One-pot Bi-enzymatic cascade synthesis of novel ganoderma triterpenoid saponins

Te Sheng Chang, Chien Min Chiang, Tzi Yuan Wang, Yu Li Tsai, Yu Wei Wu, Huei Ju Ting, Jiumn Yih Wu

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Ganoderma lucidum is a medicinal fungus whose numerous triterpenoids are its main bioactive constituents. Although hundreds of Ganoderma triterpenoids have been identified, Gano-derma triterpenoid glycosides, also named triterpenoid saponins, have been rarely found. Ganoderic acid A (GAA), a major Ganoderma triterpenoid, was synthetically cascaded to form GAA-15-O-β-glucopyranoside (GAA-15-G) by glycosyltransferase (BtGT_16345) from Bacillus thuringiensis GA A07 and subsequently biotransformed into a series of GAA glucosides by cyclodextrin glucanotransferase (Toruzyme® 3.0 L) from Thermoanaerobacter sp. The optimal reaction conditions for the second-step biotransformation of GAA-15-G were found to be 20% of maltose; pH 5; 60 C. A series of GAA gluco-sides (GAA-G2, GAA-G3, and GAA-G4) could be purified with preparative high-performance liquid chromatography (HPLC) and identified by mass and nucleic magnetic resonance (NMR) spectral analysis. The major product, GAA-15-O-[α-glucopyranosyl-(1→4)-β-glucopyranoside] (GAA-G2), showed over 4554-fold higher aqueous solubility than GAA. The present study demonstrated that multiple Ganoderma triterpenoid saponins could be produced by sequential actions of BtGT_16345 and Toruzyme®, and the synthetic strategy that we proposed might be applied to many other Ganoderma triterpenoids to produce numerous novel Ganoderma triterpenoid saponins in the future.

Original languageEnglish
Article number580
JournalCatalysts
Volume11
Issue number5
DOIs
Publication statusPublished - May 2021

Keywords

  • Cyclodextrin glucanotransferase
  • Ganoderic acid A
  • Ganoderma lucidum
  • Glycosyltransferase
  • Saponin
  • Triterpenoid

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Fingerprint

Dive into the research topics of 'One-pot Bi-enzymatic cascade synthesis of novel ganoderma triterpenoid saponins'. Together they form a unique fingerprint.

Cite this