantly to a wide range of biological activities [ 81 ].…”

Thermal Decomposition of Carbamoyl Meldrum's Acids: A Starting Point for the Preparation of 1,3‐Oxazine Derivatives

“…Depending on the type of Meldrum's acid derivative used and in addition the conditions of the process, various compounds can be prepared, for example, β‐lactams , 1,3‐oxazinones , pilicides , isooxazolols , tetramic acid derivatives , cyclic nitrones , prodigiosin family antibiotics analogs, or substituted pyridines . Also, valuable noncyclic compounds can be easily prepared using Meldrum acid as a β‐ketoacylium synthon, for example, we can cite formation of 1,3‐diones , ketoesters , and ketoamides . The main stream of the aforementioned reactions of Meldrum's acid derivatives is connected with their tendency to form ketenes during thermal decomposition; once formed, ketene may react with various types of nucleophiles.…”