Etudes sur les matières végétales volatiles CLXXII. Présence de (+)‐nopinène et de sabinène dans l'huile essentielle de lavande

Naves, Y. R.; Tullen, Paul

doi:10.1002/hlca.19600430736

Cited by 6 publications

(1 citation statement)

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“…Reference data for p -1,8-menthadienols were from the NIST webbook (including p -1,8-menthadien-4-ol; p -1,8-menthadien-6-ol = carveol; p -1,8-menthadien-7-ol; p -menthadien-9-ol) as well as from literature sources (e.g., cis- and trans carveol: Garneau et al 1997 ; p -1,8-menthadien-3-ol = isopiperitenol: Lücker et al 2004 ). Generally, p -1,8-menthadien-5-ol appears to be a rare compound in nature: we only found one old report on its occurrence, namely in the oil of a particular population of lemongrass Cymbobogon flexuosus (Naves 1961 ). A rudimentary mass spectrum for trans - and cis - p -1,8-menthandien-5-ol (showing the three most prominent ions only and not sufficient for a comparison) is given by Brenna et al ( 2006 ).…”

Section: Discussionmentioning

confidence: 84%

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

et al. 2023

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The oil gland secretion of the oribatid mite Nothrus palustris 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 N. palustris by GC–MS and NMR spectroscopy, eventually identifying the unknown compounds as p-menthane monoterpenoids. The major components were two isomeric 6-isopropenyl-3-methyl-cyclohex-3-en-1-yl formates (= p-1,8-menthadien-5-yl formates), which accounted for about 75% of the secretion. These were accompanied by five additional, only partly identified p-menthanes (or p-methane-derivatives), all of which represented minor or trace components. In addition, adult secretions contained two C21-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 N. palustris, we assume that both geranial and p-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 p-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.

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