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1. (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: 21946057Publication DOI: 10.1016/j.fitote.2011.09.001Journal NLM ID: 16930290RPublisher: 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
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: 18529
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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
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