1,2,3,4,6-pentagaloil-glucosa Knowpia

1,2,3,4,6-pentagaloil-glucosa
Nombre IUPAC
	[(2S,3R,4S,5R,6R)-2,3,5-tris[(3,4,5-trihydroxybenzoyl)oxy]-6-[(3,4,5-trihydroxybenzoyl)oxymethyl]oxan-4-yl] 3,4,5-trihydroxybenzoate
General
Otros nombres	1,2,3,4,6-penta-O-galoil-β-D-glucosa; 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose; beta-penta-O-galloyl-glucose; PGG; 1,2,3,4,6-Penta-O-galloyl-beta-D-glucose
Fórmula estructural
Fórmula molecular	C41H32O26
Identificadores
Número CAS	14937-32-7
ChEBI	18082
ChEMBL	382408
ChemSpider	58735
PubChem	65238
UNII	3UI3K8W93I
KEGG	C04576
	SMILES C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O
	InChI InChI=1S/C41H32O26/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/t27-,33-,34+,35-,41+/m1/s1; Key: QJYNZEYHSMRWBK-NIKIMHBISA-N
Propiedades físicas
Masa molar	940,67 g/mol
	Valores en el SI y en condiciones estándar; (25 ℃ y 1 atm), salvo que se indique lo contrario.
	[editar datos en Wikidata]

1,2,3,4,6-pentagaloil-glucosa es la pentahidroxi ácido gálico, éster de glucosa. Es el precursor común de los galotaninos y los relacionados elagitaninos.^[2]

Pentagaloil glucosa puede precipitar las proteínas^[3] incluyendo las salivales humanas, α-amilasa.^[4]

También se puede utilizar en la radioprotección.^[5]

Presencia natural

1,2,3,4,6-pentagaloil-glucosa se puede encontrar en el grando Punica granatum, el granado,^[6] en Elaeocarpus sylvestris^[5] o en Rhus typhina.^[7] También se puede encontrar en Paeonia suffruticosa

Biosíntesis

La enzima beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase usa 1-O-galloyl-beta-D-glucose y 1,2,3,6-tetrakis-O-galloyl-beta-D-glucose para producir D-glucosa y Pentagaloil glucosa.

Metabolismo

Metabolismo de los elagitaninos

Tellimagrandin II, primero de todos los elagitaninos, forma glucosa pentagalloyl por deshidrogenación oxidativa y el acoplamiento de 2 grupos galoil.

β-glucogallin: 1,2,3,4,6-pentagalloyl-β-d-glucose galloyltransferase es una enzima que se encuentra en las hojas de Rhus typhina, el zumaque cuerno de ciervo, que cataliza la galoilación de 1,2,3,4,6-penta-O-galloyl-β-d-glucose to 3-O-digalloyl-1,2,4,6-tetra-O-galloyl-β-d-glucose (hexa-galloylglucose).^[7]

Química

Pentagaloil glucosa puede sufrir reacciones de oxidación que están en función del pH.^[8]

