Journal of natural products vol:71 issue:11 pages:1833-1836
While classic raffinose family oligosaccharides (RFOs) such as raffinose and stachyose are common in plants, stachyose is absent in the Caryophyllaceae. Instead the tetrasaccharide lychnose alpha- d-Gal-(1-->6)alpha- d-Glc-(1-->2)beta- d-Fru-(1-->1)alpha- d-Gal can accumulate. Stellaria media, a representative member of this family, was used to isolate alpha- d-Gal-(1-->6)-[alpha- d-Gal-(1-->4)]alpha- d-Glc-(1-->2)beta- d-Fru-(1-->1)alpha- d-Gal, a novel pentasaccharide with a lychnose backbone. Complete NMR characterization using COSY, HSQC, HSQC-TOCSY, HMBC, and NOESY experiments was performed to unequivocally resolve its structure. This is the first report of a natural compound containing a Gal alpha(1-->4)Glc linkage. The trivial name stellariose is proposed for this new pentasaccharide.