Insecticidal, Anti-juvenile Hormone, and Fungicidal Activities of Organic Extracts from Different Penicillium Species and Their Isolated Active Components

Abstract

Organic extracts from mycelium and culture broth of 21 Penicillium isolates have been tested for insecticidal, insect anti-juvenile hormone (anti-JH), and antifungal activities. Culture broth extracts were the most active, mainly against insects; nearly 25% of them have shown high entomotoxicity (100% mortality at 100 microg/cm(2)). A strong in vivo anti-JH activity against Oncopeltus fasciatus Dallas was detected in the culture broth extracts from P. brevicompactum P79 and P88 isolates. The two new natural products isolated from P79, N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline (1) and 2-hept-5-enyl-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo[2,1-b]-1, 3-oxazine (2), possessed anti-JH and insecticidal activity, respectively, against O. fasciatus. Synthesized natural compound 1 has shown an ED(50) of 0.7 microg/nymph when assayed on newly molted fourth-instar nymphs of O. fasciatus. Promising biological activities have also been detected in the synthetic precursors.

Biosynthesis of two dihydropyrrole-polyketides from a marine-derived Penicillium citrinum

“…After toxicity evaluation with unlabeled sodium acetate, added to the growth medium of P. citrinum (up to 5 g L -1 ), for which no morphology alterations of the fungus in the growth medium or even alterations in the production yield of 1 and 2 were observed, experiments with sodium[1-13 C]acetate, sodium[1,2-13 C 2 ]acetate, sodium [2,[3][4][5][6][7][8][9][10][11][12][13] C 2 ]propionate, [methyl-13 C]methionine, [U-13 C 5 ]ornithine and [U-13 C 5 ]proline were performed. 13 C-Labeled precursors were added at the fourth day of growth, at a final concentration of 1 mg mL -1 for each precursor, using previously optimized growth conditions.…”

“…7 However, such alkaloids are extremely rare in fungi, the only examples found in literature 8 include the dihydropyrrole-bearing peptide brevigellin isolated from Penicillium brevicompactum, 9 the dihydropyrrole b-keto amides 1 and 2 also isolated from P. brevicompactum, [10][11][12] the mildly antibiotic scalusamides A−C (3-5), which have been isolated from a marine-derived P. citrinum, 13 as well as the tetrahydropyrrole-citrinin conjugate perinadine A, isolated from P. citrinum of marine origin. 14 Compounds 1 and 2 display insecticidal, fungicidal activities and induce precocious metamorphosis in the milkweed bug Oncopeltus fasciatus (Insecta).…”

“…14 Compounds 1 and 2 display insecticidal, fungicidal activities and induce precocious metamorphosis in the milkweed bug Oncopeltus fasciatus (Insecta). 12 We have recently isolated the same compounds 1 and 2 from a marine-derived P. citrinum, 15 and became interested to Braz. Chem.…”

“…14 Compounds 1 and 2 display insecticidal, fungicidal activities and induce precocious metamorphosis in the milkweed bug Oncopeltus fasciatus (Insecta). 12 We have recently isolated the same compounds 1 and 2 from a marine-derived P. citrinum, 15 and became interested to establish the actual biosynthetic pathway leading to 1 and 2. This is because while pyrrole, dihydropyrrole or pyrrolidine alkaloids isolated from non-fungal sources are typically derived from proline, 16,17 ornithine, 1 or even from acetate, 16 the biosynthesis of the above mentioned dihydropyrroles isolated from fungi have not yet been investigated.…”

Fungal Secondary Metabolism in the Light of Animal–Fungus Interactions: From Mechanism to Ecological Function

“…Numerous studies have used protocols for secondary metabolite isolation in combination with animal exposure assays to determine the toxicity of fungal chemicals (e.g., [34][35][36][37][38][39][40][41][42]). By using several insect systems, many metabolites turned out to have insecticidal properties; i.e., killed juveniles and adults or inhibited juvenile development ( Fig.…”