Referencias

↑ Número CAS
↑ Biosynthesis of gallotannins: β-Glucogallin-dependent formation of 1,2,3,4,6-pentagalloylglucose by enzymatic galloylation of 1,2,3,6-tetragalloylglucose. Cammann J., Denzel K., Schilling G. and Gross G. G., Archives of Biochemistry and Biophysics, Volume 273, Issue 1, 15 August 1989, Pages 58-63
↑ Mechanisms of protein precipitation for two tannins, pentagalloyl glucose and epicatechin16 (4→8) catechin (procyanidin). Hagerman A. E., Rice M. E. and Ritchard N. T., Journal of agricultural and food chemistry, 1998, vol. 46, no7, pp. 2590-2595
↑ Evidence for pentagalloyl glucose binding to human salivary α-amylase through aromatic amino acid residues. Gyöngyi Gyémánt, Ágnes Zajácz, Bálint Bécsi, Chandran Ragunath, Narayanan Ramasubbu, Ferenc Erdődi, Gyula Batta and Lili Kandra, Biochimica et Biophysica Acta (BBA) - Proteins & Proteomics, Volume 1794, Issue 2, February 2009, pp. 291-296
↑ ^a ^b Elaeocarpus sylvestris modulates gamma-ray-induced immunosuppression in mice: implications in radioprotection. Park E, Lee NH, Baik JS and Jee Y, Phytother Res., August 2008, volume 22, issue 8, pages 1046-1051, doi 10.1002/ptr.2430, PubMed
↑ Punicafolin, an ellagitannin from the leaves of Punica granatum. Takashi Tanaka, Gen-Ichiro Nonaka and Itsuo Nishioka, Phytochemistry, Volume 24, Issue 9, 1985, Pages 2075–2078, doi 10.1016/S0031-9422(00)83125-8
↑ ^a ^b Gallotannin biosynthesis: purification of β-glucogallin: 1,2,3,4,6-pentagalloyl-β-d-glucose galloyltransferase from sumac leaves. Ruth Niemetz and Georg G Gross, Phytochemistry, Volume 49, Issue 2, 28 September 1998, pages 327-332, doi 10.1016/S0031-9422(98)00014-4
↑ Reaction pH and protein affect the oxidation products of β-pentagalloyl glucose. Yumin C. and Hagerman A.E., Free radical research, 2005, vol. 39, no2, pp. 117-124

Enlaces externos

Esta obra contiene una traducción derivada de «1,2,3,4,6-Pentagalloyl glucose» de Wikipedia en inglés, publicada por sus editores bajo la Licencia de documentación libre de GNU y la Licencia Creative Commons Atribución-CompartirIgual 4.0 Internacional.
http://onlinelibrary.wiley.com/doi/10.1111/j.1471-4159.2009.06069.x/pdf

Datos: Q4545645

[1] Número CAS

[2] Biosynthesis of gallotannins: β-Glucogallin-dependent formation of 1,2,3,4,6-pentagalloylglucose by enzymatic galloylation of 1,2,3,6-tetragalloylglucose. Cammann J., Denzel K., Schilling G. and Gross G. G., Archives of Biochemistry and Biophysics, Volume 273, Issue 1, 15 August 1989, Pages 58-63

[3] Mechanisms of protein precipitation for two tannins, pentagalloyl glucose and epicatechin16 (4→8) catechin (procyanidin). Hagerman A. E., Rice M. E. and Ritchard N. T., Journal of agricultural and food chemistry, 1998, vol. 46, no7, pp. 2590-2595

[4] Evidence for pentagalloyl glucose binding to human salivary α-amylase through aromatic amino acid residues. Gyöngyi Gyémánt, Ágnes Zajácz, Bálint Bécsi, Chandran Ragunath, Narayanan Ramasubbu, Ferenc Erdődi, Gyula Batta and Lili Kandra, Biochimica et Biophysica Acta (BBA) - Proteins & Proteomics, Volume 1794, Issue 2, February 2009, pp. 291-296

[Park-5] Elaeocarpus sylvestris modulates gamma-ray-induced immunosuppression in mice: implications in radioprotection. Park E, Lee NH, Baik JS and Jee Y, Phytother Res., August 2008, volume 22, issue 8, pages 1046-1051, doi 10.1002/ptr.2430, PubMed

[Tanaka-6] Punicafolin, an ellagitannin from the leaves of Punica granatum. Takashi Tanaka, Gen-Ichiro Nonaka and Itsuo Nishioka, Phytochemistry, Volume 24, Issue 9, 1985, Pages 2075–2078, doi 10.1016/S0031-9422(00)83125-8

[Niemetz-7] Gallotannin biosynthesis: purification of β-glucogallin: 1,2,3,4,6-pentagalloyl-β-d-glucose galloyltransferase from sumac leaves. Ruth Niemetz and Georg G Gross, Phytochemistry, Volume 49, Issue 2, 28 September 1998, pages 327-332, doi 10.1016/S0031-9422(98)00014-4

[8] Reaction pH and protein affect the oxidation products of β-pentagalloyl glucose. Yumin C. and Hagerman A.E., Free radical research, 2005, vol. 39, no2, pp. 117-124

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