38963-94-9Relevant articles and documents
Glycosidically Bound Norisoprenoids from Vitis vinifera Cv. Riesling Leaves
Skouroumounis, George K.,Winterhalter, Peter
, p. 1068 - 1072 (1994)
HRGC and HRGC-MS identifications of glycosidically bound Riesling leaf constituents were achieved after extraction with MeOH, Amberlite XAD-2 adsorption, and subsequent enzymatic hydrolysis of the glycoconjugates.Among the enzymatically liberated aglycons 23 bound C13 norisoprenoids were identified.With the aid of multilayer coil countercurrent chromatography (MLCCC) five major C13 glycosides were purified, and their structures were elucidated by high-field NMR, i.e., the β-D-glucopyranosides of vomifoliol, 4,5-dihydrovomifoliol, 3-hydroxy-5,6-epoxy-β-ionone, grasshopper ketone, and 3-oxo-megastigman-9-ol.The latter glucoside with a saturated megastigmane skeleton is reported here for the first time.In addition, the β-D-glucopyranosides of benzyl alcohol and raspberry ketone have been isolated.
Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent
Wadzinski, Tyler J.,Steinauer, Angela,Hie, Liana,Pelletier, Guillaume,Schepartz, Alanna,Miller, Scott J.
, p. 644 - 652 (2018/05/04)
Glycosylated natural products and synthetic glycopeptides represent a significant and growing source of biochemical probes and therapeutic agents. However, methods that enable the aqueous glycosylation of endogenous amino acid functionality in peptides without the use of protecting groups are scarce. Here, we report a transformation that facilitates the efficient aqueous O-glycosylation of phenolic functionality in a wide range of small molecules, unprotected tyrosine, and tyrosine residues embedded within a range of complex, fully unprotected peptides. The transformation, which uses glycosyl fluoride donors and is promoted by Ca(OH)2, proceeds rapidly at room temperature in water, with good yields and selective formation of unique anomeric products depending on the stereochemistry of the glycosyl donor. High functional group tolerance is observed, and the phenol glycosylation occurs selectively in the presence of virtually all side chains of the proteinogenic amino acids with the singular exception of Cys. This method offers a highly selective, efficient, and operationally simple approach for the protecting-group-free synthesis of O-aryl glycosides and Tyr-O-glycosylated peptides in water.
PHENYLBUTAN-2-ONE β-D-GLUCOSIDES FROM RASPBERRY FRUIT
Pabst, Anni,Barron, Denis,Adda, Jacques,Schreier, Peter
, p. 3853 - 3858 (2007/10/02)
From a methanolic extract of raspberry fruit, the 4'-O-β-D-glucopyranoside of 4-(4'-hydroxyphenyl)butan-2-one (raspberry ketone) and the 3'-O-β-D-glucopyranoside of 4-(3',4'-dihydroxyphenyl)butan-2-one were isolated by liquid chromatography on XAD-2, Sephadex LH-20 and RP-18 as well as by HPLC on a diol phase.Identifications were carried out by 1H and 13C NMR spectroscopy, using synthetic reference compounds.Assignment of the carbon resonances was made by DEPT and INADEQUATE experiments.The effects of glucosylation on the 13C NMR spectra of phenylbutanone derivatives are discussed.
Tannins and Related Compounds. X. Rhubarb (2): Isolation and Structures of a Glycerol Gallate, Gallic Acid Glucoside Gallates, Galloylglucoses and Isolindleyin
Nonaka, Gen-Ichiro,Nishioka, Itsuo
, p. 1652 - 1658 (2007/10/02)
Six tannin-related compounds (I-VI) have been isolated from commercial rhubarb, and their structures have been established on the basis of chemical and spectroscopic data to be 1-O-galloylglycerol (I), gallic acid 3-O-β-D-(6'-O-galloyl)-glucopyranoside (II), gallic acid 4-O-β-D-(6'-O-galloyl)-glucopyranoside (III), 1,6-di-O-galloyl-β-D-glucose (IV), 6-O-galloylglucose (V) and 4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2"-O-galloyl)-glucopyranoside (VI, named isolindleyin).Keywords - rhubarb; Polygonaceae; glycerol gallate; gallic acid glucoside gallate; galloylglucose; isolindleyin; tannin-related compound
