Gypenoside XVII - CAS 80321-69-3
Catalog number:
80321-69-3
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C48H82O18
Molecular Weight:
947.15
COA:
Inquire
Targets:
Others
Description:
Gypenoside XVII is a natural product extracted from the roots of Panax notoginseng (Burk.) F.H.Chen. It confers protection against Aβ25-35-induced neurotoxicity through estrogen receptor-dependent activation of PI3K/Akt pathways, inactivation of GSK-3β and activation of Nrf2/ARE/HO-1 pathways.
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Purity:
>98%
Appearance:
Solid powder
Synonyms:
3β-(β-D-Glucopyranosyloxy)-12β-hydroxy-5α-dammar-24-en-20-yl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside;(3beta,12beta)-3-(beta-D-Glucopyranosyloxy)-12-hydroxydammar-24-en-20-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside;Gynosaponin S;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2S)-2-[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol
Solubility:
10 mM in DMSO
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
Gypenoside XVII confers protection against Aβ25-35-induced neurotoxicity through estrogen receptor-dependent activation of PI3K/Akt pathways, inactivation of GSK-3β and activation of Nrf2/ARE/HO-1 pathways.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Grams to Kilograms
Boiling Point:
1013.5±65.0 °C | Condition: Press: 760 Torr
Density:
1.38±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
ZRBFCAALKKNCJG-SJYBZOGZSA-N
InChI:
InChI=1S/C48H82O18/c1-22(2)10-9-14-48(8,66-43-40(60)37(57)34(54)27(64-43)21-61-41-38(58)35(55)32(52)25(19-49)62-41)23-11-16-47(7)31(23)24(51)18-29-45(5)15-13-30(44(3,4)28(45)12-17-46(29,47)6)65-42-39(59)36(56)33(53)26(20-50)63-42/h10,23-43,49-60H,9,11-21H
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)COC7C(C(C(C(O7)CO)O)O)O)O)O)O)C
1.Biotransformation of gypenoside XVII to compound K by a recombinant β-glucosidase.
Zhong FL1, Dong WW1, Wu S1, Jiang J1, Yang DC2, Li D3, Quan LH4. Biotechnol Lett. 2016 Apr 8. [Epub ahead of print]
OBJECTIVE: To study the β-glucosidase gene (bgy1) from Lactobacillus brevis that was cloned and expressed in Escherichia coli BL21 (DE3) and then using it for the biotransformation of gypenoside XVII.
2.Gypenoside XVII Enhances Lysosome Biogenesis and Autophagy Flux and Accelerates Autophagic Clearance of Amyloid-β through TFEB Activation.
Meng X1, Luo Y1, Liang T2, Wang M3, Zhao J3, Sun G1, Sun X1. J Alzheimers Dis. 2016 Apr 5. [Epub ahead of print]
A strategy for activating transcription factor EB (TFEB) to restore autophagy flux may provide neuroprotection against Alzheimer's disease. Our previous study reported that gypenoside XVII (GP-17), which is a major saponin abundant in ginseng and Panax notoginseng, ameliorated amyloid-β (Aβ)25-35-induced apoptosis in PC12 cells by regulating autophagy. In the present study, we aimed to determine whether GP-17 has neuroprotective effects on PC12 cells expressing the Swedish mutant of APP695 (APP695swe) and APP/PS1 mice. We also investigated the underlying mechanism. We found that GP-17 could significantly increase Atg5 expression and the conversion of LC3-I to LC3-II in APP695 cells, which was associated with a reduction in p62 expression. GP-17 also elevated the number of LC3 puncta in APP695 cells transduced with pCMV-GFP-LC3. GP-17 promoted the autophagy-based elimination of AβPP, Aβ40, and Aβ42 in APP695swe cells and prevented the formation of Aβ plaques in the hippocampus and cortex of APP/PS1 mice.
3.Attenuation of Aβ25-35-induced parallel autophagic and apoptotic cell death by gypenoside XVII through the estrogen receptor-dependent activation of Nrf2/ARE pathways.
Meng X1, Wang M1, Sun G2, Ye J3, Zhou Y4, Dong X5, Wang T1, Lu S1, Sun X6. Toxicol Appl Pharmacol. 2014 Aug 15;279(1):63-75. doi: 10.1016/j.taap.2014.03.026. Epub 2014 Apr 12.
Amyloid-beta (Aβ) has a pivotal function in the pathogenesis of Alzheimer's disease. To investigate Aβ neurotoxicity, we used an in vitro model that involves Aβ25-35-induced cell death in the nerve growth factor-induced differentiation of PC12 cells. Aβ25-35 (20μM) treatment for 24h caused apoptotic cell death, as evidenced by significant cell viability reduction, LDH release, phosphatidylserine externalization, mitochondrial membrane potential disruption, cytochrome c release, caspase-3 activation, PARP cleavage, and DNA fragmentation in PC12 cells. Aβ25-35 treatment led to autophagic cell death, as evidenced by augmented GFP-LC3 puncta, conversion of LC3-I to LC3-II, and increased LC3-II/LC3-I ratio. Aβ25-35 treatment induced oxidative stress, as evidenced by intracellular ROS accumulation and increased production of mitochondrial superoxide, malondialdehyde, protein carbonyl, and 8-OHdG. Phytoestrogens have been proved to be protective against Aβ-induced neurotoxicity and regarded as relatively safe targets for AD drug development.
4.Enzymatic Biotransformation of Ginsenoside Rb1 and Gypenoside XVII into Ginsenosides Rd and F2 by Recombinant β-glucosidase from Flavobacterium johnsoniae.
Hong H1, Cui CH, Kim JK, Jin FX, Kim SC, Im WT. J Ginseng Res. 2012 Oct;36(4):418-24. doi: 10.5142/jgr.2012.36.4.418.
This study focused on the enzymatic biotransformation of the major ginsenoside Rb1 into Rd for the mass production of minor ginsenosides using a novel recombinant β-glucosidase from Flavobacterium johnsoniae. The gene (bglF3) consisting of 2,235 bp (744 amino acid residues) was cloned and the recombinant enzyme overexpressed in Escherichia coli BL21(DE3) was characterized. This enzyme could transform ginsenoside Rb1 and gypenoside XVII to the ginsenosides Rd and F2, respectively. The glutathione S-transferase (GST) fused BglF3 was purified with GST-bind agarose resin and characterized. The kinetic parameters for β-glucosidase had apparent Km values of 0.91±0.02 and 2.84±0.05 mM and Vmax values of 5.75±0.12 and 0.71±0.01 μmol·min(-1)·mg of protein(-1) against p-nitrophenyl-β-D-glucopyranoside and Rb1, respectively. At optimal conditions of pH 6.0 and 37℃, BglF3 could only hydrolyze the outer glucose moiety of ginsenoside Rb1 and gypenoside XVII at the C-20 position of aglycon into ginsenosides Rd and F2, respectively.
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CAS 80321-69-3 Gypenoside XVII

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