| Identification | Back Directory | [Name]
GINSENOSIDE F2 | [CAS]
62025-49-4 | [Synonyms]
GINSENOSIDE F2
20(S)-Ginsenoside-F2
Ginsenoside F2, >=98%
-D-glucopyranosidederiv.
20(S)-Ginsenoside F2 ,98%
Ginsenoside F2, 98%, from Panax ginseng C. A. Mey.
(20S)-3β,20-Bis(β-D-glucopyranosyloxy)-5α-dammar-24-ene-12β-ol
12β-Hydroxy-5α-dammar-24-ene-3β,20-diylbis(β-D-glucopyranoside)
b-D-Glucopyranoside, (3b,12b)-12-hydroxydammar-24-ene-3,20-diyl bis-
β-D-Glucopyranoside, (3β,12β)-12-hydroxydammar-24-ene-3,20-diyl bis-
(20S)-3β-(β-D-Glucopyranosyloxy)-20-(β-D-glucopyranosyloxy)dammar-24-ene-12β-ol | [Molecular Formula]
C42H72O13 | [MDL Number]
MFCD06410948 | [MOL File]
62025-49-4.mol | [Molecular Weight]
785.01 |
| Chemical Properties | Back Directory | [Melting point ]
195-200°C | [Boiling point ]
871.5±65.0 °C(Predicted) | [density ]
1.30±0.1 g/cm3(Predicted) | [storage temp. ]
Hygroscopic, -20°C Freezer, Under inert atmosphere | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
12.91±0.70(Predicted) | [color ]
White to Off-White | [Stability:]
Hygroscopic | [InChIKey]
SWIROVJVGRGSPO-IGNDSYMUNA-N |
| Hazard Information | Back Directory | [Description]
Ginsenoside F2 is a ginsenoside that has been found in P. ginseng and has diverse biological activities.1,2,3 It increases the proliferation of human hair dermal papilla cells (HHDPCs) and HaCaT human keratinocytes when used at concentrations of 0.01, 0.1, and 1 μM.1 Ginsenoside F2 (0.5 and 2.5 mg/kg) induces hair growth and increases hair density following depilation in mice. It is cytotoxic to U373MG glioblastoma cells in vitro (IC50 = 50 μg/ml) and reduces tumor growth in a U373MG mouse xenograft model when administered at a dose of 35 mg/kg every other day.2 Ginsenoside F2 (1 mg/ear) reduces ear edema induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in mice.3 It is a human intestinal bacterial metabolite of ginsenoside Rb1 (Item No. 15319) via the intermediate ginsenoside Rd (Item No. 15329).4 | [Chemical Properties]
White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from ginseng rhizomes and Gynostemma pentaphyllum. | [Uses]
Ginsenoside F2 is a bioactive metabolite of the ginsenoside component of Panax ginseng with the ability to regulate element-binding protein cleavage activating protein and transforming growth factor-β pathways. This control over apoptosis can lead to a control over hair growth and hair loss in mammals. | [Definition]
ChEBI: A ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy groups at positions
3 and 20 have been converted to the corresponding beta-D-glucopyranosides, and in which a double bond has been introduced at the 24-25 position. | [Synthesis]
GENERAL STEPS: In a 1-liter stirred kettle reactor, 200 mL of reaction mixture (containing 50 mM phosphate buffer, pH 5.5) was mixed with 5 mg/mL of substrate PPDGM and crude recombinant CcBg11A (final protein concentration of 1 mg/mL). The reaction conditions were set to 30°C and stirred at 100 rpm for 2 hours. After completion of the reaction, the mixture was extracted twice in equal volumes using n-butanol. The n-butanol extracts were combined, concentrated by vacuum evaporation, and purified by a preparative HPLC system (Shimadzu, Japan) using a Shim-pack PREP-ODS(H) column (20 mm × 250 mm, 5 μm). The elution conditions were as follows: flow rate of 5.0 mL/min and a gradient elution program (0-10 min, 32% acetonitrile aqueous solution; 10-40 min, acetonitrile concentration was increased from 32% to 60%; and 40-50 min, 60% acetonitrile was maintained). The elution process was monitored by absorbance at 203 nm, and eluates were collected every 5 mL. The eluates containing the target product were combined and finally concentrated by vacuum evaporation. | [References]
[1] Chemistry of Natural Compounds, 2014, vol. 50, # 4, p. 691 - 696
[2] Khim. Prir. Soedin., 2014, vol. 50, # 4, p. 598 - 603,6
[3] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 120, p. 60 - 67 |
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