Show legend Show as text

Structure type: monomer ; 659.4137 [M+Na]+
C₃₆H₆₀O₉
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7266
  Liu X, Qiao LR, Xie D, Dai JG "Microbial deglycosylation and ketonization of ginsenosides Rg1 and Rb1 by Fusarium oxysporum" - Journal of Asian Natural Products Research 13(7) (2011) 652-658
  

  Two major ginsenosides, ginsenoside-Rg1 (1) and ginsenoside-Rb1 (2), were transformed by the fungus Fusarium oxysporum f. sp. Lycopersici (Z-001). 1 was converted into five metabolites, ginsenoside-F1 (3), 6α,12β-dihydroxydammar-3-one-20(S)-O- β-D-glucopyranoside (4), 3a-oxa-3a-homo-6α,12β-dihydroxydammar- 3-one-20(S)-O-β-D-glucopyranoside (5), 20(S)-protopanaxatriol (6), and 3-oxo-20(S)-protopanaxatriol (7). 2 was converted into four metabolites, ginsenoside-Rd (8), ginsenoside-F2 (9), compound K (10), and 12β-hydroxydammar-3-one-20(S)-O-β-D-glucopyranoside (11). The structures of these metabolites were determined by the analysis of extensive spectroscopic data. Among them, 4 and 5 were two new compounds. Deglycosylation and ketonization at C-3 were recognized as the characteristic reactions of this strain.

  deglycosylation, Fusarium oxysporum, ginsenosides, ketonization

  Publication DOI: 10.1080/10286020.2011.585607
  Journal NLM ID: 100888334
  Publisher: Harwood Academic Publishers; London: Informa Healthcare
  Correspondence: jgdai@imm.ac.cn
  Institutions: Key Laboratory of Biosynthesis of Natural Products, Ministry of Public Health, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China, Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China
  Methods: 13C NMR, 1H NMR, TLC, ESI-MS, FTIR, HPLC, extraction, CC, HR-ESI-MS
  
   
  
  Fusarium oxysporum f.sp. lycopersici Z-001
  CSDB ID 43450 (all data & tools)

Show legend Show as text

Structure type: monomer
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7290
  Liu X, Qiao L, Xie D, Zhang Y, Zou J, Chen X, Dai J "Microbial transformation of ginsenoside-Rg1 by Absidia coerulea and the reversal activity of the metabolites towards multi-drug resistant tumor cells" - Fitoterapia 82(8) (2011) 1313-1317
  

  Biotransformation of ginsenoside-Rg1 (1) by the fungus Absidia coerulea AS 3.2462 yielded five metabolites (2-6). On the basis of spectroscopic data analyses, the metabolites were identified as ginsenoside-F1 (2), 6α,12β-dihydroxydammar-3-one-20(S)-O-β-D-glucopyranoside (3), 3-oxo-20(S)-protopanaxatriol (4), 3-oxo-7β-hydroxy-20(S)-protopanaxatriol (5), and 3-oxo-7β,15α-dihydroxy-20(S)-protopanaxatriol (6), respectively. Among them, 5 and 6 are new compounds. These results indicated that Absidia coerulea AS 3.2462 could catalyze the specific C-3 dehydrogenation of derivatives of ginsenoside-Rg1, as well as hydroxylation at the 7β and 15α positions. Metabolites 2, 4 and 5 exhibited moderate reversal activity towards A549/taxol MDR tumor cells in vitro.

  hydroxylation, microbial transformation, ginsenoside-Rg1, Absidia coerulea AS 3.2462, dehydrogenation, tumor MDR reversal activity

  NCBI PubMed ID: 21946057
  Publication DOI: 10.1016/j.fitote.2011.09.001
  Journal NLM ID: 16930290R
  Publisher: Elsevier
  Correspondence: jgdai@imm.ac.cn
  Institutions: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Ministry of Public Health, Beijing, China, Key Laboratory of Biosynthesis of Natural Products, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Ministry of Public Health, Beijing, China
  Methods: 13C NMR, 1H NMR, TLC, FTIR, HPLC, extraction, HR-ESI-MS, antitumor activity assay
  
   
  
  Absidia coerulea AS 3.2462
  CSDB ID 43510 (all data & tools)