62025-49-4

Basic information

• Product Name: GINSENOSIDE F2
• Synonyms: GINSENOSIDE F2;(20S)-3β-(β-D-Glucopyranosyloxy)-20-(β-D-glucopyranosyloxy)dammar-24-ene-12β-ol;(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);20(S)-Ginsenoside-F2;20(S)-Ginsenoside F2 ,98%;-D-glucopyranosidederiv.;Ginsenoside F2, >=98%
• CAS NO: 62025-49-4
• Molecular Formula: C₄₂H₇₂O₁₃
• Molecular Weight: 785.01
• Product Categories: Ginseng series;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 62025-49-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 871.488 °C at 760 mmHg
• Flash Point: 480.858 °C
• Appearance: /
• Density: 1.303 g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.91±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: GINSENOSIDE F2(CAS DataBase Reference)
• NIST Chemistry Reference: GINSENOSIDE F2(62025-49-4)
• EPA Substance Registry System: GINSENOSIDE F2(62025-49-4)

Safety Data

• Hazardous Substances Data: 62025-49-4(Hazardous Substances Data)

Usage

Description

Ginsenoside F2 is a ginsenoside that has been found in P. ginseng and has diverse biological activities. 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. 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. Ginsenoside F2 (1 mg/ear) reduces ear edema induced by phorbol 12-myristate 13-acetate (TPA; ) in mice. It is a human intestinal bacterial metabolite of ginsenoside Rb1 via the intermediate ginsenoside Rd .

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.

Synthetic route

ginsenoside Rd (52705-93-8) → ginsenoside F2 (62025-49-4)

Conditions	Yield
With water at 30℃; Microbiological reaction;	74%
With recombinant β-glucosidase CcBgl1A from Cellulosimicrobium cellulans sp. 21 In aq. phosphate buffer at 30℃; for 2h; pH=5.5; Enzymatic reaction;	62 mg
With Aspergillus oryzae β-galactosidase; water In aq. phosphate buffer at 50℃; for 1h; pH=4.5; Enzymatic reaction;

Ginsenoside Rb1 (41753-43-9, 132929-86-3) → ginsenoside F2 (62025-49-4) + 3-O-(β-D-glucopyranosyl)-20-O-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]-3β,12β,20β-trihydroxydammar-24-ene (80321-69-3)

Conditions	Yield
With water at 30℃; for 36h; Microbiological reaction;	A 58% B n/a
With recombinant β-glycosidase from Microbacterium sp. Gsoil 167, Ile184Ala, Ile389Ala, Phe390Ala mutant for 1h; Time; Enzymatic reaction;

3,20-di-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)dammar-24-en-3β,12β,20S-triol (108194-57-6) → ginsenoside F2 (62025-49-4)

Conditions	Yield
With sodium methylate In methanol Yield given;

(20S)-dammar-24-ene-3α,12β,20-triol (6892-79-1) → ginsenoside F2 (62025-49-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: chromic anhydride / pyridine 2: sodium borohydride / propan-2-ol 3: silver oxide / CH2Cl2 4: 0.1M sodium methoxide / methanol View Scheme
Multi-step reaction with 4 steps 1: chromic anhydride / pyridine 2: sodium borohydride / propan-2-ol 3: silver oxide / CH2Cl2 4: 0.1M sodium methoxide / methanol View Scheme
Multi-step reaction with 4 steps 1: chromic anhydride / pyridine 2: sodium borohydride / propan-2-ol 3: silver oxide / CH2Cl2 4: 0.1M sodium methoxide / methanol View Scheme
Multi-step reaction with 4 steps 1: chromic anhydride / pyridine 2: sodium borohydride / propan-2-ol 3: silver oxide / CH2Cl2 4: 0.1M sodium methoxide / methanol View Scheme

protopanaxadiol (6892-79-1, 7755-01-3, 30636-90-9, 38243-15-1, 53368-76-6, 103834-30-6) → ginsenoside F2 (62025-49-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: silver oxide / CH2Cl2 2: 0.1M sodium methoxide / methanol View Scheme
Multi-step reaction with 2 steps 1: silver oxide / CH2Cl2 2: 0.1M sodium methoxide / methanol View Scheme
Multi-step reaction with 2 steps 1: silver oxide / CH2Cl2 2: 0.1M sodium methoxide / methanol View Scheme
Multi-step reaction with 2 steps 1: silver oxide / CH2Cl2 2: 0.1M sodium methoxide / methanol View Scheme

