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Identification of beta-hydroxy fatty acid esters and primary, secondary-alkanediol esters in cuticular waxes of the moss Funaria hygrometrica

TitleIdentification of beta-hydroxy fatty acid esters and primary, secondary-alkanediol esters in cuticular waxes of the moss Funaria hygrometrica
Publication TypeJournal Article
Year of Publication2016
AuthorsBusta, L, Budke, JM, Jetter, R
JournalPHYTOCHEMISTRY
Volume121
Pagination38-49
Date PublishedJAN
ISSN0031-9422
Abstract

The plant cuticle, a multi-layered membrane that covers plant aerial surfaces to prevent desiccation, consists of the structural polymer cutin and surface-sealing waxes. Cuticular waxes are complex mixtures of ubiquitous, typically monofunctional fatty acid derivatives and taxon-specific, frequently bifunctional specialty compounds. To further our understanding of the chemical diversity of specialty compounds, the waxes on the aerial structures of the leafy gametophyte, sporophyte capsule, and calyptra of the moss Funaria hygrometrica were surveyed. Respective moss surfaces were extracted, and resulting lipid mixtures were analyzed by gas chromatography-mass spectrometry (GC-MS). The extracts contained ubiquitous wax compound classes along with two prominent, unidentified classes of compounds that exhibited some characteristics of bifunctional structures. Microscale transformations led to derivatives with characteristic MS fragmentation patterns suggesting possible structures for these compounds. To confirm the tentative structure assignments, one compound in each of the suspected homologous series was synthesized. Based on GC-MS comparison with the authentic standards, the first series of compounds was identified as containing esters formed by beta-hydroxy fatty acids and wax alcohols, with ester chain lengths varying from C-42 to C-50 and the most prominent homolog being C-46. The second series consisted of fatty acid esters of 1,7-alkanediols, linked via the primary hydroxyl group, with ester chain lengths C-40-C-62 also dominated by the C-46 homolog. The beta-hydroxy acid esters were restricted to the sporophyte capsule, and the diol esters to the leafy gametophyte and calyptra. Based on their homolog and isomer distributions, and the presence of free 1,7-triacontanediol, possible biosynthetic reactions leading to these compounds are discussed. (C) 2015 Elsevier Ltd. All rights reserved.

DOI10.1016/j.phytochem.2015.10.007