LC/MS/MS identification of glycosides produced by biotransformation of cinnamyl alcohol in Rhodiola rosea compact callus aggregates

Abstract

Cinnamyl alcohol was added to the media of compact callus aggregates (CCA) of Rhodiola rosea for stimulating the production of cinnamyl glycosides. The biotransformation reaction produced high amounts of rosin, while only a very low amount of rosavin was produced. As the consumption rate of cinnamyl alcohol was much higher than production of rosin, the aqueous methanol extracts of compact callus aggregates were studied by liquid chromatography-mass spectrometric methods and four new unexpected biotransformation products of cinnamyl alcohol were identified.

Qualitative and Quantitative Analysis of Different Rhodiola rosea Rhizome Extracts by UHPLC-DAD-ESI-MSn

“…This was due to the content of cinnamyl alcohol glycosides being inversely correlated to the amount of cinnamyl alcohol in the extract. As salidroside and cinnamyl alcohol glycosides are thought to be responsible for the pharmacological activity of Rhodiola rosea extracts [13], a high content of cinnamyl alcohol could be considered an unfavorable trait for preparations of the plant, although it might be reasoned that glycosides are mostly transformed and absorbed in their aglycone form after oral consumption. Overall, ASE can be recommended for production of extracts for medicinal use.…”

“…Subsequently, rosarin (9), rosavin (11), rosin (12) and compound (13), cinnamyl-(6'-O-β-D-xylopyranosyl)-O-β-glucopyranoside, were found to be glycosides of (15). Their sugar moieties consist of arabinopyranosyl-glucopyranoside for (9), arabinofuranosyl-glucopyranoside for (11), glucopyranoside for (12) and xylopyranosyl-glucopyranoside for (13).…”

“…About 140 compounds have been found in the underground organs of Rhodiola rosea, comprising monoterpene alcohols, cyanogenic glycosides, aryl glycosides, phenylethanoids, phenylpropanoids, flavonoids, proanthocyanidins, as well as gallic acid derivatives [3]. Compounds thought to be responsible for activities are phenylethanoids salidroside, and its aglycone tyrosol, as well as a group of phenylpropanoids, namely the cinnamyl alcohol glycosides rosin, rosarin, and rosavin [13]. Pharmacological studies investigating isolated compounds are most abundant for salidroside.…”

Rhodiola rosea L.: from golden root to green cell factories

“…In the control samples, none of these metabolites were produced (Furmanowa et al 1999;György et al 2004). After feeding R. rosea callus culture with CA, several new glycosides as products of biotransformation were identified Tolonen et al 2004). With addition of 2.5 mM CA, a remarkable increase in the content of rosin in the hypocotyle originated callus was observed, while the axially bud originated callus line produced 1.2-fold less rosin and 2-fold more rosavin rosea, proved that TyrDC has an organ-specific expression.…”

Two-dimensional Mapping Using Different Chromatographic Separations Coupled with Mass Spectrometry for the Analysis of Ginsenosides in Panax Ginseng Root and Callus

“…Additionally, the identification of glycosides was studied using LC-MS/MS, [19][20][21] but it seemed to be difficult because the separation of LC is not enough to analyze the glycosides by LC-MS/MS. Therefore, a rapid and simple method is required to understand the effective combinations of glycosides from the pattern of components in the Panax ginseng, and to identify the differences between callus extracts, themselves, that have been derived using different culture conditions, and between callus extracts and root extracts.…”