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Moving beyond the ubiquitous: the diversity and biosynthesis of specialty compounds in plant cuticular waxes

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Abstract

Cuticular waxes coat aerial plant surfaces to protect tissues against biotic and abiotic stress. The waxes are complex mixtures of fatty-acid-derived lipids formed on modular biosynthetic pathways, with varying chain lengths and oxygen functional groups. The waxes of most plant species contain C26–C32 alcohols, aldehydes, alkanes, and fatty acids together with their alkyl esters, and comparisons between diverse wax mixtures have revealed matching chain length distributions between some of these compound classes. Based on such patterns, the biosynthetic pathways leading to the ubiquitous wax constituents were hypothesized early on, and most of these pathway hypotheses have since been confirmed by biochemical and molecular genetic studies in model species. However, the most abundant wax compounds on many species, including many important crop species, contain secondary functional groups and thus their biosynthesis differs at least in part from the ubiquitous wax compounds with which they co-occur. Here, we survey the chemical structures of these species-specific specialty wax compounds based on a comprehensive CAS SciFinder search and then review relevant reports on wax compositions to help develop and refine hypotheses for their biosynthesis. Across the plant kingdom, specialty wax compounds with one, two, and three secondary functional groups have been identified, with most studies focusing on Angiosperms. Where multiple specialty wax compounds were reported, they frequently occurred as homologous series and/or mixtures of isomers. Among these, it is now possible to recognize series of homologs with predominantly odd- or even-numbered chain lengths, and mixtures of isomers with functional groups on adjacent or on alternating carbon atoms. Using these characteristic molecular geometries of the co-occurring specialty compounds, they can be categorized and, based on the common structural patterns, mechanisms of biosynthesis may be predicted. It seems highly likely that mixtures of isomers with secondary functions on adjacent carbons arise from oxidation catalyzed by P450 enzymes, while mixtures of isomers with alternating group positions are formed by malonate condensation reactions mediated by polyketide synthase or ketoacyl-CoA synthase enzymes, or else by the head-to-head condensation of long-chain acyls. Though it is possible that some enzymes leading to ubiquitous compounds also participate in specialty wax compound biosynthesis, comparisons between co-occurring ubiquitous and specialty wax compounds strongly suggest that, at least in some species, dedicated specialty wax compound machinery exists. This seems particularly true for the diverse species in which specialty wax compounds, most notably nonacosan-10-ol, hentriacontan-16-one (palmitone), and very-long-chain β-diketones, accumulate to high concentrations.

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Notes

  1. The presence of a compound in multiple species of the same genus is denoted in the tables with the species abbreviation as “xx”, here for example representing multiple Brassica species as “B.xx”.

Abbreviations

VLC:

Very-long-chain

TCN:

Total carbon number

R:

Head group oxidation state

CoA:

Coenzyme A

ACP:

Acyl carrier protein

KAS:

Ketoacyl-ACP synthase

KAR:

Ketoacyl-ACP reductase

HAD:

Hydroxyacyl-ACP dehydratase

EAR:

Enoyl-ACP reductase

FAE:

Fatty acid elongase

KCS:

Ketoacyl-CoA synthase

KCR:

Ketoacyl-CoA reductase

HCD:

Hydroxyacyl-CoA dehydratase

ECR:

Enoyl-CoA reductase

RED:

Reductase

EST:

Esterase

FAR:

Fatty acyl reductase

AD:

Aldehyde decarbonylase

WS:

Wax ester synthase

FA:

Fatty acid

FAS:

Fatty acid synthase

PKS:

Polyketide synthase

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Acknowledgements

The authors would like to thank S. Hessam M. Mehr for expertise in preliminary data analysis using d3.js libraries that made great contributions to the development of the manuscript.

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  1. Lucas Busta

    Present address: Center for Plant Science Innovation, 1901 Vine Street, Lincoln, NE, 68588, USA

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  1. Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z4, Canada

    Lucas Busta & Reinhard Jetter

  2. Department of Botany, University of British Columbia, 6270 University Boulevard, Vancouver, BC, V6T 1Z4, Canada

    Reinhard Jetter

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Busta, L., Jetter, R. Moving beyond the ubiquitous: the diversity and biosynthesis of specialty compounds in plant cuticular waxes. Phytochem Rev 17, 1275–1304 (2018). https://doi.org/10.1007/s11101-017-9542-0

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