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1-α-O-Galloylpunicalagin

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1-α-O-Galloylpunicalagin
Chemical structure of 1-α-O-galloylpunicalagin
Names
Other names Combreglutinin
Teroblongin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C55H32O34/c56-13-1-8(2-14(57)30(13)62)48(75)89-55-47-46(87-51(78)10-4-16(59)31(63)35(67)20(10)21-11(52(79)88-47)5-17(60)32(64)36(21)68)43-19(83-55)7-82-49(76)9-3-15(58)33(65)37(69)22(9)24-28-26-27-29(54(81)86-44(26)41(73)39(24)71)25(40(72)42(74)45(27)85-53(28)80)23-12(50(77)84-43)6-18(61)34(66)38(23)70/h1-6,19,43,46-47,55-74H,7H2/t19?,43-,46-,47+,55?/m1/s1Key: PMOWTIMRSISLEU-NTBKRYJNSA-N
SMILES
  • C1C2(3(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5C6=C(C(=C(C=C6C(=O)O3)O)O)O)O)O)O)OC(=O)C7=CC(=C(C(=C7C8=C(C(=C9C2=C8C(=O)OC3=C(C(=C(C4=C(C(=C(C=C4C(=O)O1)O)O)O)C(=C23)C(=O)O9)O)O)O)O)O)O)O
Properties
Chemical formula C55H32O34
Molar mass 1236.827 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

1-α-O-Galloylpunicalagin is an ester of gallic acid and punicalagin, a type of ellagitannin. It is found in the pomegranate (Punica granatum) and in Combretum glutinosum.

A study in Taiwan showed that 1-α-O-galloylpunicalagin induced nitric oxide production in a dose-dependent manner in endothelial cells via the PI3K/AKT/mTOR pathway.

References

  1. Combreglutinin, a Hydrolyzable Tannin from Combretum glutinosum. Akino Jossang, Jean-Louis Pousset and Bernard Bodo, J. Nat. Prod., 1994, volume 57, issue 6, pages 732–737, doi:10.1021/np50108a008
  2. Chen, LG; Liu, YC; Hsieh, CW; Liao, BC; Wung, BS (2008). "Tannin 1-alpha-O-galloylpunicalagin induces the calcium-dependent activation of endothelial nitric-oxide synthase via the phosphatidylinositol 3-kinase/Akt pathway in endothelial cells". Molecular Nutrition & Food Research. 52 (10): 1162–71. doi:10.1002/mnfr.200700335. PMID 18435486.
Types of pomegranate ellagitannins
Aglycones
Sugars
Examples
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