Collect. Czech. Chem. Commun. 2010, 75, 175-186
Published online 2010-02-20 11:51:13

Modified approach for preparing (E)-stilbenes related to resveratrol, and evaluation of their potential immunobiological effects

Jan Šmidrkala, Juraj Harmathab,*, Miloš Buděšínskýb, Karel Vokáčb, Zdeněk Zídekc, Eva Kmoníčkovác, Roman Merkla and Vladimír Filipa

a Department of Dairy and Fat Technology, Faculty of Food and Biochemical Technology, Institute of Chemical Technology, Prague, 166 28 Prague 6, Czech Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., 166 10 Prague 6, Czech Republic
c Institute of Experimental Medicine, Academy of Sciences of the Czech Republic, v.v.i. 142 20 Prague 4, Czech Republic


Resveratrol and closely related stilbenoids belong to the most intensively studied biologically active compounds. This interest evoked several attempts to prepare such compounds in a convenient synthetic way. Our approach allowed obtaining largely methoxystilbenes, formed as E-isomers only (using Wittig–Horner synthesis as the key step), which were further demethylated by boron tribromide. The hydroxymethoxystilbenes (e.g. pterostilbene) were prepared using isopropyl protection, later selectively deprotected by boron trichloride. The method is suitable for preparing such compounds in a large amount. Effects of the obtained stilbene derivatives on immunobiological responses triggered by lipopolysacharide and interferon-γ were tested under in vitro conditions. Namely production of nitric oxide (NO) was investigated, and relation between the molecular structure and immunobiological activity was assessed.

Keywords: Stilbene; Resveratrol; Pinosylvin; Pterostilbene; Polyphenols; Antioxidants; Stilbenes; Nitric oxide (NO) bioassay; Immunobiological in vitro activity.

References: 44 live references.