Insecticidal Activity of Penitrems, Including Penitrem G, a New Member of the Family Isolated from Penicillium crustosum

Abstract

Penitrem G (7), a new indole-diterpenoid compound, has been isolated together with the already known mycotoxins penitrems A−D (1−4) and F (6) from the mycelium of Penicillium crustosum Thom. The structure of penitrem G was established on the basis of spectroscopic data. In addition, paspaline (8), another indole-diterpenoid mycotoxin that has not been previously described in this fungus, was also isolated. These compounds were tested for insecticidal activity against the hemipteran Oncopeltus fasciatus Dallas and the dipteran Ceratitis capitata Wiedemann. Penitrems A−D and F showed convulsive and insecticidal activities against both insect species. In addition, important reductions in the fecundity and fertility of the surviving C. capitata females were observed. In contrast, penitrem G and paspaline did not show any kind of activity. Mortality data and sublethal effects of the treatments have allowed preliminary structure−activity relationships to be proposed. Keywords: Penicillium crustosum; penitrems; penitrem G; indole-diterpenoid; mycotoxin; insecticidal activity; Oncopeltus fasciatus; Ceratitis capitata; fecundity; fertility