Quantitative Analysis of Anti-inflammatory and Radical Scavenging Triterpenoid Esters in Evening Primrose Seeds

Abstract

Lipophilic triterpenoidal esters with radical scavenging and cyclooxygenase inhibitory properties were recently found in cold-pressed, nonraffinated evening primrose oil (EPO). A quantitative assay for the analysis of 3-O-trans-caffeoyl derivatives of betulinic, morolic, and oleanolic acid in evening primrose seeds was developed and validated. Extraction efficiency >99% was achieved by means of pressurized liquid extraction with two extraction cycles and 80% (v/v) ethanol at 120 degrees C. Analysis of esters was by normal-phase high-performance liquid chromatography on a Diol column and hexane/ethyl acetate (containing 0.1% formic acid) (65:35) as the eluent. The analytes were determined without further prepurification. Seeds from defined cultures of Oenothera biennis, Oenothera lamarckiana, and Oenothera ammophila, grown under identical conditions, were analyzed. The cultures originated from seeds from eight collections in the wild and from selections from five cultivars. The content of total triterpenoidal esters in seeds varied between 1.34 and 2.78 mg/g. Three types of qualitative patterns were observed for the triterpenoidal esters. The influence of different harvest times and plant treatments was studied with the cultivar Anothera. Variations between 1.5 and 2.3 mg/g were found.

Polyphenol Composition of Extract from Aerial Parts of Circaea Lutetiana L. and its Antioxidant and Anti-Inflammatory Activity in Vitro

“…The presence of ellagic acid derivatives as well as ellagic acid itself has also been confirmed in C. lutetiana (Granica and Kiss, 2013). In the literature there are no studies of the bioactivity of extracts prepared from enchanter's nightshade, though there are quite extensive studies of the bioactivities, especially the antioxidant and anti-inflammatory properties, of other medicinal plants of the Oenotheraceae family (Shikov et al, 2006;Zaugg et al, 2006;Wojdyło et al, 2007;Hevesi et al, 2009;Márquez-Flores et al, 2009;Kiss et al, 2010Kiss et al, , 2011. In this study we examined the anti-inflammatory and antioxidant activity of standardized extract from the herb of Circaea lutetiana.…”

Anti‐wrinkling effects of the mixture of vitamin C, vitamin E, pycnogenol and evening primrose oil, and molecular mechanisms on hairless mouse skin caused by chronic ultraviolet B irradiation

“…It was also reported to show protective effects against UV‐induced skin damage in a human clinical study (3, 4). Antioxidant and anti‐inflammatory effects (5), and promising natural treatments for scleroderma by evening primrose oil have also been demonstrated (6). However, the precise molecular mechanism of the photoprotective effects of these antioxidants remains unclear.…”

Anxiolytic activity of a supercritical carbon dioxide extract of Souroubea sympetala (Marcgraviaceae)

“…The extraction was conducted with 85% ethanol at 110°C, pressure of 120 bar (12 MPa), for two 5 min static cycles. This method was optimized for triterpene extraction (Zaugg et al, 2006). Supercritical CO2 extraction.…”