12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one (51116-90-6) → ginsenoside F2 (62025-49-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium borohydride / propan-2-ol 2: silver oxide / CH2Cl2 3: 0.1M sodium methoxide / methanol View Scheme
Multi-step reaction with 3 steps 1: sodium borohydride / propan-2-ol 2: silver oxide / CH2Cl2 3: 0.1M sodium methoxide / methanol View Scheme
Multi-step reaction with 3 steps 1: sodium borohydride / propan-2-ol 2: silver oxide / CH2Cl2 3: 0.1M sodium methoxide / methanol View Scheme
Multi-step reaction with 3 steps 1: sodium borohydride / propan-2-ol 2: silver oxide / CH2Cl2 3: 0.1M sodium methoxide / methanol View Scheme

Ginsenoside Rb1 (41753-43-9, 132929-86-3) → ginsenoside F2 (62025-49-4) + compound K (39262-14-1)

Conditions	Yield
With Fusarium sp.,(YMF1.02193) In methanol at 28℃; Microbiological reaction;
With recombinant β-glycosidase from Microbacterium sp. Gsoil 167, Ile184Ala, Ile389Ala, Phe390Ala mutant for 24h; Kinetics; Time; Enzymatic reaction;

Ginsenoside Rb1 (41753-43-9, 132929-86-3) → ginsenoside F2 (62025-49-4)

Conditions	Yield
With Fusarium oxysporum(YMF1.02670) In methanol at 28℃; Microbiological reaction;	5 mg
Multi-step reaction with 2 steps 1: water / 36 h / 30 °C / Microbiological reaction 2: water / 72 h / 30 °C / Microbiological reaction View Scheme
With β-galactosidase from Aspergillus saponins; water In methanol at 60℃; for 96h; Enzymatic reaction;

3-O-(β-D-glucopyranosyl)-20-O-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]-3β,12β,20β-trihydroxydammar-24-ene (80321-69-3) → ginsenoside F2 (62025-49-4)

Conditions	Yield
With water at 30℃; for 72h; Microbiological reaction;

Ginsenoside Rb3 (11021-13-9, 68406-26-8, 82166-13-0, 82166-14-1, 146987-67-9) → ginsenoside F2 (62025-49-4) + 3-O-β-D-glucopyranosyl-20-O-[β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl]-20(S)-protopanaxadiol

Conditions	Yield
With recombinant β-glycosidase from Microbacterium sp. Gsoil 167, wild-type for 120h; Enzymatic reaction;

Ginsenoside Rb1 (41753-43-9, 132929-86-3) → ginsenoside F2 (62025-49-4) + ginsenoside Rd (52705-93-8)

Conditions	Yield
With recombinant β-glycosidase from Microbacterium sp. Gsoil 167, wild-type for 24h; Enzymatic reaction;

ginsenoside Rb2 (11021-13-9, 68406-26-8, 82166-13-0, 82166-14-1, 146987-67-9) → ginsenoside F2 (62025-49-4) + 3-O-(β-D-glucopyranosyl)-20-O-[α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]-3β,12β,20β-trihydroxydammar-24-ene

Conditions	Yield
With recombinant β-glycosidase from Microbacterium sp. Gsoil 167, Ile184Ala, Ile389Ala, Phe390Ala mutant for 1h; Time; Enzymatic reaction;

ginsenoside Rb2 (11021-13-9, 68406-26-8, 82166-13-0, 82166-14-1, 146987-67-9) → ginsenoside F2 (62025-49-4) + ginsenoside Rd (52705-93-8)

