Alkyl Cinnamates from Pollen of Pinus sylvestris

Alkyl cinnamates 1–8 were isolated for the first time from pollen of Pinus sylvestris L. Their structures were determined using UV, IR, and NMR spectroscopy and mass spectrometry. The known compounds 1,16-dioxohexadecan-7-yl 7- O-cis-p -coumarate ( 1 ), 1-hydroxy-16-oxohexadecan-7-yl 7- O-trans-p -c...

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Published inChemistry of natural compounds Vol. 59; no. 2; pp. 207 - 211
Main Authors Olennikov, D. N., Shishmarev, V. M., Shiretorova, V. G.
Format Journal Article
LanguageEnglish
Published New York Springer US 01.03.2023
Springer
Springer Nature B.V
Subjects
Biological activity
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Infrared spectroscopy
Mass spectrometry
NMR spectroscopy
Nuclear magnetic resonance spectroscopy
Organic Chemistry
Plant Sciences
Pollen
Tyrosine
alkyl cinnamates
PTP1B
Pinaceae
pollen
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Summary:Alkyl cinnamates 1–8 were isolated for the first time from pollen of Pinus sylvestris L. Their structures were determined using UV, IR, and NMR spectroscopy and mass spectrometry. The known compounds 1,16-dioxohexadecan-7-yl 7- O-cis-p -coumarate ( 1 ), 1-hydroxy-16-oxohexadecan-7-yl 7- O-trans-p -coumarate ( 2 ), and 1,16-dihydroxyhexadecan-7-yl 7- O-trans-p -coumarate ( 3 ), and five new alkyl cinnamates 1,16-dioxohexadecan-7-yl 7- O-trans -caffeate (pinuspollenine I, 4 ), 1,16-dioxohexadecan-7-yl 7- O-trans-m -coumarate (pinuspollenine II, 5 ), 1-hydroxy-16-oxohexadecan-7-yl 7- O-trans-m- coumarate (pinuspollenine III, 6 ), 1,16-dioxohexadecan-7-yl 7- O-trans-p -methoxycinnamate (pinuspollenine IV, 7 ), and 1-hydroxy-16-oxohexadecan-7-yl 7- O-trans-p -methoxycinnamate (pinuspollenine V, 8 ) were detected. A study of the biological activity showed that 1–3 inhibited protein tyrosine phosphatase 1B activity.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-023-03957-1