Biogenesis of nonacosan-15-one in brassica oleracea

Kolattukudy, Pappachan E.; Jaeger, R.H.; Robinson, Robert

doi:10.1016/s0031-9422(00)97349-7

Cited by 11 publications

(5 citation statements)

References 9 publications

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“…In these instances, a second stage of the pathway is additionally involved, transforming alkanes first into secondary alcohols and then into ketones (Figure 2). This reaction sequence is well-supported by chemical evidence correlating chain-length and isomer compositions of all three compound classes (Jenks et al, 1995), and by biochemical evidence provided by feeding experiments and detailed studies of label positions in resulting products (Kolattukudy and Liu, 1970;Kolattukudy et al, 1971Kolattukudy et al, , 1973. Recently, a reverse genetic approach led to the discovery of a cytochrome P450 enzyme that is involved in secondary alcohol and ketone formation in A. thaliana .…”

Section: Compound Classesmentioning

confidence: 77%

Plant surface lipid biosynthetic pathways and their utility for metabolic engineering of waxes and hydrocarbon biofuels

2008

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SummaryDue to their unique physical properties, waxes are high-value materials that are used in a variety of industrial applications. They are generated by chemical synthesis, extracted from fossil sources, or harvested from a small number of plant and animal species. As a result, the diversity of chemical structures in commercial waxes is low and so are their yields. These limitations can be overcome by engineering of wax biosynthetic pathways in the seeds of high-yielding oil crops to produce designer waxes for specific industrial end uses. In this review, we first summarize the current knowledge regarding the genes and enzymes generating the chemical diversity of cuticular waxes that accumulate at the surfaces of primary plant organs. We then consider the potential of cuticle biosynthetic genes for biotechnological wax production, focusing on selected examples of wax ester chain lengths and isomers. Finally, we discuss the genes/enzymes of cuticular alkane biosynthesis and their potential in future metabolic engineering of plants for the production of renewable hydrocarbon fuels.

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Section: Compound Classesmentioning

confidence: 77%

Plant surface lipid biosynthetic pathways and their utility for metabolic engineering of waxes and hydrocarbon biofuels

2008

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“…Compelling evidence exists that the VL-CFA precursors described above are utilized for alkane biosynthesis. This conclusion was first drawn from feeding experiments in diverse plant species that showed incorporation of elongation products into various classes of wax compounds, including alkanes, secondary alcohols, and ketones (63,64,69,72). These biochemical results were confirmed by molecular genetic studies in Arabidopsis, where two mutants known to be defective in VLCFA elongation, cer6 and cer10, showed drastic reductions of the longer acyl chains together with depleted levels of all the odd-numbered wax constituents (alkanes, secondary alcohols, and ketones) (54,105).…”

Section: Synthesis Of Alkanes Secondary Alcohols and Ketonesmentioning

confidence: 99%

Sealing Plant Surfaces: Cuticular Wax Formation by Epidermal Cells

Samuels

Kunst

Jetter

2008

Annu. Rev. Plant Biol.

919

768

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The vital importance of plant surface wax in protecting tissue from environmental stresses is reflected in the huge commitment of epidermal cells to cuticle formation. During cuticle deposition, a massive flux of lipids occurs from the sites of lipid synthesis in the plastid and the endoplasmic reticulum to the plant surface. Recent genetic studies in Arabidopsis have improved our understanding of fatty acid elongation and of the subsequent modification of the elongated products into primary alcohols, wax esters, secondary alcohols, and ketones, shedding light on the enzymes involved in these pathways. In contrast, the biosynthesis of alkanes is still poorly understood, as are the mechanisms of wax transport from the site of biosynthesis to the cuticle. Currently, nothing is known about wax trafficking from the endoplasmic reticulum to the plasma membrane, or about translocation through the cell wall to the cuticle. However, a first breakthrough toward an understanding of wax export recently came with the discovery of ATP binding cassette (ABC) transporters that are involved in releasing wax from the plasma membrane into the apoplast. An overview of our present knowledge of wax biosynthesis and transport and the regulation of these processes during cuticle assembly is presented, including the evidence for coordination of cutin polyester and wax production.

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“…The position and geometry of the double bonds found in the diunsaturated hydrocarbons of B. brauni (Knights et al, 1970) suggest that they are probably formed by the elongation of oleic acid to A 3 unsaturated C 2 8 , C 3 0 , C 3 2 acids followed by decarboxylation (Kolattukudy, 1976b). Experiments with specifically labeled pre cursors showed that the carbonyl carbon of nonacosan-15-one was derived from the C-2, C-4, and C-6 of C 1 6 , C 1 8 , and C 2 0 acids, respectively (Kolattu kudy, 1968d;Kolattukudy et al, 1968Kolattukudy et al, , 1971a. Although no direct experimental evidence to support involvement of the elongation-decarboxylation mechanism in the biosynthesis of olefins is cur rently available, the structures of all the olefins thus far isolated from plants are consistent with the elongation-decarboxylation mechanism.…”

Section: C]methionine and [mentioning

confidence: 99%

“…Exogenous nonacosan-15-one was not incorporated into C 2 9 alkane in B. oleracea or roses (Kolattukudy, 1966;Mondeshki et al, 1969), and the carbonyl carbon of the ketone was shown to be derived from the C-2 and C-4 of exogenous C 1 6 and Cjg acids, respectively (Kolattukudy et al, , 1971a. Exogenous nonacosan-15-one was not incorporated into C 2 9 alkane in B. oleracea or roses (Kolattukudy, 1966;Mondeshki et al, 1969), and the carbonyl carbon of the ketone was shown to be derived from the C-2 and C-4 of exogenous C 1 6 and Cjg acids, respectively (Kolattukudy et al, , 1971a.…”

mentioning

confidence: 99%