Bisorbicillinoids Produced by the Fungus Trichoderma citrinoviride Affect Feeding Preference of the Aphid Schizaphis graminum

Abstract

We report the effects of some bisorbicillinoids isolated from biomass of the fungus Trichoderma citrinoviride on settling and feeding preference of the aphid Schizaphis graminum. Purification of the fungal metabolites was carried out by a combination of column chromatography and thin-layer chromatography using direct and reverse phases. Chemical identification was performed by spectroscopic methods including nuclear magnetic resonance and mass spectrometry. The identified bisorbicillinoids appeared to be bislongiquinolide, its 16,17-dihydro derivative, trichodimerol, and dihydrotrichodimerol. A feeding preference test with alate morphs of S. graminum was used to identify the active fractions. Among the four bisorbicillinoids, dihydrotrichodimerol and bislongiquinolide influenced aphid feeding preference, restraining specimens from settling on leaves treated with metabolites. Taste neurons sensitive to these compounds, particularly to bislongiquinolide, were located on tarsi of the S. graminum alate morphs.

Sorbicillinoids from Fungi and Their Bioactivities

“…Dihydrotrichodimerol (44) and bislongiquinolide (=bisorbibutenolide=trichotetronine, 49) from Trichoderma citrinoviridev influenced aphid feeding preferences [48]. Isobisvertinol (38) from Aspergillus sp.…”

“…[22] Bisvertinolone (34) Inhibitory effect on β-l,6-glucan biosynthesis [42] Isobisvertinol (38) Inhibitory effect on lipid droplet accumulation in mouse macrophages [40] Trichodimerol (42) Inhibitory effect on bacterial endotoxin-induced production of tumor necrosis factor (TNF-α) in murine macrophages and human peripheral blood monocytes [46] Inhibitory effect on lipopolysaccharide-induced eicosanoid secretion in THP-1 human monocytic cells [66] Suppression of the production of tumor necrosis factor-α and nitric oxide in LPS-stimulate RAW264.7 cells [50] Dihydrotrichodimerol (44) Activation of peroxisome proliferator-activated recptor γ (PPAR γ) with an ED 50 of 80 ng/mL [50] Suppression of the production of tumor necrosis factor-α and nitric oxide in LPS-stimulate RAW264.7 cells [50] Effect on feeding perference of the aphid [48] Bislongiquinolide (49) Effect on feeding perference of the aphid [48] Sorbiterrin A (79) Inhibitory effect on acetylcholinesterase activity with IC 50 value of 25 µg/mL [61] Note: "ED 50 " means the median effective dose. "IC 50 " means the median inhibitory concentration.…”

The Effect of Stereochemistry on the Biological Activity of Natural Phytotoxins, Fungicides, Insecticides and Herbicides

“…graminum alate morphs. These allowed us to characterize bislongiquinolide ( 39 ) and dihydrotrichodimerol ( 38 ) as two additional Trichoderma metabolites that influence aphid feeding preference, restraining them from settling on treated leaves …”

Production and chemical characterization of pigments in filamentous fungi

“…This compound reduced the feeding preference of the aphid Schizaphis graminum, one of the most important pests of cereal crops, suggesting a potential for the development of new agrochemicals for control of this pest (Evidente et al, 2009). Moreover, dihydrotrichodimerol previously isolated from P. terrestre and from unidentified fungal strains, showed, respectively, cytotoxic effects to cancer cell lines and effects on the activation of PPARc (peroxisome proliferator-activated receptor c), a nuclear receptor with therapeutic potential in the treatment of type 2 diabetes, inflammatory disease, and certain cancers (Lee et al, 2005;Liu et al, 2005).…”