Planta Med 2008; 74 - PB79
DOI: 10.1055/s-0028-1084424

A novel complex phenolic constituent from medium matured Sorbus domestica (Rosaceae) fruits

A Termentzi 1, M Zervou 2, E Kokkalou 1
  • 1Laboratory of Pharmacognosy, Department of Pharmacognocy-Pharmacology, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki, 54124, Greece
  • 2Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation, Vas. Konstantinou 48, Athens, 11635, Greece

Sorbus domestica fruits are traditionally used in Greece as a remedy against long term diabetic complications. Previous studies have already proved the potent antioxidant capacity of fruit extracts [1], as well as the efficient inhibition of the aldose reductase enzyme (ALR2) which is implicated in the long term diabetic complications. The detailed phytochemical LC-DAD-MS (ESI+) analysis showed the existence of several flavonoids, hydroxybenzoic and hydroxycinnamic acids [2]. The preparative phytochemical analysis resulted to the isolation of several flavonoids, phenolic acids and a novel polyphenolic acid, identified as 3-{4-(bis[4-hydroxy-3-(5-hydroxy pentanoyloxy)phenyl)methoxy]-3,5-dihydroxyphenyl}propanoic acid was isolated from the diethyl ether fractions of fruits collected unripe and left for maturation for one week at room temperature. The substance was isolated as white powder using preparative chromatographic techniques and the identification was achieved by UV and NMR spectroscopy (1H, 13C, COSY, HSQC, HMBC). The estimation of the exact molecular weight of the substance (628.2145 amu), as well as the MS/MS experiments were performed at a quadrupole-TOF mass spectrometer with a nanoelectrospray source (nano-ESI QqTOF MS/MS) in positive ion mode.

Acknowledgements: Biomedical Research Foundation, Academy of Athens, Dr. S. Garbis (for the TOF MS/MS spectrum)

References:1. Termentzi, A. et al. (2006) Food Chem. 98: 599–608.

2. Termentzi, A. et al. (2008) Food Chem. 106: 1234–1245.