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G7548

Penta-O-galloyl-β-D-glucose hydrate

≥96% (HPLC), apoptosis inducer, powder

Sinónimos:

1,2,3,4,6-Penta-O-galloyl-b-D-glucopyranose, 1,2,3,4,6-pentakis(3,4,5-trihydroxybenzoate)-b-D-Glucopyranose, Gallic acid, pentaester with b-D-glucopyranose, Glucopyranose, pentagallate, b-D, PGG, Penta-1,2,3,4,6-O-galloyl-b-D-glucose, Penta-O-galloyl-beta-D-glucose

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Acerca de este artículo

Fórmula empírica (notación de Hill):
C41H32O26 · xH2O
Número CAS:
14937-32-7
Peso molecular:
940.68 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329799964
NACRES:
NA.77
MDL number:
MFCD18632553
Assay:
≥96% (HPLC)
Form:
powder
Quality level:
100
Servicio técnico
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Nombre del producto

Penta-O-galloyl-β-D-glucose hydrate, ≥96% (HPLC)

Quality Level

100

assay

≥96% (HPLC)

form

powder

optical activity

[α]/D +14 to +26°, c = 0.2 in acetone-d6

color

light brown

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

O=C(O[C@H]([C@H]([C@@H]([C@@H](COC(C1=CC(O)=C(O)C(O)=C1)=O)O2)OC(C3=CC(O)=C(O)C(O)=C3)=O)OC(C4=CC(O)=C(O)C(O)=C4)=O)[C@@H]2OC(C5=CC(O)=C(O)C(O)=C5)=O)C6=CC(O)=C(O)C(O)=C6.O

InChI

1S/C41H32O26.H2O/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16;/h1-10,27,33-35,41-56H,11H2;1H2/t27-,33-,34+,35-,41+;/m1./s1

InChI key

JCJIMLXECAATFH-ZSJSDXHXSA-N

Application

Penta-O-galloyl-β-D-glucose hydrate (PCG) has been used as an inhibitor of abdominal aortic aneurysms (AAA) and matrix metalloproteinase (MMP) related metastatic activity.

Biochem/physiol Actions

Autophagy inducer in human PC-3 and mouse TRAMP-C2 prostate cancer cells
PGG induces predominantly (caspase dependent) apoptosis in DU145 and LNCaP cells, while inducing autophagy in more resistant PC3 and TRAMP-C2 cells. It appears that PGG targeted signaling downstream of rather than the mTOR itself. Polyphenolic pyranoses were reported (J Biol Chem. 2010, 285 (11), 7892-902) to inhibit the plasminogen activator inhibitor type 1 (PAI-1).
Penta-O-galloyl-β-D-glucose hydrate (PCG) is a polyphenolic gallotannin compound produced by plants. It has an ability to inhibit matrix metalloproteinase (MMP) related metastatic activity. Thus, PCG can be used for treating metastatic activity in squamous cell carcinoma. In addition, it also acts as a potential drug for stabilizing small abdominal aneurysms.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000506115
0000506115
0000432700
0000432700
0000399139

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Renate R Baumgartner et al.
Journal of natural products, 73(9), 1578-1581 (2010-09-02)
The inhibition of protein tyrosine phosphatase 1B (PTP1B) is of substantial interest for the treatment of type-2 diabetes mellitus. Using an in vitro enzyme assay with human recombinant PTP1B 1,2,3,4,6-penta-O-galloyl-D-glucopyranose was isolated from the roots of Paeonia lactiflora as an
Mei-Hui Lin et al.
Antimicrobial agents and chemotherapy, 55(3), 1021-1027 (2010-12-22)
1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose (PGG) is an active ingredient in plants that are commonly used in Chinese medicine to treat inflammation. We demonstrate here that PGG, at 6.25 μM, does not inhibit the growth of Staphylococcus aureus, and yet it prevents biofilm formation
Hyo-Jung Lee et al.
Kidney international, 79(5), 538-545 (2010-11-19)
Adhesion of calcium oxalate (CaOx) crystals to kidney cells may be a key event in the pathogenesis of kidney stones associated with marked hyperoxaluria. Previously, we found that 1,2,3,4,6-penta-O-galloyl-β-D-glucose (PGG), isolated from a traditional medicinal herb, reduced CaOx crystal adhesion
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