Macrotermitinae termites have farmed fungi in the genus Termitomyces as a food source for millions of years. However, the biochemical mechanisms orchestrating this mutualistic relationship are largely unknown. To deduce fungal signals and ecological patterns that relate to the stability of this symbiosis, we explored the volatile organic compound (VOC) repertoire of Termitomyces from Macrotermes natalensis colonies. Results show that mushrooms emit a VOC pattern that differs from mycelium grown in fungal gardens and laboratory cultures. The abundance of sesquiterpenoids from mushrooms allowed targeted isolation of five drimane sesquiterpenes from plate cultivations. The total synthesis of one of these, drimenol, and related drimanes assisted in structural and comparative analysis of volatile organic compounds (VOCs) and antimicrobial activity testing. Enzyme candidates putatively involved in terpene biosynthesis were heterologously expressed and while these were not involved in the biosynthesis of the complete drimane skeleton, they catalyzed the formation of two structurally related monocyclic sesquiterpenes named nectrianolins.

数百万年来，巨白蚁亚科白蚁一直以Termitomyces属的真菌为食。然而，协调这种互惠关系的生化机制在很大程度上是未知的。为了推断与这种共生稳定性相关的真菌信号和生态模式，我们探索了来自Macrotermes natalensis的Termitomyces的挥发性有机化合物 (VOC) 库群落。结果表明，蘑菇散发出的 VOC 模式不同于真菌花园和实验室培养物中生长的菌丝体。蘑菇中丰富的倍半萜类化合物允许从平板栽培中有针对性地分离出五种 drimane 倍半萜。其中一种、drimenol 和相关 drimanes 的全合成有助于挥发性有机化合物 (VOC) 的结构和比较分析以及抗菌活性测试。推测参与萜烯生物合成的候选酶被异源表达，虽然这些不参与完整的 drimane 骨架的生物合成，但它们催化了两种结构相关的单环倍半萜烯的形成，称为 nectrianolins。