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Phytochemical diversity is an effective plant defensive attribute, but much more research has focused on genetic and environmental controls of specific defensive compounds than phytochemical diversityper se. Documenting plasticity in phytochemical richness and plant chemical composition as opposed to individual compounds is important for understanding plant defense. This study outlines a multi-site transplant experiment in Cerrado gallery forests in central Brazil, utilizingPiper arboreum(Piperaceae), a prevalent and widespread neotropical shrub. Clones from four distinct populations were planted either at their origin site or in a different forest. Secondary metabolite composition varied between populations initially and then changed after transplanting. Interestingly, clones with chemical profiles that were distinct from the populations where they were introduced experienced reduced specialist chrysomelid herbivory compared to clones that were more chemically similar to the existingP. arboreumpopulations where they were planted. Specialist Lepidoptera herbivory also declined in clones transplanted to a new forest, but this change could not be ascribed to chemical profiles. In contrast, generalist herbivory was unaffected by chemical dissimilarity and transplanting. This research adds to the expanding body of evidence suggesting that phytochemical diversity is a dynamic trait exerting unique effects on different herbivore guilds.