Enterocin (Vulgamycin) is isolated from Streptomyces in the bacterial kingdom and is a polyketide natural product that is easily proteolytically degraded in the gastrointestinal tract. It has a series of weak to moderate biological activities, such as antibacterial efficacy against Lactobacillus monocytogenes, Listeria and Bacillus, cytotoxicity against HeLa and HepG2 cancer cells, herbicidal activity, and inhibitory activity against β-amyloid fibrillation.

Enterocin 结构非常特殊，具有一个独特且高度氧化的三环笼状核心骨架，带有一个α-吡喃酮单元和一个苄基。该化合物的生物合成途径始于由连接酶组装苯甲酸单元，随后通过与丙二酰辅酶 A 进行脱羧克莱森缩合反应，在 II 型聚酮合酶介导下经过经七次迭代延伸步骤合成而来。特别引人关注的是黄素蛋白催化的 C4 亚甲基的氧化反应，这进一步引发了类法沃斯基重排以及两次分子内醛醇缩合反应，从而构建出三环笼状骨架。