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Chemical Characteristic

Product NameGypenosides
CAS No.15588-68-8
Molecular Weight 1791.83
FormulaC80H126O44
Smiles[C@H]1([C@@H]([C@H](C(O[C@@H]1CO)O[C@H]1[C@@H]([C@H](C(O[C@@H]1CO)O[C@H]1[C@@H]([C@H](C(O[C@@H]1C(=O)O)O[C@H]1CC[C@]2([C@H]([C@]1(C)C=O)CC[C@@]1([C@@H]2CC=C2[C@]1(CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)OC1O[C@H]([C@@H]([C@H]([C@H]1OC1OC[C@H]([C@@H]([C@H]1O)OC1OC
Chemical Structure

Biological activities

Gypenosides are the major components which are extracted from folk medicine Gynostemma pentaphyllum Makino. Gypenosides are used to treat hepatiti, hyperlipoproteinemia, cardiovascular disease and cancer. Gypenosides possess anti-inflammatory, anti-thrombotic, anti-oxidative and anti-cancer characteristics. Gypenosides show cytotoxic to Colo 205 cells with an IC50 of 113.5 mg/mL. Gypenosides induce apoptosis in human hepatoma cells through the activation of the caspase cascade and regulation of the Bcl-2 family. Gypenosides also affect N-acetyltransferase activity and gene expression in human cervical cancer cells.[1] Gypenosides induce suppression of human tongue squamous cell carcinoma SCC4 cell growth, induce apoptosis in response to overexpression of reactive oxygen species, calcium (Ca2+) and decrease mitochondrial membrane potential in vitro.[2] Pretreatment with gypenosides (100-400 mg/mL) significantly protect cells from glutamate-induced cell death. Gypenosides significantly up-regulate mRNAs encoding g-glutamylcysteine synthetase (g-GCS) and glutathione reductase (GR) and enhance their activities for GSH synthesis as well as recycle.[3] Gypenosides treatment at concentrations ranging from 50 to 200 mg/mL effectively attenuates MPP+-induced injury of dopaminergic neurons in a dose-dependent manner. Gypenosides (50 mg/mL) can sufficiently inhibit MPP+-induced injury. Gypenosides at the concentration of 200 mg/mL have the maximum protective effect.[4]

References

[1] Chen JC, et al. Gypenosides induced apoptosis in human colon cancer cells through the mitochondria-dependent pathways and activation of caspase-3. Anticancer Res. 2006, 26(6B): 4313-4326.
[2] Lu KW, et al. Gypenosides inhibited invasion and migration of human tongue cancer SCC4 cells through down-regulation of NFkappaB and matrix metalloproteinase-9. Anticancer Res. 2008, 28(2A): 1093-1099.
[3] Shang L, et al. Gypenosides protect primary cultures of rat cortical cells against oxidative neurotoxicity. Brain Res. 2006, 1102(1): 163-174.
[4] Wang P, et al. Gypenosides protects dopaminergic neurons in primary culture against MPP(+)-induced oxidative injury. Brain Res Bull. 2010, 83(5): 266-271.

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