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Biotransformation of Glycosylated Saponins in Balloon Flower Root Extract into 3-O-β-ᴅ-Glucopyranosyl Platycosides by Deglycosylation of Pectinase from Aspergillus aculeatus

  • Ju, Jung-Hun (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Kang, Su-Hwan (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Kim, Tae-Hun (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Shin, Kyung-Chul (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Oh, Deok-Kun (Department of Bioscience and Biotechnology, Konkuk University)
  • Received : 2020.01.22
  • Accepted : 2020.03.10
  • Published : 2020.06.28

Abstract

Platycodon grandiflorum root (Platycodi radix) saponins, platycosides, have been used as health supplements and food items for the treatment of respiratory disorders and pulmonary diseases. Deglycosylated saponins have been known to exert stronger biological effects than their glycosylated forms. In the present study, glycosylated platycosides in Platycodi radix extract were biotransformed into deglycosylated 3-O-β-ᴅ-glucopyranosyl platycosides, including 3-O-β-ᴅ-glucopyranosyl platycodigenin, 3-O-β-ᴅ-glucopyranosyl polygalacic acid, and 3-O-β-ᴅ-glucopyranosyl platyconic acid, by pectinase from Aspergillus aculeatus. This is the first report on the quantitative enzymatic production of 3-O-β-ᴅ-glucopyranosyl platycosides. The chemical structures of 3-O-β-ᴅ-glucopyranosyl platycosides were identified with LC/MS. Moreover, the biotransformation pathways of the three types of platycosides in Platycodi radix into 3-O-β-ᴅ-glucopyranosyl platycosides were established.

