Structure and biosynthesis of cleomeprenols from the leaves of Cleome spinosa

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Abstract
Cleomeprenols isolated from Cleome spinosa L. (Capparidaceae) have been identified as nonaprenol (1), decaprenol (2), and undecaprenol (3), which are composed of an ω-terminal isoprene, three internal E-isoprene, and the remaining Z-isoprene residues, respectively. Feeding experiments using stereospecifically double-labelled radioactive mevalonate showed that all the cleomeprenols are composed of four biogenetically E- and the remaining biogenetically Z-isoprene residues. Occurrence of the successive cis-condensation of isoprene residues with (2E, 6E,10E)-geranylgeranyl pyrophosphate was demonstrated by comparing the incorporation of a homologue of all-E-prenyl pyrophosphates with that of the corresponding 2Z-isomer.