Journal
PHYTOCHEMISTRY
Volume 203, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2022.113396
Keywords
Lepidosperma congestum; L; gunnii; laterale; Cyperaceae; Resveratrol; Piceatannol; Prenylation; Oxyprenylation; Melatonin receptors; Quinone reductase 2 inhibitors
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Funding
- Hanson Bay Company, Karatta SA
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A series of prenylated and hydroxyprenylated compounds were isolated from resin produced by certain Australian plants, showing strong binding affinity and inhibition activity towards melatonin receptors and enzymes.
Prenylated and hydroxyprenylated piceatannol, resveratrol and pinosylvin derivatives were isolated from resin produced by three Australian Lepidosperma Labill. Species (Cyperaceae). From L. congestum R.Br. one known compound, 3 ',5 '-bis-prenyl-E-resveratrol, and five undescribed compounds were isolated, 3 '-O-prenyl-5 '-prenylE-piceatannol, 5 ',6 '-bis-prenyl-E-piceatannol, 5 '-prenyl-E-piceatannol, 3 ',5 '-bis(3-hydroxy-3-methylbutyl)-Eresveratrol and 3 ',5 '-bis-E-hydroxyprenyl-E-resveratrol. From L. gunnii Boeckeler one undescribed compound was isolated, 3 '-E-hydroxyprenyl-5 '-Z-hydroxyprenyl-E-resveratrol. From L. laterale R.Br. six undescribed compounds were isolated, 3-O-prenyl-E-pinosylvin, 3-O-Z-hydroxyprenyl-E-pinosylvin, 3 '-Z-hydroxyprenyl-E-resveratrol, 3O-Z-hydroxyprenyl-E-resveratrol, 3-O-Z-hydroxyprenyl-4 '-O-methyl-E-resveratrol, and 3-O-prenyl-3 ' 8,8 '-dihydroxyprenyl-E-resveratrol. Compounds, including a reference compound 3-O-prenyl-3 '-O-methyl-Epiceatannol, were screened in an assay for melatoninergic binding to MT1 and MT2 receptors and binding to QR2/MT3 enzyme, and for inhibition of QR2/MT3 in a functional assay. Strong binding was observed for 3-O-Zhydroxyprenyl-E-resveratrol with a Ki of 0.022 nM and the strongest inhibition of QR2/MT3 observed was for the reference compound, 3-O-prenyl-3 '-O-methyl-E-piceatannol, with an inhibition of 61% at 1 mu M and 95% at 10 mu M. The three most active binders and inhibitors of QR2/MT3 were found to have a common substructure corresponding to 3-O-prenylresveratrol.
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