Design and synthesis of ten biphenyl-neolignan derivatives and their in vitro inhibitory potency against cyclooxygenase-1/2 activity and 5-lipoxygenase-mediated LTB4-formation.

A set of ten derivatives of methylhonokiol, an anti-inflammatory active biphenyl-type neolignan from Magnolia grandiflora, has been evaluated for their in vitro cyclooxygenase-1/2 (COX-1/2) inhibitory activity using assays with purified prostaglandin H synthase (PGHS)-1 and PGHS-2 enzymes as well as for their 5-lipoxygenase (5-LOX) mediated LTB(4) formation inhibitory activity using an assay with activated human polymorphonuclear leukocytes. The derivatization reactions included methylation, acetylation, hydrogenation, epoxydation and isomerization. Five of the derivatives are new to science. The most active compound against COX-1 and COX-2 was methylhonokiol with IC(50) values of 0.1 microM, whereas the most active compound against LTB(4) formation was (E)-3'-propenyl-5-(2-propenyl)-biphenyl-2,4'-diol with an IC(50) value of 1.0 microM. Structure-activity relationship studies showed that the polarity of the derivatives plays a crucial role in their activity towards COX-1/2 enzyme and 5-LOX mediated LTB(4) formation.

An improved method to discover adulteration of Styrian pumpkin seed oil.

Pumpkin seed oil is rather expensive compared to other vegetable oils. Therefore, it is often adulterated by the addition of cheaper oils. In contrast to other edible oils, the content of Delta 5-sterols is very low, while Delta 7-sterols are dominating. The determination of Delta 5-sterols, especially beta-sitosterol has proven to be a good possibility to detect admixture of cheap vegetable oils to a level below which the economic profit is not significant any more. The presented method is a variant of an analysis concept, which has been published previously in European Food Research and Technology by Mandl et al. [Eur. Food Res. Technol. 209 (1999) 400. ]. It includes saponification of the triglycerides as a first step followed by separation of the potassium salts of the fatty acids from the unsaponifiable fraction by adsorption chromatography. In order to enhance gas chromatographic properties of the analytes, the hydroxyl function of the sterols is derivatized with N-Methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) to the trimethylsilylether. Finally, the analytes are separated on a capillary column of medium polarity (HP 35 MS) in a temperature programmed run within 18 min. Detection of the analytes was done by flame ionization. Special attention was set onto the precision and repeatability of the method.