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Item E-cinnamic acid derivatives and phenolics from chilean strawberry fruits, Fragaria chiloensis ssp. chiloensisAutores: Cheel, J.; Theoduloz, C.; Rodriguez, J.; Saud, G.; Caligari, P.D.S.; Schmeda-Hirschmann, G.Three E-cinnamic acid glycosides, tryptophan, and cyanidin-3-O-β-D-glucopyranoside were isolated from ripe fruits of the Chilean strawberry Fragaria chiloensis ssp. chiloensis. 1-O-E-Cinnamoyl-β-D-xylopyranoside, 1-O-E-cinnamoyl-β-D-rhamnopyranoside, and 1-O-E-cinnamoyl-α-xylofuranosyl-(1→6)-β-D-glucopyranose are reported for the first time. The cinnamic acid glycosides and aromatic compound patterns in F. chiloensis fruits were determined by high-performance liquid chromatography (HPLC). HPLC analyses of extracts showed that cyanidin-3-O-β-D-glucopyranoside and free ellagic acid are present in achenes while the E-cinnamoyl derivatives and tryptophan were identified only in the thalamus. The free radical scavenging effect of the fruit extract can be associated with the anthocyanin contentItem Free radical scavengers from Cymbopogon citratus (DC.) stapf plants cultivated in bioreactors by the temporary immersion (TIS) principleAutores: Tapia, A.; Cheel, J.; Theoduloz, C.; Rodriguez, J.; Schmeda-Hirschmann, G.; Gerth, A.; Wilken, D.; Jordan, M.; Jimenez-Gonzalez, E.; Gomez-Kosky, R.; Mendoza, E.Q.The biomass production of Cymbopogon citratus shoots cultivated in bioreactors according to the temporary immersion (TIS) principle was assessed under different growth conditions. The effect of gassing with CO2-enriched air, reduced immersion frequency, vessel size and culture time on total phenolic and flavonoid content and free radical scavenging effect of the methanolic extracts was measured. From the TIS-culture of C. citratus, seven compounds were isolated and identified as caffeic acid (1), chlorogenic acid (2), neochlorogenic acid (3), p-hydroxybenzoic acid (4), p-hydroxybenzoic acid 3-O--d-glucoside (5), glutamic acid (6) and luteolin 6-C-fucopyranoside (7). The occurrence of compounds 1Ð7 and their variability in C. citratus grown under different TIS conditions was determined by HPLC. The free radical scavenging effect of the methanolic extract and compounds was measured by the discoloration of the free radical 1,1- diphenyl-2-picrylhydrazyl (DPPH). The main metabolites in 6- and 8-week-old cultures, both in 5 and 10 l vessels, were chlorogenic acid (2) (100Ð113 mg%) and neochlorogenic acid (3) (80Ð 119 mg%), while in the cultures with CO2-enriched air and reduced immersion frequency the main compound detected in the extracts was glutamic acid (6) (400 and 670 mg% for the green and white biomass and 619 and 630 mg% for the green and white biomass, respectively). The most active compounds, as free radical scavengers, in the DPPH discoloration assay were caffeic acid (1), chlorogenic acid (2), neochlorogenic acid (3) and the flavonoid luteolin 6-C-fucopyranoside (7).Item Free radical scavengers and antioxidants from lemongrass (Cymbopogon citratus (DC.) Stapf.)Autores: Cheel, J.; Theoduloz, C.; Rodriguez, J.; Schmeda-Hirschmann, G.Methanol, MeOH/water extracts, infusion, and decoction of Cymbopogon citratus were assessed for free radical scavenging effects measured by the bleaching of the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical, scavenging of the superoxide anion, and inhibition of the enzyme xanthine oxidase (XO) and lipid peroxidation in human erythrocytes. The extracts presented effect in the DPPH and superoxide anion assay, with values ranging between 40 and 68% and 15-32% at 33 and 50 mu g/mL, respectively, inhibited lipid peroxidation in erythrocytes by 19-71% at 500 mu g/mL and were inactive toward the XO at 50 mu g/mL. Isoorientin, isoscoparin, swertiajaponin, isoorientin 