Loline Alkaloids: Currencies of Mutualism

Abstract

Organic chemistry Z 0200 Loline Alkaloids: Currencies of Mutualism -[87 refs.]. -(SCHARDL*, C. L.; GROSSMAN, R. B.; NAGABHYRU, P.; FAULKNER, J. R.; MALLIK, U. P.; Phytochemistry 68 (2007) 7, 980-996; Dep. Plant Pathol., Univ. Ky., Lexington, KY 40546, USA; Eng.) -Nuesgen 30-211

Loline alkaloid production by fungal endophytes of Fescue species select for particular epiphytic bacterial microflora

“…As B. ambifaria exhibited the highest growth rate and achieved the highest population size when grown on lolines and was likely to be the most genetically tractable, it was chosen for further analysis. As several substituted forms of loline can occur in infected plants (Schardl et al, 2007), we examined which forms were present in our extracts by both thin layer chromatography (TLC) and GC-MS analysis (Supplementary Figures S1 and S2). N-Formylloline was preferentially consumed by B. ambifaria, as indicated by GC analysis (Yates et al, 1990).…”

“…Lolines are saturated 1-aminopyrrolizidine alkaloids having a variety of substitutions on the 1-amino group and an epoxide oxygen bridge between C 2 and C 7 (Schardl et al, 2007). They are broadly toxic to many insect herbivores of grasses (Wilkinson et al, 2000).…”

“…They are broadly toxic to many insect herbivores of grasses (Wilkinson et al, 2000). However, unlike the hepatoxic/carcinogenic pyrrolizidines produced by plants, loline alkaloids are non-toxic to mammalian herbivores (Schardl et al, 2007). Of the several loline alkaloids produced by Neotyphodium strains, N-formylloline is typically found in the highest concentrations (Justus et al, 1997).…”

Butterflies Extracts Show Antibacterial Activity

“…Several of the grass food plants are known to contain modified or precursors of PAs [14]. Loline alkaloids are also produced by mutualistic fungi symbiotic with grasses, and may be the source of the PAs we have found in the adult butterflies [15] [16] [17] [18]. The association of the symbiotic fungal endophytes with the food plants of these species is widespread, but erratic.…”

Variable Effects of Grass-Neotyphodium Associations on Cereal Leaf Beetle (Coleoptera: Chrysomelidae) Feeding, Development and Survival

“…All of these alkaloid classes have anti-insect activity (Siegel et al 1990;Siegel and Bush 1996;Lane et al 2000;Schardl et al 2007;Potter et al 2008). However, only pyrrolizidine loline derivatives (N-formyl loline, N-acetyl loline, N-acetyl norloline) and peramine (pyrrolopyrazine) are widely viewed as important in the insect resistance of E+ grasses because, unlike ergot and lolitrem alkaloids in E+ grasses, they have no known toxic effects on vertebrates (Bush et al 1997;Lane et al 2000).…”