Conditions	Yield
With recombinant β-glycosidase from Microbacterium sp. Gsoil 167, wild-type for 24h; Enzymatic reaction;

ginsenoside Rb2 (11021-13-9, 68406-26-8, 82166-13-0, 82166-14-1, 146987-67-9) → ginsenoside F2 (62025-49-4) + compound K (39262-14-1)

Conditions	Yield
With recombinant β-glycosidase from Microbacterium sp. Gsoil 167, Ile184Ala, Ile389Ala, Phe390Ala mutant for 120h; Kinetics; Enzymatic reaction;

Upstream product

• 108194-57-6 3,20-di-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)dammar-24-en-3β,12β,20S-triol 
• 6892-79-1 (20S)-dammar-24-ene-3α,12β,20-triol 
• 6892-79-1 protopanaxadiol 
• 51116-90-6 12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one 
• 41753-43-9 Ginsenoside Rb₁ 
• 80321-69-3 3-O-(β-D-glucopyranosyl)-20-O-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]-3β,12β,20β-trihydroxydammar-24-ene 
• 11021-13-9 ginsenoside Rb₂ 
• 11021-13-9 Ginsenoside Rb₃ 
• 52705-93-8 ginsenoside Rd 

Relevant articles and documents

Overexpression and characterization of a glycoside hydrolase family 1 enzyme from Cellulosimicrobium cellulans sp. 21 and its application for minor ginsenosides production

Abstract A novel β-glucosidase gene (ccbgl1a) was cloned from the ginsenosides-transforming strain Cellulosimicrobium cellulans sp. 21. This enzyme was overexpressed in Escherichia coli, the recombinant β-glucosidase (CcBgl1A) containing N-terminal His-tag was sufficiently purified by nickel metal affinity chromatography with purification factor of 1.9-fold and specific activity of 31.5 U/mg. The molecular mass of recombinant CcBgl1A was estimated to be approximately 46 kDa. CcBgl1A exhibited optimal activity at 35°C and pH 5.5. However, above 40°C, the enzyme stability significantly decreased. The enzyme showed high bioconversion ability on protopanaxadiol-type ginsenosides mixture (PPDGM), which could hydrolyze the outer C-3 glucose moieties of ginsenosides Rb1, Rb2, Rc and Rd into the rare ginsenosides Gypenoside XVII (Gyp XVII), compound O, ginsenoside Mb and ginsenoside F2. Scaled-up production using 1 g of the PPDGM resulted in 292 mg Gyp XVII, 134 mg CO, 184 mg Mb, and 62 mg F2, with chromatographic purities. These results suggest that CcBgl1A would be potentially useful in the preparation of pharmacologically active minor ginsenosides Gyp XVII, CO, Mb and F2.

Rational design of a β-glycosidase with high regiospecificity for triterpenoid tailoring

Triterpenoids with desired glycosylation patterns have attracted considerable attention as potential therapeutics for inflammatory diseases and various types of cancer. Sugar-hydrolyzing enzymes with high substrate specificity would be far more efficient than other methods for the synthesis of such specialty triterpenoids, but they are yet to be developed. Here we present a strategy to rationally design a β-glycosidase with high regiospecificity for triterpenoids. A β-glycosidase with broad substrate specificity was isolated, and its crystal structure was determined at 2.0 ? resolution. Based on the product profiles and substrate docking simulations, we modeled the substrate binding modes of the enzyme. From the model, the substrate binding cleft of the enzyme was redesigned in a manner that preferentially hydrolyzes glycans at specific glycosylation sites of triterpenoids. The designed mutants were shown to produce a variety of specialty triterpenoids with high purity.

Biotransformation of the principal ginsenosides of Panax ginseng into minor glycosides through the action of bacterium Paenibacillus sp. BG134

The bacterium Paenibacillus sp. BG134 was capable of biotransforming the principal 20(S)-protopanaxadiol ginsenosides Rc, Rb2, Rd, and Rb1 into the corresponding minor glycosides C-Mc1, C-O, and F-2. The specificity of Paenibacillus