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1. (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: 10.1080/10286020.2011.585607Journal NLM ID: 100888334Publisher: 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
The publication contains the following compound(s):
- Compound ID: 18479
Structure type: monomer
Trivial name: ginsenoside-F1, 20(S)-ginsenoside-Rh1, ginsenoside F1
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Reference(s) to other database(s): CCSD:
40243, CBank-STR:1127
- Compound ID: 18480
|
b-D-Glcp-(1-20)-Subst
Subst = 3-oxo-20(S)-protopanaxatriol = SMILES C/C(C)=C\CC{20}[C@](C)(O)[C@H]1CC[C@]4(C)[C@@H]1{12}[C@H](O)C[C@@H]3[C@@]2(C)CCC(=O)C(C)(C)[C@@H]2{6}[C@@H](O)C[C@]34C |
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Structure type: monomer
; 659.4137 [M+Na]+
C36H60O9
- Compound ID: 18481
|
b-D-Glcp-(1-20)-Subst
Subst = 3a-oxa-3a-homo-6α,12β,20S-dihydroxydammar-3-one = SMILES C/C(C)=C\CC{20}[C@](C)(O)[C@H]1CC[C@]4(C)[C@@H]1{12}[C@H](O)C[C@@H]3[C@@]2(C)CCC(=O)OC(C)(C)[C@@H]2{6}[C@@H](O)C[C@]34C |
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Structure type: monomer
; 675.4094 [M+Na]+
C36H60O10
- Compound ID: 18482
|
b-D-Glcp-(1-20)-+
|
b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Protopanaxadiol20s |
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Structure type: monomer
Trivial name: ginsenoside-Rd
- Compound ID: 18483
Structure type: monomer
Trivial name: ginsenoside-F2
- Compound ID: 18484
Structure type: monomer
Trivial name: compound K
- Compound ID: 18485
|
b-D-Glcp-(1-20)-Subst
Subst = 12β,20(S)-dihydroxydammar-3-one = SMILES C/C(C)=C\CC{20}[C@](C)(O)[C@H]1CC[C@]4(C)[C@@H]1{12}[C@H](O)C[C@@H]3[C@@]2(C)CCC(=O)C(C)(C)[C@@H]2CC[C@]34C |
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Structure type: monomer
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