2"-O-rhamnoside, orientin, chlorogenic acid, and caffeic acid were isolated and identified by spectroscopic methods. Isoorientin and orientin presented similar activities toward the DPPH (IC50: 9-10 mu M) and inhibited lipid peroxidation by 70% at 100 gamma g/mL. Caffeic and chlorogenic acid were active superoxide anion scavengers with IC50 values of 68.8 and 54.2 mu M, respectively, and a strong effect toward DPPH. Caffeic acid inhibited lipid peroxidation by 85% at 100 mu g/mLItem Free radical scavenging activity and secondary metabolites from in vitro cultures of Sanicula graveolensAutores: Cheel, J.; Schmeda-Hirschmann, G.; Jordan, M.; Theoduloz, C.; Rodriguez, J.; Gerth, A.; Wilken, D.An in vitro propagation system was developed to obtain shoot and root cultures from the Andean spice Sanicula graveolens (Apiaceae). Propagation of shoots, roots and plantlets was achieved by the temporary immersion system. The free radical scavenging effect of the methanol/ water (7 :3 v/v) extracts was determined by the discoloration of the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH). Total phenolic, flavonoid, chlorogenic acid (CA) and quercetin 3-O-glucoside content in the samples was assessed by spectrophotometry and DAD-HPLC analysis, respectively. On a dry weight basis, the crude extracts showed total phenolic values ranging from 3.57 to 6.93%, with highest content for the root culture sample. Total flavonoid content ranged from 1.23 to 2.23% and was lower for the root culture. Chlorogenic acid and neochlorogenic acid were identified by TLC in all samples. Highest free radical scavenging effect was observed for the root culture which also presented the highest CA content. Two of the shoot culture samples, with similar IC50 values in the DPPH discoloration assay, also presented close quercetin-3-O-glucoside content.Item Free radical scavenging activity and phenolic content in achenes and thalamus from Fragaria chiloensis ssp chiloensis, F. vesca and F. x ananassa cv. ChandlerAutores: Cheel, J.; Theoduloz, C.; Rodriguez, J.; Caligari, P.D.S.; Schmeda-Hirschmann, G.The total phenolic, flavonoid and anthocyanin content of achenes (true fruit) and thalamus (receptacle) from the native South American Fragaria chiloensis ssp. chiloensis (f. patagonica and f. chiloensis), Fragaria vesca and Fragaria x ananassa cv. Chandler was determined by spectrophotometric means. Highest phenolic content was found in F. vesca while lowest content was measured for white strawberry (F. chiloensis ssp. chiloensis, f. chiloensis). The total anthocyanin and total flavonoid contents in the samples investigated was lower for the white strawberry and higher in F. x ananassa cv. Chandler. Total flavonoid content showed a better correlation than total anthocyanins with the free radical scavenging effect of the extracts measured by means of the DPPH discoloration assay. In the superoxide anion assay all the acetone extracts of strawberries showed similar activity. The data presented in this study demonstrate that the amount of phenolic compounds differ significantly between species and subspecies and determine the free radical scavenging activity of fruits. On a w/w basis, higher total phenolics including flavonoids was found in achenes. The highest total anthocyanin content was found in the achenes of F. chiloensis and F. vesca, while F. ananassa presented higher antocyanin content in thalamus. The main anthocyanin in thalamus of F. ananassa (95%) were pelargonidin derivatives which were also present in F. chiloensis ssp. chiloensis f. patagonica (62.6%) but were not detected in F. vesca and F. chiloensis ssp. chiloensis f. chiloensis. In F. vesca and F. chiloensis ssp. chiloensis f. chiloensis only cyanidin derivatives were found both in thalamus and achenes.
