(3b,6a,12b,24R)-20,24-Epoxy-3,12,25-trihydroxydammaran-6-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-bet

Introduction：Basic information about (3b,6a,12b,24R)-20,24-Epoxy-3,12,25-trihydroxydammaran-6-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-bet, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

(3b,6a,12b,24R)-20,24-Epoxy-3,12,25-trihydroxydammaran-6-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside Basic information

• Product Name: (3b,6a,12b,24R)-20,24-Epoxy-3,12,25-trihydroxydammaran-6-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
• Synonyms: PSEUDOGINSENOSIDE F11;GINSENOSIDE A1;(3b,6a,12b,24R)-20,24-Epoxy-3,12,25-trihydroxydammaran-6-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside;(20S,24R)-6α-(2-O-α-L-Rhamnopyranosyl-β-D-glucopyranosyloxy)-20,24-epoxy-5α-dammarane-3β,12β,25-triol;(24R)-Pseudoginsenoside F11;[(24R)-20,24-Epoxy-3β,12β,25-trihydroxy-5α-dammaran-6α-yl]2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside;17β-[[(2S)-2β-Methyl-5α-(1-hydroxy-1-methylethyl)tetrahydrofuran]-2-yl]-3β,12β-dihydroxy-4,4,8β,10β,14α-pentamethyl-5α-gonane-6α-yl 2-O-α-L-rhamnopyranosyl-β-D-glucopyranoside;PSEUDOEPHEDRINE HCl, (+)-1S,2S- AMP 1.0mg/ml(P)(DISCONTINUED)
• CAS: 69884-00-0
• MF: C42H72O14
• MW: 801.01
• Product Categories: Ginsenoside series;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Saponins
• Mol File: 69884-00-0.mol

(3b,6a,12b,24R)-20,24-Epoxy-3,12,25-trihydroxydammaran-6-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside Chemical Properties

• Melting point: >196°C (dec.)
• Boiling point: 885.3±65.0 °C(Predicted)
• density: 1.33±0.1 g/cm3(Predicted)
• storage temp.: 2-8°C
• solubility: Methanol (Slightly), Pyridine (Slightly)
• pka: 12.85±0.70(Predicted)
• form: Solid
• color: White
• InChIKey: JBGYSAVRIDZNKA-VQZATTJQNA-N

Safety Information

• Hazard Codes: Xn
• Risk Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• HS Code: 29389090
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Acute Tox. 4 Oral

(3b,6a,12b,24R)-20,24-Epoxy-3,12,25-trihydroxydammaran-6-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside Usage And Synthesis

Description

Pseudoginsenoside F₁₁ is an ocotillol-type ginsenoside that has been found in P. ginseng and has diverse biological activities. In vivo, pseudoginsenoside F₁₁ (10 mg/kg) prevents tubular cell apoptosis, decreases in renal glutathione peroxidase (GPX) and superoxide dismutase (SOD) levels, and increases in renal lipid peroxide levels in a rat model of nephrotoxicity induced by cisplatin . It reduces infarct size, brain water content, and cortical accumulation of autophagosomes in a rat model of ischemic stroke induced by permanent middle cerebral artery occlusion. Pseudoginsenoside F₁₁ (4 and 8 mg/kg) inhibits morphine-induced memory impairment in the Morris water maze and development of morphine-induced conditioned place preference in mice. It also reduces hippocampal advanced glycation end product (AGE) and malondialdehyde (MDA) levels, increases hippocampal SOD activity and glutathione (GSH) levels, and attenuates cognitive impairment in the Morris water maze in a mouse model of D-galactose-induced mild cognitive impairment.

Chemical Properties

White solid

Uses

Pseudoginsenoside F11 is an oxotillol-type ginsenoside which displayes neuroprotective activity.

in vivo

One in vivo model of cisplatin-induced acute renal failure was performed. The results showed that pretreatment with Pseudoginsenoside Pseudoginsenoside F11 (Ginsenoside A1) reduced cisplatin-elevated blood urea nitrogen and creatinine levels, as well as ameliorated the histophathological damage [1]. We tested the effects of Pseudoginsenoside Pseudoginsenoside F11 (Ginsenoside A1) on morphine-induced development of behavioral sensitization and alterations in glutamate levels in the medial prefrontal cortex (mPFC) in freely moving mice by using in vivo microdialysis. As the results shown, Pseudoginsenoside Pseudoginsenoside F11 (Ginsenoside A1) antagonized the development of behavioral sensitization and decrease of glutamate in the mPFC induced by morphine^[3].

References

[1] HONGBO WANG. The pseudoginsenoside F11 ameliorates cisplatin-induced nephrotoxicity without compromising its anti-tumor activity in vivo.[J]. Scientific Reports, 2014: 4986. DOI: 10.1038/srep04986
[2] YUE-YANG LIU. Pseudoginsenoside-F11 attenuates cerebral ischemic injury by alleviating autophagic/lysosomal defects[J]. CNS Neuroscience & Therapeutics, 2017, 23 7: 567-579. DOI: 10.1111/cns.12702
[3] ZHU LI . Antagonistic Effect of Pseudoginsenoside-F11 on the Behavioral Actions of Morphine in Mice[J]. Pharmacology Biochemistry and Behavior, 2000, 66 3: Pages 595-601. DOI: 10.1016/s0091-3057(00)00260-4
[4] ZHEN ZHANG. Pseudoginsenoside-F11 attenuates cognitive impairment by ameliorating oxidative stress and neuroinflammation in d?galactose-treated mice[J]. International immunopharmacology, 2019, 67: Pages 78-86. DOI: 10.1016/j.intimp.2018.11.026