Nitidane: An Irregular Prenylated Diterpene from the Cuticle of the Springtail <i>Heteromurus nitidus</i>

Collembola are closely related to insects, but our knowledge of their often unique chemistry is limited. Here we report the identification of the epicuticular lipid nitidane, representing a novel class of epicuticular lipids. Nitidane (4) is an irregular terpene consisting of seven isoprene units, made up of a diterpene core that is modified by a geranyl moiety that is itself prenylated. The observed [46+(22+11)1]-terpene structure has not been reported before.