Sphinganine-analog mycotoxins (SAMs) including fumonisins and f. sp. (AAL) toxins are a group of related mycotoxins produced by plant pathogenic fungi in the genus and in f. sp. Lycopersici, respectively. SAMs have shown diverse cytotoxicity and phytotoxicity, causing adverse impacts on plants, animals, and humans, and are a destructive force to crop production worldwide. This review summarizes the structural diversity of SAMs and encapsulates the relationships between their structures and biological activities. The toxicity of SAMs on plants and animals is mainly attributed to their inhibitory activity against the ceramide biosynthesis enzyme, influencing the sphingolipid metabolism and causing programmed cell death. We also reviewed the detoxification methods against SAMs and how plants develop resistance to SAMs. Genetic and evolutionary analyses revealed that the (fumonisins biosynthetic) gene cluster was responsible for fumonisin biosynthesis in spp. Sequence comparisons among species within the genus suggested that mutations and multiple horizontal gene transfers involving the gene cluster were responsible for the interspecific difference in fumonisin synthesis. We finish by describing methods for monitoring and quantifying SAMs in food and agricultural products.