68406-26-8 , Ginsenoside Rb3 ,
Gypenoside IV ,
(3b,12b)-3-[(2-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 6-O-(b-D-glucopyranosyl)-b-D-glucopyranoside;
Gypenoside IV
Cas:68406-26-8
C53H90O22 / 1079.27
MFCD10566396
(3b,12b)-3-[(2-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 6-O-(b-D-glucopyranosyl)-b-D-glucopyranoside; Gypenoside IV
Ginsenoside Rb3 is a natural product that belongs to the group of ginseng saponins. It is a major active component of ginseng, which has been demonstrated to have various biological effects, such as anti-inflammatory and hypoglycemic effects. Ginsenoside Rb3 inhibits the activation of pro-inflammatory pathways, including NF-κB and MAPKs, and induces apoptosis in tumor cells through the mitochondrial membrane potential. Ginsenoside Rb3 also has antioxidant properties, which may be due to its ability to inhibit oxidative stress-induced DNA damage. In addition, this compound has been shown to have an effect on glucose metabolism by acting on insulin receptors and inhibiting the activity of enzymes involved in energy metabolism. Ginsenoside Rb3 can prevent cardiac myocardial infarction and improve energy metabolism by activating AMPK.
Ginsenoside Rb3 is a steroid glycoside that has been found in Panax and has diverse biological activities. It inhibits JNK-mediated activation of NF-κB and apoptosis induced by oxygen-glucose deprivation (OGD) in H9c2 mouse cardiac myoblasts in vitro and reduces myocardial apoptosis and production of reactive oxygen species (ROS) in a rat model of myocardial ischemia-reperfusion injury when administered at a dose of 20 mg/kg. Ginsenoside Rb3 (10 and 20 mg/kg per day for 10 days) prevents increases in serum creatinine, blood urea nitrogen (BUN), and malondialdehyde (MDA) levels, and decreases in superoxide dismutase (SOD) activity and glutathione (GSH) levels, as well as inhibits renal cell apoptosis in a mouse model of nephrotoxicity induced by cisplatin. It decreases the abundance of cancer cachexia-associated gut microbiota and the number of polyps in the ApcMin/+ mouse model of colon cancer. Ginsenoside Rb3 also decreases immobility time in the forced swim and tail suspension tests, indicating antidepressant-like activity, in mice.
Ginsenoside Rb3 analytical standard provided with w/w absolute assay, to be used for quantitative titration.
Ginsenoside Rb3 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-glucopyranosyl-(1->2)-beta-D-glucopyranoside and beta-D-xylopyranosyl-(1->6)-beta-D-glucopyranoside respectively, and in which a double bond has been introduced at the 24-25 position. It has a role as a plant metabolite, an antioxidant, an antidepressant, a cardioprotective agent, a NMDA receptor antagonist and a neuroprotective agent. It is a 12beta-hydroxy steroid, a beta-D-glucoside, a disaccharide derivative, a ginsenoside and a tetracyclic triterpenoid. It derives from a hydride of a dammarane.
CAS Number | 68406-26-8 |
Product Name | Unii-W6V49A8fjq |
IUPAC Name | (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]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]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol |
Molecular Formula | C53H90O22 |
Molecular Weight | 1079.3 g/mol |
InChI | InChI=1S/C53H90O22/c1-23(2)10-9-14-53(8,75-47-43(67)39(63)37(61)29(72-47)22-69-45-41(65)34(58)26(57)21-68-45)24-11-16-52(7)33(24)25(56)18-31-50(5)15-13-32(49(3,4)30(50)12-17-51(31,52)6)73-48-44(40(64)36(60)28(20-55)71-48)74-46-42(66)38(62)35(59)27(19-54)70-46/h10,24-48,54-67H,9,11-22H2,1-8H3/t24-,25+,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39-,40-,41+,42+,43+,44+,45-,46-,47-,48-,50-,51+,52+,53-/m0/s1 |
InChI Key | NODILNFGTFIURN-DEJGUFKASA-N |
SMILES | CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)C)OC7C(C(C(C(O7)COC8C(C(C(CO8)O)O)O)O)O)O)C |
Solubility | Soluble in DMSO |
Synonyms | Ginsenoside C, Ginsenoside-Rb3, HY-N0041, HYN0041, HY N0041, FT-0626701, FT0626701, FT 0626701, CS-3831, CS3831, CS 3831 |
Canonical SMILES | CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)C)OC7C(C(C(C(O7)COC8C(C(C(CO8)O)O)O)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@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O)O)C |
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