J. Agric. Food Chem., 53 (22), 8512 -8518, 2005. 10.1021/jf051294g S0021-8561(05)01294-X
Web Release Date: October 7, 2005

Copyright © 2005 American Chemical Society

E-Cinnamic Acid Derivatives and Phenolics from Chilean Strawberry Fruits, Fragaria chiloensis ssp. chiloensis

José Cheel, Cristina Theoduloz, Jaime Rodríguez, Guillermo Saud, Peter D. S. Caligari, and Guillermo Schmeda-Hirschmann*

Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Laboratorio de Cultivo Celular, Facultad de Ciencias de la Salud, Centro de Investigaciones en Biotecnología Silvoagrícola, and Instituto de Biología Vegetal y Biotecnología, Universidad de Talca, Talca, Chile

Received for review June 1, 2005. Revised manuscript received August 23, 2005. Accepted August 23, 2005. J.C. thanks the Universidad de Talca for a doctoral grant. G.S. thanks the Universidad de Talca and Centro de Investigaciones en Biotecnología Silvoagrícola for financial support in a doctoral program. We acknowledge financial support from the research programs on "Productos Naturales Bioactivos" and "Frutilla Chilena Integral", Universidad de Talca.

Abstract:

Three E-cinnamic acid glycosides, tryptophan, and cyanidin-3-O--D-glucopyranoside were isolated from ripe fruits of the Chilean strawberry Fragaria chiloensis ssp. chiloensis. 1-O-E-Cinnamoyl--D-xylopyranoside, 1-O-E-cinnamoyl--D-rhamnopyranoside, and 1-O-E-cinnamoyl--xylofuranosyl-(16)--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--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 content.

Keywords: Fragaria chiloensis; Chilean strawberry; E-cinnamic acid derivatives; free radical scavengers; antioxidants; anthocyanin


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