Nitidane: An Irregular Prenylated Diterpene from the Cuticle of the Springtail Heteromurus nitidus .

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 [4 6 +(2 2 +1 1 ) 1 ]-terpene structure has not been reported before.