Long-chain syn-1-phenylalkane-1,3-diyl diacetates, related phenylalkane derivatives, and sec-alcohols, all possessing dominantly iso-branched chain termini, and 2/3-methyl-branched fatty acids from Primula veris L. (Primulaceae) wax

• Published in: Phytochemistry (Oxford) Vol. 186; p. 112732
• Main Authors: Radulović, Niko S., Živković Stošić, Milena Z.
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01.06.2021
• Subjects: 1-Phenylalkane-1,3-diones; 2-Methylalkanoic and 3-methylalkanoic acids; 3-Oxo-1-phenylalkan-1-yl acetates; Alcohols; Branched long-chain wax constituents; Chromatography, Gas; Fatty Acids; Primula; Primula veris L; Primulaceae; sec-Alcohols; syn-1-Phenylalkane-1,3-diyl diacetates; sec-Alcohols; Primula veris L; syn-1-Phenylalkane-1,3-diyl diacetates; Branched long-chain wax constituents; Primulaceae; 1-Phenylalkane-1,3-diones; 3-Oxo-1-phenylalkan-1-yl acetates; 2-Methylalkanoic and 3-methylalkanoic acids
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2021.112732

Herein, the results of the first study of non-flavonoid constituents of aboveground surface-wax washings of Primula veris L. (Primulaceae) are presented. Chromatography of the washings yielded a minor fraction composed of n-, iso-, and anteiso-series of long-chained syn-1-phenylalkane-1,3-diyl diacetates, 3-oxo-1-phenylalkan-1-yl acetates, 1-phenylalkane-1,3-diones, 1-hydroxy-1-phenylalkan-3-ones, sec-alcohols (2- to 10-alkanols), and n-, iso-, anteiso-, 2-methylalkanoic and 3-methylalkanoic acids; 118 of these constituents represent up to now unreported natural compounds. The structural/stereochemical elucidation was accomplished by the synthesis of authentic standards, derivatization reactions, the use of gas chromatographic retention data and detailed 1D and 2D-NMR analyses of the obtained complex chromatographic fraction. Primula veris produces unusually high amounts of branched long-chained metabolites (>60%) except for the fatty acids where the percentage of branched isomers is comparable to the ones with n-chains. Noteworthy is the fact that long-chained α- and β-methyl substituted fatty acids were detected herein for the first time in the kingdom Plantae. [Display omitted] •Non-flavonoid constituents of P. veris surface waxes were analyzed in detail.•118 unreported natural compounds were identified in a wax chromatographic fraction.•Unusually, branched-chain metabolites dominated in the detected compound series.•α- and β-methyl substituted fatty acids were detected for the first time in Plants.•Identification required synthesis, derivatization, GC-MS and NMR analyses.