Show legend Show as text

Structure type: monomer
Trivial name: ganoderic acid C2 (GAC2)-3-O-β-glucoside
Compound class: triterpenoid saponin
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9613
  Ding HY, Wang TY, Wu JY, Zhang YR, Chang TS "Novel Ganoderma triterpenoid saponins from the biotransformation-guided purification of a commercial Ganoderma extract" - Journal of Bioscience and Bioengineering 135(5) (2023) 402-410
  

  Ganoderma sp. contains high amounts of diverse triterpenoids; however, few triterpenoid saponins could be isolated from the medicinal fungus. To produce novel Ganoderma triterpenoid saponins, biotransformation-guided purification (BGP) process was applied to a commercial Ganoderma extract. The commercial Ganoderma extract was partially separated into three fractions by preparative high-performance liquid chromatography, and the separated fractions were then directly biotransformed by a Bacillus glycosyltransferase (BsUGT489). One of the biotransformed products could be further purified and identified as a novel saponin: ganoderic acid C2 (GAC2)-3-O-β-glucoside by nucleic magnetic resonance (NMR) and mass spectral analyses. Based on the structure of the saponin, the predicted precursor should be the GAC2, which was confirmed to be biotransformed into four saponins, GAC2-3-O-β-glucoside, GAC2-3,15-O-β-diglucoside and two unknown GAC2 monoglucosides, revealed by NMR and mass spectral analyses. GAC2-3-O-β-glucoside and GAC2-3,15-O-β-diglucoside possessed 17-fold and 200-fold higher aqueous solubility than that of GAC2, respectively. In addition, GAC2-3-O-β-glucoside retained the most anti-α-glucosidase activity of GAC2 and was comparable with that of the anti-diabetes drug (acarbose). The present study showed that the BGP process is an efficient strategy to survey novel and bioactive molecules from crude extracts of natural products.

  glycosyltransferase, glycosylation, Ganoderma lucidum, biotransformation, triterpenoid

  NCBI PubMed ID: 36889998
  Publication DOI: 10.1016/j.jbiosc.2023.02.004
  Journal NLM ID: 100888800
  Publisher: Osaka, Japan, Amsterdam, The Netherlands: Society for Bioscience and Bioengineering
  Correspondence: T.S. Chang
  Institutions: Department of Cosmetic Science, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan, Biodiversity Research Center, Academia Sinica, Taipei 115, Taiwan, Department of Food Science, National Quemoy University, Kinmen 892, Taiwan, Department of Biological Sciences and Technology, National University of Tainan, Tainan 700, Taiwan
  
   
  
  Ganoderma lucidum
  CSDB ID 41034 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: ganoderic acid C2 (GAC2)-3,15-O-β-glucoside
Compound class: triterpenoid saponin
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9613
  Ding HY, Wang TY, Wu JY, Zhang YR, Chang TS "Novel Ganoderma triterpenoid saponins from the biotransformation-guided purification of a commercial Ganoderma extract" - Journal of Bioscience and Bioengineering 135(5) (2023) 402-410
  

  Ganoderma sp. contains high amounts of diverse triterpenoids; however, few triterpenoid saponins could be isolated from the medicinal fungus. To produce novel Ganoderma triterpenoid saponins, biotransformation-guided purification (BGP) process was applied to a commercial Ganoderma extract. The commercial Ganoderma extract was partially separated into three fractions by preparative high-performance liquid chromatography, and the separated fractions were then directly biotransformed by a Bacillus glycosyltransferase (BsUGT489). One of the biotransformed products could be further purified and identified as a novel saponin: ganoderic acid C2 (GAC2)-3-O-β-glucoside by nucleic magnetic resonance (NMR) and mass spectral analyses. Based on the structure of the saponin, the predicted precursor should be the GAC2, which was confirmed to be biotransformed into four saponins, GAC2-3-O-β-glucoside, GAC2-3,15-O-β-diglucoside and two unknown GAC2 monoglucosides, revealed by NMR and mass spectral analyses. GAC2-3-O-β-glucoside and GAC2-3,15-O-β-diglucoside possessed 17-fold and 200-fold higher aqueous solubility than that of GAC2, respectively. In addition, GAC2-3-O-β-glucoside retained the most anti-α-glucosidase activity of GAC2 and was comparable with that of the anti-diabetes drug (acarbose). The present study showed that the BGP process is an efficient strategy to survey novel and bioactive molecules from crude extracts of natural products.

  glycosyltransferase, glycosylation, Ganoderma lucidum, biotransformation, triterpenoid

  NCBI PubMed ID: 36889998
  Publication DOI: 10.1016/j.jbiosc.2023.02.004
  Journal NLM ID: 100888800
  Publisher: Osaka, Japan, Amsterdam, The Netherlands: Society for Bioscience and Bioengineering
  Correspondence: T.S. Chang
  Institutions: Department of Cosmetic Science, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan, Biodiversity Research Center, Academia Sinica, Taipei 115, Taiwan, Department of Food Science, National Quemoy University, Kinmen 892, Taiwan, Department of Biological Sciences and Technology, National University of Tainan, Tainan 700, Taiwan
  
   
  
  Ganoderma lucidum
  CSDB ID 41404 (all data & tools)