Lolines are a class of alkaloids produced by fungi in the genus Neotyphodium that are in symbiotic relationships with cool-season grasses (Poaceae subfamily Po�ideae). Lolines possess antifeedant and insecticidal properties that protect the plant from insect herbivory without any concomitant antimammalian activity; they also increase their hosts' phosphate uptake and tolerance towards drought and heat. Lolines are pyrrolizidines with an ether bridging C atom 2 and 7 . The ether bridge is in an unusual context in biological compounds, which raises interesting questions about the lolines' biosynthesis. We have synthesized various proposed biosynthetic intermediates in isotopically labeled form and used them in feeding experiments, helping us to propose a biosynthetic pathway for the lolines.

Synthesis of intermediates of loline biosynthesis pathway

247th National Meeting (2014)

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