After chemo-metamorphosis: -menthane monoterpenoids characterize the oil gland secretion of adults of the oribatid mite, .

The oil gland secretion of the oribatid mite is known to show the phenomenon of juvenile-adult polymorphism, i.e., juvenile instars produce secretions predominated by geranial, whereas adults secrete dehydrocineole along with a number of chemically unidentified compounds. We here re-analyzed the secretions of adult by GC-MS and NMR spectroscopy, eventually identifying the unknown compounds as -menthane monoterpenoids. The major components were two isomeric 6-isopropenyl-3-methyl-cyclohex-3-en-1-yl formates (= -1,8-menthadien-5-yl formates), which accounted for about 75% of the secretion. These were accompanied by five additional, only partly identified -menthanes (or -methane-derivatives), all of which represented minor or trace components. In addition, adult secretions contained two C-hydrocarbons, 1,12-heneicosadiene (major) and a heneicosatriene (minor). Menthane monoterpenoids represent a novel sub-class of terpene compounds in the oil gland secretions of Oribatida. In case of , we assume that both geranial and -menthane monoterpenoids arise via the mevalonate pathway which obviously shows a split at the level of geranyl pyrophosphate, leading to geranial in juveniles and to -menthanes in adults. The significance of methane occurrence in oil glands as well as the taxonomic distribution of juvenile-adult polymorphism in oribatid oil gland secretions is discussed. The latter phenomenon-i.e., "chemo-metamorphosis" of secretions-is not known from early- and middle-derivative Oribatida nor from Astigmata, but appears to be more common in some derivative desmonomatan and brachypyline oribatid groups.