5ObetaDglucoside

5ObetaDglucoside refers to a class of β-D-glucosides in which a glucose moiety is linked to another molecule (the aglycone) by an O-glycosidic bond at the aglycone’s 5-hydroxyl position. In this naming convention, the glucose unit is in the beta configuration and attaches through its anomeric carbon to the hydroxy group on the aglycone, forming a 5-O-glycosidic linkage. The result is a glycoside where the glucose unit can be cleaved enzymatically or chemically to release the aglycone and glucose.

Structure and properties vary with the aglycone, but the common feature is the β-D-glucosyl attachment via a stable O-glycosidic bond. This modification typically increases the compound’s water solubility and can alter properties such as stability, polarity, color, or bioactivity. The glycosidic bond is susceptible to hydrolysis by β-glucosidases, as well as acidic conditions, which can liberate the aglycone and glucose.

Biological occurrence and function: 5-O-β-D-glucosidic linkages are widespread in plant secondary metabolism. Glycosylation often serves to store, transport, detoxify, or modulate the activity of phenolic, flavonoid, terpenoid, and other aglycones. The process is catalyzed by UDP-glucose-dependent glycosyltransferases, using UDP-glucose as the sugar donor.

Analytical and practical notes: compounds of this class are analyzed by standard glycoside methods (HPLC, LC-MS) after enzymatic or acid hydrolysis to determine the aglycone and sugar composition. They are used as standards or references in natural product research and pharmacognosy.