Gypenoside XLIXCAS# 94987-08-3 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 94987-08-3 | SDF | Download SDF |
| PubChem ID | 16007240 | Appearance | White powder |
| Formula | C52H86O21 | M.Wt | 1047.23 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | DMSO : 125 mg/mL (119.36 mM; Need ultrasonic) | ||
| Chemical Name | (3S,5S,8R,9S,10S,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-3-[(2S,3R,4S,5S)-5-hydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,4,8,14-tetramethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde | ||
| SMILES | CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C5CCC6C(CCC6(C5(CCC4C3(C)C)C)C)C(CCC=C(C)C)(COC7C(C(C(C(O7)CO)O)O)O)O)C=O)O)OC8C(C(C(CO8)O)O)O)O)O)O | ||
| Standard InChIKey | AFEVCSJFNQWWDF-AZFNEDKCSA-N | ||
| Standard InChI | InChI=1S/C52H86O21/c1-24(2)9-8-15-52(65,23-68-45-40(63)38(61)36(59)30(19-53)70-45)27-12-16-49(6)26(27)10-11-32-50(49,7)17-13-31-48(4,5)33(14-18-51(31,32)22-54)71-47-43(73-46-41(64)37(60)34(57)25(3)69-46)42(29(56)21-67-47)72-44-39(62)35(58)28(55)20-66-44/h9,22,25-47,53,55-65H,8,10-21,23H2,1-7H3/t25-,26+,27-,28+,29-,30+,31-,32-,33-,34-,35-,36+,37+,38-,39+,40+,41+,42-,43+,44-,45+,46-,47-,49+,50+,51+,52+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Gypenoside XLIX, a naturally occurring gynosaponin, inhibits NF-kappaB activation via a PPAR-alpha-dependent pathway, it may treat inflammatory and cardiovascular diseases, including atherosclerosis. |
| Targets | PPAR | TNF-α | NF-kB | p65 |
| In vitro | Gypenoside XLIX isolated from Gynostemma pentaphyllum inhibits nuclear factor-kappaB activation via a PPAR-alpha-dependent pathway.[Pubmed: 16525884]J Biomed Sci. 2006 Jul;13(4):535-48.Nuclear factor (NF)-kappaB is important in the generation of inflammation. Besides regulating lipid metabolism, peroxisome proliferator-activated receptor (PPAR)-alpha activators also reduce NF-kappaB activation to terminate activation of inflammatory pathways. Gynostemma pentaphyllum (GP) has been used to treat various inflammatory diseases and hyperlipidemia.
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| Cell Research | Gypenoside XLIX, a naturally occurring gynosaponin, PPAR-alpha dependently inhibits LPS-induced tissue factor expression and activity in human THP-1 monocytic cells.[Pubmed: 17141290]Toxicol Appl Pharmacol. 2007 Jan 1;218(1):30-6.Tissue factor (TF) is involved not only in the progression of atherosclerosis and other cardiovascular diseases, but is also associated with tumor growth, metastasis, and angiogenesis and hence may be an attractive target for directed cancer therapeutics. Gynostemma pentaphyllum (GP) is widely used in the treatment of various cardiovascular diseases including atherosclerosis, as well as cancers. Gypenoside (Gyp) XLIX, a dammarane-type glycoside, is one of the prominent components in GP. We have recently reported Gypenoside XLIX to be a potent peroxisome proliferator-activated receptor (PPAR)-alpha activator.
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| Structure Identification | Yao Xue Xue Bao. 1997 Jul;32(7):524-9.[Studies on the chemical constituents of Gynostemma longipes C.Y. Wu].[Pubmed: 11596278]
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Gypenoside XLIX Dilution Calculator
Gypenoside XLIX Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 0.9549 mL | 4.7745 mL | 9.549 mL | 19.098 mL | 23.8725 mL |
| 5 mM | 0.191 mL | 0.9549 mL | 1.9098 mL | 3.8196 mL | 4.7745 mL |
| 10 mM | 0.0955 mL | 0.4775 mL | 0.9549 mL | 1.9098 mL | 2.3873 mL |
| 50 mM | 0.0191 mL | 0.0955 mL | 0.191 mL | 0.382 mL | 0.4775 mL |
| 100 mM | 0.0095 mL | 0.0477 mL | 0.0955 mL | 0.191 mL | 0.2387 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Gypenoside XLIX, a naturally occurring PPAR-alpha activator, inhibits cytokine-induced vascular cell adhesion molecule-1 expression and activity in human endothelial cells.[Pubmed:17434475]
Eur J Pharmacol. 2007 Jun 22;565(1-3):158-65.
Vascular cell adhesion molecule-1 (VCAM-1) is involved in several diseases, including chronic inflammation and atherosclerosis. Inhibition of the expression of this adhesion molecule is one of the key targets of anti-inflammatory, anti-cancer and anti-atherosclerotic drugs. Gynostemma pentaphyllum is a traditional medicine widely used in the treatment of respiratory inflammation, hyperlipidemia and atherosclerosis. However, its molecular mechanisms of action are still largely unknown. Gypenoside XLIX, a dammarane-type glycoside, is a prominent component of G. pentaphyllum. We have recently demonstrated Gypenoside XLIX to be a selective peroxisome proliferator-activated receptor (PPAR)-alpha activator. Here we demonstrate that Gypenoside XLIX concentration-dependently (0-300 microM) inhibited VCAM-1 promoter activity after induction by cytokine tumor necrosis factor (TNF)-alpha in human umbilical vein endothelial cells (HUVECs) transfected with promoter-reporter construct pVCAM-1-LUC. Furthermore, Gypenoside XLIX inhibited TNF-alpha-induced VCAM-1 mRNA and protein overexpression in HUVECs. The result of the enzyme immunoassay demonstrated that Gypenoside XLIX inhibited TNF-alpha-induced increase in cell surface VCAM-1 protein levels in HUVECs. In the present study we show that activities of Gypenoside XLIX are similar to those of Wy-14643, a potent synthetic PPAR-alpha activator. Furthermore, Gypenoside XLIX-induced inhibition on TNF-alpha-stimulated VCAM-1 promoter hyperactivity was completely abolished by a selective blocker of PPAR-alpha, MK-886. Thus, our findings suggest that Gypenoside XLIX inhibits cytokine-induced VCAM-1 overexpression and hyperactivity in human endothelial cells via a PPAR-alpha-dependent pathway. These data provide new insight into the rational basis of the use of the traditional Chinese herbal medicine G. pentaphyllum in the treatment of inflammatory and cardiovascular diseases, including atherosclerosis.
