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

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Title:Modified approach for preparing (E)-stilbenes related to resveratrol, and evaluation of their potential immunobiological effects
Creators:
Šmidrkal, Jan
Harmatha, Juraj
Buděšínský, Miloš
Vokáč, Karel
Zídek, Zdeněk
Kmoníčková, Eva
Merkl, Roman
Filip, Vladimír
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 75, 2, pp. 175-186
Uncontrolled Keywords:Immunobiological in vitro activity, Antioxidants, Pinosylvin, Resveratrol, Stilbene, Nitric oxide (NO) bioassay, Pterostilbene, Stilbenes, Polyphenols

Abstract

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 <i>E</i>-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.

Title:Modified approach for preparing (E)-stilbenes related to resveratrol, and evaluation of their potential immunobiological effects
Creators:
Šmidrkal, Jan
Harmatha, Juraj
Buděšínský, Miloš
Vokáč, Karel
Zídek, Zdeněk
Kmoníčková, Eva
Merkl, Roman
Filip, Vladimír
Uncontrolled Keywords:Immunobiological in vitro activity, Antioxidants, Pinosylvin, Resveratrol, Stilbene, Nitric oxide (NO) bioassay, Pterostilbene, Stilbenes, Polyphenols
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:75
Number:2
Page Range:pp. 175-186
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2009531UNSPECIFIED
ID Code:5236
Item Type:Article
Deposited On:08 Mar 2010 12:31
Last Modified:08 Mar 2010 11:31

Citation

Šmidrkal, Jan; Harmatha, Juraj; Buděšínský, Miloš; Vokáč, Karel; Zídek, Zdeněk; Kmoníčková, Eva; Merkl, Roman; Filip, Vladimír (2010) Modified approach for preparing (E)-stilbenes related to resveratrol, and evaluation of their potential immunobiological effects. Collection of Czechoslovak Chemical Communications, 75 (2). pp. 175-186.

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