Discrimination and Classification of Ginsenosides and Ginsengs Using Bis‐Boronic Acid Receptors in Dynamic Multicomponent Indicator Displacement Sensor Arrays

Abstract

Ginsenosides are complex natural products with a diverse array of biological activities, but their molecular recognition and sensing is challenging. A library of simple bis-boronic acid-based receptors with various spacers was synthesized for the sensing of ginsenosides. The incorporation of two boronic acids allowed the pairing of two indicators, which can simultaneously bind the receptors or two saccharides within the ginsenosides. A cross-reactive sensing array was therefore constructed using the receptors in conjunction with different pairs of indicators. LDA plots created from the colorimetric response of the hosts and indicator pairs reveal excellent classification of the ginsenosides, and the corresponding loading plots reveal the cross-reactivity of the receptors. In addition, several commercial ginseng extracts were unambiguously classified using the same sensing array. The assay reported here should be applicable to the analysis of other large saccharide-based natural products.

Molecular recognition with boronic acids—applications in chemical biology

“…Each analyte will have its own specific pattern of displacement, and in this way, complex mixtures can be deconvoluted. These sensing systems have been developed for many saccharide mixtures including monosaccharides and saccharide derivatives [16,23], ginsenosides [85] and nucleotides [66].…”

Discrimination of vicinal-diol-containing flavonoids and black teas by arrays of host–indicator ensembles

“…We recently reported a series of multi-boronic acid receptors ( Figure 2) in the context of studies on ginseng (22,23). The reason for introducing more than one boronic acid into the hosts was for the binding with two different indicators, which led to a larger wavelength span and a greater variation of the optical signal than with one indicator.…”

“…Alternatively, boronic acids are suitable for binding flavonoids because most flavonoids contain catechol groups which can reversibly associate with phenyl boronic acids to form cyclic boronic esters (19 -21). Using bis-boronic acidbased receptors, a series of sensing arrays for the discrimination and classification of ginsenosides and ginseng extracts have also been reported recently by our group (22). This paper sought to explore the potential of these sensing arrays for the discrimination of vicinal-diolcontaining flavonoids and black teas.…”

Responsive Boronic Acid-Decorated (Co)polymers: From Glucose Sensors to Autonomous Drug Delivery

“…Formation of a boronate ester with ARS then blocks this quenching, causing fluorescent enhancement on complexation with BA moieties [71]. This competitive binding strategy is frequently used to calculate the association constants of various boronic acid moieties towards a range of different potential binding agents through monitoring of the decrease in fluorescence [72,73,74,75,76]. The fluorescence quenching can also be employed to visually report the presence of saccharides through dissociation of the BA-ARS complex through competitive binding with the saccharide present [25,77].…”