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Applied Biochemistry and Microbiology

, Volume 55, Issue 4, pp 360–370 | Cite as

Cyclodextrin Glycosyltransferase-Catalyzed Synthesis of Pinoresinol-α-D-glucoside Having Antioxidant and Anti-Inflammatory Activities

  • N. Khummanee
  • P. Rudeekulthamrong
  • J. KaulpiboonEmail author
Article
  • 3 Downloads

Abstract

Enzymatic synthesis of pinoresinol-α-glucosides (PGs) was performed through the transglycosylation reaction catalyzed by the recombinant cyclodextrin glycosyltransferase (CGTase) from Bacillus circulans A11 using β-cyclodextrin as the glycosyl donor and pinoresinol as the acceptor molecule. Incubation of 0.5% (wt/vol) β-cyclodextrin with 1.5% (wt/vol) pinoresinol (P) and 80.0 U/mL of CGTase in 20 mM of Tris–HCl buffer (pH 9.0) at 50oC for 60 h was optimal for PGs synthesis. Under these conditions, two PG transfer products with molecular weights of 544 and 682 Da corresponding to pinoresinol monoglucoside (PG1-I and PG1-II) and pinoresinol diglucoside (PG2), respectively, were detected by TLC and MS. The structures of PG1 and PG2 were confirmed as pinoresinol-α-D-glucopyranoside and pinoresinol-α-D-diglucopyranoside, respectively, by 1H-NMR analysis. The free-radical scavenging and anti-inflammatory activities of PG1 and PG2 were reduced as compared with the original P using α,α-diphenyl-β-picrylhydrazyl radical scavenging reactions and the β-glucuronidase inhibition assay. The loss of antioxidant and anti-inflammatory activities might result from the addition of glucose in the position 4-OH of P that may have disturbed its electron rotation. In vivo, PGs are converted to Ps before they are absorbed and so loss of activity may be minimal. Interestingly, the α-glycosylated compounds which showed the change of physicochemical properties such as increase of solubility and sweetness could promote a positive effect on the bioavailability of original P.

Keywords:

Antibacterial activity anti-inflammatory activity cyclodextrin glycosyltransferase intermolecular transglycosylation pinoresinol-α-glucoside 

Notes

ACKNOWLEDGMENTS

We also thank the Drug Discovery and Development Center, and Center of Scientific Equipment for Advanced Research, Thammasat University for special service rate 1 of HPLC.

FUNDING

The authors gratefully acknowledge financial s-upport from the Thammasat University Research Fund under the TU Research Scholar, Contract no. TP 2/26/2559 and the Phramongkutklao College of Medicine Research Fund (Thailand).

COMPLIANCE WITH ETHICAL STANDARDS

The authors declare that they have no conflict of interest. This article does not contain any studies involving animals or human participants performed by any of the authors.

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Copyright information

© Pleiades Publishing, Inc. 2019

Authors and Affiliations

  • N. Khummanee
    • 1
  • P. Rudeekulthamrong
    • 2
  • J. Kaulpiboon
    • 3
    Email author
  1. 1.Protein Research Laboratory, Faculty of Medicine, Thammasat UniversityPathumthaniThailand
  2. 2.Department of Biochemistry, Phramongkutklao College of MedicineBangkokThailand
  3. 3.Division of Biochemistry, Department of Preclinical Science, Faculty of Medicine, Thammasat UniversityPathumthaniThailand

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