Abstract
Plants synthesize and accumulate a wide variety of compounds called secondary metabolites. Secondary metabolites serve as chemical barriers to protect plants from pathogens and herbivores. Antimicrobial secondary metabolites are accumulated to prevent pathogen infection. These metabolites are classified into phytoalexins (induced in response to pathogen attack) and phytoanticipins (present prior to pathogen infection). The antimicrobial compounds in the grass family (Poaceae) were studied from the viewpoint of evolution. The studies were performed at three hierarchies, families, genera, and species and include the following: 1) the distribution of benzoxazinoids (Bxs) in the grass family, 2) evolutionary replacement of phytoanticipins from Bxs to hydroxycinnamic acid amide dimers in the genus Hordeum, and 3) chemodiversity of flavonoid and diterpenoid phytoalexins in rice. These studies demonstrated dynamic changes in secondary metabolism during evolution, indicating the adaptation of plants to their environment by repeating scrap-and-build cycles.