Chemical investigations of several genera of North American fireflies have shown the presence of steroidal pyrones known as lucibufagins (LBGs). These compounds have been shown to have potent anti-predator activity. Lucibufagins are a subclass of bufadienolides, toxins that affect sodium-potassium ATPase, that includes compounds known from toads, a snake, and at least six families of plants. Due to the wide variety of taxa that contain bufadienolides and their medically-relevant bioactivity, there is great interest in their biosynthesis. Here we describe the presence of LBGs from Pyractomena borealis and show evidence of endogenous biosynthesis of these compounds. Analysis of NMR spectra of extracts of P. borealis adults indicated the presence of a LBG previously known from Lucidota atra. HPLC-MS studies were performed to show incorporation of doubly 13C labeled cholesterol into the steroid core of the P. borealis LBG.

Composition and endogenous biosynthesis of the chemical defense of Pyractomena borealis

255th National Meeting (2018)

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