Ligstroside

Oleuropein (the most abundant bitter principle) and its analog ligstroside, both sec-oiridoid biophenols, were extracted from Hojiblanca black olives (Piperno and others 2004). Secoiridoids are present exclusively in plants of the Oleraceae family (Tripoli and others 2005). Oleuropein is present in high amounts (6000 90 mg/100 g DW) in the leaves of the olive tree (Le Tutour and others 1992), but it is also present in all constituent parts of the fruit peel, pulp, and seed (Servili and others 1999). 

Compound 22, ligstroside, is very similar to oleuropein from which it differs for the presence of a tyrosol unit instead of hydroxy-tyrosol [24]. 

Secoiridoid glucosides of oleoside (28) type frequently occur in Oleaceae family. Usually, in Fraxinus species they are present as mono- or diesters of p-hydroxyphenylethanol (29) derivatives. Our phytochemical studies on Fraxinus ornus resulted in the isolation of ligstroside (14), oleuropein (18), framoside (19) and of the new compounds ornoside (15), hydroxyornoside (17), hydroxyframoside A (20a) and hydroxyframoside B (20b) [15-17],... 

Acid hydrolysis of hydroxyomoside (17) using 16.0% methanolic H2SO4 resulted in a complex reaction mixture from which 32a,b could be isolated as a minor product and 33a,b as a major one. Under the same reaction conditions insularoside (15) afforded 32a,b and 34a,b, while ligstroside produced only 32a,b. 

Decarboxymethyl ligstroside Ri-OH (304) aglycon(3,4-DHPEA-EDA) Decarboxymethyl oleuropein Rj-H (320) aglycon(p-HPEA-EDA)... 

Andrews, P., Busch, J. L. H. C., Joode, T. D., Groenewegen, A., and Alexandre, H. 2003. Sensory properties of virgin ohve oil polyphenols Identification of deace-toxy-ligstroside agglycon as a key contributor to pungency. J. Agric. Food Chem. 51 1415-1420. 

Rios JJ, Gil MJ, Gutierrez-Rosales F (2005) Solid-phase extraction gas chrranatography-ion trap-mass spectrometry qualitative method for evaluation of phenolic compounds in virgin olive oil and structural confirmation of oleuropein and ligstroside aglyctnis and their oxidation products. J Chromatogr A 1093 167-176... 

Recently, it has been shown that ligstroside aglycone (oleocanthal) inhibits COX-1 and COX-2 activity in the same way as the anti-inflammatory drug ibupro-fen does [134], Starting from these results, we speculated a similar activity for... 

Ligstrohemiacetal B (66) (revised structure of jasmolactone A), 3032 Ligstroside, 3041, 3052 Liliaceae, 1554 Liliopsida, 979... 

Rosendal Jensen S, Juhl Nielsen B 1976 A new coumarin, fraxidin 8-0-)ff-D-glucoside and 10-hy-droxy-ligstroside from bark of Fraxinus excelsior. Phytochemistry 15 221-223... 

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