Given that plants cannot outrun their predators, they often rely on chemical defenses to protect themselves and their offspring (seeds). These chemical defenses, often unique to particular plants or groups of plants, are valuable resources for developing natural pesticides that may carry fewer risks for ecosystems and for consumers. This project focuses on a group of plants in the tomato family that produce a promising class of natural insecticides called acylsugars. These sticky sugars are produced by gland-tipped hairs and act as traps for insect predators, but they are non-toxic to humans and degrade quickly in the environment. While most acylsugar research has examined their importance in leaf defense, this research will explore their role in protecting the fruit and its enclosed seeds, studying the tomatillos and their wild relatives. Many of these species cover their fruit in a balloon-like sac that develops from the outer organ of the flower (the calyx), and they decorate this inflated calyx with dense sticky acylsugar-coated hairs. This research will investigate the relationship between the repeated evolutionary origins of the inflated calyx across tomatillos and the production of insecticidal acylsugars, providing the foundation for developing novel natural insecticides. This project is built upon a collaborative network of tomatillo researchers from the U.S. and abroad and will advance international collaborations. It will provide training opportunities for early ca