A beta-D-glucoside that is beta-D-glucopyranose in which the hydroxy group at position 1R is substituted by a (2-hydroxybenzyl)oxy group. It is isolated from the flowers of Filipendula ulmaria.

Identification

IUPAC Names

2-hydroxybenzyl beta-D-glucopyranoside

Molecular Formula
C13H18O7
Mass
286.280
Monoisotopic Mass
286.10525
Charge
0
InChI
InChI=1S/C13H18O7/c14-5-9-10(16)11(17)12(18)13(20-9)19-6-7-3-1-2-4-8(7)15/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
InChIKey
VBSPBYNZPRRGSB-UJPOAAIJSA-N
SMILES
O1[C@@H]([C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OCC=2C=CC=CC2O)CO
Synonyms

(2-hydroxyphenyl)methyl beta-D-glucopyranoside

(2R,3R,4S,5S,6R)-2-[(2-hydroxybenzyl)oxy]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

2-(beta-D-glucopyranosyloxymethyl)phenol

isosalicin

Species

filipendula ulmaria

NCBI:txid57917Book: Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients, Shmuel Yannai, CRC Press, 2003, pg 771, I-161.

Europe PubMed Central results


Glucosylation of salicyl alcohol by cell suspension cultures of Solanum laciniatum.

Author: Syahrani A, Widjaja I, Indrayanto G, Wilkins AL.

Abstract: Cell suspension cultures of Solanum laciniatum were able to transform exogenously inoculated salicyl alcohol into salicyl alcohol 7-O-beta-D-glucopyranoside (isosalicin). The highest level of isosalicin (54.6 mg/g dry weight) in the cells was formed within 2 days after inoculation with salicyl alcohol (37.5 mg/flask containing 50 ml of medium). The biotransformation capacity of the cell suspension cultures was about 31.1%.

HPLC-MS/MS analysis of willow bark extracts contained in pharmaceutical preparations.

Author: Kammerer B, Kahlich R, Biegert C, Gleiter CH, Heide L.

Abstract: Preparations containing willow bark extract are popular herbal remedies, but they are mostly standardised with respect to only one compound (usually salicin). RP-HPLC using a C18-column eluted with water:methanol:tetrahydrofuran and coupled to electrospray triple-quadrupole MS and MS/MS was used for the characterisation of dried extracts of Salix spp. and for the identification of their constituents. Comparison with reference substances led to the identification of 13 compounds (saligenin, salicylic acid, salicin, isosalicin, picein, salidroside, triandrin, salicoylsalicin, salicortin, isosalipurposide, salipurposide, naringenin-7-O-glucoside and tremulacin). Two pharmaceutical preparations containing willow bark extract, used in clinical trials and labelled Salix daphnoides and S. purpurea x daphnoides extracts, were compared using the described method and exhibited several clear differences, the most prominent of which was the possible presence of picein in the former preparation. The described method may be utilised for the characterisation of herbal medicines in order to ensure comparability of medication in further clinical trials.

Predicting the substrate specificity of a glycosyltransferase implicated in the production of phenolic volatiles in tomato fruit.

Author: Louveau T, Leitao C, Green S, Hamiaux C, van der Rest B, Dechy-Cabaret O, Atkinson RG, Chervin C.

Abstract: The volatile compounds that constitute the fruit aroma of ripe tomato (Solanum lycopersicum) are often sequestered in glycosylated form. A homology-based screen was used to identify the gene SlUGT5, which is a member of UDP-glycosyltransferase 72 family and shows specificity towards a range of substrates, including flavonoid, flavanols, hydroquinone, xenobiotics and chlorinated pollutants. SlUGT5 was shown to be expressed primarily in ripening fruit and flowers, and mapped to chromosome I in a region containing a QTL that affected the content of guaiacol and eugenol in tomato crosses. Recombinant SlUGT5 protein demonstrated significant activity towards guaiacol and eugenol, as well as benzyl alcohol and methyl salicylate; however, the highest in vitro activity and affinity was shown for hydroquinone and salicyl alcohol. NMR analysis identified isosalicin as the only product of salicyl alcohol glycosylation. Protein modelling and substrate docking analysis were used to assess the basis for the substrate specificity of SlUGT5. The analysis correctly predicted the interactions with SlUGT5 substrates, and also indicated that increased hydrogen bonding, due to the presence of a second hydrophilic group in methyl salicylate, guaiacol and hydroquinone, appeared to more favourably anchor these acceptors within the glycosylation site, leading to increased stability, higher activities and higher substrate affinities.