(20S)-Protopanaxatriol - CAS 34080-08-5
Catalog number: 34080-08-5
Category: Inhibitor
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Molecular Formula:
C30H52O4
Molecular Weight:
476.73
COA:
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Targets:
Others
Description:
20S-Protopanaxatriol (g-PPT), a dammarane-type tetracyclic terpene sapogenin, may be used to study its binding to and modulation of cell function via glucocortoid (GR) and oestrogen (ER) receptors.
Purity:
>98%
Synonyms:
20(S)-APPT; g-PPT
MSDS:
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InChIKey:
SHCBCKBYTHZQGZ-CJPZEJHVSA-N
InChI:
InChI=1S/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,21-,22+,23-,24-,25-,27+,28+,29+,30-/m0/s1
Canonical SMILES:
CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CC(C4C3(CCC(C4(C)C)O)C)O)C)O)C)O)C
1.Both GPER and membrane oestrogen receptor-α activation protect ventricular remodelling in 17β oestradiol-treated ovariectomized infarcted rats.
Lee TM1, Lin SZ, Chang NC. J Cell Mol Med. 2014 Dec;18(12):2454-65. doi: 10.1111/jcmm.12430. Epub 2014 Sep 25.
Clinical and experimental studies have established that gender is a factor in the development of ventricular hypertrophy. We investigated whether the attenuated hypertrophic effect of oestradiol was via activation of phosphatidylinositol 3-kinase (PI3K)/Akt/endothelial nitric oxide synthase (eNOS) through non-genomic action. Twenty-four hours after coronary ligation, female Wistar rats were randomized into control, subcutaneous oestradiol treatment or a G-protein coupled oestrogen receptor (GPER) agonist, G-1 and treated for 4 weeks starting from 2 weeks after bilateral ovariectomy. Ventricular hypertrophy assessed by cardiomyocyte size after infarction was similarly attenuated by oestradiol or G-1 in infarcted rats. The phosphorylation of Akt and eNOS was significantly decreased in infarcted rats and restored by oestradiol and G-1, implying the GPER pathway in this process. Oestradiol-induced Akt phosphorylation was not abrogated by G-15 (a GPER blocker).
2.Identification of 20(S)-protopanaxatriol metabolites in rats by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry and nuclear magnetic resonance spectroscopy.
He C1, Zhou D, Li J, Han H, Ji G, Yang L, Wang Z. J Pharm Biomed Anal. 2014 Jan;88:497-508. doi: 10.1016/j.jpba.2013.09.031. Epub 2013 Oct 14.
20(S)-Protopanaxatriol (PPT), one of the aglycones of ginsenosides, has been shown to exert cardioprotective effects against myocardial ischemic injury. However, studies on PPT metabolism have rarely been reported. This study is the first to investigate the in vivo metabolism of PPT following oral administration by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-Q/TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy. The structures of the metabolites were identified based on the characteristics of their MS data, MS(2) data, and chromatographic retention times. A total of 22 metabolites, including 17 phase I and 5 phase II metabolites, were found and tentatively identified by comparing their mass spectrometry profiles with those of PPT. Two new monooxygenation metabolites, (20S,24S)-epoxy-dammarane-3,6,12,25-tetraol and (20S,24R)-epoxy-dammarane-3,6,12,25-tetraol, were chemicallly synthesized and unambiguously characterized according to the NMR spectroscopic data.
3.Bioactive protopanaxatriol type saponins isolated from the roots of Panax notoginseng (Burk.) F. H. Chen.
Zhang Y1, Han LF, Sakah KJ, Wu ZZ, Liu LL, Agyemang K, Gao XM, Wang T. Molecules. 2013 Aug 26;18(9):10352-66. doi: 10.3390/molecules180910352.
Seven new protopanaxatriol type saponins, 20S-sanchirhinosides A1 (1), A2 (2), A3 (3), A4 (4), A5 (5), and A6 (6), and sanchirhinoside B (7) were obtained as minor constituents from the root extract of Panax notoginseng (Burkill, F. H. Chen), which showed protection effects against antimycin A induced mitochondrial oxidative stress. Their structures were elucidated by chemical and spectroscopic methods (IR, HRESI-TOF-MS, 1D and 2D NMR). Among them, compounds 4, 6 and 7 showed significant protective effects against antimycin A-induced L6 cell injury.
4.Biotransformation of saponins by endophytes isolated from Panax notoginseng.
Luo SL1, Dang LZ, Li JF, Zou CG, Zhang KQ, Li GH. Chem Biodivers. 2013 Nov;10(11):2021-31. doi: 10.1002/cbdv.201300005.
The biotransformation of the major saponins in Panax notoginseng, including the ginsenosides Rg1, Rh1, Rb1, and Re, by endophytes isolated from P. notoginseng was studied. One hundred and thirty-six endophytes were isolated and screened for their biotransformational abilities. The results showed that five of the tested endophytes were able to transform these saponins. These five strains were identified based on their ITS or 16S rDNA sequences, which revealed that they belonged to the genera Fusarium, Nodulisporium, Brevundimonas, and Bacillus genera. Ten transformed products were isolated and identified, including a new compound 6-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranosyldammarane-3,6,12,20,24,25-hexaol (3), and nine known compounds, compound K (1), ginsenoside F2 (2), vinaginsenoside R13 (4), vinaginsenoside R22 (5), pseudo-ginsenoside RT4 (6), (20S)-protopanaxatriol (7), ginsenoside Rg1 (8), vinaginsenoside R15 (9), and (20S)-3-O-β-D-glucopyranosyl-6-O-β-D-glucopyranosylprotopanaxatriol (10).
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CAS 34080-08-5 (20S)-Protopanaxatriol

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