Quantitative gas chromatographic analysis of plant cuticular waxes containing long-chain aldehydes

Phytol derived from chlorophyll hydrolysis in plants is metabolized via phytenal

“…Phytol ( cis - and trans -isomers) was obtained from Sigma Aldrich. Phytenal was synthesized by oxidation of phytol with pyridinium chlorochromate ( 22 , 23 ). Briefly, a solution of phytol and pyridinium chlorochromate (in a nanomolar ratio of 0.01–0.09) in dichloromethane was stirred for 90 min.…”

Chemical Variation among Castes, Female Life Stages and Populations of the Facultative Eusocial Sweat Bee Halictus rubicundus (Hymenoptera: Halictidae)

“…To identify the double bond positions in n-alkenes and macrocyclic lactones, we separated pools of extracts into polar (macrocyclic lactones) and unpolar (n-alkenes) fractions using the SPE-method (solid-phase extraction) according to Naß et al ( 1998 ). The double bond positions were identified by derivatizing with dimethyl disulfide (DMDS) according to Carlson et al ( 1989 ).…”

The Chemical Landscape of Leaf Surfaces and Its Interaction with the Atmosphere

“…However, other plant species may have more reactive molecules in their leaf cuticles. For example, more than 50% of the fatty acids in the cuticles of some mangrove species are unsaturated, while Fagus sylvatica and other plants have traces of alkyl coumarates and other unsaturated compounds (Figure B). , Notably, an early study reported significant production of 4-oxopentanal, 6-methyl-5-hepten-2-one, and geranyl acetone upon ozonation of isolated cuticles of various oak species (e.g., Quercus ilex and Quercus suber ) and other common Mediterranean plants . Although the authors did not investigate the nature and location of the parent molecule(s), some Quercus species show a remarkably high proportion of terpenes and terpenoids in their cuticle, in addition to a few aromatic compounds. , (However, metabolites excreted from glandular trichomes , (section ) and/or sampling artifacts (i.e., skin lipids) may also be responsible for the reactivity observed in Fruekilde et al) Third, physically damaged leaves may expose chemicals embedded within the cuticle to atmospheric oxidantse.g., phenolics in the cuticle , and in other leaf tissues may react with gas-phase oxidants. − In conclusion, the cuticle’s reactivity may warrant a reassessment, as it may be relevant in damaged leaves and in plant species with traces of unsaturated chemicals in their leaf cuticle.…”

“…For example, more than 50% of the fatty acids in the cuticles of some mangrove species are unsaturated, 90 while Fagus sylvatica and other plants have traces of alkyl coumarates and other unsaturated compounds (Figure 2B). 64,79 Notably, an early study reported significant production of 4-oxopentanal, 6-methyl-5-hepten-2one, and geranyl acetone upon ozonation of isolated cuticles of various oak species (e.g., Quercus ilex and Quercus suber) and other common Mediterranean plants. 91 Although the authors did not investigate the nature and location of the parent molecule(s), some Quercus species show a remarkably high proportion of terpenes and terpenoids in their cuticle, in addition to a few aromatic compounds.…”

“…(A) Schematic representation of a cuticle showing the location of its primary components. (B) Major chemicals in the leaf cuticles of Fagus sylvatica (European beech). − Epi- and intracuticular waxes are reported together, although the distribution of each chemical may vary depending on its location within the cuticle (see Supporting Information for additional details).…”