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Targeted gene inactivation, metabolic profiling, and bioassays led to the discovery of the gladiofungins as previously\u2010overlooked components of the antimicrobial armory of the beetle symbiont, which are highly active against the entomopathogenic fungus <jats:italic>Purpureocillium lilacinum<\/jats:italic>. By mutational analyses, isotope labeling, and computational analyses of the modular polyketide synthase, we found that the rare butenolide moiety of gladiofungins derives from an unprecedented polyketide chain termination reaction involving a glycerol\u2010derived C3 building block. 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