Show legend Show as text

Structure type: monomer ; 459.2008 [M+H]+
C₂₅H₃₀O₈
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8289
  Liang W, Li Z, Ji S, Wang Q, Qiao X, Guo D, Ye M "Microbial glycosylation of tanshinone IIA by Cunninghamella elegans AS 3.2028" - RSC Advances 5(78) (2015) 63753-63756
  

  Tanshinone IIA (TIIA) is a natural product with significant anti-atherogenic activities. However, poor water-solubility and low bioavailability hinder its further exploitation as a drug candidate. In this study, microbial transformation of TIIA by Cunninghamella elegans AS 3.2028 was conducted to obtain two new glycosylated derivatives. Their structures were identified as hydroquinone TIIA 11-O-β-D-glucopyranoside (1) and hydroquinone TIIA 12-O-β-D-glucopyranoside (2) based on extensive NMR and MS spectral analyses. The solubility of 1 in 50% MeOH-H2O solution was approximately 50-fold that of TIIA, and 1 showed remarkably improved oral absorption in mice. Furthermore, 1 and 2 exhibited similar Nrf2 activation activity to TIIA

  glycosylation, biotransformation, Cunninghamella elegans, tanshinone IIA

  Publication DOI: 10.1039/c5ra09745b
  Journal NLM ID: 101581657
  Publisher: Cambridge, UK: Royal Society of Chemistry
  Correspondence: yemin@bjmu.edu.cn
  Institutions: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, China
  Methods: 13C NMR, 1H NMR, IR, MS/MS, biological assays, HPLC, UV, optical rotation measurement, CC, cell growth, HR-ESI-MS, antioxidant activities, HMBC, LC, HPLC-DAD, IC-PAD, LC-SRM-MS
  
   
  
  Cunninghamella elegans AS 3.2028
  CSDB ID 47891 (all data & tools)

Show legend Show as text

Structure type: monomer ; 459.2009 [M+H]+
C₂₅H₃₀O₈
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8289
  Liang W, Li Z, Ji S, Wang Q, Qiao X, Guo D, Ye M "Microbial glycosylation of tanshinone IIA by Cunninghamella elegans AS 3.2028" - RSC Advances 5(78) (2015) 63753-63756
  

  Tanshinone IIA (TIIA) is a natural product with significant anti-atherogenic activities. However, poor water-solubility and low bioavailability hinder its further exploitation as a drug candidate. In this study, microbial transformation of TIIA by Cunninghamella elegans AS 3.2028 was conducted to obtain two new glycosylated derivatives. Their structures were identified as hydroquinone TIIA 11-O-β-D-glucopyranoside (1) and hydroquinone TIIA 12-O-β-D-glucopyranoside (2) based on extensive NMR and MS spectral analyses. The solubility of 1 in 50% MeOH-H2O solution was approximately 50-fold that of TIIA, and 1 showed remarkably improved oral absorption in mice. Furthermore, 1 and 2 exhibited similar Nrf2 activation activity to TIIA

  glycosylation, biotransformation, Cunninghamella elegans, tanshinone IIA

  Publication DOI: 10.1039/c5ra09745b
  Journal NLM ID: 101581657
  Publisher: Cambridge, UK: Royal Society of Chemistry
  Correspondence: yemin@bjmu.edu.cn
  Institutions: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, China
  Methods: 13C NMR, 1H NMR, IR, MS/MS, biological assays, HPLC, UV, optical rotation measurement, CC, cell growth, HR-ESI-MS, antioxidant activities, HMBC, LC, HPLC-DAD, IC-PAD, LC-SRM-MS
  
   
  
  Cunninghamella elegans AS 3.2028
  CSDB ID 47892 (all data & tools)