62025-49-4 , 20-(S)-Ginsenoside F2
Cas:62025-49-4
C42H72O13 / 785.01
MFCD06410948
20-(S)-Ginsenoside F2 is a ginsenoside that has been shown to have biological properties, including signal pathways and anti-inflammatory effects. It can inhibit the activation of mitogen-activated protein kinase (MAPK) pathways, which are important in the regulation of cellular functions. 20-(S)-Ginsenoside F2 has also been shown to inhibit mitochondrial membrane potential and induce apoptosis. This compound is cytotoxic to brain cells, and significantly decreases malignant brain tumor cell viability in vitro. The analytical method for this compound is preparative high performance liquid chromatography. 20-(S)-Ginsenoside F2 binds to the polymerase chain reaction (PCR) primer site, preventing DNA replication.
Apoptotic and antiproliferative agent. Minor ginsenoside converted from Rb1. Induces apoptosis through multiple pathways (IC50 = 60 nM). Shows antitumor effects in vivo. Orally active.
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.
Ginsenoside F2 is 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. It has a role as an apoptosis inducer, an antineoplastic agent and a plant metabolite. It is a ginsenoside, a tetracyclic triterpenoid, a 12beta-hydroxy steroid and a beta-D-glucoside. It derives from a hydride of a dammarane.
CAS Number | 62025-49-4 |
Product Name | ginsenoside F2 |
IUPAC Name | 2-(hydroxymethyl)-6-[[12-hydroxy-4,4,8,10,14-pentamethyl-17-[6-methyl-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol |
Molecular Formula | C42H72O13 |
Molecular Weight | 785 g/mol |
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 |
InChI Key | SWIROVJVGRGSPO-JBVRGBGGSA-N |
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 |
Solubility | Soluble in DMSO |
Synonyms | Ginsenoside F2; FT-0686625; FT0686625; FT 0686625; N1568; N 1568; N-1568; X1142; X-1142; X 1142; C20779; C 20779; C-20779; Q-100717; Q 100717; Q 100717 |
Canonical 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 |
Isomeric SMILES | CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C |
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