Two New Isomers of Palmityl-4-hydroxycinnamate from Flowers of Taraxacum Species

Two isomers, (Z)- and (E)-palmityl 4-hydroxycinnamate [hexadecyl(2Z)-3-(4-hydroxyphenyl)prop-2-enoate and hexadecyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate] were isolated for the first time from ligulate flowers of Taraxacum linearisquameum Soest (sect. Taraxacum). The highest amount of these compounds...

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Bibliographic Details
Published in:Natural product communications 2016-06, Vol.11 (6), p.837-840
Main Authors: Dudáš, Matej, Vilková, Mária, Béres, Tibor, Repčák, Miroslav, Mártonfi, Pavol
Format: Article
Language:English
Subjects:
Cinnamates - chemistry
Flowers - chemistry
Isomerism
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure
Plant Extracts - chemistry
Taraxacum - chemistry
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Summary:Two isomers, (Z)- and (E)-palmityl 4-hydroxycinnamate [hexadecyl(2Z)-3-(4-hydroxyphenyl)prop-2-enoate and hexadecyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate] were isolated for the first time from ligulate flowers of Taraxacum linearisquameum Soest (sect. Taraxacum). The highest amount of these compounds was detected in pollen grains; 0.26 mg/100 mg DW of the (E)-isomer and 0.096 mg/100 mg DW of the (Z)-isomer. The structures of these compounds were elucidated by a combination of HPLC-ESI-Qtof-MS and ID and 2D NMR spectroscopy. Their presence was confirmed in other species of Taraxacum, but they were not found in the male-sterile triploid agamospermous taxon T. parnassicum.
ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X1601100635