Conversion of Glycosylated Platycoside E to Deapiose-Xylosylated Platycodin D by Cytolase PCL5

Abstract

Platycosides, the saponins abundant in Platycodi radix (the root of Platycodon grandiflorum), have diverse pharmacological activities and have been used as food supplements. Since deglycosylated saponins exhibit higher biological activity than glycosylated saponins, efforts are on to enzymatically convert glycosylated platycosides to deglycosylated platycosides; however, the lack of diversity and specificities of these enzymes has limited the kinds of platycosides that can be deglycosylated. In the present study, we examined the enzymatic conversion of platycosides and showed that Cytolase PCL5 completely converted platycoside E and polygalacin D3 into deapiose-xylosylated platycodin D and deapiose-xylosylated polygalacin D, respectively, which were identified by LC-MS analysis. The platycoside substrates were hydrolyzed through the following novel hydrolytic pathways: platycoside E → platycodin D3 → platycodin D → deapiosylated platycodin D → deapiose-xylosylated platycodin D; and polygalacin D3 → polygalacin D → deapiosylated polygalacin D → deapiose-xylosylated polygalacin D. Our results show that cytolast PCL5 may have a potential role in the development of biologically active platycosides that may be used for their diverse pharmacological activities.

A candidate gene identified in converting platycoside E to platycodin D from Platycodon grandiflorus by transcriptome and main metabolites analysis

“…It has been found that platycoside E is a precursor of platycodin D, and PE can be converted to PD by enzyme catalysis. Their biological activities can be increased and their bioavailability and cell permeability would be improved due to their reduced size resulted by de-glycosylation of saponins 17 .…”

Improved production of deglucosylated platycodin D from saponins from balloon flower leaf by a food-grade enzyme using high hydrostatic pressure

“…(Jeong et al, 2014) converted platycoside E into platycodin D, which indicates that these enzymes hydrolyze only the glucose moiety at the C-3 position of the platycosides. In contrast, crude enzyme and cytolase from A. niger (Shin et al, 2020), and pectinase from Aspergillus aculeatus (Ju et al, 2020) converted platycoside E into deapiose-dexylosylated platycodin D and glucosylated platyconic acid, respectively, hydrolyzing glycosides at the C-28 position. However, the enzyme that converts into deglucosylated platycodin D is only the recombinant β-glucosidase from D. turgidum (Kang et al, 2019).…”

“…Therefore, various methods such as heating (Kim et al, 2000), acid treatment (Bae et al, 2004), and biotransformation (Kim et al, 2019a;Shin et al, 2018) have been used to deglycosylate saponins. Among these, the enzymatic biotransformation of platycosides shows the highest selectivity and productivity, which has been demonstrated in diverse studies using a crude enzyme from Aspergillus niger (Wie et al, 2007), β-galactosidase from Aspergillus oryzae (Ha et al, 2010), β-glucosidase from Aspergillus usamii (Ahn et al, 2018), recombinant β-glucosidases from Caldicellulosiruptor bescii (Kil et al, 2019), Caldicellulosiruptor owensensis (Shin et al, 2019), and Dictyoglomus turgidum (Kang et al, 2019), and commercial enzymes, such as cellulase (Ha et al, 2010), laminarinase (Jeong et al, 2014), snailase (Li et al, 2012), pectinase (Ju et al, 2020), and cytolase (Shin et al, 2020). β-Glucosidase from D. turgidum was the only enzyme that produced deglucosylated platycodin D and showed the highest lipoxygenase inhibitory activity among all platycosides.…”

Improved Biotransformation of Platycoside E into Deapiose-Xylosylated Platycodin D by Cytolase PCL5 under High Hydrostatic Pressure

“…Platycoside E, platycodin D3, platycodin D, and deapiosylated platycodin D were purchased from Ambo Laboratories (Daejeon, Republic of Korea). Deapiose-xylosylated platycodin D was prepared as previously reported [23] and used as a standard. All other reagents were purchased from Sigma-Aldrich (St. Louis, MO, USA).…”

“…Caldicellulosiruptor bescii [18], Caldicellulosiruptor owensensis [19], Dictyoglomus turgidum [20], and cellulase [21], pectinase [22], and cytolase PCL5 [23]. Among these, cytolase PCL5 is the only enzyme that can hydrolyze the outer glucose at C-3 and xylose and apiose at C-28 in platycoside E, the most abundant saponin in balloon flower (Figure 1).…”