Composition of Plant Cuticular Waxes

Jetter, Reinhard; Kunst, Ljerka; Samuels, Lacey

doi:10.1002/9780470988718.ch4

Cited by 342 publications

(318 citation statements)

References 122 publications

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“…Wax crystals were either of the same dimensions as epicuticular crystals in plants [16–17] or even smaller, because we used alkanes with the same or longer chain lengths, when comparing to plant wax compounds (20 to 40 carbons [22–23]). Microscopy studies of our bioinspired wax surfaces showed differences in both crystal size and density among the samples: The length and thickness of the crystals decreased with an increase of the chain length of the alkanes that formed these surfaces, whereas the density of the wax coverage showed an opposite relationship.…”

Section: Discussionmentioning

confidence: 99%

“…[16–17], which originate from the self-assembly of specific molecules (e.g., [14,18–21]). The morphology of crystals is coherent with the chemical composition of the wax, representing a complex mixture of long-chain aliphatic and cyclic hydrocarbons, fatty acids, aldehydes, ß-diketones, primary and secondary alcohols, and is usually determined by the dominating chemical compound or compound class [16,22–23]. …”

Section: Introductionmentioning

confidence: 99%

“…To avoid the possible influence of chemical diversity and crystal shape, we decided, instead of using native plant wax surfaces, to use bioinspired wax surfaces covered by crystals having a similar morphology. Bioinspired surfaces were made of long-chain hydrocarbons, which can be dominating chemical constituents in plant waxes [22]. Four n -alkanes of varying chain lengths (C 36 H 74 , C 40 H 82 , C 44 H 90 , and C 50 H 102 ) were used to form crystalline wax coatings having a different size and density of crystals.…”

Section: Introductionmentioning

confidence: 99%

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Insect attachment on crystalline bioinspired wax surfaces formed by alkanes of varying chain lengths

Gorb

Böhm

Jacky

et al. 2014

Beilstein J. Nanotechnol.

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SummaryThe impeding effect of plant surfaces covered with three-dimensional wax on attachment and locomotion of insects has been shown previously in numerous experimental studies. The aim of this study was to examine the effect of different parameters of crystalline wax coverage on insect attachment. We performed traction experiments with the beetle Coccinella septempunctata and pull-off force measurements with artificial adhesive systems (tacky polydimethylsiloxane semi-spheres) on bioinspired wax surfaces formed by four alkanes of varying chain lengths (C36H74, C40H82, C44H90, and C50H102). All these highly hydrophobic coatings were composed of crystals having similar morphologies but differing in size and distribution/density, and exhibited different surface roughness. The crystal size (length and thickness) decreased with an increase of the chain length of the alkanes that formed these surfaces, whereas the density of the wax coverage, as well as the surface roughness, showed an opposite relationship. Traction tests demonstrated a significant, up to 30 fold, reduction of insect attachment forces on the wax surfaces when compared with the reference glass sample. Attachment of the beetles to the wax substrates probably relied solely on the performance of adhesive pads. We found no influence of the wax coatings on the subsequent attachment ability of beetles. The obtained data are explained by the reduction of the real contact between the setal tips of the insect adhesive pads and the wax surfaces due to the micro- and nanoscopic roughness introduced by wax crystals. Experiments with polydimethylsiloxane semi-spheres showed much higher forces on wax samples when compared to insect attachment forces measured on these surfaces. We explain these results by the differences in material properties between polydimethylsiloxane probes and tenent setae of C. septempunctata beetles. Among wax surfaces, force experiments showed stronger insect attachment and higher pull-off forces of polydimethylsiloxane probes on wax surfaces having a higher density of wax coverage, created by smaller crystals.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Insect attachment on crystalline bioinspired wax surfaces formed by alkanes of varying chain lengths

Gorb

Böhm

Jacky

et al. 2014

Beilstein J. Nanotechnol.

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“…However, before the development of suitable analytical methods, triterpenoid content of cuticular waxes was considered as rather not interesting and poor in contrast to the rich composition of these compounds occurring in the entire organs. The lack of appropriate methods and standards caused the misleading opinion that only a few structures are present in the cuticular waxes of diverse plant taxa [15]. The recent intensive studies on the occurrence of triterpenoids in surface waxes covering plant organs have demonstrated that the chemical composition of cuticles shows great variability, not only among different plant species, but also between different organs of an individual plant.…”

Section: Digital Signaturementioning

confidence: 99%

Triterpenoid profile of fruit and leaf cuticular waxes of edible honeysuckle Lonicera caerulea var. kamtschatica

2017

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Edible honeysuckle (honeyberry) Lonicera caerulea is becoming popular as a novel berry crop with several useful features such as early fruit ripening and exceptional hardiness, particularly resistance to pests and diseases as well as severe frosts in winter and droughts in summer. The triterpenoid profile of fruit and leaf cuticular waxes of edible honeysuckle (a Russian cultivar Chernichka) was analyzed by GC-MS. The major compounds identified were the tetracyclic triterpenoids campesterol, cholesterol, cycloartanol, cycloart-23-ene-3,25-diol, 24-methylenecycloartanol (only in leaves), sitosterol, stigmasta-3,5-dien-7-one, and stigmasterol; and the pentacyclic triterpenes: α-amyrin, β-amyrin, hop-22(29)-en-3-one, oleanolic acid, and ursolic acid. Several remarkable features of the analyzed triterpenoid contents were revealed, including the relatively low abundance of triterpenoids in fruit waxes (6.5% of wax extract) compared to leaf waxes (22%), and a particularly high proportion of tetracyclic triterpenoids (tetracyclic to pentacyclic compound ratios of 4:1 in fruits and almost 7:1 in leaves). These rare features distinguish the triterpenoid profile of the cuticular waxes of L. caerulea var. kamtschatica from the majority of triterpenoid profiles in plant cuticular waxes investigated to date. To our knowledge, this is the first quantitative compositional study on triterpenoid compounds in the cuticular waxes of edible honeysuckle, supplementing the knowledge of cuticular triterpenoid diversity and distribution.

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“…[1,2] (S)-Nonacosan-10-ol [(+)-Ginnol] is the major component of tubular microcrystalline wax aggregates, which are found on leaf surfaces of several plants such as Nasturtium (Tropaeolum majus L.), the sacred Lotus (Nelumbo nucifera Gaertn.) and Ginkgo (Ginkgo biloba L.).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (S)‐Nonacosan‐10‐ol, the Major Component of Tubular Plant Wax Crystals

et al. 2007

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Abstract(S)‐Nonacosan‐10‐ol [(+)‐Ginnol] is the main component of the tubular wax aggregates, which are found on many plant leaves. To investigate the role of this lipid for the formation of super hydrophobic self‐cleaning plant surfaces, both enantiomers of the title compound were prepared in six steps. Key steps are the resolution of the allylation product of decanal with (R)‐O‐methylmandelic acid, and a chain elongation by cross metathesis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Composition of Plant Cuticular Waxes

Cited by 342 publications

References 122 publications

Insect attachment on crystalline bioinspired wax surfaces formed by alkanes of varying chain lengths

Insect attachment on crystalline bioinspired wax surfaces formed by alkanes of varying chain lengths

Triterpenoid profile of fruit and leaf cuticular waxes of edible honeysuckle Lonicera caerulea var. kamtschatica

Synthesis of (S)‐Nonacosan‐10‐ol, the Major Component of Tubular Plant Wax Crystals

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