[Studies on the chemical constituents of Gynostemma longipes C.Y. Wu].[Pubmed:11596278]
Yao Xue Xue Bao. 1997 Jul;32(7):524-9.
A new triterpenoid saponin named gylongiposide I was isolated from the aerial parts of Gynostemma longipes C.Y. Wu. On the basis of chemical evidence and spectral data the structure of gylongiposide I was elucidated as 19-oxo-3 beta, 20(S), 21-trihydroxydammar-24-ene-3-O-([alpha-L-rhamnopyranosy(1-->2)] [beta-D-xylpyranosyl(1-->3)]) alpha-L-arabinopyranoside (G). The known compounds were identified as Gypenoside XLIX(F) and ginsenoside Rb1(A).
Gypenoside XLIX, a naturally occurring gynosaponin, PPAR-alpha dependently inhibits LPS-induced tissue factor expression and activity in human THP-1 monocytic cells.[Pubmed:17141290]
Toxicol Appl Pharmacol. 2007 Jan 1;218(1):30-6.
Tissue factor (TF) is involved not only in the progression of atherosclerosis and other cardiovascular diseases, but is also associated with tumor growth, metastasis, and angiogenesis and hence may be an attractive target for directed cancer therapeutics. Gynostemma pentaphyllum (GP) is widely used in the treatment of various cardiovascular diseases including atherosclerosis, as well as cancers. Gypenoside (Gyp) XLIX, a dammarane-type glycoside, is one of the prominent components in GP. We have recently reported Gyp XLIX to be a potent peroxisome proliferator-activated receptor (PPAR)-alpha activator. Here we demonstrate that Gyp XLIX (0-300 microM) concentration dependently inhibited TF promoter activity after induction by the inflammatory stimulus lipopolysaccharide (LPS) in human monocytic THP-1 cells transfected with promoter reporter constructs pTF-LUC. Furthermore, Gyp XLIX inhibited LPS-induced TF mRNA and protein overexpression in THP-1 monocyte cells. Its inhibition of LPS-induced TF hyperactivity was further confirmed by chromogenic enzyme activity assay. The activities of Gyp XLIX reported in this study were similar to those of Wy-14643, a potent synthetic PPAR-alpha activator. Furthermore, the Gyp XLIX-induced inhibitory effect on TF luciferase activity was completely abolished in the presence of the PPAR-alpha selective antagonist MK-886. The present findings suggest that Gyp XLIX inhibits LPS-induced TF overexpression and enhancement of its activity in human THP-1 monocytic cells via PPAR-alpha-dependent pathways. The data provide new insights into the basis of the use of the traditional Chinese herbal medicine G. pentaphyllum for the treatment of cardiovascular and inflammatory diseases, as well as cancers.
Gypenoside XLIX isolated from Gynostemma pentaphyllum inhibits nuclear factor-kappaB activation via a PPAR-alpha-dependent pathway.[Pubmed:16525884]
J Biomed Sci. 2006 Jul;13(4):535-48.
Nuclear factor (NF)-kappaB is important in the generation of inflammation. Besides regulating lipid metabolism, peroxisome proliferator-activated receptor (PPAR)-alpha activators also reduce NF-kappaB activation to terminate activation of inflammatory pathways. Gynostemma pentaphyllum (GP) has been used to treat various inflammatory diseases and hyperlipidemia. Here, we demonstrate that GP extract and one of its main components, Gypenoside XLIX (Gyp-XLIX) inhibited LPS-induced NF-kappaB activation in murine macrophages. Furthermore, Gyp-XLIX restored the LPS- and TNF-alpha-induced decrease in cytosolic I-kappaBalpha protein expression and inhibited the translocation of NF-kappaB(p65) to the nucleus in THP-1 monocyte and HUVEC cells. The inhibition of LPS- and TNF-alpha-induced NF-kappaB luciferase activity in macrophages was abolished by MK-886, a selective PPAR-alpha antagonist. GP extract and Gyp-XLIX (EC(50): 10.1 microM) enhanced PPAR-alpha luciferase activity in HEK293 cells transfected with the tK-PPREx3-Luc reporter plasmid and expression vectors for PPAR-alpha. Additionally, Gyp-XLIX specifically enhanced PPAR-alpha mRNA and protein expression in THP-1-derived macrophage cells. The selectivity of Gyp-XLIX for PPAR-alpha was demonstrated by the activation of only PPAR-alpha in HEK293 cells transfected with expression vectors for PPAR-alpha, PPAR-beta/delta or PPAR-gamma1 plasmids and in THP-1-derived macrophage naturally expressing all three PPAR isoforms. The present study demonstrates that Gyp-XLIX, a naturally occurring gynosaponin, inhibits NF-kappaB activation via a PPAR-alpha-dependent pathway.
