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  7. Ginsenoside F2
Ginsenoside F2
Ginsenoside F2 Chemical Structure

Ginsenoside F2

Catalog NO.: B0005-465151 CAS NO.: 62025-49-4 Brand: BOC Sciences

Category
Carbohydrates, Nucleosides & Nucleotides
Application/Structure
Glycosides
Molecular Formula
C42H72O13
Molecular Weight
785.01
Size Price Stock Quantity
20 mg $285 In stock

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cGMP Capacity

  • kg to MT scale
  • GMP batches production
  • Over 20 years of experience
  • HPAPI production with OEL < 1 μg/m³
  • Cleanroom Class 100 to Class 100,000
  • Special type of reactions in cGMP workshop
  • Cleaning level: Class A B C
  • cGMP synthesis workshop
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Product Description

Ginsenoside F2 is extracted from the root of Panax ginseng C. A. Mey. It was assessed for its antiproliferative activity against breast cancer stem cells (CSCs). It induced apoptosis in breast CSCs by activating the intrinsic apoptotic pathway and mitochondrial dysfunction. It decreased the expression of TGF-β2 and SCAP proteins.

Quantity
Milligrams-Grams
InChI Key
SWIROVJVGRGSPO-JBVRGBGGSA-N
InChI
InChI=1S/C42H72O13/c1-21(2)10-9-14-42(8,55-37-35(51)33(49)31(47)25(20-44)53-37)22-11-16-41(7)29(22)23(45)18-27-39(5)15-13-28(38(3,4)26(39)12-17-40(27,41)6)54-36-34(50)32(48)30(46)24(19-43)52-36/h10,22-37,43-51H,9,11-20H2,1-8H3/t22-,23+,24+,25+,26-,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-,37-,39-,40+,41+,42-/m0/s1
SMILES
CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)C)C)O)C)OC6C(C(C(C(O6)CO)O)O)O)C
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1.Microbial conversion of ginsenoside Rb1 to minor ginsenoside F2 and gypenoside XVII by Intrasporangium sp. GS603 isolated from soil.
Cheng LQ;Na JR;Kim MK;Bang MH;Yang DC J Microbiol Biotechnol. 2007 Dec;17(12):1937-43.
A new strain, GS603, having beta-glucosidase activity was isolated from soil of a ginseng field, and its ability to convert major ginsenoside Rb(1) to minor ginsenoside or gypenoside was studied. Strain GS603 was identified as an Intrasporangium species by phylogenetic analysis and showed high ginsenoside-converting activity in LB and TSA broth but not in nutrient broth. The culture broth of the strain GS603 could convert ginsenoside Rb(1 )into two metabolites, which were analyzed by TLC and HPLC and shown to be the minor ginsenoside F(2) and gypenoside XVII by NMR.
2.The Bioconversion of Red Ginseng Ethanol Extract into Compound K by Saccharomyces cerevisiae HJ-014.
Choi HJ;Kim EA;Kim DH;Shin KS Mycobiology. 2014 Sep;42(3):256-61. doi: 10.5941/MYCO.2014.42.3.256. Epub 2014 Sep 30.
A β-glucosidase producing yeast strain was isolated from Korean traditional rice wine. Based on the sequence of the YCL008c gene and analysis of the fatty acid composition, the isolate was identified as Saccharomyces cerevisiae strain HJ-014. S. cerevisiae HJ-014 produced ginsenoside Rd, F2, and compound K from the ethanol extract of red ginseng. The production was increased by shaking culture, where the bioconversion efficiency was increased 2-fold compared to standing culture. The production of ginsenoside F2 and compound K was time-dependent and thought to proceed by the transformation pathway of: red ginseng extract→Rd→F2→compound K. The optimum incubation time and concentration of red ginseng extract for the production of compound K was 96 hr and 4.5% (w/v), respectively.
3.Comparative analysis on microbial and rat metabolism of ginsenoside Rb1 by high-performance liquid chromatography coupled with tandem mass spectrometry.
Chen G;Yang M;Song Y;Lu Z;Zhang J;Huang H;Guan S;Wu L;Guo DA Biomed Chromatogr. 2008 Jul;22(7):779-85. doi: 10.1002/bmc.1001.
Ginsenoside Rb1 is an active protopanaxadiol saponin from Panax species. In order to compare the similarities and differences of microbial and mammalian metabolisms of ginsenoside Rb1, the microbial transformation by Acremonium strictum and metabolism in rats were comparatively studied. Microbial transformation of ginsenoside Rb1 by Acremonium strictum AS 3.2058 resulted in the formation of eight metabolites. Ten metabolites (M1-M10) were detected from the in vivo study in rats and eight of them were identified as the same compounds as those obtained from microbial metabolism by liquid chromatography-tandem mass spectrometry analysis and comparison with reference standards obtained from microbial metabolism. Their structures were identified as ginsenoside Rd, gypenoside XVII, 20(S)-ginsenoside Rg3, 20(R)-ginsenoside Rg3, ginsenoside F2, compound K, 12beta-hydroxydammar-3-one-20(S)-O-beta-d-glucopyranoside, and 25-hydroxyl-(E)-20(22)-ene-ginsenoside Rg3, respectively. The structures of the additional two metabolites were tentatively characterized as 20(22),24-diene-ginsenoside Rg3 and 25-hydroxyginsenoside Rd by HPLC-MS/MS analysis. M7-M10 are the first four reported metabolites in vivo.
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