Isolation and characterization of a pentasaccharide from Stellaria media.
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 α-d-Gal-(1→6)α-d-Glc-(1→2)β-d-Fru-(1→1)α-d-Gal can accumulate. Stellaria media, a representative member of this family, was used to isolate α-d-Gal-(1→6)-[α-d-Gal-(1→4)]α-d-Glc-(1→2)β-d-Fru-(1→1)α-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 α(1→4)Glc linkage. The trivial name stellariose is proposed for this new pentasaccharide.
Vanhaecke
Mieke
M
Laboratory of Molecular Plant Physiology, Institute of Botany and Microbiology, K. U. Leuven, Kasteelpark Arenberg 31, B-3001 Heverlee, Belgium.
Van den Ende
Wim
W
Lescrinier
Eveline
E
Dyubankova
Natalia
N
D002240:Carbohydrate Sequence; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry / Q000302:isolation & purification*; D011887:Raffinose / Q000737:chemistry / Q000302:isolation & purification; D029752:Stellaria / Q000737:chemistry*
D009844:Oligosaccharides; C515781:galactopyranoyl-1-6-glucopyranosyl-1-2-fructofuranosyl-1-1-galactopyranoside; C567993:stellariose; C005695:stachyose; D011887:Raffinose