Very-long-chain secondary alcohols and alkanediols in cuticular waxes of Pisum sativum leaves

In cuticular waxes from leaves of Pisum sativum, 19 secondary alcohols, 10 primary/secondary alkanediols and three secondary/secondary alkanediols were identified by various chemical transformations with product assignment employing GC-MS. The homologous series Of C-29-C-33 secondary alcohols (1.1 mu g/cm(2)) was dominated by hentriacontanol isomers (94%). Only octacosanediols and trace amounts of hexacosanediols (< 1%) were detected in the primary/secondary alkanediol faction (0.7 mu g/cm(2)). The secondary/secondary alkanediols (0.12 mu g/cm(2)) contained a single homologue with chain length C-31. All three compound classes showed characteristic isomer distributions with secondary functional groups predominantly located between C-14 and C-16. Based on the isomer compositions, the sequence of biosynthetic steps introducing the hydroxyl functions is discussed. (c) 2006 Elsevier Ltd. All rights reserved.