Keywords

References

  1. Zhao HL, Harding SV, Marinangeli CP, Kim YS, Jones PJ. 2008. Hypocholesterolemic and anti-obesity effects of saponins from Platycodon grandiflorum in hamsters fed atherogenic diets. J. Food Sci. 73: H195-200. https://doi.org/10.1111/j.1750-3841.2008.00915.x
  2. Chung JW, Noh EJ, Zhao HL, Sim JS, Ha YW, Shin EM, et al. 2008. Anti-inflammatory activity of prosapogenin methyl ester of platycodin D via nuclear factor-kappaB pathway inhibition. Biol. Pharm. Bull. 31: 2114-2120. https://doi.org/10.1248/bpb.31.2114
  3. Jang KJ, Kim HK, Han MH, Oh YN, Yoon HM, Chung YH, et al. 2013. Anti-inflammatory effects of saponins derived from the roots of Platycodon grandiflorus in lipopolysaccharidestimulated BV2 microglial cells. Int. J. Mol Med. 31: 1357-1366. https://doi.org/10.3892/ijmm.2013.1330
  4. Halliwell B. 2006. Oxidative stress and neurodegeneration: where are we now? J. Neurochem. 97: 1634-1658. https://doi.org/10.1111/j.1471-4159.2006.03907.x
  5. Park S, Yoo J, Kim H, Choi Y, Choi H, Song J. 2013. The physiochemical characteristics and anti-oxidant activity of extracts of Platycodon grandiflorus (Jacquin) A. De Candolle. Planta Med. 79: 1267-1268.
  6. Choi YH, Kim YS, Yeo SJ, Roh SH, Jeong YC, Kang JS, et al. 2008. Ameliorating effect of balloon flower saponin on the ethanolinduced memory impairment in mice. Phytother. Res. 22: 973-976. https://doi.org/10.1002/ptr.2394
  7. Yoo KY, Park OK, Hwang IK, Li H, Ryu SY, Kang IJ, et al. 2008. Induction of cell proliferation and neuroblasts in the subgranular zone of the dentate gyrus by aqueous extract from Platycodon grandiflorum in middle-aged mice. Neurosci. Lett. 444: 97-101. https://doi.org/10.1016/j.neulet.2008.07.057
  8. Chun J, Joo EJ, Kang M, Kim YS. 2013. Platycodin D induces anoikis and caspase-mediated apoptosis via p38 MAPK in AGS human gastric cancer cells. J. Cell Biochem. 114: 456-470. https://doi.org/10.1002/jcb.24386
  9. Park CS, Yoo MH, Noh KH, Oh DK. 2010. Biotransformation of ginsenosides by hydrolyzing the sugar moieties of ginsenosides using microbial glycosidases. Appl. Microbiol. Biotechnol. 87: 9-19. https://doi.org/10.1007/s00253-010-2567-6
  10. Shin KC, Oh DK. 2016. Classification of glycosidases that hydrolyze the specific positions and types of sugar moieties in ginsenosides. Crit. Rev. Biotechnol. 36: 1036-1049. https://doi.org/10.3109/07388551.2015.1083942
  11. Li W, Zhao LC, Wang Z, Zheng YN, Liang J, Wang H. 2012. Response surface methodology to optimize enzymatic preparation of deapio-platycodin D and platycodin D from radix platycodi. Int. J. Mol. Sci. 13: 4089-4100. https://doi.org/10.3390/ijms13044089
  12. Jeong EK, Ha IJ, Kim YS, Na YC. 2014. Glycosylated platycosides: Identification by enzymatic hydrolysis and structural determination by LC-MS/MS. J. Sep. Sci. 37: 61-68. https://doi.org/10.1002/jssc.201300918
  13. Ha IJ, Kang M, Na YC, Park Y, Kim YS. 2011. Preparative separation of minor saponins from platycodi radix by high-speed countercurrent chromatography. J. Sep. Sci. 34: 2559-2565. https://doi.org/10.1002/jssc.201100326
  14. Ahn HJ, You HJ, Park MS, Johnston TV, Ku S, Ji GE. 2018. Biocatalysis of platycoside E and platycodin D3 using fungal extracellular beta-glucosidase responsible for rapid platycodin D Production. Int. J. Mol. Sci. 19: 2671. https://doi.org/10.3390/ijms19092671
  15. Wie HJ, Zhao HL, Chang JH, Kim YS, Hwang IK, Ji GE. 2007. Enzymatic modification of saponins from Platycodon grandiflorum with Aspergillus niger. J. Agric. Food Chem. 55: 8908-8913. https://doi.org/10.1021/jf0716937
  16. Kang SH, Kim TH, Shin KC, Ko YJ, Oh DK. 2019. Biotransformation of food-derived saponins, platycosides, into deglucosylated saponins including deglucosylated platycodin D and their anti-inflammatory activities. J. Agr. Food Chem. 67: 1470-1477. https://doi.org/10.1021/acs.jafc.8b06399
  17. Tang ZY, Hou YY, Hu XY, Liu AN, Yau LF, Tong TT, et al. 2017. Metabolite identification and pharmacokinetic study of platycodi radix (Jiegeng) in vivo. Rsc. Adv. 7: 37459-37466. https://doi.org/10.1039/C7RA04814A
  18. Son JW, Kim HJ, Oh DK. 2008. Ginsenoside Rd production from the major ginsenoside Rb(1) by beta-glucosidase from Thermus caldophilus. Biotechnol. Lett. 30: 713-716. https://doi.org/10.1007/s10529-007-9590-4
  19. Kil TG, Kang SH, Kim TH, Shin KC, Oh DK. 2019. Enzymatic biotransformation of balloon flower root saponins into bioactive platycodin D by deglucosylation with Caldicellulosiruptor bescii beta-glucosidase. Int. J. Mol. Sci. 20: 3854. https://doi.org/10.3390/ijms20163854
  20. Nyakudya E, Jeong JH, Lee NK, Jeong YS. 2014. Platycosides from the Roots of Platycodon grandiflorum and their health benefits. Prev. Nutr. Food Sci. 19: 59-68. https://doi.org/10.3746/pnf.2014.19.2.059
  21. Ryu CS, Kim CH, Lee SY, Lee KS, Choung KJ, Song GY, et al. 2012. Evaluation of the total oxidant scavenging capacity of saponins isolated from Platycodon grandiflorum. Food Chem. 132: 333-337. https://doi.org/10.1016/j.foodchem.2011.10.086

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